Josh Kopelman

We just helped Airbnb hire their first GTM engineer. Now, we want to help you do the same! Last year, I went to our team with a problem: too many enterprise companies were asking me how to hire GTM engineers and I needed help finding them. So, we launched @Clay's Talent Marketplace for GTM Engineers, which now has over 1,500 candidates across the ecosystem!! But soon we realized there was still a gap between the number of companies looking for great GTMEs and the number of people who can do the job at the highest levels. Teams like Decagon, Notion, and Lovable are quickly adopting the role, and the demand is outpacing the supply. That’s why next month we’re launching Clay’s first GTME Career Prep Bootcamp: Alpha Forge. It's an intense 4-week, 20-hour-per-week program designed to teach you how to think and operate like a world-class GTM engineer. This is not about learning Clay or any one tool. We'll teach you the mindset, core concepts, the full tech stack you could use, workshop creative strategies, and help you execute plays at scale. Graduates get priority introductions to top companies that are actively hiring GTM Engineers. For our first cohort, the bootcamp is 100% free. If you want to break into one of the fastest-growing roles in tech, this is your chance. The bootcamp starts April 6th. Learn more and apply here: clayhq.typeform.com/to/BtPYbo3Y

We're hiring salespeople at @Clay! And I made this video to recruit you :) Want to know what a day in the life of a seller at Clay looks like? Watch below to meet the humans selling Clay, and how they're operating at the cutting edge of AI and GTM. In the age of AI, you need different skills to be the best seller. Come join the company that's charting the future of GTM, and we'll help you become the best seller for the post-AI world. We're hiring in New York, San Francisco and London. Apply here: clay.com/jobs

Our new product, @Clay Ads, is officially live! This might be the most electric product-market fit we've ever seen. I met with 8 prospects last week and they couldn't get enough. In just two months, our team used Clay Ads to cut LinkedIn CPL from $250 to $25. Here's how it works: Exclusion lists that auto-sync to Salesforce so ads only reach people who can actually buy. If you’re an existing customer, open opp, or partner, you won’t see our ads. This is by design! Meta became a real B2B channel for us too. Work emails rarely match personal profiles, so most B2B teams skip it entirely. Clay enriches contacts with personal emails before audiences ever hit the platform. 60%+ match rates. One recent campaign generated 200 leads at $10 each within 24 hours. And the audiences stay fresh on their own. When someone becomes a customer, they stop seeing your ads the next day. When sales shifts priorities, targeting shifts with them. This all happens automatically -- across both platforms. And no CSV exports or manual rebuilds required! Customers like Slack, Anthropic and Rippling are already hitting 90%+ match rates on LinkedIn and 60%+ on Meta. That is 2-4x what they were getting before. This is a massive win for marketing teams. Learn more here: clay.com/ads

Visiting Miami next week with @akothari and looking forward to meet local founders. Who’s free on Tuesday night?

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…

It’s a special privilege to be able to partner with companies building on the frontier. Because of this deep partnership with the team at @harvey, AI agents can now search and access content on the web that hasn’t been indexed by search engines built for humans.

New AI infrastructure is enabling a new generation of companies that are effectively tech enabled services. The prior generation struggled for these reasons (not an exhaustive list.) If you can clear these bottlenecks, you likely have a great opportunity in front of you.

I wouldn't be surprised to see Citrini propose rolling up private security and barbed wire manufacturers.

At @NotionHQ, we believe every business deserves powerful & beautiful tools. AI is the most important technology of this era. It shouldn't only belong to companies that have AI teams or can afford forward deployed engineers. Today we're launching Custom Agents: — The first multiplayer agents built for business. — No coding. Minutes to set up. Hosted in the cloud. — Run autonomously 24/7 with all your business apps. — Switch between the best LLMs (usually the same day they're released). — One person builds it, the whole company benefits. Rolling out for Business and Enterprise customers today. The AI era should leave no one behind 👌

Anyone have a @Waymo invite code for Miami they can share with me?

Calling it now: 2026 will bring the first SAFE that converts at a 20% PREMIUM to the next round. We’ve officially reached that part of the cycle.

This is Episode 3 of Executive Function with Stevie Case, Chief Revenue Officer at Vanta. There are few roles at a startup more perilous than being the early go to market hire. Against all odds, Stevie has played that role at Vanta to an extraordinary degree. Partnering closely with @christinacaci she helped Vanta transition from founder led selling into a real GTM engine now in the hundreds of millions in ARR. In our deep dive, we explore what it takes to win in this uniquely demanding role. Here are just a handful of the things that jumped out to me from our conversation: - Pedigree can be an anti-signal for early sales hires. Stevie says one of the most common reasons for failure with an early sales hire is bringing on someone with big logos on their resume. She says the more ideal profile is someone she calls a "a Renaissance rep," somebody who's more creative, entrepreneurial, and curious. But they're not going to have prettiest resume. - The CRO role isn't a "VP of Sales plus-plus." The CRO is fundamentally more analytical than a sales leadership role. Stevie doesn't consider herself a sales leader. She hires them. The CRO's job is to hit top-line revenue goals, and sales is just one avenue for that. - CROs in 2028 will be technical. Stevie thinks the next gen of CROs will be a different breed from the crop today: They'll be technical, systems thinks. They might come from disciplines like growth, RevOps, or GTM engineering. She thinks they're no longer going to be career salespeople. And she thinks only 10% of today's CROs will be able to make this transition. - But human sellers will still have a place in AI-native company org charts. While Stevie is bullish on AI tooling for efficiency, she thinks SDRs picking up the phone and having a conversation with someone will cut through the noise in a way AI-generated cold emails can't. - On hiring coin-operated versus mission-driven sellers early on: There's a maxim that the best sales folks are coin-operated. But Stevie says these folks are best suited for a repeatable, post-PMF GTM motion where they can take an ICP and run. But before extreme PMF, when you've got some customers and some revenue but it's not entirely repeatable, you want to find people who also have some long-term motivation and an interest in equity, because you need them to help work toward repeatability. - Confidence and velocity are under-measured and under-valued GTM metrics. The confidence with which reps can get on a call and tell your company's story successfully, and the speed with which they can act on an opportunity and close a deal, are key revenue metrics that aren't strictly quantifiable. Sure, there's time to close and win rate, but she says the only way to really get a pulse is listening to sales calls. - One of the most effective things you can do as a revenue exec is take ownership of what's not working. One of Stevie's early sales mentors was George Hu, who was COO of Twilio when she was coming up in the sales org. Stevie put together a presentation about how marketing wasn't giving them enough leads. George told her, "So what can you do about it?" She realized they could do more outbound. That's a lesson she's taken with her as CRO: Take control over your own destiny. - The key to a healthy CEO-CRO relationship is unfiltered information exchange. It's easy to only report up to the CEO to tell them what's working. Stevie says a big unlock in her relationship with Vanta CEO Christina Cacioppo was when she felt comfortable sharing everything, warts and all. - A perfect first sales call is 60% discovery. A lot of sellers make the mistake of frontloading why the product is so great. Stevie says the optimal first call is mostly customer discovery, and in fact rarely even gets to a product demo. - The single best thing you can do to become a CRO is learn under somebody great, not optimizing for title. Stevie says a mistake a lot of early career sales operators make is taking a VP of Sales job just for the sake of proving they can do it. She says the better way to carve a path toward the executive level is to find an excellent mentor and figure out how to work for them. And here are the timestamps: 00:00 Why early revenue hires fail 02:23 Who to hire at $5M in revenue 04:16 Coin-operated sellers vs. long-term builders 05:57 What excellence looks like in the CRO role 07:44 Metrics, confidence, and velocity 12:04 Should CROs lead sales? 14:39 From shy seller to revenue leader 16:36 Learning to scale at Twilio 17:44 "There is no CRO playbook 19:58 Stevie's scaling mistake at Vanta 22:16 Why Vanta stays 100% sales-led 23:16 The value of planning 24-26 months ahead 29:54 When trusting intuition was the wrong call 30:49 Do humans still have a place in the future of GTM? 33:33 Stevie's leadership non-negotiables 36:36 The myth of hiring for industry expertise 40:00 What stays centralized in a 600-person company 47:09 The hidden leverage of a customer's first 30 days 53:42 Why the CRO role will face enormous changes by 2028 58:42 What leaders must do now to stay relevant 01:02:30 Unpacking the CEO-CRO dynamic

.@fal just published their first State of Generative Media report. The report is super thorough and worth checking out if you’re deep on this space (or want to be) and want to nerd out!!

What an amazing run @davegirouard! I know that @Upstart is in great hands with @paulxgu -- and can't wait to see the company's next chapter!

