The Official SaaStr Podcast: SaaS | Founders | Investors

Fouad ElNaggar is the Founder & CEO @ Sapho, the only employee experience portal designed for the digital workforce. To date, Ray has raised over $27m in funding with Sapho from some real favourites of ours including Ray @ Caffeinated, Felicis, Uncork, Bloomberg Beta, Clark Landry and Howard Lindzon @ Social Leverage, just to name a few. Prior to founding Sapho, Fouad was the Chief Strategy Officer at CBS Interactive overseeing strategy, operations, partnerships, and M&A. At CBSi, Fouad structured deals with partners such as Yahoo, IAC, and Twitch and acquired premium brands such as TV Guide and Giant Bomb. Prior to CBSi, Fouad was a VC at Redpoint Ventures overseeing the firm's LA office and helping establish a dedicated fund in Brazil. Fouad has previously founded three venture-backed companies – Marketing Technology Solutions (acquired), Liquid Light (acquired), and Hark. In Today's Episode You Will Learn: How Fouad made his way from the world of VC to the world of CBS and media to founding SaaS companies being a serial SaaS founder with his 4th company, Sapho? What does Fouad mean when he says the role of the CEO is to be an "inspirational asshole"? Why is this role so crucial and how is it embodied both in the approach to inspiring a team and driving goals and decision-making? How does Fouad think about structuring decision-making internally? Where do so many go wrong in implementing a decision-making process? Why is Fouad a believer that "it is about coaching and promoting rather than signal hiring"? What does Fouad really interpret as signal hiring? When does signal hiring work well? How does Fouad determine when a stretch VP is a stretch too far? What are the leading indicators? Does Fouad agree with Mariam Naficy that rotation of function is key to internal upscaling? What does Fouad believe are the 2 fundamental benefits of "being old" in SaaS? How would Fouad respond to the suggestion that the rate of decay on experience has never been greater with Moore's law effect on technology? Applied to hiring, how does Fouad think about the decision to hire a jack of all trades vs a specialist? When is the time to make the transition? Fouad's 60 Second SaaStr What does Fouad know now that he wishes he had known at the beginning? A moment in Fouad's business life that changed the way he thinks? What would Fouad most like to change in the world of SaaS today? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Fouad ElNaggar

Christoph Janz is the Managing Partner @ Point Nine Capital, one of Europe's leading early stage funds with a portfolio that includes the likes of ZenDesk, Algolia, Delivery Hero, Revolut, Contentful and many more incredible companies. Before that, he co-founded two Internet startups (DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio, FreeAgent – and his love for SaaS. Christoph is also the writer of the phenomenal blog, The Angel VC, a must read for me. In Today's Episode You Will Learn: How Christoph made his way from serial founder to angel in ZenDesk to today, founding one of Europe's most successful early stage funds in the form of Point Nine Capital? Product market fit is one of the most used words in the industry, so wtf really is product market fit? What does product market fit look like in terms of metrics across the core disciplines: MRR, churn and conversion from free to paid? What is the hailed question that all Series A and B investors want to know? What does it take to make the graduation from Seed to Series A today? In terms of scaling, why does pouring fuel on the marketing fire not always equal more leads? How does Christoph view the role of outbound? Why is it such high hanging fruit? What is core to executing outbound successfully? Point Nine did a comprehensive assessment of how founders view the fundraising process, what were the biggest elements founders dislike about the process? From now on, what is the thinking behind the strategy that Point Nine will always do their pro-rata in the Series A? How does this affect reserve allocation? Christoph's 60 Second SaaStr What does Christoph know now that he wishes he had known in the beginning? What does it take for European founders to make it big in the US? Most common mistakes CEOs make in the scaling process? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Christoph Janz

Tom Bogan is the CEO of Adaptive Insights, the company that proves a new generation of business planning software for finance and beyond. Prior to their reported $1.55Bn acquisition to WorkDay, Adaptive Insights raised over $175m in VC funding from the likes of Bessemer, Salesforce Ventures, Norwest Venture Partners and many more incredible investors. Prior to Adaptive Insights, Tom was a partner at Greylock Partners where he focused on enterprise software investments. He was also president and COO at Rational Software until its acquisition by IBM. Before Rational, Tom served as CEO at Avatar Technologies and Pacific Data. He began his career as a financial officer in both public and private companies, serving as CFO at SQA and Orange Nassau, Inc., as well as vice president of finance at SCA Services. In Today's Episode You Will Learn: How Tom made his way into the world of SaaS, came to be a Partner with Greylock and then made the move back into operations with Adaptive Insights? Elad Gil has previously said the role of CEO is to "find product market fit, ensure the company does not run out of money and ensure the team does not implode", how does Tom define his role as CEO of a $100m+ SaaS company? How does the role of CEo fundamentally change over time? What aspect of the role does Tom find most challenging? What core role of CEO is constant throughout the lifecycle of the company? From seeing many of the world's best SaaS CEOs, what are the commonalities in how the very best CEOs hire the very best execs? How does Tom think about the debate of hiring externally or promoting from within? How does Tom look to reduce internal discontent when hiring externally rather than promoting? At $100m Jyoti Bansal said on the show, this stage is about "creating and sustaining operational efficiency". What have been Tom's biggest learnings on the creation and maintenance of operational efficiency? What has worked? What has not worked? How does Tom think about internal asset allocation? Why does Tom believe that ultimately, ARR growth is the metric to rule them all? How does Tom think about and prioritise the metric stack in SaaS? How does he approach payback period vs CAC/LTV? In terms of services components of businesses, does Tom believe these should be baked into the CAC? What should the financial targets be for these services businesses? Tom's 60 Second SaaStr What does Tom know now that he wishes he had known at the beginning? Tom's favourite business reading material and why? What would Tom most like to change in the world of SaaS today? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr

Jonah Goodhart is the CEO @ Moat, the SaaS analytics and intelligence company focused on transforming brand advertising online. Prior to their acquisition by Oracle for a reported $850m Moat raised over $67m in VC funding from the likes of Insight Venture Partners, Founders Fund, Mayfield, Founder Collective, SV Angel and more incredible names. Prior to founding Moat, Jonah was the founding investor and board member at Right Media, acquired by Yahoo for a reported $680m. Jonah was also the founding partner of WGI Group and co-founder of Billions.org. If all of that was not enough, Jonah is also an angel investor including the likes of adroll, Namely and fitmob all in his personal portfolio. In Today's Episode You Will Learn: How Jonah made his way into SaaS with is founding investor role in Right Media? How did experiencing both bubbles change the way Jonah thinks about operations today? How does Jonah fundamentally define "North Star"? How plastic and flexible does Jonah believe a North Star should be? What was a time where Jonah's decision was guided in a certain direction by his strong North Star? Why does Jonah believe that in B2B your roadmap is given to you by your customers? What can founders do to clearly and quickly determine what their customers want from their conversations with them? What questions are crucial to ask? What response suggests real intent to buy from them? How does one prevent this from falling into heavy customisation? How does Jonah approach the element of "brand" in the world of B2B today? What does Jonah believe is the secret to brand? How does this affect how Jonah both onboards, trains and engages with new and existing employees? Was brand core to Moat being able to sell to enterprise so successfully in the early days? Jonah's 60 Second SaaStr What does Jonah know now that he wishes he had known at the beginning? Quality or quantity of logos in the early days? How important is it for SaaS founders to be involved in the process? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jonah Goodhart

Sam Blond is Chief Sales Officer @ Brex, the startup that provides corporate cards for startups. To date they have raised over $57m in funding from the likes of Y Combinator, Peter Thiel, Max Levchin, Yuri Milner, Elad Gil and many more incredible names. Prior to Brex, Sam Was Chief Revenue Officer at Rainforest QA. Before Rainforest, Sam saw firsthand the hypergrowth scaling of Zenefits as VP of Sales where he saw the company grow from 18 employees and $1m in ARR to over 1,800 employees and over $70m in ARR. Sam got his start in the SaaS industry with Jason Lemkin @ Echosign as Director of Sales. In Today's Episode You Will Learn: How Sam made his way into the world of sales and came to join Jason Lemkin with his first role in sales at Echosign? Why does Sam believe that more sales reps does not always equal more revenue? What are the benchmarks that suggest founders really need to add to their sales team? Does Sam agree Founders should be selling up to $1m in ARR? How does Sam assess who is the best person to hire for the role? What have been Sam's lessons on what it fundamentally takes to attract the best talent? In the early days how does Sam think about both role allocation and whether to hire the young jack of all trades vs the more senior executive? Why does Sam believe that founders need to spend more time on top of funnel? Why does Sam believe that not all opportunities are created equal? How does Sam think about the right structure and time it should take to pass from lead to MQL to SAL to opportunity to deal? Where does this most commonly breakdown? Why does Sam believe the key to success in SaaS sales teams is "urgency"? Literally, how can reps instil a sense of urgency in their current pipeline? Why does Sam disagree with the conventional wisdom and say discounting is a great tool? How does Sam determine the right level of discount to give? How does Sam assess pilots as an alternative approach to getting leads over the line? Sam's 60 Second SaaStr What does Sam know now that he wishes he had known at the beginning? Quality or quantity of logos in the early days? Sales rep productivity, what does Sam believe is good? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Sam Blond

Eoghan McCabe is the Co-Founder & CEO @ Intercom, one of the fastest growing saas companies of the day providing a new and better way to acquire, engage and retain customers. Due to their phenomenal growth they have raised over $240m in funding from some of the best in the world including Kleiner Perkins, Social Capital, Bessemer and Index, just to name a few. As for Eoghan, prior to co-founding Intercom, he founded an award-winning software design consultancy called Contrast, and co-founded Exceptional, a developer tool startup acquired in 2011 and now a part of Rackspace. In Today's Episode You Will Learn: How did Eoghan come to be founder of one of the hottest growing startups in SaaS from founding a software design firm in Ireland? What does Eoghan believe are the core pillars for success in making the move from SME to enterprise? How does one reinvent oneself to make this transition? How has Eoghan seen te org structure and internal decision-making change with the adoption of many more enterprise clients? How does Eoghan determine between the decision to hire the young jack of all trades vs the much more experienced senior exec? Why does Eoghan believe you can never be too early to bring someone more senior than you onto the team? What makes Eoghan say, "we are all learning on the fly"? How does Eoghan look to create a culture of experimentation and accountability without the fear of failure? What must the leader do to imbue this culture? Where does Eoghan see many going wrong in trying to make this happen? How does Eoghan think about "transparency" with SaaS companies today? Why does he think that not only is it not healthy but also largely not possible? Instead, what is a better, more sustainable solution to transparency? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Eoghan McCabe

Steve Lucas is the CEO @ Marketo, the world leader in marketing automation for companies of any size. Prior to their IPO and eventual sale to Vista Equity partners for $1.79Bn they raised over $100m in VC funding from the likes of Battery Ventures, IVP, Mayfield and Lead Edge Capital. As for Steve, prior to joining Marketo, he served in many leadership positions at SAP, Salesforce, Microsoft, BusinessObjects, and Crystal Decisions. If that wasn't enough Steve also sits on the board of Tivo, SendGrid and The American Diabetes Society. In Today's Episode You Will Learn: How did Steve make his way into the world of SaaS and come to be CEO @ Marketo? Why does Steve describe his experience at Salesforce to be life-changing? What were the core takeaways for Steve? How has that impacted how he operates today with Marketo? What does Steve mean when he says Marc Benioff is a "master of relevance"? Why does Steve believe the key to success as a CEO is accessibility? How can CEOs be both vulnerable and strong in today's SaaS world? What are the 2 different types of CEOs and how they engage with their CMOs? What do the best do? What do the worst do? Why does Steve believe that the "CRM" term is incomplete? How does Steve fundamentally believe the way that customers want to be engaged with has changed? How can marketers enact this level of personalisation and engagement with such large customer bases? How does the role of artificial intelligence fit into this mass scale personalisation? How does Steve view the broader martech landscape? Why does Steve strongly believe that we will be entering a period of consolidation in martech? How does Steve view the emergence of new categories such as ABM? How does this impact his overarching view on the next wave for martech? Steve's 60 Second SaaStr What does Steve know now that he wishes he had known when he started? Management upgrade is the most important role of CEO, agree? What keeps Steve up at night? How does that influence his running and operations of Marketo? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Steve Lucas

Jerry Jao is the Founder & CEO @ Retention Science, the startup that brings intelligence to your marketing automation through artificial intelligence that delivers a personalized customer experience, at scale. To date, Jerry has raised over $10m in VC funding with Retention Science from great friends of the show in Forerunner Ventures, Upfront Ventures, Clark Landry, Andy Rankin and more fantastic names. Prior to founding Retention Science, Jerry founded two other e-Commerce marketing technologies and served as Strategic Innovation Officer to Clear Channel Radio. Jerry is also a Guest Lecturer at The Kellogg School of Management and sits on the board of Penango. In Today's Episode You Will Learn: How did Jerry make his way into the world of SaaS with the founding of his first company? What have been the top 3 mistakes that Jerry has made since founding Retention Science? With P&G, Unilever and Olay all as enterprise clients, how did Jerry first sell into them as a small startup? What is required to give these large enterprises confidence in buying from startups? What does the perfect case study look like to convert these mega accounts? In the early days is it a quality or quantity of logos game? How important is it for the founder to be really actively involved in the sales process to these mega corporations? How does Jerry divide his time now between new and existing customers, as well as team and investor management How does Jerry approach multi-year and prepaid deals with these incumbents? What is the line of reasoning for suggesting prepaid is fair? Retention Science have been profitable since 2018, how does Jerry look to balance the mindset of fast growth and profitability? How does Jerry think about payback period for enterprise sales reps with this profitability mindset? How does this affect his thoughts and views on internal asset allocation? Jerry's 60 Second SaaStr A moment in Jerry's life that has changed the way he thinks? When I say success in SaaS who embodies this to Jerry? What does Jerry know now that he wishes he had known at the beginning? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jerry Jao

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David's successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David's amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today. In Today's Episode You Will Learn: What are the leading indicators that early stage VCs dig deep on to assess the strength of product market fit? What level of traction both in enterprise and SMB would an early stage investor deem exciting enough to pursue? What levels of engagement are sufficient enough to suggest cause for a much larger and increased round? How should founders assess sales rep productivity? What can they do to actively shorten the ramp time? How will early stage investors analyse the ramp time? What suggests repeatability of process? Why does David believe there is no point focusing on CAC/LTV in the early days? What is the single biggest thing that founders can do to show repeatability of process and revenue as fast as possible? What is the most common reason that people miss plan? How must the mindset of the founder switch from extreme frugality to hyper growth scaling? When is the right time for this transition to take place? What are the inherent challenges to this switch? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Skok If you're looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr. MonkeyLearn allows companies to easily analyze text with Machine Learning. Customers like Clearbit and Segment are using MonkeyLearn to turn emails, support tickets, customer feedback, and documents into actionable data. Their platform makes it super easy to classify texts by topic, sentiment or intent or to extract specific data such as keywords, names, and companies. MonkeyLearn makes teams more efficient by automating business processes, getting insights and saving hours of manual text data processing. And if you would like to learn more, head to monkeylearn.com/saastr, that is www. m o n k e y l e a r n .com/saastr. Plus, listeners of the SaaStr podcast will have a very special opportunity to purchase monthly plans for half the price. So, check out MonkeyLearn and start getting more out of your text today.

Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M) and big data leader Aster Data (acquired by Teradata for $325M). In Today's Episode You Will Learn: Why does Dave believe it is foundational to be an ARR first company? How does Dave think startups can show their ARR first mentality from the first investor meeting? How does this help drive operational efficiency? How does Dave segment ARR into 3 distinct camps? Why does Dave argue that SaaS metrics are not nearly as simple as they seem? Which metrics does Dave believe most founders confuse? What metrics will the best VCs pick apart and dig deep on? How can founders respond with accuracy and confidence? How does Dave respond to multi-year deals? Under what conditions are they acceptable and not acceptable? How must they be reported in accounting? Where do many startups go wrong when considering multi-year deals? How important is it for them to be pre-paid? Why does Dave argue that renewals do not measure customer satisfaction?What is an accurate measurement to determine customer satisfaction? How often should this be conducted? What sample size of customer gives the right amount of data? How does Dave approach comp with regards to sales team cross-sell and upsell? Why is it not as black and white as boards often portray? Under which circumstances does Dave believe double comp is justified and not justified? How can you communicate this to your board successfully? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Dave Kellogg If you're looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr.

Phil Fernandez is a Silicon Valley veteran, with more than 35 years of experience building and leading breakout technology companies. Phil co-founded Marketo in 2006 and led the company as Chairman and CEO for a decade, overseeing its successful IPO and acquisition by Vista Equity Partners. Prior to Marketo, Phil served as president and COO of Epiphany, an enterprise customer relationship management (CRM) software company. Today, Phil is a Venture Partner with Shasta Ventures, the fund with a portfolio including the likes of Nest, eero, Zuora, Canva and many more incredible companies. In Today's Episode You Will Learn: When is the right time to hire your first CRO? Where did Phil make a big mistake in who owns what revenue numbers? What are the traits that make the best CROs? How should they look to work with both sales and marketing to drive efficiency internally? Why does Phil believe you must hire the most senior Chief People Officer as soon as you can? What does the role of "Chief People Officer" really embody? How should they look to work with HR internally? Who should they report to? How does this role change with a scaling organisation? How has Phil seen the relationship between average contract value and potential for expansion change? What is the correlation between and ongoing services component and both customer NPS and expansion? Where did Phil go wrong with this at Marketo? How should emerging SaaS startups today be thinking about technical legacy debt? Why does Phil believe it is never to early to have a Head of Research function? How should this function work with the team to build the latest technology into new products? Why did Steve sell Marketo to Vista Equity Partners? What was the thesis and big learnings from that experience? What does Phil mean when he says he did not "watch the clock properly''? How can founders today be proactively thinking about ramp time for sales reps, new product engagement etc. Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Phil Fernandez

Bill Binch is a leader and expert in the SaaS sales industry, currently CRO @ Pendo.io, the startup that helps you understand and guide your users, creating a product experience they can't live without. They have raised over $58m in VC funding from some of the best in their space with the likes of Battery Ventures, Spark Capital and Salesforce Ventures, all backing them. As for Bill, prior to Pendo, Bill was the Senior Vice President of Global Sales at Marketo for 8 years. He joined when it was a small venture-backed startup with a mission to reinvent marketing automation. It was his sales leadership and expertise that formed a critical component in building Marketo into one of the fastest-growing enterprise software companies in the world, recognized through his being awarded worldwide VP of sales in 2011. In Today's Episode You Will Learn: How Bill made his way into the world of SaaS and came to be employee #18 at Marketo before making the transition to today, as CRO @ Pendo? Bill has said before that career paths are for B players. First, what is wrong with the current thinking around career paths? Why does that inherently mean that A players do not align with them? How can one determine when is the right time to step away from the career paths? What characteristics and attributes do those truly special opportunities have? Bill has successfully made the transition from transactional business to enterprise business many times, what have been his core learnings on what it takes to make this transition successfully? What are the biggest challenges in making the transition? How does the internal structure of the team change when making this transition? What does Bill mean when he says you have to "rig the recruiters"? What incentives can be placed in front of them that ensure you will be a priority for them? On the flip side, what incentives do you have to give the recently on boarded employees to encourage grassroots, word of mouth on the company brand? How does the company and sales cycle fundamentally change when moving from $0-1m ARR? What does that mean for the company policy on discounting and pilots? How does the company alter when transitioning from $1-10m in ARR? How can sustainable social validity be built in this stage? How does a company successfully move from $15m-100m in ARR? 60 Second SaaStr? What does Bill know now that he wishes he had known at the beginning? What keeps Bill up at night? What does Bill mean when he says you have to check your ego? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Bill Binch If you're looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit www.egnyte.com/SaaStr.

Kristina Shen is a Partner @ Bessemer Venture Partners, one of the world's leading venture funds with a portfolio including the likes of Pinterest, Skype, Box, LinkedIn, Yelp and many more incredible companies. As for Kristina, she serves on the boards of DoubleDutch, Glint, Retail Solutions and Zoosk and is also a board observer with RainforestQA, Vidyard, Gainsight and ServiceTitan. Kristina is also one of the best data gurus as the co-author of Bessemer's State of the Cloud 2016 and 2017 and Bessemer 10 Laws of Cloud, which captures the top trends among leading public and private cloud computing and enterprise mobile companies. Due to Kristina's success she has been named to both Forbes and Business Insider's 30 Under 30 in 2014 and 2016, respectively. In Today's Episode You Will Learn: How Kristina made her way into the world of cloud investing and came to be the data guru for much of the cloud landscape? What does Kristina fundamentally mean when she states the key question is, is there velocity in this SaaS business? Is velocity just about revenue or ARR growth? How can startups present real velocity with their sales funnel? How can startups present further velocity through their SQL process? Why does Kristina believe that "private SaaS multiples are not expensive and we need a new framework"? What makes the existing framework inaccurate? What does this mean for the way Kristina assess ARR multiple and growth rates? How does this framework alter Kristina's perception of the often hailed "Rule of 40"? How does it change with scaling? What are the core elements Series A SaaS investors focus on today? With regards to revenue benchmarks for the A round, where do they need you to be both on the low and high end? Where do Series A investors expect startups to be for y/y ARR growth? What core metrics are required to successfully raise your Series B in SaaS today? What does Kristina think is the fundamental difference between Series A and B today in SaaS? What can founders do to show repeatability and reliability of revenue streams as they move into the B round? 60 Second SaaStr? What does Kristina know now that he wishes he had known at the beginning? Questions from Jeremy Levine: What would Kristina like her legacy to be as an investor in 20 years time? What keeps Kristina up at night? Is it worse to see an amazing deal and pass on it or to have never seen it at all? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Kristina Shen

Jason Lemkin is the Founder @ SaaStr, the world's largest SaaS event with over 20,000 of the world's best SaaS founders and investors attending every year. Jason also invests from SaaStr's debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies. In Today's Episode You Will Learn: How does Jason think founders should approach long sales cycles in the early days? Why does Jason believe that ultimately long sales cycles do not matter? What can the truly great VPs do to impact those long sales cycles? How does Jason think founders can tackle lead optimisation with their team? How can founders determine which leads to send to which AEs? What will the effect of this tailored lead distribution be? When is the right time for the founder to begin to take a step back from sales? Why does Jason believe that the founder must always be involved in the sales process? How does this look at scale when selling to thousands of customers? How does this mean the founder works with the growing scaling team over time? Why does Jason believe that SaaS companies have to raise so much money today? What is the core decision that founders must make when determining how much they need to raise? How should founders approach the topic of cloning? What are the 3 core advantages they have over their clones? What must they be mindful of when being cloned by incumbents? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr

Timo Rein is the Founder & CEO @ Pipedrive, the startup that helps sales people focus on actions that close deals. To date, Timo has raised over $30m from the likes of Atomico, Bessemer Venture Partners, TransferWise Founder Taavet Hinrikus and Andy MCloughlin and has scaled the team to over 330 people across multiple continents. Prior to founding Pipedrive, Timo was a Partner @ Vain & Partners acting in a consultancy role on how to get the best ROI from your sales process and before that was himself a door-to-door salesman with SouthWestern Company selling high ACV products. In Today's Episode You Will Learn: How Timo made his way into the world of SMB CRM with the founding of Pipedrive from the days of being a door-to-door salesman of high ACV products? Why did Timo choose to go global with Pipedrive from day 1? What are the benefits of founders having this global mindset from the start? What are Timo's biggest learnings in terms of acquiring customers globally early on? What worked? What did not work? How did Timo think about pricing on an individual country perspective? What are the challenges with this? Having raised from both US and UK VCs, how does fundraising differ when comparing Europe to the US? If Timo had to say the West Coast, East Coast and European VCs each had one area they focus, what would that area be? What are the challenges with these inherent focus points? What advice would Timo have for foreign founders looking to make it big in the US? How does Timo look to manage a team so spread across the globe? What are the core challenges of this? What works? What does not work? What functions can be split up by geography? What must remain in one location? Now at 300 people, how does Pipedrive ensure for the same values fit when hiring at scale? Many VCs say with such low ACV and such high churn, the SMB market is too difficult. How does Timo respond to this? How does Timo think about ensuring the continuous refilling of top of funnel? How does Timo think about acquiring such small customers in a cost efficient manner? 60 Second SaaStr? What does Pipedrive look like at $100m ARR? What keeps Timo up at night? Who is Timo's favourite angel investor? What does Timo know now that he wishes he had known at the beginning? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Timo Rein

Jason Lemkin is the Founder @ SaaStr, the world's largest SaaS event with over 20,000 of the world's best SaaS founders and investors attending every year. Jason also invests from SaaStr's debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies. In Today's Episode You Will Learn: When is the right time to hire your first sales rep? What characteristics must those sales have? Why does Jason believe it is impossible to poach a rockstar from another fast scaling startup? Should you then hire the stretch VP or the more experienced, potentially burnt out exec? How does Jason think about aligning compensation to company objectives? Within the company, which functions serve as the best test areas for variable compensation? What must you be wary of when installing a system of variable compensation? When is a stretch VP a stretch too far? What must a stretch Head of Sales have done to make him ready? What must a VP of Product done before to make him ready? What resources can you build around stretch VPs to provide them with additional support? How does Jason think about the first time you spend to acquire customers? Why does Jason suggest just trying to make $1 for every $1 you spend? Why is it crucial to think of your marketing spend on a blended basis? How can you create alignment between the marketing teams number and the cadence of sales? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr

Jon Lee is the Founder & CEO @ ProsperWorks, the #1 recommended CRM for G Suite. To date, ProsperWorks have raised over $85m in VC funding from the likes of True Ventures, Norwest, GV, Bloomberg Beta and more incredible names. As for Jon, prior to ProsperWorks, he started in investment banking at Merrill Lynch before moving to run a large operations team at Yahoo. Jon then founded Bazaar Advertising Solutions, a business self funded from a Palo Alto apartment that Jon scaled into a highly profitable $47m business in less than 2 years. Jon then sold Bazaar to Epic Media in 2006. Following the acquisition, Jon founded DNA Games, the number one casino simulation game on Facebook with more than 20 million players, ultimately acquired by Zynga in May 2011. In Today's Episode You Will Learn: How Jon made his way into the world of CRM having successfully founded and sold 2 prior business in the lead gen and gaming space? Why does Jon believe building a SaaS business is very much like building a gaming business? How does on think about the scaling of company culture with the scaling of headcount? Where does Jon see the inflection points where this culture starts to break down? What does Jon mean when he suggests "the importance of a culture of innovation"? Why does Jon believe it is so important to insert a culture of risk into the organisation? How does this risk mindset differ and look across different segments of the business? How does Jon aim to create a culture of risk and ambition without a fear of failure and not hitting targets? Why does Jon think it is always better to start in SMB and move to enterprise? How does this decision change how one thinks about product roadmap? How does this change how one approaches traction building ahead of fundraising? What should one look to learn from rapid iteration and testing before moving to the enterprise market? 60 Second SaaStr? What does Jon know now that he wishes he had known at the beginning? What keeps Jon up at night? What is Jon's favourite SaaS reading material? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jon Lee

Chetan Puttagunta is a General Partner @ NEA, one of the world's largest venture capital firms in the world with over $3Bn in their latest fund and a portfolio including the likes of Mulesoft, Jet.com, Uber, Houzz and many more incredible companies. As for Chetan, Chetan focuses on enterprise software and has made investments in MuleSoft, MongoDB, Elastic, Heap, just to name a few. Due to his phenomenal track record, Chetan has been named to GrowthCap's Top 40 under 40 Growth Investors, Forbes 30 under 30 All-Star Alumni List, and Forbes' 30 under 30 in Venture Capital. In Today's Episode You Will Learn: How Chetan made his from the world of leveraged buyouts to the world of enterprise VC investing with NEA? Why does Chetan have such conviction with regards to open source companies today? Why does he feel the big question of "Can open source product multi-billion dollar companies" has been proven"? How does Chetan think about the underlying business models of open source when comparing the likes of Red Hat with 85% gross margin to Hortonworks at negative gross margins? What does Chetan believe is a healthy ratio between professional services vs closed premium features? Does Chetan believe this is the end for per seat pricing in SaaS? How does Chetan approach market sizing today when evaluating potential enterprise opportunities? Why does Chetan believe there is a mental trap in the VC requirement for large markets? How can founders present the niche market they are attacking, in an exciting enough way to satiate the investor appetite for large market? Chatan has said before, "if you have conviction and vision, you should not be afraid to raise capital and go big". Does every founder not have conviction and vision in the early days? How does Chetan determine when truly is the right time to pour fuel on the fire and raise that mega war chest? 60 Second SaaStr? A moment in Chetan's life that has changed the way he thinks about the world? Fave SaaS reading material? What does Chetan know now that he wishes he had known at the beginning? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Chetan Puttagunta

Rob Reid is the Executive Vice President & Managing Director @ Sage Intacct, the undisputed global leader serving finance teams of any size. With over 10,000 employees and and over 3m customers, their financial solutions generate over $2Bn in revenue. As for Rob, prior to Sage Intacct, Rob led Intacct over an incredible 8 year journey culminating in their, reported $850m exit to Sage in 2017. Before that he was CEO and President of LucidEra, a market leader for on-demand business intelligence. Prior to LucidEra Rob was group Vice President of industry leading Siebel CRM for Oracle, managing the SMB sector. Fun fact, over his phenomenal 30 year career, Rob has been involved with 8 startups, 7 of which have had successful exits. In Today's Episode You Will Learn: How Rob made his way into the world of SaaS over 30 years ago from wanting to be in advertising and hating computer science? As a multi-time CEO, how has Rob seen his role and understanding of what it takes to be a great CEO changed over the last 30 years? Does Rob agree that "management upscaling is the most important role a CEO can do"? What does Rob mean when he says, "the old school CEO approach is upside down and backward"? How should it be in that case? Why does Rob believe that an executive team is like a boat of oarsman? What are the fundamentals to ensuring your executive team are aligned and working in tandem? Why is transparency across the organisation fundamental to both efficiency and culture? How does Rob think about internal promotion vs external hire when it comes to the exec team? Why is Rob adamant that "cloud companies like never before have to be customer-centric"? What does this mean for thinking about optimising the structure of your organisation? How does one think about such high levels of customer success and touch points when serving the immense SMB landscape? How is this feasible? What have been Rob's key learnings? 60 Second SaaStr? Following many successful outcomes, what is Rob's biggest splurge to date? Why does Greg Sands call Rob "The Big Fundamental"? What does Rob know now that he wishes he had known at the beginning of his career? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Rob Reid

Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems. To date, they have raised over $8m in VC funding from some of the best in the business including the likes of Mike Volpi @ Index Ventures and Mike Dauber @ Amplify Partners. Prior to Gremlin, Kolton was a Chaos Engineer at Netflix improving streaming reliability and operating the Edge services. Fun fact, Kolton also designed and built Netflix's failure injection service. Before that he improved the performance and reliability of the Amazon Retail website. At both companies he has served as a 'Call Leader', managing the resolution of company-wide incidents. In Today's Episode You Will Learn: How a conversation in the hallway of a conference with a VC gave Kolton the confidence that he could leave the corporate world of Netflix and Amazon and start a startup? What were Kolton's biggest takeaways from seeing the first hand scaling of behemoths like Amazon and Netflix? How did they fundamentally alter how he views goal setting today? How does Kolton look to achieve the balance of ambitious goal setting without the team losing motivation if they do not hit the goals? Why does Kolton believe that a decentralised workforce is merely an evolution in how we do business? What are the core fundamentals to achieving success in creating and scaling a remote workforce? What have been some of the biggest challenges in structuring the team this way? What is the single biggest tip Kolton has for other founders in ensuring high conversion rates from trials? Where do most founders go wrong with this? Today, is engineering buy in the only necessity to succeed in a bottoms up sales world? 60 Second SaaStr? What does Kolton know now that he wishes he had known at the beginning? If an investor can provide one thing, what is most important for Kolton? What are Kolton's favourite SaaS reading materials? When is a stretch a stretch too far for a team member? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Kolton Andrus

Ryan Williams is the Founder @ SalesCollider, the organisation that helps technical founders jumpstart sales. Ryan got his start as the first sales manager at Adroll where he grew the team from 3 to 32 reps in just 8 months, a team that was responsible for ARR growing from $4m to $58m in under 2 years. Ryan then became an advisor to the early team at InVision where he coached both CEO and sales reps to close the first dozen enterprise deals. Then his last stop before founding SalesCollider was as VP of Sales at LeadGenius where he grew enterprise sales by over 400% and added clients such as Ebay, IBM and Google, just to name a few. Ryan is also an Entrepreneur in Residence @ 500 Startups and a Mentor with First Round Capital. In Today's Episode You Will Learn: How Ryan made his way into the world of sales as first sales manager at Adroll and how that led to advising the CEO of InVision on gaining their first enterprise clients? 70% of VPs of Sales fail when they join early stage startups, why is this? How can founders know when is the right time to bring in their first VP of Sales? What can they do to maximise the chances of success when bringing them into the organisation? What is the right profile type for the first VP of Sales? What are the core foundations to assessing the strength of the VP in the interview, especially for engineering minded founders? What is the one question that Ryan loves to ask potential sales candidates? What answer does he look for? Does Ryan agree with a recent guest, "discounting is now table stakes"? Where do most early stage startups go wrong when thinking about discounts? What framework must startups utilise to analyse the right discount to offer? Why must they know the internal value they are providing to their customer in such a detailed way when discounting? 60 Second SaaStr What does Ryan know now that he wishes he had known at the beginning? SDR's are the most important function in sales, agree or disagree? Sales rep productivity, what is good and what is bad? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Ryan Williams

Pieterjan (PJ) Bouten is the Founder & CEO @ Showpad, the world's leading sales enablement platform that allows for the creation of amazing buyer experiences. To date they have raised over $89m in VC funding from the likes of Insight Venture Partners, Dawn Capital and Hummingbird. As for PJ, Showpad is the second company he has founded. In 2010 he co-founded the mobile development agency, In The Pocket and still serves on its board. Prior to In The Pocket, Pieterjan held senior roles at Netlog and Accenture. In Today's Episode You Will Learn: How PJ made his way from the world of Accenture to founding the world's leading sales enablement platform in Showpad? What was the most challenging element for PJ and Showpad in scaling from $1m-10m in ARR? How does the go-to-market change with this scaling? How does the team structure and composition alter? How does the branding and positioning change? PJ has said before that you must "reiterate value at every touchpoint", what does he mean by this? How can one look to build a structure and framework to ensure one is effective with this? How does one scale this when serving thousands of SMBs? What were PJs biggest lessons from their experiences of discounting? What advice would PJ give to founders on when and how much to discount? How does PJ think about the use of pilots and trials? How can one ensure optimal efficiency of conversion with both methods? 60 Second SaaStr Does the role of CEO ever get easier? What does PJ know now that he wishes he had known at the beginning? What keeps PJ up at night? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Pieterjan Bouten

Clate Mask is the CEO of Infusionsoft, the leading cloud-based CRM platform for growth-minded small businesses with more than 145,000 users worldwide. Under Clate's leadership, InfusionSoft has grown from a fledgling startup housed in a worn-down strip mall into a 550 person company, raising over $130m in VC funding in the process. If that was not enough, Clate is also an angel investor with the likes of CampusLogic, where he also sits on the board and is co-author of Conquer the Chaos: How to Grow a Successful Small Business Without Going Crazy. In Today's Episode You Will Learn: How Clate made his way into the world of SaaS and came to found the leading CRM for small businesses? Enterprise vs SMB: Why does Clate fundamentally believe that not everyone has to move to enterprise with time? Why do so many founders believe they need to? Why is it such a preference for investors? How does the decision to remain in SMB change the future structure of the team and product roadmap? What was the hardest challenge for Clate about staying in SMB? The Metrics Stack: What is the core metric that founders must observe to analyse the state of their business? How does this core metric affect every other metric? How does Clate view the significance of payback period, what is good to him? How does sales rep productivity change when serving SMB vs enterprise? What is good sales rep productivity? Why does Clate fundamentally believe CAC/LTV is the mothership? What is it solely driven by? Partnerships 101: How can a founder know whether they have the right model and product for a partnerships model? How do partnership models change both the service and sales process of your company? What are the biggest risks to implementing a full-scale partnerships model? What have been the biggest challenges for Clate of scaling this partnerships model? 60 Second SaaStr What does Clate know now that he wishes he had known at the beginning? What is the most important element an investor can provide? A moment in Clate's life that has changed the way he thinks and sees the world? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Clate Mask

Harry Glaser is the Founder & CEO @ Periscope Data, the startup that allows you to transform your business with the fastest, most powerful analytics platform. To date, Periscope have raised over $34m in funding from some of the very best in the business including Bessemer, SV Angel, DFJ, Susa Ventures and Data Collective, just to name a few. With this funding they now serve over 975 customers including Adobe, Flexport, Tinder, NewRelic and more. Prior to founding Periscope, Harry was a Product Manager @ Google. Fun fact about Periscope, it was voted the best small company to work for in 2017. In Today's Episode You Will Learn: How Harry made his way from being a PM at Google to convincing his co-founder Tom to leave his comfortable corporate job in Seattle to chase the startup dream in the valley? Diverse Teams: There a a lot of all white male teams in SaaS, what should they do to create a more diverse, well-rounded team? What is the first step? What is the framework for achieving this hiring ambition? What are the biggest challenges? Where does Harry see founders most often making mistakes in building diverse teams? Data Teams: Why does Harry believe that founding teams must have data professionals within them from Day 1? Why does Harry believe this makes those startups more successful? What are the fundamental benefits? How does this data-centricity change the decision-making of the organisation? What are the core challenges in scaling this data team? Moving Upmarket: Why does Harry believe that it is better to do SMB to enterprise than enterprise to SMB? How does the product fundamentally change when addressing the enterprise market? How does the structure of the team change with the move? How does the messaging of the company alter with the move to a more enterprise focus? 60 Second SaaStr What does Harry know now that he wishes he had known at the beginning? Harry recently tweeted "you don't choose the kind of CEO you are", what kind of CEO are you then? A moment in Harry's life that has served as an inflection point and changed the way he thinks? What can a founder do today to instantly make a better workplace culture? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Harry Glaser

Mark Godley is the President of LeadGenius, the startup that provides the power of human intelligence with the scale of machine learning. To date they have raised $16m in funding from the likes of a16z, Initialized Capital, Scott and Cyan Banister and SV angel just to name a few. As for Mark, he most recently served as Chief Revenue Officer for HG Data and before that was VP of Market Development for ConnectandSell. If that was not enough, mark also holds advisory roles in the salestech and martech space, including Omniquo, ZenIQ.io and The Big Willow. In Today's Episode You Will Learn: How Mark made his way into the world of SaaS over 25 years ago? How has he seen the industry change so remarkably over that time? Why does Mark believe that many startups today are created with the wrong intentions? Who is ultimately to blame for this, the founders or the investors who back them? Why does Mark believe that SaaS founders should "ignore fundraising and sign customers"? What are the unidentified consequences to Mark of taking external money? How does Mark view the function played by discounting in onboarding your first few key customers? What does Mark think of pilots? How willing should founders be to engage with unpaid pilots? How can enterprise founders solve the 2 big problems today of. A.) Standing out in the sea of enterprise startups? Gain trust from enterprise CIOs when they are still a small team with little brand or track record? What does Mark believe is the secret to selling to enterprise effectively? Why must founders be both credible and vulnerable when selling? What is the difference between helping someone buy and selling them a product? 60 Second SaaStr What does Mark know now that he wishes he had known at the beginning? Why are data vendors their own worst enemy? What would Mark like to change about the world of VC and startups? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Mark Godley If you have a digital product, whether it's mobile or web, Amplitude's product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

Wade Foster is the Founder & CEO @ Zapier, the startup that moves information between your web apps automatically, so you can focus on your most important work. A couple of incredible achievements from Zapier, they have scaled to a phenomenal $35m in ARR, they have built a time of over 130 people, all without a central office and they have done this with just $1.2m in early stage funding from the likes of Bessemer, Y Combinator and DFJ. In Today's Episode You Will Learn: How Wade made his way into the world of SaaS and came to found Zapier? Why does Wade believe that founders need to put in place traditional management sooner than they normally do? What should this structure look like? When is the optimal time to start considering it and then implementing it? Wade has said before that most startups should "ignore fundraising", why does he believe this? How has bootstrapping Zapier influenced how he manages and scales the company? What lessons has he taken from VC backed founders that he has applied to the growth of Zapier? Zapier is a completely remote team, what is the secret to seamless communication and company culture when building a team to 130 with no central office? What are the core benefits? What are the fundamental challenges? 60 Second SaaStr What does Wade know now that he wishes he had known at the beginning? Why should everyone on the team do support? How does Wade look to scale himself as CEO? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Wade Foster If you have a digital product, whether it's mobile or web, Amplitude's product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

Olof Mathé is the Founder & CEO @ Mixmax, the startup that allows you to be a sales pro, providing powerful analytics, automation and enhancements for your outbound communication and a product that has achieved almost the impossible in SaaS, true viral growth and a $0 CAC. As for Olof, prior to Mixmax he led the team that built Inkling Habitat, now adopted by the world's largest publishers and before that he was an entrepreneur and worked at Skype and McKinsey. In Today's Episode You Will Learn: How Olof made his way to the bay and how he made his way into the world of SaaS with the founding of Mixmax? Why does Olof believe that customer success is the new marketing? What does this mean for the right time to hire your first customer success rep? What are the other subsequent advantages of instilling an early customer success team? Why does Olof believe that every company must have some haters? What does this suggest about your product? How should startup founders react to this? Is there a method of damage limitation with these segments Why does Olof think it is ok if they come from your core user base? With regards to growth, how important does Olof view the differing forms of metrics? How many should founders be focussed on? How does this approach affect your internal decision-making? How does it affect product roadmap? How does Olof break down the structure of Mixmax into 3 subsequent parts? Why does Olof not like employees in SF working from home? What are the drawbacks to this? What is the right way to recruit remote employees? Why is not all inbound poor quality? 60 Second SaaStr What does Olof know now that he wishes he had known at the beginning? How to cost effectively deal with inbound hiring applications? What is the least discussed but most worthy topic in SaaS? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Olof Mathé If you have a digital product, whether it's mobile or web, Amplitude's product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

Brad Feld is one of the world's leading VCs having Co-Founded Foundry Group, Brad has made investments in the likes of Zynga, Makerbot and Fitbit, just to name a few. Brad is also Co-Founder of Techstars, one of the world's most prominent startup accelerators, whose portfolio companies have raised over $1.3bn in funding. If that wasn't enough Brad is also a best selling author having co-authoured Venture Deals: Be Smarter Than Your Lawyer and VC and Startup Communities: Building An Entrepreneurial Ecosystem In Your Community. In Today's Episode You Will Learn: How Brad made his way into the world of VC and came to found Foundry Group? Brad has previously stated that companies can be segmented into 3 different core components? What does he mean by this? How can startups be structured internally for scalability? Why does Brad hate the word culture? How should culture be viewed and approach internally within startups? How has Brad seen his personal development with regards to being a board member? What has he got better at? What does he believe makes a great board member? Why is CAC the easiest metric to game in SaaS? How should the CAC/LTV ratio be approached? How can entrepreneurs use this to attract VC investment? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Brad Feld If you have a digital product, whether it's mobile or web, Amplitude's product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download. User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

Mark Mader is the CEO @ Smartsheet, the company that allows firms the best way to plan, track, automate and report on work. To date, they have raised over $105m in funding from some of the best in the business including Insight Venture Partners. Prior to Smartsheet, Mark served as senior vice president of global services for Onyx Software, leading the consulting and customer operations teams in the Americas, Europe, and Asia. Due to this success, in 2015, he was recognized as Ernst & Young Entrepreneur of the Year in Technology for the Pacific Northwest. In Today's Episode You Will Learn: Why Mark's being disrupted by Salesforce led to his entry into the world of SaaS and how he came to be CEO @ Smartsheet? How does Mark think that startups should approach hiring across market cycles? What have been some core lessons Mark has learnt in frothy markets and the war to win "hot talent"? How does Mark think about "paying up" for certain candidates? How flexible should startup founders be on moving their compensation bands? Why does Mark believe that too many people over index culture fit? How does Mark look to balance between raw IQ and culture fit? How does Mark look to really stress test someone's ability to perform a role, pre-hire? Where do most startups go wrong in their early hiring processes? How does Mark think about creating a structured framework for giving employee feedback? Why do people overestimate the importance of the feedback itself? What else should they be focusing on? In terms of providing that feedback, how does Mark assess the importance of output? How does Mark look to balance the complicated elements of output vs input? Is it really all about activity? 60 Second SaaStr What does Mark know now that he wishes he had known at the beginning? Management upscaling is the most important role of CEO? When is a stretch VP a stretch too far? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Mark Mader

Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston's premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce and Atlas Venture. Prior to founding InsightSquared, Fred was a corporate development associate with Salesforce Ventures and before that he held several key roles at Bessemer Venture Partners including associate and Director of IT. He is also a board member of TUGG, an organization that brings together tech entrepreneurs with social enterprises that support at-risk youth. In Today's Episode You Will Learn: How Fred made his way into the world of SaaS, hustled his way to being a VC with Bessemer and then came to found InsightSquared from Boston? Why does Fred strongly argue that it is easier to start with SMB and move to enterprise than enterprise down? What are both the technical and personnel considerations of the decision? Why is it the product manager's job to lose complexity as slowly as possible? Why does Fred disagree and state that CAC/LTV is not the guiding metric for SaaS startups? What are the core problems of CAC/LTV? What alternatives should founders consider as their guiding metrics? Where does Fred believe most founders go wrong when assessing their metrics? What metric keeps Fred up at night? What does Fred believe are the fundamentals to successfully building an inside sales team from scratch? What is the lowest ACV that an inside sales team can justify? How does Fred look to create a culture of accountability and responsibility without the element of fear of not hitting quota? Why does Fred go against conventional wisdom and suggest that customer success is the responsibility of the entire organisation? Why is this advantageous compared to a dedicated CS team? How does this mean both time and teams are allocated towards customer success? 60 Second SaaStr What does Fred know now that he wishes he had known at the beginning? What is the least discussed but most worthy topic in SaaS? What would Fred's biggest advice to emerging SaaS founders be? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Fred Shilmover

Mike McDerment is co-founder and CEO of FreshBooks, the #1 cloud-based accounting software designed exclusively for service-based small business owners. Starting from his parent's basement, Mike has grown Freshbooks to more than 10m users worldwide and raising over $75m in VC funding from the likes of Accomplice and Georgian Partners. Mike is also the co-author of Breaking the Time Barrier, downloaded more than 250,000 downloads since its release. In Today's Episode You Will Learn: How Mike came to enter the world of SaaS with the founding of Freshbooks from his parent's basement? Why does Mike disagree with the common notion of the "pivot"? How does Mike balance between realism when something is not working and vision? From Mike's conversation with USV's Fred Wilson, what does he believe are the 3 most important roles of the CEO? Why is the No 1 rule in SaaS, you do not replatform your software? What are the inherent dangers? How does it affect your ability to drive revenue? Where do most SaaS startups make big mistakes when replatforming? Where are the inflection points in SaaS team scaling? What is the biggest challenge at 20 people? How does collaboration change when your team hits 40 people? How can one maintain seamless communication when one hits 80 people? 60 Second SaaStr Why is Mike so bullish on SaaS outside of Silicon Valley? How does being outside the Valley affect his ability to hire? What does Mike know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Mike McDerment

