In Depth

Today’s episode is with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. In addition to Pilot, Waseem co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014. In today’s conversation, we pay particular attention to the earliest days of Pilot. Waseem takes us behind the scenes of the ideation stage for what would eventually become Pilot, and how the founding team gained conviction to actually start building. He also explains why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers. Next, we talk about building out Pilot’s ICP, and how he started getting the product into the hands of paying customers. He’s got some great tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. Finally, he looks out to the horizon and shares how he prioritizes which offerings to add to Pilot’s product suite. Today’s conversation is an absolute must-listen for founders and folks that have goals to one day become founders. Product pros also won’t want to miss learning from Waseem’s playbook honed over the course of building three companies. You can follow Waseem on Twitter at @waseem. For more startup real talk from Waseem, you can subscribe to his Substack: https://waseem.substack.com/ You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO. In today’s conversation, Shannon shares the comms and leadership lessons she’s picked up along the way. In addition to sharing her broader philosophy around the role of comms and her thoughts on why it’s one of the more underappreciated functions, Shannon gets into the tactical weeds on everything from killing stories and creating new categories, to her frameworks for building relationships with reporters. There’s plenty of career advice as well, from how she approaches selecting companies to work for, to what the transition from head of comms to CMO was like, to what she’s learned from mentors and bosses like Jeff Weiner. Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/ You can follow Shannon on Twitter at @sstubo. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson

Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma. With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow. We kick this conversation off with Colleen’s explanation of why she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly. Colleen also shares why she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. She gives a detailed look at how she approaches many of those systems, from how rewards and recognition were incredibly different at Zynga and Credit Karma, to why career growth isn’t just about a promotion. Colleen also shares her take on whether we should double down on strengths or focus on correcting weaknesses when it comes to performance. Given her experience as a 4X Chief People Officer, today’s episode is a must-listen for first-time founders and early people leaders looking for a roadmap as their startups scale. You can follow Colleen on Twitter at @Chiefpplofficer, and you can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company. Bowery’s mission to democratize access to fresh, locally grown food. It’s no doubt an extremely complex problem, so it might surprise you that its founder, Irving, didn’t have any background in agriculture before starting Bowery. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio. But looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In today’s conversation, he walks us through his multi-pronged approach to developing the idea for what would become Bowery, which includes paying just as much attention to the doubters as to the folks who believed in the vision. Next we switch gears and talk about assembling Bowery’s small-but-mighty team of five, which Irving kept deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. Whether you’re a founder yourself or have long-term career goals to make the leap, today’s episode is packed with equal parts inspiration and tactical takeaways. You can follow Irving on Twitter at @ifain You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/

Today’s episode is with Kelly Watkins, CEO of Abstract, a platform for structure and transparency in the design process. In joining Abstract last year, Kelly is one of very few folks from a marketing background to take on the CEO seat. She brings a wealth of experience leading incredibly high-performing marketing teams for Slack, Github, and Bugsnag. In today’s conversation, we start by reflecting on her first year as CEO. She shares her alternative to yearly planning, borrowing from famed military strategist John Boyd. Kelly also walks us through Abstract’s most recent product launch, and how it clearly crystallized her leadership point of view to constantly optimize for trade-offs, rather than clear-cut right and wrong. Next we switch gears to talk about some of the lessons from her storied marketing career. She unpacks her jobs-to-be-done approach for crafting a product story when there’s loads of competition. She also takes us behind the scenes in developing Slack’s “where work happens” tagline, and crossing the chasm from a passionate early adopter customer base to the ubiquitous product it is today. Today’s conversation is a must-listen for marketing folks, who will surely appreciate the peek behind the curtain. But all sorts of leaders with goals to more effectively collaborate with the org will come away with a deeper understanding of marketing’s art and science. You can follow Kelly on Twitter at @_kcwatkins You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson To learn more about Kelly’s advice on hiring your first head of marketing, read her Medium article: https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73 For more on the jobs-to-be-done framework, check out this article on the Review: https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework

Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital. Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona. From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world. Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers. You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/ You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Eric Berg, CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft. In today’s conversation, he opens up his executive playbook as he weaves together each of those experiences — and covers a lot of ground along the way. He starts by talking about early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground. He also dives into the often-maligned “messy middle,” particularly when it comes to moving upmarket and developing a pricing and packaging model that, when done well, takes a company to new heights. We then switch gears and discuss more broadly about team building and company building — particularly the cultural lessons that stick with him from his tenure at each stop in his career. His biggest learnings include hiring folks up and down the org chart with the right ego to talent ratio and the tactical steps he takes to implement a “disagree and commit’ value so it’s not just a long-forgotten team motto. Finally, we touch on the biggest surprises as he approaches one year of sitting in the CEO seat. Today’s conversation is a must-listen particularly for product folks, as well as others who want to more deeply understand the trade-offs that nearly every great company faces on the path to scale. You can follow Eric on Twitter at @ericberg. You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s conversation is with Elliot Shmukler, founder and CEO of Anomalo, which is a platform that validates and documents all of your data. Elliot founded Anomalo after a storied career as a product and growth leader at some of the most interesting companies around. Most recently, he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. His jam-packed resume also includes stops at Wealthfront as the VP of Product and Growth and as a product leader at LinkedIn and eBay. In today’s conversation, we pull on threads from his newest role as a founder of a startup going from zero to one, including his biggest surprises in the transition from executive to CEO. We also touch on how he prioritizes his time at a startup still in the earliest stages of company-building, and how to avoid wasting your time on prospects that are not all that interested in actually buying. Next, we turn our attention to his history of picking incredible companies to work for — from the questions he asks as a candidate to the decision-making frameworks he borrows from his poker playing. Finally, we end with his biggest lessons from the best CEOs he’s worked with, including habits that set the best communicators apart from the pack, and the tactics for keeping office politics at bay so the best ideas are able to surface. All sorts of folks will find something worthwhile in today’s conversation — whether you’re a founder still in the early phases of customer discovery, an executive with long-term goals to start your own company, or someone earlier in their career that wants to get better at spotting the next unicorn. You can follow Elliot on Twitter at @eshmu. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

