In Depth

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

Today’s episode is with Sydney Strader, VP of Customer Success at Catalyst. Prior to joining Catalyst, Sydney was the VP of Customer Success at InVision.In our conversation we focus on founder-led customer success, an area of early company building that’s often overlooked. Here’s a preview of her tactical advice: How to structure early customer check-ins, plus a framework to help surface more specific feedback.  The most impactful questions that founders and customer success managers should ask all their customers. Why everyone at the company owns the net revenue retention metric — not just the customer success function. How to make your first customer success hire, from the ideal profile to structuring the interview process and setting comp.  You can follow Sydney on Twitter at @sydneystrader. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Steven Bartel, co-founder and CEO of Gem.Before building the talent acquisition platform, Steven was an early engineer at Dropbox, where he spent 5 years working on analytics, Dropbox Paper, and hiring as the company grew from 25 to 1500 people.This experience from Dropbox, combined with his lessons from building out Gem’s own team and talking to his customer base of recruiters makes Steven the perfect person to talk to about early-stage recruiting.In our conversation we focus on how to make those fourth, fifth, or tenth hires — those really early days when your startup has zero brand recognition or recruiting help. Here’s a preview of his tactical advice: A trick for sourcing second-degree network connections The power of sending a “break-up” message in your candidate outreach.  How Gem brought candidates on to work with them in very structured trial periods before making a full-time offer.  Advice for working on your recruiting pitch and nurturing passive talent The similarities between early-stage hiring and founder-led sales You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson 

Today’s episode is with Snir Kodesh, Head of Engineering at Retool, which is a development platform for building custom business tools. Before joining Retool, Snir spent six years as a Senior Director of Engineering at Lyft.In our conversation, we cover some of the biggest differences between leading engineering teams for a consumer product versus an enterprise platform — and the things that are consistent across both orgs.First, Snir pulls back the curtain on the software development cycle, starting with setting the product roadmap while balancing a diverse set of customer needs. He outlines who’s in the room to represent product, engineering and design, and what those meetings actually look and sound like.Next, he dives into how engineering actually starts taking that product roadmap and making a plan of action using the “try, do, consider” framework. He makes the case for leaning on QBRs instead of OKRs, why scope creep gets a bad rap, and his advice for getting better at estimating how long a feature will actually take to complete.Finally, we zoom out and cover his essential advice for engineering leaders — especially folks who are scaling quickly from leading a small team to a much bigger one.You can follow Snir on Twitter at @snirkodeshYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Claire Butler, Senior Director of Marketing at Figma, and one of the company’s first 10 employees.In today’s conversation, she sketches out Figma’s five phases of community-led growth — and shares tons of advice along the way for startups who also are looking to build an organic growth engine.In the first phase, Claire covers the biggest lessons from Figma’s years of stealth mode — and how you can start planting the seeds for a community when you don’t have a fully-formed product. She also unpacks the decision to eventually emerge from stealth, after years of quietly building.In the second phase, Claire opens up the pages of Figma’s launch playbook — from taking over design Twitter, to marketing to folks who tend to bristle at traditional SaaS marketing.In the third phase, she shares how Figma leveraged the community to get folks to try the product, even if they weren’t going to switch over right away to designing in Figma full-time. In this phase of community-building, Figma built out its evangelist strategy and Claire shares tons of tips for generating excitement around your nascent product.In the final two phases, Figma needed to connect the individual users that loved the product with a larger enterprise strategy. They didn’t layer in a sales team until four years after the product launched, and didn’t add a paid product tier until another two years after that. Claire explores the ins and outs of these GTM trade-offs.You can follow Claire on Twitter at @clairetbutlerYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Todd Jackson’s filling in as host again this week. (As a reminder, he’s hosting a few product-focused episodes this season — all about finding product-market fit.)Today, Todd chats with Andrew Ofstad, co-founder of Airtable. In our conversation, we go deep into Airtable’s early days, and how they navigated the journey of finding traction and scaling.Here’s a preview of what Todd and Andrew cover:How the founders came together, their vision for the product, and what the initial prototypes looked like. Airtable’s alpha, beta, and launch timelines, as well as their early traction.The challenges of creating a horizontal product that can do many things, including identifying initial use cases and figuring out how to describe what they were building.How to approach pricing and competition, as well as their early go-to-market strategy.What the next 3 years will look like for Airtable, and how they’ve navigated scaling while staying true to their vision.Whether you’re a founder validating your own idea, or a product leader looking for growth advice, there are tons of tactics here that go much deeper than the typical founding stories you hear.You can follow Andrew on Twitter at @aofstad. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

Today’s episode is with Ian Wong, co-founder and CTO of Opendoor. Before founding Opendoor, Ian was Square’s first data scientist, where he developed machine learning models and infrastructure for fraud detection.In today’s conversation, we cover his essential advice for how to integrate data science into your startup. As Ian puts it, in the early innings it might make sense for your startup to be operations heavy. But as you start to scale, data science becomes a critical component for running a business with longevity in mind. We dive into how both Square and Opendoor approached this transition.Along those lines, we discuss some of the early considerations for your fledgling data science team, including the type of folks to hire for the early team, like whether to look for generalists or specialists, and how to set up your interview loops. Ian also dives into his lessons on structuring the data science function so that it’s deeply integrated with the rest of the technical org.Next, we dive into some of his biggest lessons as a first-time founder and CTO, including his practice with Opendoor’s leadership team of doing pre-mortems to predict why something might not work. He also encourages founders to run through a bi-yearly exercise of re-writing their job rec.You can follow Ian on Twitter at @ihatYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.) Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a repeat founder, Sidharth picked up a ton of valuable lessons, particularly when it comes to company culture and management. Right from the start, he knew he wanted to build Subscript to be global, distributed, and asynchronous. That’s why there are no internal company meetings. Everyone also operates autonomously, deciding what to work on for themselves.We dive into both the philosophy behind this unique approach and the nitty gritty details of how exactly it works in practice. Here’s a preview: How to share company updates asynchronously every week. Advice on how to approach goal-setting and performance feedback, while minimizing micromanagement. Tips for improving transparency and documentation, plus details on Subscript’s running product/market fit journal.  Thoughts on how to assess asynchronous communication skills when hiring. How this culture impacts a founder’s role and schedule. There’s tons of food for thought in here, whether you’re a founder thinking about shaping your company culture, or a manager looking for some fresh ideas. You can follow Sidharth on Twitter at @sikakkar. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.