Ross Mason is the Founder & VP of Product Strategy @ MuleSoft, one of the world's leading software platforms making it easy to connect the world's applications, data and devices. Following over $250m in VC funding from the likes of Lightspeed, Salesforce Ventures, Sapphire Ventures and NEA, MuleSoft then went public in March 2017, popping as much as 45% on it's first day of trading. As for Ross, prior to MuleSoft, he was CEO of SymphonySoft, an EU-based company providing services and support for large-scale integration projects. Previously, Ross was Lead Architect for RaboBank and played a key role in developing one of the first large-scale ESB implementations in 2002. In Today's Episode You Will Learn: How Ross made his way into the world of SaaS with the founding of MuleSoft? Why did Ross decide to move full time to the West Coast having started the company in Europe? What were the biggest challenges about the move to the US? What advice would Ross give to prospective entrepreneurs, looking to make the move? Where does Europe exceed the US and vice versa? What does it really mean to be a SaaS platform? What 3 elements of a company benefit when a product unbundles into a SaaS platform? How does unbundling change the process for building products and services? How does unbundling change the ability to drive new revenue streams? How does unbundling change core operational elements of the business? What does Ross mean when he says we are shifting from verticals into value chains? Does Ross believe it is even possible to own the entire customer lifecycle today, from start to finish? 60 Second SaaStr What does Ross know now which he wishes he had known at the beginning? How did it feel the day MuleSoft went public? What advice does Ross commonly hear being given that he most disagrees with? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Ross Mason

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David's successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David's amazing blog here! In Today's Episode You Will Learn: How did David make his way into the world of SaaS? What was it about Matrix that made him want to make the transition from operations to VC? Metrics: Why are metrics so important? What role do they play in an organisation? How do good founders respond to questions on not achieving sales targets? What metrics in SaaS really determine the trajectory of the business? How can founders examine unit economics to determine whether they have a sustainable SaaS business? How does David address sales rep productivity? How much in ARR should they be booking in relation to their annual comp package? Negative Churn: What is negative churn? Why is it fundamental for SaaS startups to have a strong grasp of their negative churn? How does negative churn affect the pricing axis? What can startups do if they have no alternative product to upsell to? Upsell: To what extent should founders be willing to engage in customisation in order to upsell a product? What are the dangers? What should founders be mindful of? To what extent is upsell the responsibility of customer success? Should they have a hand in the sales process? What are the dangers and concerns? How important is it for a startup to track their champion with the customer company? Does it matter if your champion leaves? What should you do if so? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Skok

Des Traynor is the Co-Founder, Chief Strategy Officer and VP of Marketing at Intercom, one of the world's hottest startups that simply put, makes communicating with customers easy and efficient. They have raised over $115m in funding from some of the world's leading investors including Social Capital, Index Ventures, Bessemer Venture Partners and then titans of industry with Mark Zuckerberg, Jack Dorsey and the Collison brothers at Stripe. Prior to Intercom, Des previously co-founded Exceptional (now a part of Rackspace), and prior was a UX designer for web applications. In Today's Episode You Will Learn: How Des made his way from founding consultancy web design businesses in Ireland to founding SaaS superstar, Intercom, with Eoghan and moving to San Francisco? Why does Des believe that "brand is the most overlooked element for new startups"? How must founders think differently when constructing their brand for a single product vs multi-product company? What is the right way to think about this brand architecture? How involved should customers be in the development of product roadmap? Where are the nuances and challenges to this? When is the right time to start thinking about releasing a second product? What is the right and the wrong way for this to be marketed? What does Des mean when he says, "there is an inverse correlation between quality and market size"? How should founders think about selling to both SMB and enterprise? How do their buying psychology and implementation process differ? 60 Second SaaStr When I say success, who is the first person that comes to Des' mind? Where do most startups go wrong with their branding? What does Des know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Des Traynor

Greg Sands is the Founder & Managing Partner @ Costanoa Ventures, one of the leading early stage enterprise funds on the West Coast with their latest $175m fund, raised earlier this year. At Costanoa, Greg has made investments in the likes of Intacct (acquired by Sage for $800m), Quizlet, DemandBase and previous guest, Grovo, just to name a few. Prior to founding Costanoa, Greg was a Managing Director at Sutter Hill, where he was an early investor in the likes of Feedburner, AllBusiness, and Return Path. Before Sutter Hill, Greg was on the other side of the table as the first hire at Netscape after its founding engineering team. As Netscape's 1st Product Manager, Greg wrote the initial business plan, coined the name Netscape, and created the SuiteSpot Business Unit, which he grew from zero to $150m in revenue. He also served as Manager of Business Development at Cisco where he architected a global channel management plan. In Today's Episode You Will Learn: How did Greg make his way into the world of SaaS as the first non-engineering hire at Netscape and then make his way into the world of SaaS investing, subsequently? Why does Greg completely disagree with the hailed notion of, "The Rule of 40"? Why does Greg believe it has achieved such status and recognition in market today? Where are the large nuances? If not the rule of 40, what metrics and benchmarks should early stage SaaS founders be focussing on? If we disregard "The Rule of 40", how does that impact the emphasis that should be placed on profitability? Tom Tunguz stated on the show, ""growth is the largest determinant of value at IPO, not profitability". What are Greg's thoughts on this? In that scaling process, Greg has said to me before, "the first hire in every function should be a Swiss army knife hire and most people go wrong". What does Greg mean when he says a Swiss Army Knife, how does that change in marketing vs sales? Where do most people go wrong within this? How does Greg define the different phases of product market fit? Why does Greg advocate that all founders approach product market fit with a "crawl, walk, run" approach? What examples does Greg have where this has worked and what specifically about this allowed it to work so well? 60 Second SaaStr Logos or expansion? Pros and cons of usage based pricing? What does Greg know now that he wishes he had known in the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Greg Sands

Spenser Skates is the Founder & CEO @ Amplitude, the only analytics solution built for modern product teams that helps you understand user behaviour and ship the right solutions fast. They have raised over 55m in VC funding from many friends of SaaStr and 20VC including Eric Vishria @ Benchmark, Neeraj Agrawal @ Battery Ventures, the teams at IVP, Data Collective, Box Group and SV angel, just to name a few of their incredible investors. Prior to Amplitude, Spenser founded Sonalight, an app that allowed users to text while they drive, backed by the likes of Y Combinator. In Today's Episode You Will Learn: How did Spenser make his way into the world of SaaS and come to found Amplitude? How did Spenser look to build and scale his sales team, as an engineering focussed founder? Where does Spenser see most engineering founders go wrong in their approach to sales? What were the stumbling blocks that Spenser found hard in this learning process? What is his biggest advice to technical founders to scale the learning curve fast? How does Spenser view the importance of a customer's willingness to pay? Does that suggest a correlated amount of value? How should this propensity to pay, change with the stage of the provider? How does Spenser suggest founders mitigate discounting? What have been Spenser's core learnings in creating an incentivised sales team? What are the core drivers that yield the behaviour desired? How does Spenser look to align this with engineering teams, traditionally disgruntled with sales' compensation packages? 60 Second SaaStr What does Spenser know now that he wishes he had known at the beginning of Amplitude? What is Spenser's fave SaaS reading material? How does that vary according to stage of business? How does Spenser view discounting? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Spenser Skates

Lars Nilsson is the VP of Global Inside Sales for Cloudera and with over twenty-five years of sales and operations experience, Lars Nilsson is a global leader in enterprise software and selling solutions. One of Lars many incredible achievements was he and his team at Cloudera built the sales methodology Account-Based Sales Development (ABSD), which has transformed how businesses approach high-value targets. Prior to Cloudera, Lars founded SalesSource, a business services consulting firm specializing in CRM customization and sales process development. Lars has also served in sales executive roles at ArcSight/Hewlett Packard, Riverbed Technology and Portal Software – all three of which achieved IPOs, in addition to Cloudera (2017). As Special Advisor at True Ventures, Lars helps True portfolio companies develop sales compensation plans from the ground up, implement best-of-breed sales technologies, and rapidly scale sales teams to meet demand. In Today's Episode You Will Learn: How did Lars make his way into the world of enterprise sales back in 1995? How has Lars seen the industry change so significantly over the last 22 years? Why does Lars believe that SDRs are the most important role in sales? How does their role of ensuring a full pipe compare to the role of demand gen and marketing? How does Lars think about setting a quota that ensures a desired behaviour beyond pure revenue chasing? What is his framework for setting and optimising the right quota? Why does Lars believe that ales is all about activities? What activities is Lars most eager to measure and test? What is Lars' biggest advice to someone looking to build out their SDR team from the ground up? What core characteristics should one look for in those initial SDR hires? What is and has been Lars' biggest challenge in building out his SDR team? Why is building SDR teams in the bay so hard? How does Lars think about setting ideal customer profiles? How big a TAM is large enough to be excited, yet narrow enough to be achievable and solve a true and inherent customer need? 60 Second SaaStr What does Lars know now that he wishes he had known at the beginning? What is Lars favourite piece of SaaS reading material? Sales rep productivity, what does Lars believe is the scale from exceptional to poor? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Lars Nilsson

Jyoti Bansal is the former Founder & CEO @ AppDynamics, backed by the likes of Lightspeed, Greylock and Kleiner Perkins just to name a few before it's ultimate acquisition by Cisco for $3.7Bn. Today, Jyoti is the Founder and CEO @ BIG Labs essentially a laboratory for creating, developing and launching innovative ideas. The first of these ideas being turned into companies being, Harness.io the industry's first continuous delivery as a service platform, where Jyoti is the Founder & CEO. As a result of his tremendous success, Jyoti has been a recipient of many leadership awards including, "Best Cloud Computing CEO to Work For", "Best CEO" by San Francisco Business Times. In Today's Episode You Will Learn: How Jyoti made his way from selling agricultural machinery with his father in India to creating one of the fastest growing enterprise companies with AppDynamics? $0-3m ARR: What is the key goal and objective for startups scaling through this phase? How can startups look to accurately determine what their North Star in this stage? To what extent should the founder involve the customer in product roadmap and development? $10-15m ARR: What are the core objectives for the business in this stage of the cycle? How should founders view competition through this phase? What does Jyoti mean when he says about "go-to-market strategy fit"? How can this be determined most accurately? $60-80m: What should be front and centre of the mind of the entrepreneur at this stage? Why does Jyoti believe it is here that it is crucial to get sales execution right? WHere are the breaking points that occur in the team scaling at this phase? How does the role CEO change here? Pre-IPO: Why is operational efficiency so crucial in this stage of the business? What did AppDynamics do best at this stage of the business? Where would Jyoti say AppDynamics could have done better in the progression through this stage? 60 Second SaaStr What does Jyoti know now that he wishes he had known at the beginning of Appdynamics? What is Jyoti's must read SaaS material? Payback period is the most important metric? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jyoti Bansal

Paul Albright is one of the valley's most experienced SaaS execs with extensive operational and capital management experience, including 3 IPOs. Most recently Paul was the Founder & CEO @ Captora, the marketing acceleration software solution that raised over $25m in VC funding from the likes of NEA and Bain Capital Ventures. Prior to Captora, Paul was Chief Revenue Officer at Marketo where he drove the overall revenue strategy across sales and marketing that delivered global revenue growth over 100% year-over-year, from $14m to $58m. In a similar position at SuccessFactors, he grew revenues to more than $200m and over 80% year-over-year growth. Previously, Paul led worldwide marketing at NetApp and at Informatica, which he joined pre-revenue through their successful IPO. If that was not enough he has also served as an entrepreneur-in-residence at Greylock. In Today's Episode You Will Learn: How Paul made his way into the world with the likes of SuccessFactors and Marketo? What were his big lessons from seeing both companies scale into hyper-growth mode? Does Paul agree with Dave Kellogg in stating, "CAC/LTV is the single most important metric for SaaS startups? What other metrics must all VPs of Demand Gen and Sales be watching constantly? What does an efficient sales and marketing engine look like? What are the core components to build that? What are the requirements to both run this engine and scale it quickly? How does the growth of this engine affect hiring in other parts of the business? Why does Paul believe that it is much harder to go SMB up than enterprise down? What are the changes that are required on both ends? For this in "no man's land of pricing" what does an efficient sales process timeline look like from lead to conversion? 60 Second SaaStr How does Paul think about picking the investors he works with? Is customisation always wrong? What is "good sales rep productivity" to Paul? What does Paul know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Paul Albright

Jack Altman is the Founder & CEO of Lattice, the #1 performance management solution for growing companies.They have raised close to $10m in funding from some of our favourites in industry including the likes of Miles Grimshaw @ Thrive, Khosla Ventures, Elad Gil, Alexis Ohanian and YC's Daniel Gross. Prior to founding Lattice, Jack was the Head of Business Development @ Teespring where he saw the firm move into hyper scaling. Jack has also build an incredible angel portfolio including the likes of Gusto, OpenDoor, Instacart, Zenefits and Soylent. In Today's Episode You Will Learn: How Jack made his way from seeing the hypergrowth of Teespring to starting Lattice? What does Jack identify as the 2 core challenges to rapid scaling in SaaS? Does Jack agree with Chris Caren in stating you have to hire for 3-4 years ahead of the role? How does Jack see the role and structure of communication change with the scaling of a firm? How did the early days of selling look with Lattice? How did Jack incorporate the team into his learnings and development within the world of SaaS? What should founders look for in the first sales hire? How does that profile change with the scaling? Why does Jack believe that each and every department should have their own North Star as well as a company North Star? Does Jack concur with Eric Ries' believe that every department must also have their own budget? In terms of metrics, how does Jack prioritise within the metric stack? What is most important for Jack to focus on? How has Jack seen this change with time? Does Jack agree with Shan Sinha @ Highfive that it is "always about payback"? 60 Second SaaStr Jack's Favourite SaaS reading material? What does Jack know now that he wishes he had known at the beginning? How much time does Jack spend talking to customers? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Jack Altman

Rajeev Batra is a Partner at Mayfield, a firm that has championed bold entrepreneurs since 1969. Rajeev's investments at Mayfield include the likes of Crunchbase, SmartRecruiters, Marketo (IPO then taken private by Vista Equity), ServiceMax (acquired by GE Digital) and more incredible companies. Prior to Mayfield, Rajeev was at Mobius (Softbank) Venture Capital and Austin Ventures. Before making the move into VC, Rajeev was on the operational side as an entrepreneur and executive with three of the companies he worked with going public and later being acquired, including the very notable Siebel Systems. In Today's Episode You Will Learn: How Rajeev made the transition from successful operator with 3 IPOs under his belt to investing in the next generation of enterprise companies with Mayfield? What does Rajeev mean when he says "startups do not die of starvation, they die of indigestion"? How does this realisation affect Rajeev's approach to customer profiling and segmenting customers? Why does Rajeev believe that "early product market fit can be misleading"? How does Rajeev look to provide context and action from numbers and analytics in the early days? How does Rajeev feel that founders should approach gross margin from the early days? How should this relationship and thought process towards gross margin change over time? Why does Rajeev believe that retention is the number 1 metric for SaaS founders to focus on? In the stack of metrics, how does this compare to gross margin, CAC/LTV and payback period? 60 Second SaaStr Enterprise investing is spreadsheet investing: True or false? How does Mayfield use an internal budget to align themselves to entrepreneurs? What does Rajeev mean when he says "I look for 2 act opportunities"? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Rajeev Batra

Shan Sinha is the Founder & CEO @ Highfive, the startup that quite simply makes insanely simple video conferencing. They have raised over $45m in funding from some of the best in the business including a16z, Lightspeed General Catalyst and Founder Collective and then individuals including Aaron Levie, Drew Houston and Marc Benioff. Prior to Highfive, Shan was the Group Product Manager for Google Apps for Enterprise, which he joined following Google's 2010 acquisition of his prior company, DocVerse, which later became part of Google Drive. In Today's Episode You Will Learn: How Shan made his way from being one of the foundations of Google Drive to changing the world of video conferencing with Highfive? As a successful second time founder, how has Shan's thesis around customer success changed? When is the right time to hire your first CS personnel? What profile should those first CS hires have? How does this vary to differing profiles in the scaling journey? Logos or expansion? What does Shan believe is crucial in the early days of SaaS scaling? What metric is the true determinant of whether a customer is attaining consistent value from your product? Why does Shan believe that not everything has to scale from Day 1? What are the benefits of implementing a model that is unable to scale? What does this show and teach the startup? How does Shan think about capturing the perfect customer experience? Why does Shan believe that payback period is the single most important metric for SaaS startups? How does Shan think about payback and margins when selling to the traditionally smaller ACV marker of SMB? What are the challenges in doing so? 60 Second SaaStr When is a stretch VP a stretch too far? What does Shan know now that he wishes had known when he started Highfive? Challenges of doing both hardware and software simultaneously? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Shan Sinha

Chris Caren is the CEO @ Turnitin, the company revolutionising the experience of writing to learn with backing from the likes of IVP, Norwest Venture Partners and GIC. Chris has scaled the company to serve over 25m students and 2m teachers across 15,000 institutions. Prior to joining Turnitin in 2009, Chris spent 4 years with Microsoft as a General Manager and before that 3 years at Business Objects as a VP of Product Marketing. In Today's Episode You Will Learn: How Chris made his way into the world of SaaS and came to be CEO @ Turnitin? What were Chris' biggest takeaways from watching both Business Objects and Microsoft as they scaled into hyper growth mode? What were his big lessons in management from Bernard Liautaud? What marketing takeaways did he have from working with Dave Kellogg? Why does Chris believe management team upgrade is the most important role a CEO can perform? What are the core characteristics that upgrade candidates must have for them to be an attractive hire? What culture must be built into the fibre of the leadership team? How does Chris look to manage internal discontent when bringing in external managers? How does Chris look to involve internal candidates for the role in the search for their next boss? What are the benefits of this? When is a stretch VP a stretch too far? What are the signs of potential strain? How does the team convey this? Once identified, what is the right post-mortem chain to take place? 60 Second SaaStr What should founders consider before selling their company? What does Chris know now that he wishes he had known at the beginning? What is Chris' favourite SaaS reading material and why? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr

Greg Schott is the Chairman and CEO @ Mulesoft, provider of the leading platform for building application networks. They have raised over $250m in funding from some of the best investors in the world including NEA and Lightspeed and then some of the largest companies of the day in Cisco, Salesforce and SAP. Greg joined Mulesoft in 2009 when the company only had 20 employees, over the last 8 years Greg has scaled the team to over 1,000 today in 18 countries. A real software industry veteran with over 20 years of experience building and leading high growth technology companies from early stage through IPO. In Today's Episode You Will Learn: How Greg made his way into the world of SaaS and came to be CEO @ Mulesoft? Greg has seen Mulesoft scale from 20 to 1,000 employees today, what have been the biggest challenges in scaling the team? Where are the breaking points? What are the signs of those impending breaking points? How does that show through the team behaviour? Where do most companies go wrong in the hiring process? What is the right and wrong way to respond when a bad hire has been made? How long is long enough to determine whether a bad hire is a bad hire? Does Greg agree with the hire fast, fire fast thesis? If Greg could go back to 2009 when he joined the firm with 20 employees, what would Greg change about the way he approached hiring? What hiring advice would Greg give to an early stage SaaS company? How does Greg think about scaling sales teams? How does Greg view specialisation in the scaling of sales? When is the right time? What should CEO's look for in their sales leaders? How does that alter at different points in the journey? 60 Second SaaStr How have things changed since IPO? When is the right time to expand product line and enter new segments? Biggest challenge with Mulesoft today? Which SaaS CEO does Greg most admire and why? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Greg Schott

