In Depth

Todd Jackson is back on the mic to guest host another product-focused episode this week with Christina Cacioppo, the co-founder and CEO of Vanta. Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way).  After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in 2018 by trying to get SOC-2 security compliance for startups — but at the time, startups didn’t even really need to have SOC-2s. But Christina and her team saw the writing on the wall and that security was going to shoot up on the priority list for even the earliest-stage companies, and kept building even when plenty of smart people told them it was a bad idea.It’s a gamble that paid off. After going through Y Combinator, the team nabbed some truly incredible early customers, including Segment, Front and Lattice. Christina tells us exactly how she went from zero selling experience to pulling off big-time deals. She also pulls back the curtain on some of Vanta’s more unconventional moves, like waiting until they acquired hundreds of customers to build a proper website and instead relying almost exclusively on word-of-mouth to grow the business. Christina also shares her thinking behind the fundraising strategy, in which Vanta operated at cash flow break-even for years before going out to raise its Series A. 

Our guest today is Ben Lang, Head of Community at Notion. Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today. But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after launching his own Notion template gallery on Product Hunt and joined as one of the first 15 employees. In our conversation today, we focus on the nuts and bolts of building a global community that drives user growth. Ben shares tactical advice on: Tackling community organically from the bottom-up, and why you shouldn’t go top-down What companies are best suited to a centralized vs. decentralized community approach  Partnering with YouTubers and other creators  His advice to founders on finding your own first community hire You can follow Ben on Twitter at @benln. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with Bryant Chou, co-founder and founding CTO of Webflow, a no-code visual web design platform built with freelance designers and developers in mind. Today, Webflow is valued at over $4 billion and has millions of users all over the world. More than 200,000 freelancers, agencies, small businesses and enterprises use Webflow to help design and power their websites at businesses large and small. But Webflow didn’t always market to such a wide customer base. In our conversation today, Bryant rewinds the clock to Webflow’s early days — when it was just a co-founder team of three building a better tool to design a website. We explore why the Webflow co-founding team had such a strong conviction that designers were their ICP, and why they took much longer to launch than other folks in their Y Combinator cohort. Bryant also explains how Webflow wrangled their viral launch on Hacker News into a sustainable revenue and shares his root cause analysis framework for collecting customer feedback. On the surface, Webflow’s path to product-market fit seems incredibly smooth. But as Bryant tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing. 

Our guest today is Don Faul, CEO of CrossFit.Don has a fascinating background where he’s been able to find success in environments as different as a combat zone and a corporate board room. After spending 8 years as a platoon commander in the U.S. Marine Corps, Don had stints at some of the most vaunted companies in tech, including Google, Facebook and Pinterest, the latter of which he served as the Head of Operations. It’s a really unique set of leadership experiences spanning very different cultures. In today’s conversation, he answers some burning questions like if micromanagement is always a bad thing, how to create a long-term company vision that genuinely gets people fired up about the future, and what folks tend to get wrong in their all-hands meetings. We also discuss what it takes to lead in this current environment, and how leadership looks different when things feel like they’re going off the rails, which plenty of startup folks are feeling right now. Don unpacks his biggest lessons on how to embrace transparency when things aren’t going well, and candidly shares his own experience of having to wind down a company. Read the article Don penned for First Round Review: The Pivotal Stories Every Startup Leader Should be Able to Tell.You can follow Don on Twitter @donfaulYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Our guest today is Brie Wolfson. Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams.In today’s conversation, we’re focused on company culture. A decade or so ago, companies like Google and Amazon dominated the cultural zeitgeist, with founders wanting to emulate their secret sauce. Today, there’s a newer guard of companies that startups want to model themselves after, with Stripe at the very top of the list. Brie peels back the layers into not just the cultural pillars that drove Stripe’s meteoric rise, but also how these showed up in day-to-day work. We also zoom out beyond Stripe to talk about her work teaming up with companies with The Kool-Aid Factory, seeing culture and company-building up close. Brie shares advice on codifying your operating principles, establishing meaningful rituals, and growing this kernel of culture as the company scales. Read the full essay Brie recommended during the interview: Reality has a surprising amount of detail and the article she penned for First Round Review: Ditch Your To-Do List and Use These Docs to Make More Impact.You can follow Brie on Twitter @zebriezYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Our guest today is Aaron Zamost.After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley's School of Law, Aaron now runs Background Partners, a communications consulting firm.In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on: Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies. The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy. A 3-question framework for simplifying your company message early on. How to prep for interviews and deal with difficult lines of questioning. How to think about commenting on events in the news, or message layoffs to the team. Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen. We also recommend checking out his two excellent Medium posts:-What’s Your Hour in ‘Silicon Valley Time’?No, you don’t need to hire an agencyYou can follow Aaron on Twitter at @zamosta. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Our guest today is Daniel Debow, a VP of Product for Demand at Shopify. Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007. In our conversation today, we focus on all the moving parts of running an M&A process as a startup . Daniel shares tactical advice on: What conditions founders should look out for at potential acquirers, as well as what established companies can do to create a more “founder-friendly” environment How to spot clear buying signals and weed out companies that are just “tire kicking” How to build meaningful relationships with executives of all types, not just corp dev teams. Techniques for including your investors in the M&A process, as well as messaging tips when opening up about the process to the wider team.  You can follow Daniel on Twitter at @ddebow. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Our guest is Anna Binder, Head of People at Asana.We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company. Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but high-performers, too. Anna also unpacks her methodology of conscious leadership, and how the best leaders always interrogate how the opposite might be true. She shares her insights from working on Asana’s executive team for nearly 7 years, and how to build habits to make sure this group is a healthy nucleus at the center of the company. We end with a rapid-fire round, with some quick hits tackling onboarding, all-hands meetings, and mentors. You can follow Anna on Twitter @annaebinder.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Mike Boufford, CTO of Greenhouse, shares insights on scaling a career at a startup. Topics include building a supportive environment, preparing for growth phases, reading books on various executive areas, and reducing attrition. He also discusses the importance of adapting, coaching team members, and evaluating hires based on versatility and adaptability.

Our guest is Peter Kazanjy, co-founder of Atrium and author of “Founding Sales: The Early Stage Go-to-Market Handbook.”As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly building and start trying to sell, things tend to get infinitely more complicated.In today’s conversation, Pete lays out the roadmap for getting founder-led sales right in the early days. From small exercises to build up your selling muscles, like his “turbo rapport” challenge to thornier topics like self-diagnosing if your selling narrative is working, he’s got tons of advice for breaking down the art of a sales call. Pete also shares tailored guidance for folks who are facing the additional hurdle of creating a new category (and trying to create a new budget), with the playbooks he used building Atrium.You can follow Peter on Twitter @Kazanjy. Check out his articles for First Round Review, including his lessons on building a customer advisory board.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson