
The Official SaaStr Podcast: SaaS | Founders | Investors
865 episodes — Page 13 of 18

SaaStr 267: Menlo Ventures Partner Naomi Ionita on 3 Lessons in Monetization - Matching Price to Value
SaaS is about creating long-term value for your customer, and being compensated appropriately for that value as a business. Learn actionable monetization tips from a Product/Growth operator turned VC, Menlo Ventures Partner Naomi Ionita. Missed the session? Here's what Naomi talks about: How to avoid underpricing your product Fitting your businesses' product to the market This podcast is an excerpt of Naomi's session at SaaStr Annual 2019. You can watch the full video on our website. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Naomi Ionita Today's sponsor: Traditional customer beta testing can't keep up with the speed of Agile or the demands of continuous delivery. Centercode's approach to real-world Delta Testing fuels product and engineering teams with actionable quality and UX insights before every new release. Visit Centercode.com to learn more.

SaaStr 266: Zoom CMO Janine Pelosi on Why MQLs and SQLs Are Not Helpful As Labels, How To Create Alignment Between Sales and Marketing & How The Role of CMO Has Changed So Dramatically Over The Years
Janine Pelosi is the CMO @ Zoom, the next-generation enterprise phone system. Prior to their very successful IPO, Zoom raised funding from some of the best in the business including Sequoia, Emergence Capital, Horizons Ventures and 2 of my favourites in the form of Matt Ocko @ Data Collective and Dan Scheinman. As for Janine before joining Zoom, she spent 11 years at Cisco where among many incredible achievements she led worldwide demand gen for WebEx and led their worldwide digital marketing team with a $25M annual budget. In Today's Episode We Discuss: How Janine made her way into the world of SaaS and came to be one of the leading CMOs today with Zoom? How has the role of the CMO changed over the last 5 years? Would Janine agree with Jason Lemkin that "the role of the CMO is to execute the vision of the CEO"? What makes Janine and Eric's relationship so successful? What makes Eric the special leader that he is? How does the changing power of the CMO affect their relationship with the CEO? When is the right time for startups to hire their first CMO? What should they look for in that ideal candidate? What should they have in place in terms of infrastructure, prior to hiring the candidate? What does the right onboarding process look like for a CMO? Where does Janine see many going wrong when hiring their first CMO? How does Janine look to create alignment between sales and marketing? Why does Janine not believe in having the labels of "MQLs and SQLs"? How does Janine look to reduce the friction when handing off between marketing and sales? What are the common causes? How are we seeing marketing also blend with customer success? Janine's 60 Second SaaStr: What does Janine know now that she wishes she had known at the start of her time at Zoom? Who does Janine most respect in the world of marketing today? Why? What would Janine most like to change about 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 Janine Pelosi

SaaStr 265: WP Engine SVP of Global Sales Matt Schatz on Building a $100M ARR Sales Team - The Second Time Around
Matt Schatz is SVP of Sales at WPEngine, responsible for defining and executing the global sales strategy. Matt has nearly two decades of senior leadership experience in sales and customer growth, specifically for technology companies with customers around the world including Bazaarvoice, CityVoice and Rackspace. Missed the session? Here's what Matt talks about: Getting your "first story" What is a lucky lead and how does that turn into predictable growth Building trust across time zones This podcast is an excerpt of Matt's session at SaaStr Annual 2019. You can watch the full session 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 SaaStr WP Engine Today's sponsor: Traditional customer beta testing can't keep up with the speed of Agile or the demands of continuous delivery. Centercode's approach to real-world Delta Testing fuels product and engineering teams with actionable quality and UX insights before every new release. Visit Centercode.com to learn more.

SaaStr 264: Gainsight COO Allison Pickens on Why Customer Success and Product Management Are The New Sales and Marketing, How To Approach Building and Scaling "Services" As A Revenue Line & How To Build A CS Team On A Tight Budget
Allison Pickens is the COO @ Gainsight, the company that provides everything you need to turn your customers into your biggest growth engine. To date Gainsight have raised over $184m from some of the world's best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures just to name a few. As for Allison, in her 5 years at Gainsight her list of achievements in endless from running all functions that drive value for Gainsight customers, now a 150 person team, to building out the corporate development function to being the right hand to the CEO. Allison is also an Entrepreneur-In-Residence at Bessemer Venture Partners and sits on the board of RainforestQA. Before Gainsight, Allison started her career in NYC with stints at Bain and The Boston Consulting Group. In Today's Episode We Discuss: How Allison made her way into the world of SaaS with Gainsight from her start in finance at Bain in New York? What does a strategic plan really mean to Allison? What is included in it? How should it be structured? In terms of ambition, how does one set ambitious enough plans to be a stretch but not a stretch too far? How does one tie their strategic plan to their financial plan? What is the right way to communicate this throughout the organisation? Why does Allison believe product marketing and customer success are the new sales and marketing? What have been Allison's biggest lessons on how to effectively measure adoption? Who is accountable to this number? CS or product management? Does Allison believe that marketing needs to be held accountable to a number directly tied to revenue? How does Allsion respond to the common negative of "services revenue"? What is an acceptable ratio of services to software revenue? How can one approach setting up a services team for scale? Why is having such a great CS team actually bad for product development in the long run? How can one mitigate this? Allison's 60 Second SaaStr: What does Allison know now that she wishes she had known at the beginning of her time with Gainsight? How often should CS check in with their customers? What does that look like? If on a tight budget, how should one staff a CS team? 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 Allison Picken

SaaStr 263: Eventbrite SVP of Platform Pat Poels on Engineering Your Own Luck - The 3 Key Rules of Building Globally Distributed Teams
Building a company made up of distributed teams presents a plethora of complex challenges that can derail productivity and impact employee retention. But with it comes immense benefits and competitive advantages such as the diversification of ideas, speedier product development, and representation in important regions and time zones. Come and hear about the typical pitfalls (and how to avoid them) from Eventbrite SVP of Platform Pat Poels, an executive with over seven years under his belt leading Eventbrite's now 300+ strong engineering team that sits across North America, South America, and Europe. Missed the session? Here's what Pat talks about: Engineering your own luck How to build an engineering team If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

SaaStr 262: Box's Jon Herstein on How Customer Success Teams Should Structure, Schedule and Execute on Customer Check Ins, Why Delight is Important But Insufficient & Why Customer Success Is Not Responsible For Upsell
Jon Herstein is the Chief Customer Officer at Box, the company that provides one platform for secure content management, workflow and collaboration. Prior to their IPO, Box had raised funding from some of the best in the business including Andreesen Horowitz, Bessemer, DST, Emergence and Meritech, just to name a few. As for Jon, prior to being Chief Customer Officer at Box, he was Senior VP of Customer Success, responsible for all post-sales services Box provides from implementation to user adoption and more. Before Box, Jon spent 4 years as VP of Professional Services at NetSuite and prior to that, close to 8 years as Senior Director of professional services at Informatica. In Today's Episode We Discuss: How did Jon make his way into the world of SaaS and come to be one of the leading figures in the rising tide of the customer success movement? What does Jon mean when he says, "you have to constantly bring your customers to the forefront of your employees minds"? For non-customer facing roles, what can one do to give them that perspective? Does it work to ensure every function spends time in customer support? What is challenging about that? What can be done in the onboarding phase to ensure the individual has the most empathy for the customer, regardless of function? For those in CS, what is the right communication cadence to check in with their accounts? What should the agenda look like? What outcomes should they drive towards? Should they be involved in the upsell process? How does Jon think about post-mortems on churned clients? How do they structure them? What lost client stands out to Jon and what would he have done differently to retain them? From Jon's experience seeing Box in hyperscaling, at what stages do SaaS orgs start to break down? Why does Jon think that is? What can be done to proactively try and mitigate this? How does Jon think about the structuring of roles and responsibilities with scale? What does this done well look like? Where do many people go wrong here? Jon's 60 Second SaaStr: What does Jon know now that he wishes he had known at the beginning of his time with Box? What motto or quote does Jon frequently revert back to? What is the most challenging element of Jon's role with Box 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 Jon Herstein

SaaStr 261: Workday EVP of the Planning Business Unit Tom Bogan on The Top Lessons Learned in Getting to $100M ARR
Tom Bogan, CEO of Adaptive Insights, a Workday company, will review the key principles to building a successful SaaS company. From team to vision to metrics to funding and more, these principles provide the framework for high-growth, high performing SaaS companies. How can you develop a winning culture? How can you set aggressive but realistic goals? What's needed to build the right team in SaaS today? Missed the session? Here's what Tom talks about: The important maxims about team building Insights on fundraising and why you might not want to always raise at the highest valuation Personal stories from his time building Adaptive Insights If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

SaaStr 260: HelloSign COO, Whitney Bouck on How Startups Can Attract The Most Seasoned Execs In SaaS, How To Determine Whether A Seasoned Exec Has True Startup Fabric & What Separates Good From Great When It Comes To COOs
Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization's go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise. In Today's Episode We Discuss: How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today's leading COOs with HelloSign? What were Whitney's biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality? What does truly successful exec leadership look like in Whitney's mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a "big company" person? What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and centre in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider? COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO? Whitney's 60 Second SaaStr: What does Whitney know now that she wishes she had known at the beginning? What makes for the optimal relationship between COO and CEO? What is the most challenging element of Whitney's role with HelloSign 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 Whitney Bouck Ever feel like you can't really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

SaaStr 259: Pipedrive SVP of Global Sales Tara Bryant on Addressing the Ugly Side of Growth
Our guest today is Pipedrive SVP of Global Sales Tara Bryant. Globalization opens up a world of opportunities for sales growth. We often focus on the positive sides of growth—but what about taking a look at the ugly sides? Even what we could consider "good problems" need preparation, and it starts by understanding your team and your goals, including knowing when and how to recruit members of your team, and building in a way that compliments your growth. Do you need more man-power on the customer facing side, or do you need to bring in new management to keep everything in line? Growth isn't always linear, and the steps to success aren't always one after the other. How do you prioritize and organize to bring the best possible results? This side of success can be scary, but knowing how to prepare can set you up to reach your companies long term growth goals. Missed the session? Here's what Tara talks about: What does the ideal candidate look like? How to hire your core staff really well Enabling salespeople to share learnings If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

SaaStr 258: Plaid CEO and Co-Founder Zach Perret on How to Build a Platform that Fuels an Ecosystem
Companies that have access to more accurate financial data have the ability to develop seamless exchanges of information, providing consumers with improved ways to manage their finances. But how do companies gain secure access to that data in the first place? Enter the platform company. Hear from Plaid co-founder and CEO, Zach Perret and CNBC's Ari Levy as he walks through his lessons learned building Plaid and how it found itself at the center of the fintech ecosystem. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Zach Perret

SaaStr 257: How To Scale Sales Culture Successfully and Sustainably, The Leading Indicators of Burnout and What To Do & The 2 Inflection Points In SaaS Growth Where Things Start To Break with Justin Welsh, Former SVP Sales @ PatientPop
Justin Welsh is the former SVP Sales @ PatientPop, the startup that offers the first all-in-one practice growth platform that's HIPAA-compliant and is proven to grow your practice. During his 5 years at PatientPop, Justin grew sales from $0 to $56m alongside the full build-out of the sales team. Before PatientPop, Justin was one of the first 10 employees at ZocDoc, where he spent 4 years in different roles including Director of Strategic Sales. In Today's Episode We Discuss: How Justin made his way into the world of Sales and came to be one of the industry's leading scale up Sales leaders with PatientPop and ZocDoc? How did Justin experience burnout? What were the first indications and signals for him that he was suffering from it? How did it manifest itself in how he carried himself and his behaviour? How did Justin communicate the situation to his bosses? What does Justin advise others in communicating burnout to their superiors? As a manager observing their team, what are signs that an individual is burning out? What is the right way to approach them to discuss the situation? What options do managers have available to them when faced with a burned out employee? How does micro-management fit into the signals that suggest clear burnout of the individual? Justin has said before that "culture must precede performance", what did he mean by this? What actions and communications must they adopt to ensure that this feeling of culture over performance is accepted by the team? With that in mind, how does Justin think about KPI and goal-setting? What can leaders do to create an environment of safety for their team? Where do many leaders go wrong here? Having seen multiple scaling culture, where do SaaS organisations tend to break down both in terms of culture and process? What are those inflection points? What can be done to actively mitigate these 2 significant points of failure? Justin's 60 Second SaaStr: What does Justin know now that he wishes he had known when he started at PatientPop? Sales leader Justin most respects and why? If Justin could change one thing about the world of SaaS today, what would it be? 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 Justin Welsh Ever feel like you can't really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

SaaStr 256: Google Cloud VP of Engineering Eyal Manor and Zenoss CMO Megan Lueders
As a global technology provider powering thousands of SaaS companies, Google is at the forefront of driving exciting and innovative technologies to market. Eyal Manor and Megan Lueders host a fireside chat between Google Cloud and Zenoss, a leader in software-defined IT operations. They discuss the most common and emerging challenges facing SaaS companies today. You'll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. Join us for this lively discussion between two innovators. Missed the session? Here's what Eyal and Megan talks about: How to develop software faster The emergence of new A.I. services Why the "strongest" conversations need to happen between engineering and marketing If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

SaaStr 255: Why Enablement Must Be An Early Investment and How To Structure It, Why The SaaS Incumbents of Today Are Not As Strong As We Think & How To Build A Sales Culture of Confidence Without Arrogance with Vikas Bhambri, SVP Sales and Customer Experi
Vikas Bhambri is SVP Sales and Customer Experience @ Kustomer, the startup providing Real-time, actionable views of customers with continuous omnichannel conversations and intelligence that automates repetitive, manual tasks. To date they have raised over $113m in financing from some of the best in the business including Tiger Global, Battery Ventures, Boldstart, Canaan, Cisco and Redpoint just to name a few. Prior to Kustomer, Vikas spent over 20 years implementing, consulting, marketing, and selling CRM and ContactCenter solutions with companies like LivePerson and Oracle. In Today's Episode We Discuss: How Vikas made his way into the world of SaaS and came to be at the rocketship that is Kustomer? Why does Vikas believe that a wave of SaaS incumbents are about to be displaced or disrupted? What about the changing tech stacks and infrastructures makes them vulnerable to up and comers? Does this not lead to a consolidatory environment? How does Vikas see the space play out in the coming years when it comes to acquisitions? What have been the dramatic changes that have happened in sales over the last few years? What is the right way for startup founders to address sales rep onboarding? Why is it so crucial to invest in enablement in the early days? How should this enablement be structured? How does this change sales rep payback periods? What is a good payback period? How does Vikas feel about discounting? If accepted, what must the startup ask for in return? How does Vikas think about multi-year deals? When are they good? What sort of terms make them less beneficial for the vendor? How does Vikas think about professional services? What is a good margin for professional services? What ratio of revenue is healthy for professional services to account for? When should one look to hire their first customer success reps? What should they look for in those reps? Vikas' 60 Second SaaStr: What does Vikas know now that he wishes he had known at the beginning? What is his secret to building diverse teams? The sales leader Vikas most respects and admirers and why? 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

SaaStr 254: HubSpot CEO Brian Halligan on The Funnel is Dead, Long Live the Flywheel.
The age-old sales funnel has worked fine for decades…until now. Flaws are being exposed, and a new model is imminent. Why is the sales funnel alone no longer an appropriate way thinking about customers? What will emerge to supplement or replace it? HubSpot CEO Brian Halligan and NEA's Hilarie Koplow-McAdams explore the evolution of the marketing and sales funnel you've been using for decades to generate traffic and convert and leads into customers. Missed the session? Here's what Brian talks about: Why a flywheel instead of a funnel? What does the Grateful Dead have to do with Marketing…? What role do T shaped people play? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Brian Halligan

SaaStr 253: TaskRabbit Founder Leah Busque on Lessons Learned from a Product Reboot
Leah Busque is currently a General Partner at Fuel Capital, an early stage venture fund located in Silicon Valley. She likes to invest across consumer, B2B saas, and technology infrastructure companies at the earliest stages. In 2008 Leah founded TaskRabbit, the leading on-demand service marketplace in the world. She spent nearly a decade involved with the company as CEO and Executive Chairwoman before she sold the company to IKEA in October of 2017. Hear about her takeaways from a product reboot with TaskRabbit. Missed the session? Here's what Leah talks about: What are the lessons learned from a product reboot? When bringing a product to market - what are the BHAGs? How to navigate a product pivot. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Leah Busque

SaaStr 252: How To Make The Transition From Founder Led Sales To Sales Team, The Truth About Raising a Series A Round As a Non-Bay Area Company and Why Employee 50 Is Such a Big Turning Point
Eric Christopher is the Founder and CEO @ Zylo, the software management system built for the cloud pioneering a new standard in software management. To date, Eric has raised over $12m for Zylo from some of the best in the business including Byron @ Bessemer, Salesforce, GGV, Semil @ Haystack and the team at High Alpha. Prior to founding Zylo, Eric was the VP of Sales @ Sprout Social leading the revenue operations for over 11,000 customers. Before Sprout Social he was VP of Sales at Shoutlet, responsible for global direct and channel sales teams and developing and managing strategic relationships. Finally, prior to Shoutlet, Eric spent over 7 years at ExactTarget as a Senior Business Development Manager which is where he met High Alpha's Scott Dorsey. In Today's Episode We Discuss: How Eric made his way into the world of startups and SaaS? What were his biggest takeaways from working with Scott Dorsey @ ExactTarget? What was the founding moment with Zylo? What have been Eric's biggest lessons when it comes to making the transition from founder led sales to sales team? What would we have done differently with the benefit of hindsight? What were the biggest challenges in the process? How does Eric think about the importance of quantity vs quality of logos when acquiring your first few customers? Do big logo brand names really provide social validity or is it over-hyped? How does Eric think about discounting in the early days? What can founders do to really extract the most value from the discount they are giving away? Why does Eric believe that hitting the employee 50 mark is a huge moment for founders and the scaling of the company? What fundamentally changes? What gets harder? What gets easier? How has Eric seen his role evolve with the scaling of the team? How does Eric think about goal and KPI setting with a much larger team? What needs to change? How does one create and retain accountability and ownership at scale? Why does Eric believe that the bar for execution in SaaS in 2019 is so much higher than in 2009? What has changed? How does this make Eric change the way he approaches benchmarking, capital allocation and growth? How did Eric find raising the Series A as a non-Bay area company? Eric's 60 Second SaaStr: What does Eric know now that he wishes he had known at the beginning? What is the toughest role to hire for today? If the money is on the table, take it. Agree or not? Why? 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 Eric Christopher

SaaStr 251: Y Combinator Michael Seibel on a Decade of Learnings from Y Combinator
Michael Seibel is CEO and a partner at Y Combinator and co-founder of two startups – Justin.tv and Socialcam. He has been a partner at Y Combinator since 2013, advised hundreds of startups, and has been active in promoting diversity efforts among startup founders. Hear his take on the future of work with a decade in learnings from YCombinator. Missed the session? Here's what Michael talks about: How quickly should you hire? When is the right time to sell a startup? How large a differentiator will investors make in your company? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Michael Seibel

SaaStr 250: Why Enterprise Is Hard Again, Why To Be Successful in SaaS Today You Have To Find The Crumbs Falling From Incumbent Mouths and Why Large Orgs Are So Dysfunctional and How To Poach Talent From Them
Peter Yared is the Founder & CEO @ InCountry, the startup that allows you to operate globally with data residency as a service meaning they store your mission-critical data in it's country of origin, without compliance. To date, Peter has raised $8m for InCountry from some of my very favourites including Bloomberg Beta, Felicis, Ray Tonsing @ Caffeinated and CRV just to name a few. Prior to InCountry, Peter founded six and sold 6 enterprise software companies that were acquired by Sun, Citrix, VMware, Oracle, Sprinklr and Prograph. Previously, Peter was also the CTO/CIO of CBS Interactive where he brought CBS into the cloud. At Sun, Peter was the CTO of the Liberty identity consortium that designed SAML 2. In Today's Episode We Discuss: How did Peter make his way into the world of enterprise SaaS with the founding and selling of 6 companies and how did InCountry come about? What is that founding moment? Why does Peter feel like it enterprise is really hard again? Why is it no longer to come into large enterprises with a small contract and expand? How does Peter think about enterprise pilots today? Do they really mean anything? What proof points suggest an enterprise is really bought in? What benchmarks should startups bake into the agreements? How does Peter think about and approach market sizing today? Why is market risk no longer a risk he is willing to take? Where do many entrepreneurs make mistakes when it comes to market timing? In terms of timing, how should entrepreneurs think about whether to start at SMB and move to enterprise or start enterprise and move to SMB? What are the considerations? Why does Peter believe that large orgs are so dysfunctional today? What can founders do to extract the truly special talent out of these large orgs with big pay packets and troves of options? How has Peter found the transition from CTO to CEO this time? What have been some of the challenges? Where has he asked for external help? Having built numerous successful remote teams, what have been Peter's biggest learnings in what it takes to successfully build remote teams? Where do many people go wrong? Does it have to be from Day 1? When is the right time to start thinking about this as a startup? Peter's 60 Second SaaStr: What would Peter most like to change about the world of Silicon Valley and tech? Who is the biggest rockstar in the valley that is less well known? Hire fast, fire fast, agree or disagree? 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 Peter Yared

SaaStr 249: New Relic CRO Erica Ruliffson-Schultz on Five Critical Steps to Scaling Enterprise
CRO Erica Ruliffson-Schultz has led New Relic through massive growth, scaling the company's enterprise business 10x since she joined the business pre-IPO. Growing a company's revenues, customer base, team, process, and product doesn't just happen without major work and strategy. Erica will share the five critical steps (and some lessons learned along the way) for scaling in the enterprise. Missed the session? Here's what Erica talks about: How to change up your marketing mix How to transition from SMB to enterprise Identifying your sweet spot target customers and leveraging your network to access those companies. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

SaaStr 248: What Early Stage SaaS Companies Can Learn Most From Late Stage SaaS Co's, How Marketing Functions Change In SaaS Co's With Scale & Why The Most Powerful Mentorship Is Mentorship From Below with Joe Chernov, VP of Marketing @ Pendo
Joe Chernov is the VP Marketing @ Pendo, the startup that understands and guides your users allowing you to create products they cannot live without. To date they have raised over $108m in funding from some of the best in SaaS including Meritech, Salesforce, Battery, Spark Capital and Sapphire just to name a few. Prior to Pendo Joe was Chief Marketing Officer at Robin and before that he was the CMO @ InsightSquared where he led the transition from an email-driven leads model to an account-based marketing model. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua. In Today's Episode We Discuss: How Joe made his way into the world of startups and SaaS marketing many years ago? Does Joe really believe in the saying that, "no one really knows what they are doing?" Where are the nuances to it? Joe has been CMO and then #2 and alternated between the 2 roles many times, so what the continuous alternating? How does switching from CMO to VP of Marketing prepare you better for each subsequent role? Does Joe agree with the saying that the best in marketing are able to "throw the playbook out of the window"? What does Joe mean when he says, "the most powerful mentorship is mentorship from below"? What makes the best #2's just so good? What do they do? What advice would Joe give to a #2 in a role today? What can the individuals do to foster a relationship of deep trust and transparency? Having worked at both early and late stage companies, what does Joe believe the early companies can learn from later stage companies? Does installing very severe ops not reduce the creativity of a young company? What does Joe believe that later stage companies can really learn and take from early-stage companies? How do the marketing functions differ in both structure and process when comparing early to late stage? What does Joe find to be the biggest challenge within each respective stage? How has Joe seen the content landscape evolve and change radically throughout his career alternating between early and late stage companies? Joe's 60 Second SaaStr: Who does Joe believe is killing it in SaaS marketing now? Why? ABM, total BS or real meaning to it? If Joe could change one thing about SaaS today, what would it be? 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 Joe Chernov

SaaStr 247: Hired CEO Mehul Patel on How to Move from Transactional to Recurring Revenue
Hear from Hired's CEO Mehul Patel on how to move from transactional to recurring revenue. Hired is a marketplace that matches tech talent with innovative companies. Hired combines job matching with unbiased career counseling to help people find a job they love. Through Hired, job candidates and companies have transparency into salary offers, competing opportunities and job details. Missed the session? Here's what Mehul talks about: How to leverage your company values to drive stability. Hiring people, strategically. Finding your pricing sweet spot. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Mehul Patel

SaaStr 246: Dropbox CCO Yamini Rangan on 5 Myths That Stop SaaS Companies From Moving Upmarket
Dropbox Chief Customer Officer Yamini Rangan draws on 20 years of experience to challenge five common misconceptions about SaaS success. From beating the competition to over (or under) relying on Outbound, she offers a practical perspective on the frameworks that are holding businesses back from reaching their full potential in a changing landscape. Missed the session? Here's what Yamini talks about: How to increase the odds of reaching $1B in ARR What is the pull upmarket, why do companies focus their attention there? Common go-to-market myths and lessons. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

SaaStr 245: The Ultimate Guide To ACVs; When and How To Increase Them, Revenue Optimisation Per Lead & What It Means To Truly Be An ARR First Company
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. Jason Lemkin is the Founder @ SaaStr, the world's largest SaaS community and leading early-stage SaaS fund with investments in Automile, TalkDesk, Algolia and more. Jason Vandeboom is the Founder of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Since 2013 with their transition to SaaS have grown to more than $50 million in ARR in less than five years, while maintaining profitability. Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor. 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. In Today's Episode We Discuss: Does David Skok believe that ACV should sit at the top of the metrics stack? What are the 4 metrics that fundamentally matter in your business? What can founders do to their pricing model to extract as much value from each customer? How do the very best businesses structure their pricing for value extraction? If ACV increase is a core focus for our startup, should we hire a sales rep solely selling to enterprise? What are the biggest mistakes founders make in this scenario? What can founders do to optimise revenue per lead? How does on need o approach lead targeting according to the individual skills of their reps? Is it best to start at enterprise and work down to SMB or does SMB and work up to enterprise work best? How does the product have to change with the scaling to enterprise? How does the messaging need to change with the scaling to enterprise? How do you need this change to be reflected in your pricing? What does it truly mean to be an ARR first company? What is the right way for founders to calculate their differing ACVs? What is the right way to present that when pitching VCs? Where do many founders go wrong in how they present and discuss ACVs with investors? 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: Harry Stebbings Jason Lemkin SaaStr David Skok Jason Vandeboom Dave Kellogg Fred Shilmover

SaaStr 244: Flexport CEO Ryan Petersen on How to Build a Truly Global Business from Day One
Flexport CEO Ryan Petersen will share what he has learned about scaling culture, expanding globally, raising venture capital (or not), and using technology to improve legacy industries. Missed the session? Here's what Ryan talks about: How Flexport grew to a multibillion-dollar business. How the company broke into the $2T freight forwarding industry. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Ryan Petersen

SaaStr 243: Twilio CMO Sara Varni on The 1 Question That Must Be Top Of Mind For All Marketers, The Truth About Enablement and How It Can Be Used Effectively & The Marketing Playbook, When To Use It vs Throw It Out Of The Window
Sara Varni is the CMO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Sara, prior to Twilio she spent 10 years with Salesforce in numerous roles including SVP of Marketing for Salesforce's Sales Cloud and CMO @ Desk.com, among other roles. If that wasn't enough, Sara is also an advisor @ Anthos Capital. In Today's Episode We Discuss: How did Sara made her way into the world of SaaS and came to be one of the industry's leading CMOs with Twilio today? What were Sara's biggest takeaways from her 10 years at Salesforce seeing the incredible hyper-growth first hand? What does Sara mean when she says, "you have to have a creative plan to get your message to market"? Does Sara really believe that there is a playbook when it comes to marketing? How does Sara determine when to throw the playbook out of the window? What resounding question do you always have to ask yourself when thinking messaging? Messaging is very dependent on the customer being targeted, how does the messaging need to be different when targeting SMB vs enterprise? How does the creative plan to get the message to the target customer change dependent on SMB vs enterprise? Where does Sara see most people go wrong here? Why does Sara so strongly believe in the power of customer stories? What makes the very best customer stories? What would Sara's advice be to someone who is wanting to start creating them? Where does Sara see so many people go wrong? What are Sara's tips for creating this alignment between the marketing team that make the stories and the sales team that sell them? Where are there often points of tension? What does the very commonly used term, "enablement", really mean to Sara? Does it mean you can hire lower quality candidates and upgrade them? How does Sara distinguish between a stretch VP and a stretch too far? What questions does Sara find most revealing in the interview process? 60 Second SaaStr: What does Sara know now that she wishes she had known at the beginning? Who is crushing it in the world of SaaS marketing today? What is the most common reason for the breakdown of an efficient funnel? 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 Sara Varni

SaaStr 242: Namely CEO Elisa Steele on How to Win the Talent War
It's the employees' market. There are more jobs than there are qualified people to do them. SaaS companies face sustained headwinds in the attracting, cultivating, driving productivity, and retaining talent. Your market competitors are your adversaries, but so is the entrepreneur sitting right next to you whose business is in a completely different sector. Namely CEO Elisa Steele shares practical advice on how to win three key Talentshare battles, which are essential to winning the Marketshare war. Missed the session? Here's what Elisa talks about: How to win Talentshare when the system is stacked against you. How to drive synchronization, productivity when your needs are constantly evolving and the talent mix is incredibly fluid and diverse. How to use Culture as the lever to maximize the ROI that you get out of the biggest investment your business will ever make. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Elisa Steele