Andy Byrne is the Co-Founder & CEO @ Clari, the startup that helps sales teams drive more revenue and increase forecast accuracy through improved deal execution and predictive analysis. They have raised over $30m in venture funding from some of the best in the business including Sequoia and Bain Capital Ventures. Prior to Clari, Andy was part of the founding executive team at Clearwell Systems—Gartner's highest ranking e-discovery company—which he helped grow from pre-product & pre-revenue in 2005 to $100 million run rate until its acquisition by Symantec (SYMC) in Q2 2011. Prior to joining Clearwell, Andy co-founded Timestock, Inc., acquired by Computer Associates (CA) via the acquisition of Wily Technology. In Today's Episode You Will Learn: How Andy made his way into the world of SaaS and came to found Clari? What were the key takeaways from his two prior successful founding experiences? Why is it important for startups to look larger than life to potential "whale" customer? What is the methodology that startups can use to gain this appearance? What role does the website play in this? Why is it important for startups to understand the risk the buyer is undertaking at large corporates when becoming a customer? How does this mean that startups should convey the product roadmap? How can startups sell the product vision and the instant value add simultaneously? How can startups look to "create theatre" with their product? What does this really mean? How can startups do this when the product is in MVP stage? Why is it so important for the startup to make the switch from vendor to partner? How can startups use execution time as the key way to achieve this? 60 Second SaaStr What hires does Andy wish he had made earlier with Clari? Recruiting in the valley, how hard and top tips? What is the most challenging element in the day to day running of Clari? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Andy Byrne

Ben Uretsky is the Co-Founder & CEO @ Digital Ocean. Under Ben's leadership, DigitalOcean has risen from a cloud startup for developers to the second largest and fastest growing cloud computing platform. To date, more than 1m developers have deployed more than 50 million cloud servers, and the company has expanded its worldwide infrastructure footprint with multiple datacenter locations around the globe. The company has raised $123 million in funding from Andreessen Horowitz, Access Industries, IA Ventures, CrunchFund, and Techstars. Prior to DigitalOcean, he co-founded and built a managed hosting provider that supported some of the top websites online and generated million-dollar annual revenues. In Today's Episode You Will Learn: How Ben made the move from co-founding a bootstrapped startup competing with Rackspace to co-founding DigitalOcean and competing with Amazon? What have been Ben's big learnings in raising $123m for DigitalOcean? How does Ben suggest building a trusted relationship with VCs? How have DigitalOcean scaled to over 1m customers without a sales team? What are the core tenets that have made this possible? How does the team prioritise customer acquisition channels at DigitalOcean? How does Ben say is the right way to build a community? Sean Rad has said before the hardest part is scaling with the firm. How has been seen his scaling as CEO with the firm? How has his personal relationship to the company changed with the scaling? Hear an inflection point in the scaling of DigitalOcean and how Ben's leadership changed as a result? 60 Second SaaStr What hire des Ben wish he had made earlier? What does Ben know now that he wishes he had known earlier? What are the key inflection points in SaaS businesses? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Ben Uretsky

Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M) and big data leader Aster Data (acquired by Teradata for $325M). In Today's Episode You Will Learn: How Dave made his way into the world of SaaS with Salesforce, came to be CMO at Business Objects and now running his own SaaS company as CEO at Host Analytics? What does David believe is the single most important metric in SaaS? How should SaaS companies structure the first four lines of their financial statements? Why is retention and renewal not always an accurate sign of customer satisfaction? How does Dave look to analyse churn? What is the post-mortem? What is more important, logos or expansion? If a startup's churn is too high, what is the top 3 things they should do? Why must you have a "standard taxonomy" for churn? How can you construct this? How does David think about taking existing customer and up-selling them? How does he view this in contrast to cross-sell? Does Dave agree with David Skok on the need for more than 1 variable pricing mechanism? Why does Dave not encourage usage based pricing? How does Dave analyse the benefits of multi-year contracts paid upfront? How does this distort TCV and inflate the figures? Does upfront payment misalign the provider and the consumer, in terms of care and support? With that in mind, how does David view billing frequency? Contract durations? 60 Second SaaStr What does Dave know now which he wishes he had known at the beginning? What is the 90 day rule? Why is it important? How much ARR should a good sales rep add in relation to comp? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Dave Kellogg

Scot Chisholm is the Founder & CEO @ Classy, the world's leading fundraising platform for nonprofit organizations As a result they have raised close to $50m in VC funding from the likes of Salesforce Ventures, our friends at BullPen Capital, Mithril Capital and many more great investors. With support and funding like this, since 2011, Classy has helped more than 3,000 nonprofits and social enterprises raise hundreds of millions of dollars and be named to "The World's Most Innovative Companies in Social Good" and to the "100 Brilliant Companies" by Entrepreneur Magazine. As for Scot, he is also a prolific angel investor, investing out of a fund called Mixture that includes investments in Change.org, inDinero, Iodine, Casetext and more. In Today's Episode You Will Learn: How Scot made his way into the world of SaaS and how a "pub crawl" came to be the founding story for Classy? What have been the key learnings for Scot in raising $50m for Classy, in an industry that is maybe not so sexy for investors? Why did Scot choose to raise both the seed and A round from angels? What advice would Scot give to aspiring founders, looking to raise? How has Scot seen the evolution of his sales team? What are the key inflection points in the scaling when elements tend to break? How important is it to segment the sales team? When should this be done? At what speed is optimal? How does Scot evaluate startups looking to move upmarket? How does the decision to move upmarket change the internal decision-making with regards to product roadmap and strategy? How does it change the role of CEO in the organisation? How does Scot look to balance the attainment of short term objectives with holding the vision for the future? How far is too far to plan ahead? How should founders think about investing in areas of the business ahead of time? 60 Second SaaStr What does Scot know now that he wishes he had known when he started? Challenges as a first time CEO/entrepreneur? The key challenges of building a SaaS company in San Diego? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Scot Chisholm

Mark Organ, Founder & CEO at Influitive. Influitive helps B2B companies mobilize their army of advocates for more rapid and profitable revenue growth. They have raised close to $50m in VC funding from some of the best in the business including the likes of Lightspeed, First Round Capital, prior guest Cindy Padnos @ Illuminate and Nick Mehta @ Gainsight, just to name a few. Prior to Influitive, Mark was the founding CEO of Eloqua, growing the business to over 150 people, hundreds of clients and a major presence around the world in 7 years. Eloqua was eventually bought by Oracle in 2012 for a reported $810m. In Today's Episode You Will Learn: How Mark made his way into the world of SaaS, came to found Eloqua and then what the catalyst was for the founding of Influitive? How did Mark make the decision to make profitability a goal? How did Mark communicate his desire to focus on profitability and unit economics over aggressive growth to his investors? What type of SaaS startups should consider this route more? To what extent is "landing whales" crucial to getting to cash flow positive? What are some of Mark's big learnings in how to attain those "whales", having done it so successfully before with Eloqua? Where do most founders go wrong and how should they approach pricing whales? Why does Mark believe paying sales reps on signing misaligns incentives? Why does he believe it is optimal to pay half on signing and half on cash being received? How do you communicate that to your sales team? To what extent should SaaS startups consider debt financing as a respectable and appropriate form of company financing? What type and stage of SaaS company does debt make perfect sense for? When is it wrong in the lifecycle to take debt? 60 Second SaaStr What hire does Mark wish he had made earlier? What does Mark know now that he wishes he had known at the beginning? Pros and cons of running a SaaS startup not in Silicon Valley? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Mark Organ

Mike Dauber is a General Partner @ Amplify Partners, the fund that backs technical founders, building technical products for technical buyers. Their portfolio consists of the likes of DataDog, Fastly, Engagio and many more incredible companies. As for Mike, prior to joining Amplify he spent more than six years at Battery Ventures, where he lead early-stage enterprise investments on the West Coast. While at Battery, he was on the Boards of Cask, Duetto, Interana, and Platfora (acquired WDAY). Mike also lead Battery's investment in Vera, which is also in Amplify's portfolio. He also previously invested in Splunk (SPLK) and RelateIQ (acquired CRM). As a result of this success, Mike was named to Forbes' Midas Brink List in 2014. In Today's Episode You Will Learn: How Mike made his way into the world of early stage enterprise investing with Battery and came to be a GP with Amplify? What does Mike mean when he says he looks for "practitioner founders"? What are the benefits of these types of founders? Why do they find product market fit faster? Does this tunnel vision not sometimes mean a lack of naivete, which can be good? Why does Mike believe that hiring sales people is like being thirsty? How can founders discover the optimal cadence for expanding the sales team? Why must founders differentiate between customers and money? Why does Mike believe that everyone needs to find their Hobbesian advisor? What characteristics should this person have? How can you find this advisor? What should their incentives be? Why does Mike believe that founders need to set the hook for VCs in the first meeting? How does this compare to how founders traditionally pitch? What should they look for in those early VC meetings? 60 Second SaaStr Why does Mike disagree with deal attribution in VC? Cyber investing: Should you invest if not a domain expert? Is enterprise investing spreadsheet investing? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Mike Dauber