Today’s episode is with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce. In today’s conversation, Kate shares a wealth of advice for building out product-led growth and self-serve motions. She shares tons of nuances around going up market, competing with sales and product planning, offering up tactical advice that any founder, product or go-to-market leader can learn from. Kate also gives us a detailed look at how they approach product prioritization at Notion, including their system of 700 tags and examples of tradeoffs they’ve had to navigate. We also get into pricing and packaging, from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based. We also chat about how to handle a wide range of use cases, as well as the “front door” customer experience her team is trying to build. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate shares some counterintuitive thoughts here. Finally, we wrap up by talking about her approach to leading teams, including why she hires for curiosity, how she tries to teach her team to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style. Kate isn’t on Twitter, but you can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor. Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In this conversation, Mark shares his approach to the CPO role and his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning. He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations. Today’s conversation is a must-listen for both founders and early-stage people leaders trying to thoughtfully scale this function, as well as for current and aspiring managers hoping to hone their leadership and development chops. You can follow Mark on Twitter at @freintime, and you can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business — and it’s his first and only job after graduating college. In today’s conversation, Marco dives into the company milestones that require a return to first principles versus pulling from a tested playbook, and the mental models he leans on when parsing through the mountains of advice he gets as a first-time founder and CEO. He connects these dots to how he manages Thumbtack’s board so those quarterly meetings are a critical resource, not just a time suck — and why he shares the board deck with the entire company. He also candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to make sure the folks that remained still had confidence in the company and his leadership moving forward. Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities. Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats. To learn more about how Marco and Thumbtack approach executive hiring, check out the article on First Round Review: https://review.firstround.com/assembling-an-executive-leadership-team-is-daunting-let-thumbtacks-ceo-help You can follow Marco on Twitter at @mlz. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Tido Carriero, the Chief Product Officer at Segment, a customer data platform which was recently acquired by Twilio. Before that, he built out the engineering teams that worked on the core product and the initial business product at Dropbox. Tido started out his career in 2008 as an early member of the Facebook ads engineering team, and went on to become an eng manager on the Pages team, a transition from IC to leadership that he talks about in this episode. In today’s conversation, we dig into his career lessons from building engineering orgs and launching new product lines at several different top tech companies. From the pros and cons of single threaded leadership to his black box analogy for assessing a team’s performance, there are tons of tactics in here on how leaders can think differently about org design, planning and execution. He also shares several gems of advice for new engineering managers and new managers-of-managers. We also chat about the path to product/market fit, especially for multi-product strategies. Tido shares his advice for going from zero to one in a new product, including the simple milestone his teams have to hit before he’ll greenlight a new project, why he prefers iterative approaches over “big bang launches,” and his thoughts on why Dropbox struggled here. (Tido shares more of his thoughts on finding product/market fit in the context of multi-product strategies here in this blog post: https://segment.com/blog/finding-product-market-fit-again/) Tido isn’t on Twitter, but you can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Russ Laraway. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work. In 2018, he joined Qualtrics as the Chief People Officer, a position he stepped away from this past January to focus on helping the company’s customers think differently about employee experience. Russ also has a book on this topic coming out soon — and we can’t wait to read it. In today’s conversation, we dig into how startups can drive employee engagement and develop high-quality managers. Russ reaches across his career to serve up some incredible wisdom, whether you’re a first-time manager or a seasoned leader. He starts by sharing his direction-coaching-career framework, along with his thoughts on where companies go wrong on OKRs. He also gets really tactical, sharing the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employment engagement surveys. Finally, Russ gives us 13 recommendations for leadership reads for managers. For more of his thinking on talent development, we recommend reading his article from a few years ago in the First Round Review: https://review.firstround.com/three-powerful-conversations-managers-must-have-to-develop-their-people You can follow Russ on Twitter at @ral1 and you can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016. In today’s conversation, Jeff looks back on some of the peaks and valleys in Twilio’s journey, and his own evolution as the CEO. He dives into some of the initial wins, like going against conventional wisdom to launch a second product in the early days of Twilio. He’s equally game to unpack some of the mistakes along Twilio’s path — like when one of their biggest customers, Uber, significantly scaled back their investment in Twilio’s products. Jeff also opens up the pages from the playbook he pulled from his time at Amazon, chiefly Twilio’s “write it down” company value, and makes his case for why PowerPoint is a terrible decision-making tool. He takes us inside Twilio’s C-suite, including why they do post-mortems when things go right — not just when they go wrong. He also sketches out his “aha” moment that his executive team needed to argue more. Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats. Jeff’s new book is titled “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292 To learn more about how Twilio approaches company values, check out this article on First Round Review: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have You can follow Jeff on Twitter at @jeffiel. You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Leah Sutton, SVP of Global HR at Elastic. Leah’s been in the HR space for over 20 years, and now leads everything from HR operations to recruiting and employee engagement for Elastic’s fully-distributed employee base, which includes over 2,000 spread across 40 countries and 48 states. In today’s conversation, we look closely under the hood of what Leah calls Elastic’s “distributed by design” company DNA. She walks us through her learnings tackling challenges companies now are paying close attention to — including how to interview for leaders that can manage well remotely — and even dives into the nitty-gritty details about payroll and compensation across regions. She also outlines a few of the tactics Elastic has leaned on to smooth over some of the language and cultural barriers that often trip up global leadership teams. Leah zooms out even further to discuss Elastic’s source code, which she describes as not so much a traditional list of values but more the things that make Elastic, Elastic. Finally, she sketches out her pitch for why companies should talk about operational debt as much as they do technical debt. Today’s conversation is a must-listen for HR leaders and founders — and for folks on the hunt for a more systematic approach to the new challenges of distributed work. Learn more about Elastic’s source code here: https://www.elastic.co/about/our-source-code You can follow Leah on Twitter at @leahesutton