So a little ways back Harry Stebbings and I did a deep dive on how to build your first sales team.  A lot of it was great, some of it needed a refresh, so I updated it and edited it to bring it into 2025.

It’s a great quick 20+ minute deep dive on many top SaaStr themes.  When to hire your first VP of Sales, what to expect from them, and more:

5 Critical Phases of Building Your SaaS Sales Machine: What Actually Works

The Early Days: Founder as Chief Revenue Officer

The #1 mistake we see? Founders raising a big round and immediately hiring a bunch of sales reps without a proven playbook. Don’t do this. Instead:

• Have the founder build and own the first sales playbook. If you’re not a natural salesperson, find a co-founder or very early employee who can. External hires at this stage fail 90% of the time.
• Don’t hire your VP of Sales too early. The best ones won’t join pre-$10M ARR anyway. They know better.

The Magic Formula: Start With Two Rockstar Reps

Here’s what actually works 80% of the time:

1. Hire two somewhat quirky sales reps that can hit quota
2. Make sure they’ve sold at your price point and ACV before
3. Ask yourself: “Would I buy from this person?”

What makes a rep truly 10x? It’s not what you think. The best reps can modify the playbook on the fly based on different personas and use cases. The other 90% just follow the script and fail.

Getting Quotas Right: A Framework That Works

Early-stage quota setting is tricky, but here’s what works:

• First 3-6 months: 100% commission on closed deals. Help them get going.
• At scale: Quota should be 3-5x fully-loaded comp
• Enterprise deals: Don’t panic about long sales cycles. They don’t matter once you hit $20-30M ARR.

The Founder’s Paradox: More Sales Time As You Scale

Here’s something counterintuitive: The best SaaS founders often spend MORE time on sales as they scale, not less. Look at Jeff Lawson at Twilio.

But there’s a key shift: Move from prospects to customers. Your time is better spent with folks already paying you money.

Building Your “Magic” Management Team

Want to avoid founder burnout? Here’s what the very best companies do:

• Find VPs who don’t just execute – they carry the load
• Look for “Romantics” – people who want more than just a paycheck
• Aim for 50% of your VPs to be true load-carriers

A key learning: Even if it takes 2 years to find these magical VPs, wait for them. When you find someone who truly shares the vision and can carry concrete blocks on their back – that’s when the real scaling begins.

The Bottom Line

Stop trying to scale sales too quickly. Instead, focus on:

1. Building a repeatable playbook yourself
2. Finding two great reps who’ve sold at your price point
3. Setting realistic quotas that normalize as you scale
4. Staying involved in sales, but shifting focus to customers
5. Building a team of “Romantics” who share your vision

Get these right, and the rest tends to fall into place.