Stripe was on his shortlist, but he chose a startup with fewer than 10 people instead. His top 1% outcome was for it to become a unicorn within five years. It took just three and a half. Meet @DeedyDas. Before joining Glean as a founding engineer, Deedy was evaluating several startup opportunities, including Stripe. But some of them already felt too far along for the experience he wanted. He didn’t want to ride a rocket ship that had already taken off. He wanted to help build one. At the time, Glean was still called SCIO, with fewer than 10 people on the team and no guarantee that the company would work. A few things gave him enough conviction to take the bet. The founder had already built and scaled an enterprise software company Experienced people were leaving comfortable jobs to join the team early Deedy deeply understood and cared about search, the problem Glean was trying to solve He dug into why enterprise search had failed before and became convinced this team had a credible shot at doing it differently Even then, Deedy put his conviction at only about six or seven out of ten, but that was enough to take the bet. His thinking was that if it didn’t work, they would probably know within a year or two, and missing the opportunity felt like the bigger risk. When he joined, Glean was still tiny. Years later, it had become the kind of company people were eager to join. And that’s part of Deedy’s lesson. If you only want to join things once they’re already seen as successful, you’ll always be making decisions based on a lagging indicator. Some of the most interesting career bets require making the decision before the outcome is obvious. You don’t need complete certainty, just enough conviction that the upside is worth the risk. Ben went much deeper with Deedy on the Next Play podcast, including how he evaluated Glean before joining, why he preferred building a rocket ship to riding one that had already taken off, moving from engineering into product, building an AI product that quickly became a meaningful part of Glean’s revenue and eventually making the jump into venture. Full conversation in the comments.

(10/13) A few of our favorite under-the-radar roles from fast-growing companies: • @n0w00j from @trymelius is hiring an account executive. • @akashraju4 from @try_glimpse is hiring a product operations manager. • @APolakof from @useflai is hiring a head of marketing and salespeople. • @akothari from @NotionHQ is hiring someone to run Notion’s Instagram account. • @20thr from @namespacelabs is hiring an account executive and an account manager. • @moritz_stephan from @hone is hiring a member of business staff and a founding designer. • @ml_angelopoulos from @arena is hiring a GTM strategy and ops lead and a growth marketer. • @tjparker from @GeneralMedicine is hiring a head of product and a strategic finance manager. • @pablorpalafox from @HappyRobot is hiring a chief of staff and a director of product marketing. • @sophiaamoruso from @trustfundvc is hiring a builder who can take briefs and ship quick products. ✨ Follow Next Play for more (and link to full list in the first comment)

He spent years building what looked like a successful career in traditional investing. Then someone at Index looked at his background and told him they had been thinking about him completely backwards. Meet @rex_woodbury Rex started his career at Goldman Sachs before moving to TPG, where he worked in growth and impact investing. He had been trained as an investor and had the kind of background that could keep him moving further down the traditional investing path. But outside of work, he kept gravitating toward technology, startups, internet culture and the way younger generations were changing how they lived and worked. When he started speaking with Index Ventures, someone on the team pointed out that they had been looking at his background the wrong way. They had initially been viewing him as the Goldman and TPG guy with an interest in next-generation technology. Then they realised it was probably the other way around. Rex was an obsessive student of the internet, technology and culture who happened to have worked at Goldman and TPG. That reframing clicked for Rex. For the first time, he felt someone had seen him the way he saw himself. The finance background was useful, but it wasn’t where he thought he could become world class. What genuinely energized him was early-stage technology, understanding people, spotting shifts before they became obvious and working with founders at the beginning. That eventually took him to Index and later to starting his own early-stage firm, Daybreak. There’s a useful career lesson in Rex’s story. Sometimes your résumé tells one version of who you are, while the things you keep reading, writing and thinking about in your free time tell another. The challenge is noticing which one actually gives you energy. Rex says it took him a few years to stop asking what the expected next step was and start asking what he could become really good at because he genuinely loved it. Ben went much deeper with Rex on the Next Play podcast, including how he moved from traditional investing into early-stage venture, how writing helped shape his career, why he left Index to start Daybreak and his advice for people trying to break into venture. Full conversation in the comments.

A few startups currently hiring with $50m-$100m raised (2/2): • @StarCatcherInd - space-based energy grid for satellites (Jacksonville) • @reactorworld - developer platform for real-time world models (Bay Area) • @Firestorm_Labs - modular UAS and expeditionary manufacturing (San Diego) • @fun - global payments infrastructure for blockchain transactions (NYC / Singapore) • @viktor__com - AI coworker for business workflows (Bay Area / NYC / Europe / Remote) • @SocketSecurity - open source supply chain security platform (US Remote / Europe Remote) • @primer_io - payments infrastructure and orchestration platform (EMEA Remote / North America Remote) • @HavocAi_USV - collaborative autonomy for uncrewed systems (San Diego / North Kingstown, RI / Remote) ✨ Follow Next Play for more (and link to full list in the first comment)

A few startups currently hiring with $50m-$100m raised (1/2): • @p0 - web research APIs for AI agents (Bay Area) • @Vapi_AI - developer platform for voice AI agents (Bay Area) • @MonacoGTM - revenue platform for startup sales (Bay Area) • @ScoutAI_ - foundation model for defense robotics (Bay Area) • @nyobolt - ultra-fast charging lithium-ion batteries (Bedford, MA) • @_MomentHQ - fixed income trading and portfolio platform (NYC) • @tesseralabsai - multi-agent AI for ERP modernization (Bay Area / NYC) • @VIKTORai - low-code platform for engineering automation (Rotterdam) • @getgarner - doctor quality analytics and reimbursements (NYC / Remote) ✨ Follow Next Play for more (and link to full list in the first comment)

(10/6) A few of our favorite under-the-radar roles from fast-growing companies: • @thazhmon from @jeeves_inc is hiring salespeople. • @arakharazian from @tryramp is hiring an economist. • @BastienDolla from @rayonapp is hiring a head of growth. • @WillBruey from @VardaSpace is hiring a people ops person. • @triekki from @zero_gtm is hiring a founding outbound person. • @anastasiacrew from @OpenRouter is hiring a community person. • @parisingh from @flowenghq is hiring a head of growth marketing. • @calvinchen from @ProximalHQ is hiring researchers and engineers. • @aakarkhanna from @joinmarble is hiring a founding operations person. • @Jerr_Wu from @HalluminateAI is hiring a chief of staff and a senior recruiter. ✨ Follow Next Play for more (and link to full list in the first comment)

She went from being a startup CEO to taking a part-time contract role. A few months later, she became The Browser Company’s first growth hire. Meet @DevinLewtan. After spending three years building Mad Realities, Devin wasn’t expecting to jump straight into another full-time job. She was still figuring out what she wanted to do next when Nash, a former boss, reached out. Nash was looking for someone to fill a growth role and asked Devin if she knew anyone in her network who might be a good fit. Devin read the role and had a different thought. It sounded like her. So they started talking and, pretty quickly, Devin began working with The Browser Company as a part-time contractor. It gave her a chance to step into the company without immediately making another big commitment after years of being a founder. She started by focusing on students, one of Arc’s strongest groups of evangelists. Early on, she created a WhatsApp group, spoke directly with students and ran user interviews to understand why they loved the product. From there, she started experimenting with campus growth, content, creators and other ways the company could reach more people. A few months later, the part-time experiment had turned into a full-time opportunity, with Devin becoming The Browser Company’s first growth hire. But the bigger adjustment wasn’t the job itself. It was going from founder back to employee. For years, Devin had been the person making the final decisions. Now she had to get comfortable focusing deeply on one area, owning experiments end to end and learning how to communicate upward instead of always being the person steering the ship. There’s something interesting about the way her next chapter started. She didn’t force herself into another big commitment immediately after leaving her company. She started smaller, gave herself room to test the fit and let the opportunity grow from there. Sometimes your next play doesn’t have to begin with a massive leap. It can start with a smaller bet that gives both you and the company enough time to figure out whether there’s something worth building on. Ben went much deeper with Devin on the Next Play podcast, including her transition from founder back to operator, how a Clubhouse side project attracted 5,000 live listeners on its first night and eventually led to Mad Realities, what she learned from building a company, and how she evaluates startups before joining them. Full conversation in the comments.