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I was with a great agentic B2B CEO this week, $100M+ ARR and still growing fast, and we got into hiring ex-founders. I’m a huge proponent. Every B2B company at scale should have 1 to 3 ex-founder CEOs on the team. They have superpowers you can’t train into an operator who has never been a founder, no matter how good that operator is. Then I said something I hadn’t planned to say out loud: “One thing to just be careful of is whether they can still do it. I know for myself, I still haven’t fully recovered from being a founder.” And it’s been a long time. More than a decade since Adobe Sign / EchoSign. Why Every Team Needs 1 to 3 Ex-Founders Ex-founders bring things almost no one else does: - They’ve owned the whole P&L, even when it was tiny. They know every dollar of burn is someone’s job, payroll, or runway. - They don’t need a playbook. Most great execs are great at running a playbook they’ve seen work before. Founders built from zero without one. In B2B + AI, something new shows up every quarter now, and ex-founders don’t freeze when it does. - They’ve hired and fired people they loved. They’ve made the hard calls, and they know what waiting too long costs. - They think like owners because they were owners. They’ll find the problem nobody assigned to them and fix it. - They understand what your week feels like. They know which problems to bring you and which ones to just handle. Get 1 to 3 of them. Ideally former CEOs who got to at least a few million in ARR, or who sold, or who fought hard for years and didn’t make it. Some Ex-Founders Are Still Running On Empty A lot of ex-founders come out of 5, 7, 10 years of running a startup and look fine. They interview well. They have the stories, the judgment, the pattern recognition, and all of it is real. But some of them don’t have the tank anymore. They can advise at a world-class level. They can’t carry a big, messy, high-stakes function for 3 or 4 years straight again, at least not right now. They can still be great hires. Just not for a role where you need someone to take a big chunk of the load off you. When you interview an ex-founder, ask directly: - How long has it been since you stepped away, and what did you do in between? - What did your last 12 months as CEO feel like? - What do you want your next 3 years to look like, day to day? - Do you want to own a number again, or help others own theirs? The honest ones will tell you, and you’ll learn a lot from the answer either way. Honestly, I’m Still A Bit Burnt, More Than A Decade Later Those of you who follow me, or use SaaStr AI, may be surprised to hear this. I know I look “high energy.” Compared to 99 out of 100 folks in the arena, I probably am. I’m running SaaStr, running two funds, writing every day, building apps every day. Being a founder still took its toll on me, and it didn’t fully come back. I love what I do. But my reserves aren’t what they were before Adobe Sign / EchoSign. My capacity to absorb one more crisis, one more bad quarter, one more key person quitting on a Friday, is lower than it was. Years of carrying everything leave a mark, and getting acquired didn’t erase it. I Had A Great Team And Am Still a Bit Burned Out I had truly great people at EchoSign. I still came out burnt. A great team takes work off your plate. Work is tasks: pipeline reviews, launches, board decks, hiring loops. A strong VP owns those. The load is what stays with you after the tasks are delegated. If the number misses, it’s on you. When two execs disagree, you make the final call. You’re the one worrying about runway at 2am. You’re the only one who can’t have a bad week. Most execs, even very good ones, take on the work and leave the load with you. If no one on your team carries any of it, it all lands on you every week, for years. We have a version of this at SaaStr today. We run with 3 humans and 20+ AI agents in production. The agents do an enormous amount of work, and the load still sits with a very small number of humans. Six Signs An Exec Is Actually Carrying Load - You’ve stopped checking their work. Six months in, their calls look like your calls, or better. - They make 51/49 decisions without you, and own them when they’re wrong. - They tell you no. They push back hard when you’re about to make a mistake. If they always agree with you, you’re still carrying it. - They run a fire without you. A big customer escalation, a key exec leaving, a bad quarter. They handle it and brief you after. - Your board trusts them directly and is comfortable talking to them without you in the room. - You can take 2 weeks off and something goes wrong, and they handle it. If no one on your team hits most of these, that’s what to fix in 2027. Put It At The Top Of Your 2027 Plan It’s mid-October. Most of you are building 2027 plans and budgets right now. Put this first. Ahead of the next product launch, the next sales hire, the new region. Bring on 1 or 2 execs in 2027 who are great at their jobs and can also take over some of the load. An ex-founder who still has the tank is often the best candidate. A long-time operator who has run a business unit end to end can be too. Look for people who have carried real load before and want to carry it again. Then hand it to them. Founders often make the hire and then never let go of the real decisions, the real accountability, the real worry. If you do that, you’ve hired another great VP and you’re still carrying everything yourself. What I’d Tell Myself In 2008 Get help. Get senior help, earlier than you think you need it. Get 1 or 2 more people on the team you can 100% trust, and hand them part of the weight. I had a great team, and I’m still a bit burnt more than a decade later. Don’t let it happen to you.
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