First Round

After @tobi published his now-famous AI memo, you probably saw similar posts from other founders and CEOs flood this platform. But most companies are still in the “memos and demos” phase — ambitious plans and mandates, “AI-first” roadmaps on board decks, flashy features and demoware. Yet scalable implementations and real results remain murky. So today, we’re launching a brand new publication to close the gap: Applied Intelligence. It aims to share how builders are using AI at their companies and the meaningful impact they’re seeing. Our inaugural essay is with none other than Shopify, following up on Tobi Lütke’s memo. We learn from VP & Head of Engineering @fnthawar about the non-obvious insights, tactics and workflows Shopify used to bring an ambitious memo to life. Read the essay below.

This is episode 5 of Executive Function, with Jeremy Epling, Chief Product Officer at Vanta. Jeremy spent 16 years at Microsoft, then moved to GitHub when it was being run by @natfriedman. Nat told him he had 9 months to ship GitHub Actions. No discussion. Jeremy says that deadline did more for the product than any strategy doc ever could have. We talk about what it actually takes to make the jump from big tech to a startup, and what great product leadership looks like once you're scaling. Here are three of a few dozen insights from our conversation: The day you become CPO, your team stops being EPD. It's the C-Suite. Every founder he asked said the same thing. Most new CPOs don't believe it until it's too late. The CPO-CRO relationship is broken by design. One runs on salary and equity, the other on quota. You have to fix that manually or it'll quietly wreck you. Spend real time with your most influential ICs — the staff engineers nobody manages but everyone listens to. They know what's actually happening before anyone else does. Timestamps: 00:00 Introduction 00:09 Why most big-tech executives fail at startups 05:38 Great product leaders stay in the details 09:21 The biggest mindset shift from VP to CPO 16:24 Revenue and product teams are always at odds 18:00 The key to a quality CPO and CRO relationship 23:21 Stop making your team fetch rocks 25:54 Who ultimately oversees the quality bar? 32:27 Why rigid hierarchies kill great companies 36:38 How to leave actionable, detailed feedback 38:55 Great CPOs should avoid comfort metrics 47:27 A glimpse into Jeremy’s working week 49:07 The case for weekly 1:1s 55:13 Why ICs are the unsung heroes of a company 58:25 Jeremy’s most formative career moments 1:07:55 The hardest skills Jeremy had to learn 1:09:31 Why great managers know when to push

Hosted a Young Builders dinner with @nickrubin from @firstround. The room was filled with UofT students and alumni building venture-backed startups, ML research, and interning at cool companies. Grateful to Nick for making the evening possible!

@zipline @Keller Keller shares more of his hiring philosophy in this episode of In Depth: youtube.com/watch?v=-i_uUB…

"Do you know when the right time to fire someone is? The first time the thought crosses your mind." @zipline co-founder and CEO @Keller explains that if you're deliberating over a new hire who's not performing, you already have the answer to your question.

@jakeserval @getserval Read here: review.firstround.com/servals-path-t…

After @jakeserval finished showing a @getserval demo to a Fortune 50 CISO, the exec asked him, “Where are you right now? I'm going to drive to see you. I'll be there in an hour.” It’s a classic “you’ll know it when you see it” PMF signal. But Stauch says it revealed a deeper truth about building for enterprise buyers: They want some consumer magic in a demo. This was an insight he’d picked up from Verkada, where he witnessed the power of a consumer-grade enterprise product. Sales reps would send prospects a text message with a live link to view Verkada security camera footage during the call. These buyers had Ring and Nest cameras at home, but were accustomed to clunky security hardware at work. The demo showed them they could raise their standards. On The Review, we sat down with the AI IT founder to pull out his PMF lessons two years into building. It’s a timely read for AI enterprise founders right now: How to take a swing at a hundred-billion dollar incumbent, the value in building the hard thing first and how to win in an existing category while actively creating a new one.

“Heat-seeking missiles for pain. That is the perfect definition of people who really succeed at startups.” @Keller is the CEO and co-founder of @Zipline, the world's largest commercial autonomous delivery system. Back in 2011, he set out to solve the un-fancy, real-world problem of transporting life-saving medicines to people who need it. To do it, he’s enlisted builders who are willing to “crack some eggs.” On In Depth, he sits down with @brettberson to share why building hardware is 10X harder than you’d think. He shares: -Why Zipline had a 1% chance of working -The blood drone delivery launch in Rwanda that was near-catastrophic -What it took to scale to 5,000 hospitals -How he hires at Zipline, from execs who aren't above "plunging the toilets" to teenagers who’ve built submarines and robots in their garage -Why the most important companies of the next 10 years will be hardware

Wow. Gumloop has gone from a side project out of a Vancouver bedroom to an AI platform that now automates daily workflows at companies like Shopify, Ramp & Instacart, and a new $50M Series B led by @benchmark (all in ~2+ years!!). It’s been a wild journey for the team, and I feel incredibly fortunate that @firstround led their 2024 seed round. If you tried it a while ago and still think of @Gumloop as just drag-and-drop workflows, I’d *strongly* recommend giving it another shot, as the product has evolved in massive ways. They’ve now added their agent builder, Gumloop Agents (lets anyone at a company build/deploy AI agents across workspaces in minutes) and Gumstack (a separate security product that lets IT teams monitor/control how agents use company data across the org). As a user of theirs said to me recently, ever since Gumstack launched, “Gumloop *IS* Gumloop for Enterprise.” As they’ve built out their product, the Gumloop team has stayed super focused on making it maximally useful to everyone – not just technical folks. IMO, this is a big part of why teams are getting hooked, and usage spreads wall-to-wall, instead of getting stuck in one department. @MaxBrodeurUrbas, @rbehal1729, and their entire team (who are all amazing btw) have been obsessed with this from day 1 and truly stay embedded with their customers, flying to their offices, running hundreds of workshops, shipping features same-day, and personally answering thousands of questions in customer Slack channels. They’re hiring across the board right now, more info below!

This is going to be killer

When hunting for ideas for his startup, @jakeserval relied on the classic “What’s your biggest pain point?” customer discovery question. He was met with shrugs. So he started asking a different question: “If you could hire somebody today to sit next to you and do your work for you, what would you have them do?” That led him to the idea for @getserval, an AI IT company that automates help desk requests and other IT workflows. He realized that the ICP he wanted to build for, IT leaders, are a problem-solving bunch. Pain points aren’t top of mind because they take pride in building solutions. So he took a different approach to these conversations. “When you frame the question as, ‘Hey, if you had somebody else here to help you, what’s the work that you'd give them?’ That's a nonjudgmental way of asking for pain points because you're saying, ‘What would you push over to this new person?’ That way, they can be much more free to say, ‘I don't like to do these things or I am doing a lot of this and I think somebody else could do it for me instead.’” Get more of Stauch’s insights from the customer discovery process on The Review: review.firstround.com/servals-path-t…

Web search infrastructure for AI is quietly becoming one of the most important layers in the stack. Great new collab between @p0 and Harvey. @paraga, @travers00 and the Parallel team built a specialized index of hard-to-reach international legal domains across 60+ countries to surface data that’s previously been effectively invisible to AI, at a scale that's difficult to pull off ("Parallel is solving it for us at a scale we couldn't build in-house.") parallel.ai/blog/case-stud…

Most CROs don’t outlast four CEOs, especially at hyper-scale companies. Chris Degnan, Snowflake’s former CRO did, joining as employee #13 and scaling revenue from $0 to $3.5B ARR during his 11-year tenure. One reason was that he refused to become what he calls a “spreadsheet manager.” “I need to know how to sell the product better than anyone else. Otherwise, how will I be able to judge if we’re hiring the right salespeople? Or what a good sales call looks like? How can I trust the forecast I’m being given?” On the latest episode of Executive Function, Degnan breaks down how the CRO role changes from $10M to $1B+, what he learned working under four different CEOs (including Frank Slootman), why he stays hyper-paranoid about competition, and more.

We hosted breakfast this AM for our @firstround portfolio founders who are parents, & man am I impressed by what ppl go through juggling both. So much respect for everyone who does it 🙌 PS how cute are these keychains?! Founders found their seat by looking for their kids’ names

It’s rare for a company’s first sales hire to survive the early chaos. It’s even rarer to span four CEOs and help scale from $0 to $3B plus in ARR without losing touch with the front line. That’s Chris Degnan, Snowflake’s first sales hire.

Suddenly every startup wants to hire forward deployed engineers. But it’s not the right fit for every company. One tell that you’re probably not a good candidate for the forward deployed model: You have a crisp vision of exactly how you want customers to use your product. Former FDE Shilpa Balaji explains that in the early days, Palantir wasn’t opinionated about how customers should use its software. Palantir FDEs helped the company build incrementally more valuable products by discovering niche uses cases while out in the field. “I think the learning the industry is taking away from the FDE’s newfound popularity is, ‘Oh, you should listen to your customers!’ Of course you should, but FDEs are for organic product growth,” she says. On The Review, we spoke with founders and operators who’ve scaled FDE teams to find out when it does — and doesn’t — make sense to adopt the model at your company: review.firstround.com/so-you-want-to…

Our team just did a deep dive on the forward deployed engineer, tracing its roots from Palantir to how newer startups like Serval are reinventing the role.

The CRO in 2028 will be technical, says @TrustVanta CRO @KillCreek. They might have come up through RevOps, or growth, or go-to-market engineering. They’ll think systems-first instead of human-capacity first. That’s not to say that companies won’t still need large GTM teams — just that the top 1% revenue leaders in the AI era will be a different breed. Get more of Stevie’s insights on how the CRO role is changing in this episode of Executive Function: youtube.com/watch?v=phPoMj…

One of the most extraordinary parts of the Notion story is that what the product has become in a post AI world is nearly identical to what Ivan outlined more than 12 years ago when he described what he wanted to build, before a single line of code was written. That may be why it’s one of the best examples of a company reinventing itself around a new technology in recent history. Congrats to the entire Notion team on their incredible execution.