One of the most common mistakes I see early-stage technical founders make is hiring AEs too early. They close a few deals, get excited, and decide it's time to "scale sales." But if you haven't figured out the motion yourself — why customers buy, what the objections are, how deals actually get across the line — you're paying someone to figure all of that out, and do so less effectively, without the cachet of the founder title. This rarely works. It results in wasting capital, burning through leads, mis hires and abrupt terminations, and then you're back where you started with less runway and nothing to show for it.

I talked to four successful founders about how they made the decision to hire their first AEs. Their companies range from early traction to serious scale, but they all went through the same messy transition from "the founders sell everything" to "okay, someone else needs to carry quota." And, it must said, they are both doing very well and growing quickly (and hiring more AEs now!).

Knowing when you're ready

There's no clean metric that says "hire salespeople now." For every founder I talked to, it was more of a gut call. Critically, though, all founders had meaningful traction they had implemented on their own, in a repeatable way, before they brought on sales resources

Jesse Zhang, CEO of Decagon, was blunt about it: "You should only hire if founder sales are going well and you feel like it's getting repeatable. If founder sales are not going well, an AE is not going to solve that." Jesse and his cofounder Ashwin got to $1M in ARR with just the two of them - no other resources at all.

Albert Gozzi, CEO of Aleph, described it as "much more gut feel than metrics. It came from feeling that we had a certain degree of repeatability — the same intro call script consistently surfaced the right pain points, and conversations with qualified leads were converting to the next stage."

Having worked with the Aleph team a fair bit, I can tell this is an understatement; Albert and team were very meticulous about their repeatability, having documented and tested multiple talk tracks and customer profiles before they even thought of bringing another seller on board. And it’s telling to me that the CEO and founder of AI for FP&A, one of the most metric-focused founders I’ve worked with, describes it as a gut feeling decision over metrics when deciding to bring on AEs.

Hagai Shapira, CEO of Daylight, had a loose target of selling the first $1M himself as a PMF signal, but what actually pushed him was simpler than that: "I felt we could move faster and that there are opps that are missed by having just me doing all sales."

This same sentiment is echoed by Han Wang, CEO of Mintlify, who's honest that he probably waited too long. Mintlify hired their first AE around $1.5M ARR, and Han thinks $500K would've been fine: "We were just so underwater with the deals that were coming in. We were often dropping the ball, missing replies, and missing times to even respond to the deals."

There are two themes embedded in these observations which are worth calling out explicitly.

1. The founders had documented, experimented, tested, and proven that a repeatable sales motion could work with themselves, before bringing on another person to sell.

They knew how to sell their product effectively, and could then replicate it with more people doing the same work.

1. Even when they reached repeatability, some of these founders didn’t immediately move to hire; they waited until they were too overwhelmed by leads and prospects and really needed the help.

Thus, erring on the side of waiting longer is worth considering, since the cost of hiring someone without first proving sales repeatability is so high.

Finding the right person

Jesse sourced through referrals. Hagai's first AE had actually advised the company before joining — he came through his co-founder's personal network, and the second was recommended by a customer.

Albert went a totally different route: "I did a lot of cold outbounding to successful AEs at companies I liked, and probably sent north of 100 messages to get a handful of meetings." Basically, he treated hiring the way you'd treat prospecting: with the same care he put into finding his first customers.

Making these first few sales hires successful

I was surprised by how strongly each of these founders focused on successful co-selling as a mechanism to onboard each AE.

Albert was on calls 3-4 hours a day for the first three months, running roughly 80% of deals together with his new hires. Hagai had both AEs report directly to him and worked opportunities side-by-side, including in-person customer visits. Han walked through deals, had his AE shadow everything, and talked through how he would've handled each situation.

Jesse frames this as intentional: "Your first AEs will be co-selling with the founder for quite some time. That lets you get a feel for how well they are doing, and it lets them truly get ramped up."

One structural thing Han did was to set quota at $500K instead of the typical $1.2M. "We really wanted them to prove out the uncertainty and the ambiguity of it all." Set a winnable quota early. You can raise it later, but nothing kills momentum faster than an AE wondering if the problem is them or your pipeline.

What I'd tell founders

After these conversations, I think it comes down to a few things:

Don't hire to fix broken sales. If you can't sell your product, neither can an AE. Hire to scale what's working, not to figure out what might work.

Source through trust. Your first AE isn't a job posting hire. Referrals, advisors, customers, or — like Albert — targeted cold outbound to AEs you've seen do great work.

Co-sell for longer than you think. Every founder here spent months in the trenches with their first hires to ensure they succeeded, and created a repeatability that could scale with additional headcount.

Set them up to win. Lower quotas, give them direct access to you, and lean in with genuine support. Then raise the bar over time.

The first AE hire isn't really about getting sales off your plate; it's about proving that your product can be sold by someone who isn't you.