Depending on which viral AI essay you agreed with on X this week, it’s already so over or we’re all playing a very expensive game of Farmville. As with most things, the real answer is a lot more unsatisfying. It’s all still messy and probably lies somewhere in the middle. While it does feel like things are shifting extremely quickly in a way that’s hard to dismiss, the hype is escalating every day. It’s impossible to tell where exactly we are on the curve. What has been more interesting to me than the debate over which camp folks are in is just how much traction these pieces are getting. I think we’re all kind of desperate to make sense of how uneven things are, and are all caught up in this moment of trying to process the whiplash. You’ll be scrolling through crazy OpenClaw workflows and mishaps that truly feel like scenes out of the future, but then skepticism starts to creep in about what’s true and what’s overengineered. And then anytime you step outside the tech bubble you can get an instant reality check on how much wood there still is to chop to get to widespread adoption. (Even if it’s just seeing how differently the ChatGPT vs. Anthropic vs. Google Super Bowl AI ads landed for tech folks vs. normies.) The gap between what people are posting about and what’s actually making a difference has never felt harder to figure out. The main thing I’ve found to be helpful as a counterweight is trying to stay diligent on spending my time as an investor where I think it matters most vs. getting caught up in the wild swings. For the past few years now, that’s meant meeting with builders who are focused on solving hard, real-world problems. To me that means taking on the biggest, most technically and operationally challenging issues in the physical world (aerospace, defense, robotics), or figuring out how to usefully inject AI into the painful, manual workflows in industries that actually make and move things. Not only because this is what personally gets me more fired up but also because it feels like this is the general direction our world is headed in. More and more of the founders I’m meeting are reorienting their approach to problem hunting and building in this way. @DideroAI is a great example here and is top of mind because they just shared their $30M Series A news today from @chemistry and @HeadlineVC. They found a problem space most of us know virtually nothing about. Procurement teams at manufacturers and distributors are managing thousands of supplier interactions across email, spreadsheets and ERPs. The bulk of this stuff is still done manually, even though it’s only getting more and more complicated as companies try to diversify their supply chains across more countries. When I led their seed in 2024, @tspencer15, @tcpetit, and @LPallhuber immediately felt like a team that was well-configured to the shape of the challenge here. They’ve been those people stuck in the mud of these workflows. (Between the 3 of them they’ve built companies, run procurement operations across countries, and dealt with the pain of trying to coordinate 100s of suppliers.) Spaces like these, where the team has the deep domain context and the agents are correctly applied, are where AI can and already is making a near-term, not-theoretical difference. In took less than a couple years, and Didero’s agents are now doing things like following up on 2K+ past due order line items that were sitting neglected, automating PO creation, and pulling info off physical bills of lading and getting it into the ERP so production doesn’t stall out waiting on someone to manually type it in. None of those are paradigm-shifting on their own, but stack up these small, boring, concrete wins week after week, company to company (and assume they continue to improve in capability at an explosive rate), and pretty soon we’ll all be surprised by just how much wood has been chopped.

Today we’re launching our newest podcast, Executive Function. The question we’re trying to answer is: what is the difference between good and truly great scale up executives? We’re beginning this journey by sitting down with Jeanne DeWitt Grosser, who’s currently the COO @vercel and previously spent almost 10 years @stripe, where her final role was Chief Business Officer. So much of her perspective can be summed up in this observation: “Most executives have a playbook and won’t contextualize it. They over pattern match and lack the intellectual curiosity to figure out what’s different. They don’t actually get their hands dirty.” Hope founders, execs, and future execs find as much value in this conversation as I did. Timestamps: (5:04) What keeps star talent from ascending to the top spot in a company (19:59) How to balance being demanding and supportive as an executive (22:47) Jeanne’s interview process for hiring executives (29:04) The thread that ties together failed executives (34:57) How Jeanne uses “driver trees” to determine metrics (43:24) Why your executive peer set needs to be your first team (57:16) How Stripe got 30 execs to operate as one team (1:02:43) Why execs should be working themselves out of a job (1:09:26) The performance review from @collision that sticks out in Jeanne’s mind

In working with so many founders, I've consistently seen that after a company has product-market-fit, the all-consuming priority shifts to building a high functioning executive team. I'm excited about our new podcast series that explores the topic of "What is the difference between a good and a great scale-up executive"... Click to signup!

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