Dear SaaStr: What Are Your Top Tips to Building Your First Sales Team?

Dear SaaStr: What Are Your Top Tips to Building A First Sales Team?

When it comes to sales hires, the key is to approach it methodically and avoid common pitfalls.

Here’s how I’d break it down:

1. Hire Two Reps to Start.  You have to A/B test it.: Always hire at least two sales reps initially. Classic SaaStr advice that is as true today as ever.  This allows you to compare performance and figure out what works. If you only hire one, you won’t know if success (or failure) is due to the individual or your process. It’s essentially an A/B test for your sales strategy.

2. Hire Reps You’d Buy From. For real.  Be honest here: This is non-negotiable. If you wouldn’t buy your own product from them, don’t hire them. It doesn’t matter how polished their resume is or how smooth they are in interviews. You need to trust that they can sell your product authentically and effectively ‌2‌‌9‌.

3. Micromanage Early On.  Until They Hit Quota: In the founder-led sales stage, you’ll need to be heavily involved. Train by osmosis—be there all day, every day, to guide and support your reps. Later, you can develop formal training processes, but in the beginning, your involvement is critical.

4. Hire Smarter, Not Just Experienced.  And Don’t Fall In Love With Their LinkedIn: Early on, prioritize intelligence and adaptability over deep domain expertise. Your first reps need to learn your product inside and out, and the learning curve will be steep. Smarter reps will adapt faster and become product experts more quickly.  And whatever you do, don’t be blinded by the fact they worked at some well known tech company.

5. Segment Your Sales Team as You Scale: As you grow, start segmenting your sales team into Small, Medium, and Large customer segments. This helps reps specialize and focus on the right type of customer. Around $10M ARR, you’ll also need to bring in a VP of Sales to structure and scale the team effectively.

6. Invest in Sales Ops Early: Once you have 8-10 salespeople, you’ll need a Sales Ops/Enablement professional to manage training, onboarding, territories, and compensation plans, unless your VP Sales happens to be great at this. Don’t wait too long to make this hire—it’s critical for scaling efficiently.

7. Trust Your Sales Leaders.  Once They Earn It, Especially: When you transition from founder-led sales to a VP or CRO-led model, you need to trust your sales leaders. Let them hire a diverse, heterogeneous team and give them room to run. A great sales leader will find and nurture talent that you might not have considered.  But that trust does have to be earned.  They have to increase sales at least a bit to earn it.

8. Don’t Wait Too Long to Hire a VP of Sales: Many founders wait until $5M or even $10M ARR to hire a VP of Sales. That’s too late. By $1M-$1.5M ARR, you should start thinking about this hire. A great VP of Sales will accelerate your growth and help you avoid costly mistakes.

9. Be Ready to Invest: Building a world-class sales team isn’t cheap. By the time you’re at $1M-$1.5M ARR, you should be prepared to invest $3M-$4M+ in your first real sales and marketing team. This investment will pay off in faster growth and better results.  More here.

10. Move On Quickly from Poor Performers: If a rep isn’t closing deals, don’t hesitate to let them go. Poor performers cost you money and drag down the team. Focus on building a team of high performers who can consistently hit their quotas.

And a great deep dive on this and more here: