Dear SaaStr: How Do I Make Sure My First 1-2 Sales Reps Are Strong?

Dear SaaStr: How Do I Hire a Great First 1-2 Sales Reps?

Hiring your first AE (Account Executive) is a pivotal moment for your startup. It’s not just about finding someone who can sell—it’s about finding someone who can sell your product in the messy, unstructured environment of an early-stage company.

Here’s how I’d approach it:

1. Hire After You’ve Done Founder-Led Sales
   You, as the founder, need to have closed the first 10-20 deals yourself. This isn’t optional. You need to understand the sales process, the objections, and what works before you can bring someone else in. If you haven’t done this yet, you’re not ready to hire an AE.

2. Look for a Problem Solver, Not Just a Closer
   Your first AE needs to be scrappy and entrepreneurial. They won’t have a playbook to follow—they’ll be helping you write it. Look for someone who’s comfortable figuring things out on their own, not someone who’s only used to executing a pre-built system. If they ask about systems and process, it’s almost certainly not a fit.

3. Passion Over Experience
   Early on, it’s often better to hire someone who’s deeply passionate about your product and mission, even if they’re not the most experienced salesperson. Selling a product without a big brand or established credibility is tough. You need someone who believes in what you’re doing and can evangelize it.

4. Match Their Experience to Your Sales Motion
   If you’re selling to SMBs, hire someone who’s great at high-velocity, transactional sales. If you’re selling to enterprise, hire someone who’s comfortable with long sales cycles and complex deals. Don’t expect someone to adapt to a completely different sales motion than what they’ve done before—it rarely works.

5. Don’t Overthink Compensation
   A good AE should pay for themselves within 3-4 months. If they’re asking for $140K OTE (On-Target Earnings), with a $70K base and $70K bonus, don’t stress too much about it. Most of that is contingent on performance, and if they’re not closing deals, they’re not earning the bonus. Focus on whether they can deliver, not just on the cost.

6. Interview 30+ Candidates
   Yes, it’s a lot. But hiring the wrong AE can set you back 3-6+ months. You need to find someone you’d personally buy from. If you wouldn’t trust them to sell to you, they’re not the right fit.

7. Set Clear Expectations and Watch for Early Results
   Your first AE should start closing deals within one sales cycle. If they’re not on the board by then, it’s a red flag. You don’t have time to wait for someone to “ramp up” indefinitely. Early-stage startups can’t afford to waste leads on someone who can’t close.

This hire is critical, so take your time and be flexible — but don’t settle for someone you wouldn’t buy from yourself.  At least don’t settle there.  Be honest.

The right AE will not only close deals but will also help you refine your sales process and set the foundation for scaling your team.