You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Kevin Fishner, Chief of Staff at HashiCorp. As the first business hire at the cloud infrastructure automation company, he previously built out the sales, marketing and product management teams. Now as chief of staff, he’s focused on building a strong foundation of company-wide systems, now that the team has grown to over 1000 people. In today’s conversation, Kevin shares a detailed look at how they run meetings, set and track progress toward goals, and make decisions through writing at HashiCorp. He also shares incredibly tactical advice for making annual planning more effective, including the unique business simulation they run, their scorecard system, and the weekly and quarterly meetings that help them stay focused on important KPIs. While today’s episode is clearly a must-listen for fellow chiefs of staff and founders spinning up a company from scratch, managers and leaders of all kinds will walk away with several takeaways on how to make their teams more effective. Because so much of what he shared is so detailed, we’ll be sharing some templates and visuals to go along with Kevin’s interview over on the First Round Review, so be sure to check that out. You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with David Lieb, the Director of Google Photos. Previously, he was the founder/CEO of Bump, an app that allowed users to swap contact information by physically bumping phones. Bump was acquired by Google in 2013, and formed the basis for the design of Google Photos, which launched in 2015 and passed the 1 billion users mark in 2019. In today’s conversation, David takes us through that journey of building a consumer product from scratch and scaling it to over a billion users in just four years. He shares the mistakes they made while building Bump, what he learned from navigating big company politics at Google, and how they pinpointed the problem in the photo-sharing space. From the precise questions they asked in user interviews, to how they stack ranked for the canonical users, there’s tons of wisdom in here for early product builders. There’s also lessons from operating at Google’s scale as well, including how his approach to planning and org design have evolved. Learn more about the Spotify “squads’ model that David mentioned in the org design section here: https://medium.com/pm101/spotify-squad-framework-part-i-8f74bcfcd761 You can follow David on Twitter at @dflieb, and you can learn more about his approach to building products on First Round Review: https://firstround.com/review/cognitive-overhead-is-your-products-overlord-topple-it-with-these-tips/ You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Bill Carr and Colin Bryar, two long-time Amazon executives who just published a new book, “Working Backwards,” which provides an inside look at how the leadership principles and business processes that have made the company so successful. Bill started at Amazon in 1999, and went on to launch and run the Prime Video, Amazon Studios, and Amazon Music businesses before he left the company in 2014. Colin joined Amazon in 1998, as the Director for Amazon Associates and Amazon Web Services Programs. He also spent two years as Jeff Bezos’ technical advisor or “shadow,” and later served as the COO for IMDb.com. In today’s conversation, Bill and Colin take us through Amazon’s culture of innovation and the origin stories of the Kindle, AWS, and Prime businesses. From granular details about the “working backwards” process, to an inside look at how players like Jeff Bezos and incoming CEO Andy Jassy operated up close, they share invaluable insights on diving deep and operational excellence. Whether it’s their lessons on why innovation can’t be a part-time job, or the perils of taking a “skills-forward” approach to exploring new opportunities, or why mechanisms are more important than good intentions, there’s lots of food for thought in here for founders and startup leaders. Learn more about “Working Backwards” here You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, and independent board member at Asana, Gusto and Patreon. Previously, she was part of the founding team at Blue Nile, spent five years in product marketing at eBay, and led marketing as an early employee at SurveyMonkey, before pivoting to operations as an SVP at Zendesk. In today’s conversation, Anne pulls on threads from across her impressive career as a founder, operator, executive and board member to deliver spot-on advice for folks with an eye for the C-suite. From what enables the best executives to scale up, to how she’s approached her own 30, 60, 90-day plans as a brand-new hire — she doles out plenty of prescriptions for getting this critical transition right and avoiding common traps. She also opens up her playbook for approaching executive recruiting, interviewing and hiring, and when to mine executive talent internally rather than defaulting to external hires. Finally, she opens up about her board work, sharing the essential ingredients for productive, impactful boards across every growth stage. Today’s conversation is a must-listen for executives, founders and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes. You can follow Anne on Twitter at @anneraimondi and you can learn more about her approach to diagnosing and repairing team trust on First Round Review: https://firstround.com/review/use-this-equation-to-determine-diagnose-and-repair-trust/ You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps. Before joining Plaid, Jean-Denis served as Director of Engineering at Dropbox, and even had a stint in law school and one year as a lawyer under his belt before diving deep into the world of CS. While he says becoming a lawyer was a “four-year detour he probably didn’t need,” there’s a lot to be said for how it’s shaped his engineering career and management philosophy. As he puts it, he strongly favors pragmatism over perfection, and it’s something he hammers home within his engineering teams. In today’s conversation, Jean-Denis pulls on threads from across his career to weave together a modern playbook for engineering leadership — and the hard-won lessons that stick with him. He also shares his insights on why his engineering org doesn’t have titles, the one question he asks every engineering manager candidate, and how his team prioritizes technical debt and keeping the lights on versus sexy, brand-new projects. Today’s conversation is a must-listen for technical leaders or those who are eyeing the engineering leadership track. From motivating a team to tracking the right KPIs, Jean-Denis has got tons of great tactics and stories from his time at Plaid and Dropbox for you to learn from. You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business. Here at First Round, we first came to know Dave when we invested in Upstart’s seed round back in 2012, and we’ve found him to be one of the most tenacious and focused founders we’ve ever backed. In today’s conversation, Dave gives us an inside look at how the business was built and what other startups can learn from its early days. In addition to unpacking the initial idea and subsequent business model pivot, Dave gets into what it felt like flying under the radar of Silicon Valley, why he “sucked at fundraising,” and how he and his co-founders have stuck together for almost a decade. From his “Are you Airbnb or Paypal?” test and why you should look at your career in landscape mode, to the three mental models he leans on to manage his psychology as a founder, Dave shares helpful frameworks that any startup leader can learn from. We also dive into his “management by exception” philosophy, what he learned from Google, how he runs his leadership team, and why he leans on references, not interviews, when hiring execs. You can follow Dave on Twitter at @davegirouard and you can read his First Round Review articles that we mentioned in the episode here: https://firstround.com/review/speed-as-a-habit/ https://firstround.com/review/how-does-your-leadership-team-rate/ https://firstround.com/review/a-founders-guide-to-writing-well/ You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello. In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity. In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup. This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/ You can follow Jay on Twitter at @jaysimons. You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson

Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort. After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways. She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart. Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone. You can follow Cristina on Twitter at @cjc. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills. You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom” For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg. To learn more about how Drift approaches storytelling, check out this article David wrote for Inc: https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/ You can email us questions directly at [email protected] or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson)

Our third episode is with Steve El-Hage, co-founder and CEO of Drop, an electronics company that creates products powered by feedback by a massive community of enthusiasts and experts. Reflecting on his 8-year, heads-down grind since becoming a first-time founder at 22, Steve shares the lessons that he figured out the hard way, from revenue dropping off a cliff and painful pivots, to hiring blunders and severe burnout.

Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas. Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape. But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders. You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App). You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Our first episode is with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. We’ve interviewed her four times on First Round Review — which might be a record — because the advice she has to share and the experiences she can draw from are unbelievably helpful to founders and startup leaders. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School. While on The Review she’s shared advice on everything from managing your emotions and struggling with scaling, to codifying your culture and setting up your first comp system, today’s conversation is focused on a different topic — management. This is a topic Molly has strong opinions on—she’s seen time and time again across her career how so many startup mistakes come down to general management issues. We cover everything from the traps that are easy to fall into, to why you should be spending more time with your highest—not your lowest—performers, to the managers she’s learned the most from, so there’s tons of insightful advice and practical tactics for both first-time managers and seasoned leaders alike. You can read more about Molly’s approach to scaling startups on First Round Review. We particularly recommend following her advice to ‘give away your Legos’ https://firstround.com/review/give-away-your-legos-and-other-commandments-for-scaling-startups/ And here’s the article on compensation that Molly mentioned in the interview: https://firstround.com/review/A-Counterintuitive-System-for-Startup-Compensation/ You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson

Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com