Dear SaaStr: I’m a Top SMB Account Executive. I Think I Want to Go Into Management, But I’m Not Sure
First off, you’ve got a solid foundation—6+ years as a successful IC. That’s a lot of experience to leverage, and it’s clear you know how to close deals and drive revenue.
But pivoting to sales leadership is a different game. It’s not for most.
It’s less about being the top performer yourself and more about building and scaling a team that can perform at a high level. Let’s work through some key questions to help you figure out if this is the right move:
1. Do You Enjoy Coaching and Developing Others?
Sales leadership is all about enabling your team to succeed. Do you get energy from mentoring others, sharing your playbook, and seeing them win? If you’ve already been informally coaching colleagues or helping others close deals, that’s a good sign.
2. Are You Ready to Step Away from Being the Top Performer?
As a leader, your success is measured by your team’s success, not your own individual performance. Are you comfortable stepping out of the spotlight and focusing on building systems, processes, and people instead of closing deals yourself?
3. Do You Have a Vision for Scaling SMB Sales?
With your experience, you’ve probably seen what works and what doesn’t in SMB sales. Can you articulate a clear strategy for hiring, onboarding, and scaling a team to dominate the SMB market? Sales leadership is as much about strategy as it is about execution.
4. Are You Comfortable with Accountability at a Higher Level?
Too many melt here. As an individual AE, missing a month or quarter is not the end of the world. As a leader, it may seem like it. As a leader, you’ll be responsible not just for your own quota but for the entire team’s performance. Are you ready to own that responsibility and navigate the pressure that comes with it?
5. What’s Your Appetite for Learning? Be Honest.
Leadership requires a different skill set than being an IC. Are you willing to invest the time and effort to learn about managing people, building culture, and driving cross-functional collaboration? It’s a steep learning curve, but one that can be incredibly rewarding.
6. What’s Your Long-Term Goal?
Do you see sales leadership as a stepping stone to something bigger, like becoming a CRO or even running your own company? Or are you looking for a new challenge that aligns with your strengths? Understanding your “why” will help you decide if this is the right move.
7. How Do You Feel About Process and Structure?
Most sales reps don’t enjoy it. SMB sales can be fast and scrappy, but scaling a team requires process and structure. Are you excited about building playbooks, implementing tools, and creating repeatable systems? If that sounds like a chore, leadership might not be the best fit.
8. Have You Talked to Other Sales Leaders?
Reach out to sales leaders you respect and ask them about their day-to-day. What do they love about the role? What challenges do they face? This can give you a clearer picture of what to expect and whether it aligns with your strengths and interests.
9. Can You Recruit a Great Team? For Real?
So many sales execs think they can — and stumble hard here. Be honest. How will you recruit the best? Not just folks willing to work for you?
If you’re leaning toward making the pivot, I’d suggest starting small. Volunteer to mentor junior reps or take on a team lead role if that’s an option.
This will give you a taste of leadership without fully committing. And if you decide to go for it, your SMB expertise is a huge asset—you’ve already lived and breathed this market, which gives you a head start in building a high-performing team.
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