SaaStr 241: Dave Kellogg on The BIggest Takeaways From Being In The Room For Sequoia's "RIP Good Times", Why Founders Should Raise As Much As Possible But Spend According To Plan & The Right Way To Think About Effective Quota Construction
Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor. Before that Dave was SVP/GM of Service Cloud @ Salesforce where he led the $500m line of business for customer service applications. Finally pre-Salesforce, Dave was CEO @ MarkLogic where he grew the team from 40 to 240 and revenues from $0 to an $80m revenue run rate. If that was not enough, Dave currently or has previously sat on the boards of Nuxeo, Alation, Aster Data and Granular. In Today's Episode We Discuss: How did Dave make his way into the world of SaaS over 20 years ago? How did seeing the boom and bust of the dot com and 2008 affect Dave's operating mentality? What were his biggest lessons from being in the Sequoia boardroom when they presented "RIP good time"? How does Dave think about when is the right time to raise? How does Dave advise founders on how much is the right amount to raise? Does Dave agree that if the money is on the table founding teams should take it? Why does Dave believe 99% of companies die? The first step in being acquired by a PE house is "making the book", what goes into "making the book"? Who is involved? How long does it take? What are the clear differences between a good book and a bad book? How should execs think about making exciting enough go-forward plans for it to be attractive to buyers but also realistic enough that they can hit it in the acquisition process? How does the selection for who receives the book look? Who decides this? What is the fundamental aim in the distribution of the book to many parties at the same time? What does Dave know now about the world of PE that he wishes he had known at the beginning? IOI's is the next step, what are they? How do they set up the process from there? How do management meetings with potential PE acquiring firms compare to founders meeting VCs in the early days? How many meetings is normal to have in this process? How long do they last? What does Dave believe is crucial to achieve in these in person meetings? How much of a role does price play in selecting the ultimate acquiror? How much of a role does their brand and reputation play? 60 Second SaaStr: What does Dave know about the process that he wishes he had known at the beginning? The biggest misconception about the world of PE and acquisitions? Burn rate is a function of the personality of the CEO? Agree or disagree? Why? 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

SaaStr 240: SaaStr 240: Brex Founder and CEO Henrique Dubugras on Lessons From a Second-Time Founder: How Brex Went From 0 - $1B in Under 2 Years
Brex Co-Founder and CEO Henrique Dubugras will talk about what he's learned building the fastest-growing B2B company. Henrique started his first company at 16 and has now built two successful companies from nothing. Learn what he did differently the second time around and the specific decisions he made to drive growth among B2B companies with Brex. Missed the session? Here's what Henrique talks about: How Brex grew from a few basic functionalities to a corporation Growing from $0 to $2B in ARR in less than two years. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Henrique Dubugras

SaaStr 239: How To Raise Prices and Still Leave Money On The Table, How To Analyse The Pros and Cons of Monthly vs Annual Deals & The Leading Indicators That Your Sales Machine Is Working with Amit Bendov, Founder & CEO @ Gong.io
Amit Bendov is the Founder and CEO @ Gong.io, the startup that provides you with powerful visibility into your customer conversations with conversation intelligence. To date, Amit has raised $68m in funding for Gong from the likes of Norwest, Battery Ventures, Cisco Investments and Wing Venture Capital just to name a few. As for Amit, prior to founding Gong, Amit was the CEO @ SiSense BI software that enables business users to connect to multiple databases of any size. Before that Amit was the CMO @ Panaya, helping companies that use SAP or Oracle to reduce 80% of their ERP upgrade. Finally before that Amit was the Founder & CEO @ SparkThis, an outsourced marketing and sales service for cloud companies. In Today's Episode We Discuss: How Amit made his way into the world of SaaS and came to found Gong, the leader in conversational intelligence driving deal conversion and rep success? How does Amit approach the process of idea validation? What can founders do to make sure their idea is a hit before they start work on it? How many customer conversations should they have? What questions are crucial to ask? What are the answers they want to hear? What is enough proof that there is a ready and willing customer base for this idea? With many products starting as free, how does Amit think about when is the right time to start charging for your product? What does Amit think about the differing variable price mechanisms that one can choose? How does one have a variable pricing mechanism without disincentivizing users to use the product? What does Amit advise founders should charge in the early days? Should they leave money on the table? How does Amit think about monthly/vs annual deals? What are the core benefits and drawbacks of each? How important is it that multi-year deals are paid upfront? What must you account for with regards to multi-year deals? How do you know when you have the right pricing mechanism in place from the sales cycles of the reps? 60 Second SaaStr: What does Amit know now that he wishes he had known in the beginning? The hardest role to hire for today? The hardest element of Amit's role as CEO of Gong? SDR is the most important function in the sales org, agree or not and why? 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 Amit Bendov

SaaStr 238: Salesforce Mobile EVP Leyla Seka and Sr. Director of Global Equality Programs Molly Ford on How They Did It: Gender Equality, Equal Pay and Racial Equality
Join Molly Ford, Salesforce Global Equality Programs Senior Director, and Leyla Seka, Salesforce VP of Mobile for actionable advice they have applied on their own journey. Here are their lessons learned on driving change in gender equality, equal pay and racial equality within Salesforce. Missed the session? Here's what Molly and Leyla talk about: Building a community of allies and allyship How to drive equality What you can be doing as an employee to help drive the culture you want If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Molly Ford Leyla Seka

SaaStr 237: Rippling's Parker Conrad on How To Clear The Bar of "Not Another System" Thinking in SaaS, Why Your Engineers Should Be Doing Support For As Long As Possible & Why Remote Teams Is The Worst Way To Build A Company, Apart From Every Other Way
Parker Conrad is the Founder & CEO @ Rippling, the startup that gives you back your time from payroll to employee computers, Rippling makes it unbelievably easy to manage your company's HR and IT - in one system. To date Parker has raised over $59m in funding from some of the best in the business including Mamoon @ Kleiner Perkins, Garry Tan @ Initialized, Justin Kan, SV Angel and Y Combinator, just to name a few. As for Parker, prior to founding Rippling, he was the Founder & CEO @ Zenefits, the startup he built from $0 to $60m in ARR in just 3 years. Before that he co-founded Sigfig where he grew assets on the platform to over $35Bn across 500k users. In Today's Episode We Discuss: How Parker made his way into the world of startups and SaaS, came to found Zenefits and what was that a-ha moment for the founding of his most recent company, Rippling? What does Parker do with regards to operational scaling that is unconventional but works? Why does Parker believe it is fundamentally better to wait for as long as possible before hiring customer support? Why should engineers also be doing customer support? Why should your engineers be heavily involved in the customer support hiring process? What are the benefits of this? How can one prevent their customer support team from being a wall of protection for the product and eng team? How can you ensure seamless collaboration and communication flow between product and customer support? Stripe last week recently announced their 5th office would be… "remote", so how does Parker feel about the building of remote teams? What are the most important things when establishing your first remote team? What do you look for in those hires? What can be done to ensure a greater feeling of community and closeness despite the distance? What have been some of the biggest challenges for Parker in building out the remote team? Parker has been a CEO with 3 different companies now and so how has he seen his style and approach change over the years? What has Parker found the hardest to get good at? When advising founders on fundraising, what advice does he give? How can founders know when is the right time to raise? How should they look to build relationships with investors between raises? 60 Second SaaStr: What does Parker know now that he wishes he had known in the beginning? What one thing would Parker like to change about tech and Silicon Valley? Biggest mentor and what has Parker learned from them? 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 Parker Conrad

SaaStr 236: Logikcull CEO Andy Wilson on $0 to $10M in 19 Months: The How, When & Why + 10 Mistakes Along the Way
Join Logikcull's CEO and Co-Founder Andy Wilson as he takes you through the mistakes made going from $0 to $10M in 19 months. Missed the session? Here's what Andy talks about: Selling the way your customers want to buy. What you need to know about hiring, firing, advisors, and culture Why SaaS is your business model, not your mission. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Andy Wilson

SaaStr 235: Scaling To 3,000+ Customers Without A Single Sales Rep, The Most Important Trait To Look For In Your First Sales Hire & How To Make Your Customers Your Best Investors with Andrew Filev, Founder and CEO @ Wrike
Andrew Filev is the Founder & CEO @ Wrike, the cloud based collaboration and project management software that scales across teams in any business. In Dec 2008, Vista Equity Partners acquired a majority stake in Wrike for a deal reportedly valuing the company at $800m. Before this transaction, Andrew had raised over $45m in funding from the likes of Rory @ Scale and Bain Capital Ventures just to name a few. As for Andrew, he started his first software development company at the age of 18 and has been running Wrike for the last 13 years alongside advisory roles with both Ditto and Appulate. In Today's Episode We Discuss: How Andrew made his way into the world of SaaS from his starting his first software business at the age of just 18 and how that led to his founding of Wrike? How does Andrew advise founders on the question of whether to start in enterprise or SMB? What are the benefits of starting in SMB? How does the founder know when is the right time to start moving to enterprise? What are those leading indicators? How does the product and what you invest in proactively need to change as you move into enterprise? Andrew has been the CEO for the last 13 years, how has the role of CEO changed over those years? What has been the most challenging phase? If the CEO is the guardian of the culture, what does a great guardian look like? What 3 elements does Andrew focus almost exclusively on today within his role as CEO? What does Andrew think are the major breaking points in the scaling of companies? Where does culture begin to breakdown? What can be done to mitigate this? How does Andrew think about using employee satisfaction surveys internally? How can one accurately determine the strength of your manager set? Andrew's 60 Second SaaStr: What does Andrew know now that he wishes he had known at the beginning? No man's land in SaaS pricing, does it exist? Sales rep productivity, what is good to Andrew? 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 Andrew Filev

SaaStr 234: PagerDuty CEO Jennifer Tejada and Duo Security CEO Dug Song on The Top Things No One Really Tells You About Scaling
Duo Security Co-Founder and CEO Dug Song and PagerDuty CEO Jennifer Tejada discuss building, enabling, and leading great teams through 10K+ customers, $100M+ ARR, $1B+ valuation and beyond - all while earning 4.5+ Glassdoor company ratings and 98%+ CEO approvals from 500+ total employees! Duo Security is a cloud-based provider of unified access security and multifactor authentication was acquired by Cisco for $2.35 billion in October 2018. PagerDuty is a leading digital operations management platform for organizations announced new financing in September 2018 at a $1.3 billion valuation. Missed the session? Here's what Jennifer and Dug talk about: When is the right time to raise money? How can you better manage the board? Should you worry about competitors? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Jennifer Tejada Dug Song

SaaStr 233: G2 Founder & CEO, Godard Abel on How To Set Ambitious But Achievable Sales Rep Quotas & The Lessons From 2 Successful Exits on The Breaking Points In The Scaling of SaaS Orgs
Godard Abel is the Founder & CEO @ G2, the company helping millions of business make better product buying decisions every month. To date, Godard has raised over $100m in funding with G2 from the likes of Accel, IVP, High Alpha, Pritzker Group and Chicago Ventures just to name a few. As for Godard, he founded his first business, BigMachines, in 2000, a business he scaled to $50m in revenue and over 300 people up until it's acquisition to Oracle 11 years later for $400m. Godard then became CEO @ Steelbrick where he took them from 5 to 200 employees and increased bookings by 37x in 7 quarters. Steelbrick was ultimately acquired by Salesforce where he spent a year and a half before starting G2. In Today's Episode We Discuss: How did Godard make his way into the world of SaaS over 20 years ago? What was the a-ha moment for the founding of G2 for Godard? Having been a Founder through the bust of 2000, how did seeing that macro environment impact his operating mentality today? What did it teach him about capital efficiency and investing ahead of time? Taking the team from 70 to 20, what were his lessons on the right way to let someone go? Where do many people get it wrong today? Why does Godard advocate for working with people that you have worked with before? How can you find the zone of genius for the people that you work with? How does Godard set a culture of ambition and determination around goals but also prevent dejection if the goals are not hit? How often should rep quota be hit? Why is that the right ratio? Where does Godard believe that things really start to break down in the scaling of an organisation? What can you do to get ahead of those moments and minimise their impact? How many direct reports does Godard believe is the optimal and then the maximum for a manager to have? How have his thoughts on this changed over time? Godard's 60 Second SaaStr: What would Godard like to change in the world of SaaS today? What does Godard know now that he wishes he had known at the beginning? If an investor can provide one value, what would it be and why? 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 Godard Abel

SaaStr 232: Fmr. Host Analytics CEO Dave Kellogg on The Top 5 Questions Every CEO Wrestles With
Dave Kellogg is CEO of Host Analytics and prolific blogger. Join him as he takes you through lessons learned from Host Analytics on the top questions every SaaS CEO wrestles with. Dave was CEO of Host Analytics from 2012 to 2018 where he quintupled ARR while halving customer acquisition costs in a highly competitive market, ultimately selling the company in a private equity transaction. Missed the session? Here's what Dave talks about: When is the right time to raise money? How can you better manage the board? Should you worry about competitors? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Dave Kellogg

SaaStr 231: Why SQLs and MQLs Are Redundant, Why You Have To Eliminate Hand Offs Between Go-To-Market Teams & Why One North Star For The Whole Company Can Be Damaging with Jason Reichl, Founder & CEO @ GoNimbly
Jason Reichl is the Founder & CEO @ GoNimbly, the first SaaS consultancy to focus on revenue operations. Currently growing 100% year over year, working with companies to un-silo their operations and create one strategic revenue ops team to support their Go To Market strategy. In the past, Go Nimbly has helped companies like Zendesk, Twilio, PagerDuty and Coursera to achieve alignment and increase revenue by 26%. As for Jason, prior to co-founding GoNimbly, he was Director of Product Management @ TradeShift and before that was VP of Product Management @ Lanetix. In Today's Episode We Discuss: How Jason made his way from Director of Product Management at Tradeshift to changing the way we think about scaling revenue operations with GoNimbly? Why does Jason believe that we have to remote handoffs between go to market teams? Why are they so damaging? How does Jason believe SaaS companies can use a "swarming" effect to create the best buyer experience for their customer? What does this involve? How does this change the type of metrics that we track? Why does Jason believe that your North Star has to be revenue in the go to market teams? Why does Jason also believe that it is damaging to have the same North Star across the entire company? How should North Star's be segregated between GTM teams and biz ops teams? What are the mistakes many companies make when setting their internal North Stars? Why does Jason believe that alignment is a dirty word? Why is alignment actually a negative for the customer experience? What does Jason view as vanity metrics? If one has vanity metrics in place, what does Jason recommend as to keeping them or phasing them out? 60 Second SaaStr: What does Jason know now that he wishes he had known in the beginning? How does Jason feel about multi-year deals? How does Jason feel about channel/partner sellers? 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

SaaStr 230: SaaStr 230: AWS VP Sandy Carter on Customer Success at Scale
We live in a Shark Tank world: competition is fierce, talent is better than ever, and we're all striving to come out on top. CEOs everywhere are seeking to innovate, but 81% say their teams are not equipped to meet the challenges needed to compete in today's marketplace. Innovation is about empathy with your customers. It's all about customer obsession! In this session, Sandy Carter, AWS Vice President will hone your superpower - not of customer focus, or customer driven, but customer obsessed. Missed the session? Here's what Sandy talks about: How to start with success and think backwards Think about how to present a feature or product before you start building. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Sandy Carter

SaaStr 229: The 2 Most Important Numbers For Your SaaS Business, Why You Should Not Have VPs Until $5m in Revenue & How To Manage Top Of Funnel Efficiently But Aggressively with Manny Medina, Founder & CEO @ Outreach
Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft's emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic. In Today's Episode We Discuss: How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft? How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel? Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR's 99% of the time not able to carry leads to completion? How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive? Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this? Why does Manny believe that you should not have a VP before $5m? 60 Second SaaStr: What does Manny know now that he wishes he had known in the beginning? What does the future of sales prospecting look like to Manny? What would Manny like to change about 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 Manny Medina

SaaStr 228: Twilio CEO Jeff Lawson and Glitch CEO Anil Dash on the Secrets to Building a Billion in ARR and Being an Ethical leader.
Join Glitch CEO Anil Dash and Twilio CEO Jeff Lawson for a discussion about the ethical implications of technology in today's society. Jeff and Anil discuss how social media and AI are changing the way we think about the impact of technology on society as well as the responsibility of tech leaders for this impact. Missed the session? Here's what Jeff talks about: How taking no stance as a business leader today, is taking a stance How to set concrete numbers for diversity goals The impact of corporate culture on employee happiness If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Jeff Lawson Anil Dash

SaaStr 227: Why Deal Size In The Early Days Does Not Matter, Why TAM In The Traditional Sense Barely Matters & Why You Have To Invest In Customer Success Before You Think You Need It with Alexandr Wang, Founder & CEO @ Scale
Alexandr Wang is the Founder & CEO @ Scale, the startup providing high quality training and validation data for AI applications. To date, Alexandr has raised over $23m with Scale from some of the best in the business including Index, Accel, Y Combinator, Dropbox's Drew Houston, Justin Kan, Thumbtack's Jonathan Swanson and more. Prior to founding Scale, Alexandr was a Tech Lead at Quora, directly responsible for all speed projects and before that a software engineer at Addepar responsible for building and maintaining financial models. In Today's Episode We Discuss: How did Alex make his way into the world of SaaS and come to found Scale? What were some of his biggest takeaways from seeing the first hand scaling of Quora and Addepar? Why does Alex take the contrarian view that "TAM in the traditional sense barely matter"? What two characteristics of the market should founders really look to examine? How does Alex approach the element of market sizing? Does he prefer top down or bottoms up and why? Why does Alex believe that you must invest in customer success before you think you need it? What were the benefits for Alex of investing early in customer success? Why does CS over sales ultimately drive the growth of your company? How does one know when is the right time to hire their first in customer success? What is the ideal profile of this candidate? How does Alex think about the integration of customer success and product teams? Why is it crucial from the product perspective that founders pick their first customers well? How can your customers drive your product decisions? How can one ensure to be customer informed and not customer driven? Why does Alex believe that in the early days it is not important to focus on the size of the deals you are signing? What should founders be focusing on with these early customers instead? When is the right time to flip the switch and opt for value extraction as a more primary objective? How does Alex respond to the fact that VCs often look at these first customer deals as an indication of the size of the pain point you are solving? 60 Second SaaStr: What does Alex know now that he wishes he had known in the beginning? What does Alex believe is the hardest role to hire for today? Who does Alex think is crushing it 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 Alexandr Wang

SaaStr 226: Survey Monkey CMO Leela Srinivasan on 7 Tips For Using Customer Feedback To Build Rabid Fans and Make More Money
Leela Srinivasan is the CMO of SurveyMonkey. Join her as she takes you through her seven tips for using customer feedback and building rabid fans. Consistently ramping your ARR is a whole lot harder if your customers don't stick around. In an age where earning customer loyalty and trust is harder than ever, the road to lifetime value is paved with customer feedback. If you take the time to listen, understand and act on what your customers are thinking and feeling, you'll create an army of advocates and drive topline revenue growth for good measure. Missed the session? Here's what Leela talks about: How to create an army of advocates How to drive topline revenue growth Real world examples from businesses that are listening and acting on customer feedback every day. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Leela Srinivasan

SaaStr 225: Biggest Lessons From The AppDynamics and GlassDoor Scaling, 3 Elements Marketing Team Comp Has To Be Tied To & How To Create True Alignment Between Marketing and Sales with Stephen Burton, VP of Smarketing at Harness.io
Stephen Burton is VP of Smarketing at Harness, the industry's first continuous delivery as a service platform. To date, Harness has raised $20m in funding from the wonderful Matt Murphy @ Menlo Ventures and BIG Labs. Prior to Harness, Stephen was VP of Marketing at Glassdoor, managing a team of 52 in product marketing, helping grow B2B revenue from $19m to $90m in just 2 years, leading to their $1.2Bn acquisition. Before Glassdoor, Stephen was VP of Product Marketing at AppDynamics where he helped grow B2B revenue from $0 to $100m in a staggering 3 year period, resulting in their $3.9Bn acquisition by Cisco. In Today's Episode We Discuss: How Steve made his way into the world of SaaS and came to be VP of marketing at 2 of the larger B2B exits of the last decade in AppDynamics and Glassdoor? What were Steve's biggest takeaways from seeing the hyper-scaling at AppDynamics? Steve has previously said, "sales and marketing must be one team". Why does he believe this is so important? What can leaders do to turn this into reality? What works? Where has Steve seen many make mistakes? Where does Steve find common points of tension between sales and marketing? WHat are the 3 elements that marketing comp should be tied and aligned to? What does Steve mean when he says, "marketers need to embrace the developer first mindset"? What does this mean for the processes used by marketing teams? Speaking of developer-first, how can startups compete in a war for talent against FB and Google? How can they integrate autonomy into their hiring process as a core advantage? For Steve, what does devops really mean? What does Steve believe is the right culture for devops teams? Does it differ from traditional dev teams? How can a CEO determine when is the right time to fundamentally invest in devops? What are the required steps to make devops teams as successful as possible? 60 Second SaaStr: What does Steve know now that she wishes she had known at the beginning? When is the right time to pour fuel on the company fire? The playbook? Is there one? Dangers? Copyability? What would Steve most like to change in the world of SaaS? 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 Stephen Burton

SaaStr 224: Zendesk CEO Mikkel Svane on Lessons from Zendesk Beyond $1B ARR
Mikkel Svane is the CEO of Zendesk and author of "Startupland". Join him as he takes you through his lessons taking Zendesk beyond a billion in ARR. Mikkel founded Zendesk in Copenhagen, Denmark in 2007 before moving the company to San Francisco in 2009. Missed the session? Here's what Mikkel talks about: The future of the cloud The rise of the public cloud and re-platforming of the tech stack How business applications are sold and delivered leveraging 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 SaaStr Mikkel Svane

SaaStr 223: Intercom COO Karen Peacock on Scaling from $1MM to $500MM ARR: 5 Strategies to Drive Your Next Wave of Growth with Intercom
Karen Peacock is COO of Intercom, one of the fastest growing SaaS businesses of all time. She has led businesses of all sizes through massive growth. Listen to her top 5 lessons learned building and scaling SaaS businesses from $1M to $500M in ARR including expanding to serve upmarket customers, moving from product to platform, and hiring to drive breakthrough customer experiences and business growth. Missed the session? Here's what Karen talks about: How should you expand your market? How to move upmarket The steps to building a product and creating an end to end experience If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Karen Peacock

