You just raised your Series A. Time to build the sales team—and fast.
It’s tempting to go big:
- “Look at the size of their deals.”
- “They closed JP Morgan Chase, Coca Cola and Ford Motor Company.”
- “If they crushed it at [insert Enterprise SaaS category leaders], they’ll crush it here too.”
Except… they probably won’t!
On paper, these enterprise AEs look impressive. In practice? Many flame out fast in startup sales roles.
Why Enterprise AEs Struggle in Startups
Hiring an AE from a Enterprise SaaS category leaders and expecting them to win in a Series A environment is like throwing a chess grandmaster into a street fight. Sure, they’re strategic—but that’s not the game you’re playing.
Structure vs. Scrappiness
- Big companies offer process, playbooks, inbound leads, SDR support—the works.
- Startups? You’re still figuring it all out. There’s no script. The right AE doesn’t just run the playbook—they help create it.
Brand Recognition vs. Cold Conviction
- Enterprise reps walk into meetings with brand cachet. Their email signature does the heavy lifting.
- Startup AEs walk into skepticism. They win by selling vision, not logos.
Process-Driven vs. Adaptive Selling
- At scale, sales is repeatable.
- At a Series A, it’s chaos. Every deal looks different. The best early-stage sellers are part AE, part scientist—testing, iterating, adjusting on the fly.
The Culture Shock Is Real
When a Enterprise SaaS category leaders AE joins a scrappy startup, here’s what typically hits them:
- No army behind them: No SDRs, no ops team, no well-oiled CRM. Early-stage AEs often run full-cycle—and that’s a steep learning curve.
- Longer, colder sales cycles: Without brand equity, it takes longer to build trust. If they’ve never had to hustle for credibility, deals stall.
- Founder-heavy sales motion: In startups, the founder’s in the trenches. Feedback is constant. Collaboration is daily. If they’re used to autonomy and silos, it’s a shock to the system.
So if the Enterprise SaaS category leaders AE isn’t the answer… who is?
What to Look for Instead
Forget the flashy logos. You don’t need the “big name” AE who closed deals with a brand doing half the work.
You need the #1 rep at the B-tier company—the one who wins deals against the category leaders, without the name recognition, the sales army behind, and often without the best product.
They’ve got something better: hunger and tenacity.
You need a builder—someone who:
- Thrives in Ambiguity: Can pivot mid-pitch, build decks from scratch, and craft messaging when marketing is still finding its footing.
- Has Grit: Startup sales is a rejection sport. They get knocked down and keep dialing.
- Embodies Founder-Mode: Owns the problem. Stays close to the customer. Builds from zero.
The best early-stage AEs often don’t have shiny resumes. They’ve sold tough products, cracked cold markets, and clawed their way to quota. They’re not brand carriers. They’re builders.
Experience Helps. Mindset Wins.
Enterprise experience isn’t useless—but it’s not enough. In startup sales roles, what matters most is mindset: hunger, hustle, and the ability to thrive in the unknown. So before you make that next hire, ask yourself: Can they build from zero?
Because at this stage, you’re not hiring a seller. You’re hiring a co-creator of your go-to-market motion.
Need help finding that kind of AE? Book a call.
We know the startup sales hiring landscape inside and out—and we specialize in connecting early-stage founders with reps who don’t just survive the chaos… they scale through it.