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Our guest today is Nadia Singer, Chief People Officer at Figma.  Nadia joined Figma in 2020 and has seen explosive growth in her own career alongside the collaborative design platform’s. Before Figma, Singer was a talent expert who has hired hundreds of talented folks at places like Quora, Facebook and Google.  In our conversation today, we dive deep into what makes someone a terrific talent evaluator. Nadia opens up her own recruiter playbook and shares: Her personal recruiting trick, which is to study how a candidate reaches an answer, rather than what they say Tactics interviewers can use to avoid pattern matching and other biases The biggest mistakes she made in her early days as a recruiter  Ways that Figma tweaked its approach to culture so it could scale alongside the company  You can follow Nadia on Twitter at @nadsinger. 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 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 @donfaul You 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 @zebriez You 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 agency You 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

For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform.  Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures. In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on: How his own motivation changed over time and how he managed his relationship with the company’s co-founders.  The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months. Why he read two books on every other executive’s area of the business when he joined the leadership team. Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition. You can follow Mike on Twitter at @mboufford. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

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

Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation.  Just last week, X1 announced a $15 million funding round. But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares: The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product. How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything. The launch strategy that crashed X1’s website and built up a 600K long waitlist. . Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times. Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here. You can follow Deepak on Twitter at @drao1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

Our guest today is Jonah Berger, a marketing professor at the Wharton School at the University of Pennsylvania and the bestselling author of “Contagious” and “Invisible Influence.”  Today we’re chatting about his follow-up book, “The Catalyst: How to Change Anyone’s Mind.” Founders start companies to change industries and behaviors, but change is hard. Going back to chemistry, Jonah notes that catalysts don't just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. (In the book Jonah offers a helpful framework about 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence.) We focus on how founders and leaders can do that in the context of building and selling products. Jonah shares his thoughts on: Whether you truly need to build a 10X better product and why a startup’s biggest competitor is actually inertia.  The role of urgency in selling or getting someone to adopt a product. How to apply the freemium approach in different contexts, like with physical products. Techniques for negotiating price, as well as the role that identity and category creation play in persuasion and product adoption. You can follow Jonah on Twitter at @j1berger. 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 David Hsu, founder and CEO of Retool, a low-code platform for developers building custom internal tools. Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform. But in this conversation, David rewinds the clock to Retool’s early days. He discusses why plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company. We explore why David had such strong conviction in his target customer, even in the face of doubters, and his early lessons on finding language-market fit. David also explains how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and shares his playbook for creating incredibly tight feedback cycles with these early evangelists. On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David 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.

Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with David Hsu, founder and CEO of Retool, a low-code platform for developers building custom internal tools. Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform. But in this conversation, David rewinds the clock to Retool’s early days. He discusses why plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company. We explore why David had such strong conviction in his target customer, even in the face of doubters, and his early lessons on finding language-market fit. David also explains how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and shares his playbook for creating incredibly tight feedback cycles with these early evangelists. On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David 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 is Rich Rao, the VP of the Small Business Group at Meta, where he manages the global revenue and operations for properties including Facebook, Instagram and WhatsApp. He also spent 10 years at Google, where he held a bunch of different go-to-market roles at the company, eventually becoming the GM for the Devices and Education verticals. In today’s conversation, Rich shares how his engineering background influences his approach to GTM, from his architecture method to the concept of refactoring. We also wind back the clock to his earliest days at Google on the team that was building and selling Gmail for your domain. There are a ton of early startup mental models that Rich shares from this period in the company’s history, including why they ended up ditching free trials and his biggest pricing lessons. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson.

Our guest is Sara Varni, CMO of Attentive, a conversational commerce platform. Before joining Attentive, Sara was Twilio’s CMO and spent 10 years as a senior marketing leader at Salesforce. In today’s conversation, we talk about what startups can learn from enterprise marketing playbooks, particularly around creating and honing a corporate message. Sara takes us behind the scenes at how companies like Twilio and Salesforce craft a corporate message from the ground up, and tweak it as the company grows. She also shares specific advice for marketers with sights on the CMO seat, including how to form collaborative, not combative relationships with sales counterparts. You can follow Sara on Twitter at @SaraVarniBright You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Todd Jackson’s back on the mic this week. (As a reminder, he’s guest hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Harry Ritter, founder of Alma, a membership-based network that helps independent mental health care providers accept insurance and build thriving private practices. In our conversation, we go deep into Alma’s early days, and how they navigated the journey of finding traction and scaling.  As you’ll hear in the episode, the Alma team essentially had to find product-market fit twice as they went from physical, co-working office spaces pre-pandemic, to quickly building out their virtual care capabilities. Here’s a preview of what Todd and Harry cover: Approaching team building as a solo founder Refining the idea and getting more insights from your customers through structured interviews, using the technique doctors are trained on Rallying your team through a pivot Staying competitor aware — not competitor obsessed The difference between building a marketplace versus a platform. Whether you’re in the early stages of starting a company or going through a tough pivot, there are tons of helpful tactics here. You can follow Harry on Twitter at @harryritter1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

Our guest is Annie Duke, a retired pro poker player and First Round’s Special Partner focused on Decision Science. She’s also the author of the bestselling book, “Thinking in Bets.” In today’s conversation, we’re talking about her follow-up to that book, titled “Quit: The Power of Knowing When to Walk Away,” which was just released this week. Quitting is not a popular topic in startup circles and history is marked by success stories of founders who refused to quit, even when just about every signal was telling them to do so. But Annie offers a counterintuitive approach. She dives into all the misconceptions about quitting, and makes the case that it can actually be a superpower, rather than a weakness. Annie explores the psychology behind why it’s so hard to walk away, and tactically what folks can do to get a clearer picture of the decisions ahead of them, rather than being clouded by biases. She also offers specific advice for advice-givers who are trying to nudge someone to change course, with tested tips for getting your message across gently, yet firmly. And after the episode be sure to check out “Quit: The Power of Knowing When to Walk Away.” You can follow Annie on Twitter at @AnnieDuke. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Our guests are Manu Sharma and Brian Rieger, co-founders of Labelbox. In this interview, we take a microscope to their co-founder DNA, exploring the ins and outs of how they’ve made the relationship work over the years. We discuss: How Manu and Brian came together as co-founders and landed on the idea for Labelbox. How they intentionally aligned their skillsets, values and responsibilities before writing a line of code. Their rituals for spending valuable time together as the company grows, including thought-starter questions for deep discussions and sharing an executive coach. How they run the executive team at scale and sketch out decision rights. Manu and Brian both have extremely valuable advice to other founders, either those in the early stages of looking for a co-founder, or folks who want to add a little magic to an existing co-founding relationship. You can follow Manu at @manuaero and Brian at @RiegerB on Twitter. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson