Scaling a startup is hard. Scaling a startup’s sales team? Even harder. I’ve seen founders make the same mistakes over and over—overpaying for roles they don’t need, hiring too senior too soon, and burning cash on titles instead of talent.
Let’s break down how to avoid these pitfalls, how much you should really be paying for sales roles, and when it’s time to promote from within. If you’re looking to build a high-performing sales team without draining your budget, keep reading.
The Problem: Overpaying and Title Inflation
One of the most common mistakes I see in startups is title inflation.Founders think they need a “VP of Sales” or “CRO” to scale, but that’s often overkill. These senior leaders come with a hefty price tag and a strategic mindset—one that doesn’t always match the tactical needs of an early-stage company.
At the same time, companies are overpaying for roles that don’t require high salaries. They hire “senior” account executives when what they really need are hungry reps with a few years of experience who are ready to prove themselves.
The Solution: Hire for Your Stage
To avoid burning cash, you need to hire for the stage your company is actually at, not the stage you hope to be at in five years. Here’s how:
Stage 1: Founder-Led Sales
Who to Hire:
Account Executive Level 2 or 3 (AE2/AE3)
3 to 5 years of experience, pipeline generators, and capable of taking direction from the founder.
Why:At this stage, you’re still proving that your product can sell consistently without you. You don’t need a sales manager because you, as the founder, are the sales manager. What you need are reps who are hungry, coachable, and willing to build alongside you.
Pay Range:
$75K to $100K annually
This is achievable outside of expensive markets like San Francisco or New York.
Common Mistake:Hiring a sales manager before you’ve proven that others can sell your product. If you can’t transition from founder-led sales to rep-led sales, it’s too early to bring in a leader.
Stage 2: Scaling from 2 to 8 Reps
Who to Hire:
Promote from within if possible.
If not, hire a Sales Manager 1:
1 to 2 years of management experience
4 to 5 years of selling experience
Still humble, open to learning, and adaptable to your vision.
Why:You’re now trying to prove that multiple reps can hit quota. A Sales Manager 1 can coach reps and maintain consistency without trying to overhaul your playbook.
Pay Range:
$175K to $225K annually
Common Mistake:Hiring too senior, too soon. A VP of Sales at this point will likely be too strategic and not tactical enough to get in the trenches with your team.
Stage 3: Building a Repeatable Sales Engine
Who to Hire:
Sales Manager 2:
3+ years of leadership experience
5+ years as a rep
Proven ability to lead teams but still willing to engage in day-to-day execution.
Why:You’re now scaling to multiple sales teams, and you need someone who can replicate what’s working across different teams. This role is about maintaining consistency, scaling processes, and ensuring your playbook is replicable.
Pay Range:
$225K to $275K annually
Common Mistake:Hiring a CRO or VP of Sales before you have a repeatable sales engine. These leaders will want to build strategy and systems that your company isn’t ready for yet.
Stage 4: Moving from Sales Execution to Sales Strategy
Who to Hire:
Sales Manager 3:
4+ years of leadership experience
8-12 years of total sales experience
Proven leader with a strategic mindset but still willing to get tactical.
Why:You’re finally ready for a strategic sales leader who can guide high-performing teams and influence the direction of your go-to-market strategy.
Pay Range:
$280K to $340K annually
Common Mistake:Jumping straight to this level without building a strong foundation. If you don’t have multiple sales teams consistently hitting quota, you’re not ready for a strategic leader.
The Trap to Avoid: Hiring Too Senior, Too Soon
I recently spoke to a founder whose company hit $20M ARR but was struggling to grow. They kept hiring senior sales leaders who wanted to focus on strategy rather than execution.The result? A disconnect between leadership and the team, stalled growth, and wasted budget.
The lesson here is simple: Don’t hire for strategy until you’re ready to scale.If you’re still proving product-market fit or transitioning from founder-led sales, you need hands-on leaders who can execute, not just strategize.
Final Thoughts: Build from Within
Promoting from within is always the best option when scaling.Your top reps already know your product, market, and customers. They’re invested in your success and can grow into leadership roles organically.
If you don’t have anyone ready, hire the least senior role that can get the job done. This keeps your budget lean and your team adaptable.
Actionable Takeaways:
Hire for Your Stage: Match your hires to where your startup is—not where you hope it’ll be.
Promote from Within: Develop your top performers into leaders to maintain continuity.
Pay Smart: Don’t overpay for roles that don’t require it.
Avoid Title Inflation: Hire for capability, not titles.
Be Patient with Strategy: Only bring in strategic leaders once you have a repeatable sales engine.
Conclusion: Scale Smart, Grow Fast
Building a high-performing sales team isn’t about titles or big salaries.It’s about hiring smart, promoting from within, and scaling at the right pace.Avoid the common mistakes of overpaying, title inflation, and hiring too senior too soon.Your budget—and your growth—will thank you.
Are you struggling with scaling your sales team? Let’s chat. Drop a comment or DM me, and let’s find a solution that works for your startup’s unique stage.