SaaStr's Lemkin: Hire 1-2 Ex-Founders in 2027 to Carry the Load

A CEO running an agentic B2B company past $100M ARR should employ one to three ex-founder executives. That is Jason Lemkin's prescription, and he frames 2027 hiring plans around a harder admission: more than a decade after selling EchoSign to Adobe, he has not fully recovered from being a founder.

The SaaStr founder laid out the argument in an October post addressed to founders building 2027 budgets. "One thing to just be careful of is whether they can still do it," Lemkin said of ex-founder hires. "I know for myself, I still haven't fully recovered from being a founder." It has been over ten years since Adobe Sign, formerly EchoSign.

Why ex-founders, specifically?

Lemkin credits ex-CEOs with capabilities operators cannot be trained into. They have owned a full P&L, however small, and know every burn dollar maps to payroll or runway. They built from zero without a playbook, so they do not freeze when B2B plus AI produces something new each quarter. They have hired and fired people they loved and know what waiting too long costs. They think like owners and know which problems to bring the CEO and which to handle alone.

The target profile: former CEOs who reached at least a few million in ARR, sold their company, or fought for years without making it.

What is the catch?

Many ex-founders exiting 5, 7, or 10 years of running a startup interview well and retain real judgment. Some no longer have the tank to carry a big, messy, high-stakes function for 3 or 4 consecutive years. They can advise at world-class level; they cannot absorb another founder-grade run. Lemkin's interview probes are direct:

• How long since you stepped away, and what did you do in between?
• What did your last 12 months as CEO feel like?
• What should your next 3 years look like, day to day?
• Do you want to own a number again, or help others own theirs?

What is the difference between work and load?

Lemkin had a strong team at EchoSign and still came out burnt. A great VP takes the work — pipeline reviews, launches, board decks, hiring loops. The load stays with the CEO regardless: the missed number, the final call between two disagreeing execs, the 2am runway worry, the fact that the CEO cannot have a bad week.

Most execs, even strong ones, take the work and leave the load. SaaStr runs today on 3 humans and more than 20 AI agents in production; the agents do enormous work, and the load still sits with very few humans.

Six signs an exec actually carries load, per Lemkin:

• You have stopped checking their work; six months in, their calls match or beat yours.
• They make 51/49 decisions without you and own the misses.
• They tell you no when you are about to err.
• They run fires — a customer escalation, a departing exec, a bad quarter — and brief you after.
• Your board trusts them directly, without you in the room.
• You can take 2 weeks off, something breaks, and they handle it.

What does this change for 2027 plans?

Lemkin ranks this hire ahead of the next product launch, sales hire, or new region. Bring on one or two execs who both perform and take load — an ex-founder with remaining tank, or an operator who has run a business unit end to end. Then actually hand over the decisions and accountability; founders who hire but never let go have bought another VP and kept all the weight.

His message to his 2008 self: get senior help earlier than seems necessary, and give 1-2 fully trusted people part of the weight.