SaaStr 222: Flexport CRO Ben Braverman on Why It Is Total Horseshit That The Best Sellers Don't Make Good Managers, Why Specialisation Does Not Lead To The Best Customer Experience & Scaling Revenue From $18k MRR in 2014 to a $472m Year In 2018
Ben Braverman is the CRO @ Flexport, one of the world's fastest growing startups combining technology, infrastructure and expertise, to build the operating system for global trade. To date they have $1.35Bn in funding from some of the biggest and best in the business including Softbank's Vision Fund, Founders Fund, DST, Susa Ventures and Y Combinator, just to name a few. As for Ben, he spearheads global sales and go to market teams. Prior to Flexport, Ben helped drive two high-growth companies to successful acquisitions: URX (acquired by Pinterest) and Heyzap (acquired by Fyber). In Today's Episode We Discuss: How Ben made his way into the world of startups and came to be CRO of one of the world's fastest growing startups in the form of Flexport? Why does Ben fundamentally disagree with the specialisation of roles within SaaS companies? What does he believes this does to the customer journey and relationship? How should one thing about role segmentation and allocation of accounts with this in mind? Where does Ben see many people going wrong here? Why does Ben believe it is "total horseshit to say the best sellers don't make the best managers"? What must founders try and figure out before hiring their sales leader? What are the leading indicators that suggest a sales rep has the ability to be a sales manager? How does Ben determine between a stretch VP and a stretch too far? What does Ben mean when he says, "there are 3 distinct buckets of sales management"? What are they and what is their relationship between one another? Why does Ben believe one does not need sales management in the early days? What is the best way to train reps and determine payback period fast? Why does Ben believe sales ops is the most underappreciated role in the valley? 60 Second SaaStr: What does Ben know now that he wishes she had known at the beginning? What is the optimal relationship between CRO and CEO? What does Ben believe in SaaS that most around his disbelieve? 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 Ben Braverman

SaaStr 221: HBS Sr. Lecturer and Former Hubspot CRO Mark Roberge on His Step by Step Guide to Revenue Growth
Mark Roberge is a senior lecturer with Harvard Business School, former CRO of Hubspot and author of the bestseller "The Sales Acceleration Formula". Join him as he takes you through his step by step guide to revenue growth. Missed the session? Here's what Mark talks about: An in-depth guide to driving revenue growth by company stage When to scale and how fast Product market fit, go-to market fit during the experiment stages If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Mark Roberge

SaaStr 220: Salesforce Mobile's EVP, Leyla Seka on Her Biggest Lessons Seeing Salesforce Scale From $500m to $16Bn, What Needs To Be In Place For Hyper-Scale & How Leaders Build Trust In Their Organisation
Leyla Seka is the executive vice president of the Salesforce Mobile platform experience. Over Leyla's incredible 11 year journey with Salesforce she has seen the team scale from 1,800 to over 40,000 and revenue scale from $500m to over $16Bn. In Leyla's role today, she leads the charge on extending the power of Salesforce with a full portfolio of mobile apps, and is responsible for driving product, go-to-market and other key programs around Salesforce's mobile offerings. Prior to her current role, Leyla was executive vice president of the Salesforce AppExchange, where she launched a refreshed AppExchange storefront, a new partner program, and built an entire AppExchange-focused team, resulting in more than 4,000 solutions, installed nearly 6 million times. Beyond her day-to-day role, Leyla is also the executive sponsor of BOLDforce, Salesforce's organization for expanding and empowering the black community at Salesforce. In Today's Episode We Discuss: How Leyla made her way into the world of SaaS with Salesforce when it had 1,800 people and $500m in revenue? What were Leyla's biggest learnings on people and business model through seeing the first hand hyper-scaling of Salesforce from $500m to $16Bn? How did Leyla evolve and scale as a leader herself in those 11 years? What advice does Leyla give to young people considering whether to found a startup, join a startup or join a hyper-growth company? Where do things start to break in the scaling of SaaS companies? What needs to be put in place to prepare for hyper-scale? What are the commonalities of where many founders go wrong in the scaling process? What does Leyla mean when she says, "growing up in product, you have to lead through influence"? How does Leyla think this influence can be created and maintained? How does Leyla think about the balance between effective influence and excessive influence? Why does Leyla believe that, "you can teach skills but you cannot teach empathy"? What have been her learnings from scaling teams when it comes to hiring and detecting candidates with true empathy? What can one do to nurture that empathy in the culture of the company? 60 Second SaaStr: What does Leyla know now that she wishes she had known at the beginning? What is the hardest element of Leyla's role at Salesforce today? What does Leyla believe in SaaS that most around her disbelieve? 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 Leyla Seka

SaaStr 219: Atlassian President Jay Simons on How to Scale an Open Culture
At Atlassian, openness is core to everything the company does: employees can access most information on Confluence; "open company, no bullshit" is one of the company's five values. But it can be risky. Atlassians knew the company was going public four months before it filed. The entire company was told about Atlassian selling its chat products Stride and Hipchat to its largest competitor in the space, Slack, four days before the news went out. Some would say that that level of openness is unnecessary, but Atlassian believes that trust and honesty are essential to maintaining the culture its worked so hard to build. Missed the session? Here's what Jay talks about: What is driving growth in the cloud? Does collaboration help founders drive growth forward? How do you scale an open 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 SaaStr

SaaStr 218: Twilio Founder, Jeff Lawson & SendGrid CEO, Sameer Dholakia on Why Developer First Is A Maturation In The Supply Chain Of Software & Why With Software Innovation Costs Being Lower Than Ever, Operators Must Maximise The Number of "At Bat" Oppor
Jeff Lawson is the Founder & CEO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Jeff, prior to founding Twilio, Jeff was the Founder & CTO @ Nine Star Inc and enjoyed a spell at Amazon as a Technical Product Manager. Sameer Dholakia is the CEO @ SendGrid, the category leader in email delivery, reaching half of the world's digital users every 3 months. Last year Twilio acquired SendGrid bringing email into one seamless customer engagement platform. As for Sameer, prior to joining SendGrid, he spent 4 years at Citrix, where he drove the company's product strategy for cloud infrastructure and server virtualization. Sameer joined the company in 2010, when Citrix acquired VMLogix, where he served as CEO and doubled revenues during each year of his tenure. Before that, he worked for 12 years at Trilogy, where he held key leadership roles helping the company grow from a start-up to a $300 million business. In Today's Episode We Discuss: How Jeff came to found Twilio and what was that a-ha moment for him? How did Sameer enter the world of SaaS and come to be CEO @ SendGrid? How did Jeff and Sameer assess the culture fit between the 2 companies when deciding whether or not to join forces? How did they formulate and approach creating a new set of values with the 2 companies coming together? How do they distinguish between culture and values? How can leaders both be authoritative and vulnerable simultaneously? What does Jeff mean when he says, "the developer first approach is a maturation of the supply chain of software"? How has Jeff seen his original thesis for "developer first" evolve and change with time? What does truly special customer experience look like in the developer first model? In terms of product strategy, how do Jeff and Sameer approach when is the right time to release a second product? What does Jeff mean when he says, "you have to maximise the number of at bat opportunities you have"? Why does Sameer think that SendGrid waited too long to release additional product lines? What were his core learnings from that? How do Jeff and Sameer think about what what truly special leadership looks like today? How do they approach speaking so that people will remember? What are some of their biggest tips to aspiring entrepreneurs with regards to that and team empowerment? Why do both Jeff and Sameer believe that so much of the management wisdom today is outdated? 60 Second SaaStr: What do Jeff and Sameer know now that they wish they had known at the beginning? The book they have gifted most often and why? What does it take to truly be a great board member? What do the next 5 years look like for Twilio? How big could it get? 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 Jeff Lawson Sameer Dholakia