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How to Choose the Right Sales Leader for Small Teams

Writer's picture: DataBased UtahDataBased Utah

Hiring the right sales leader can be one of the most pivotal decisions for a growing company, especially when your sales team consists of fewer than 20 people. At DataBased, we’ve seen this scenario play out time and time again—sometimes with great success, and other times with costly missteps. Let’s explore the key considerations and strategies to help you make the right choice for your team.


 

Avoiding the "VP Trap"

One of the most common mistakes CEOs make is defaulting to hiring a flashy Vice President of Sales. While the title might sound impressive, it often doesn’t align with the needs of a small sales organization. Many seasoned VPs have been out of the trenches for too long, focusing on high-level strategies rather than the day-to-day coaching and operational leadership that small teams require.

For teams under 20 people, you likely need a hands-on leader who can:

  • Actively manage and coach sales reps.

  • Develop and implement scalable sales processes.

  • Build playbooks and guide junior team members.

If your sales organization has fewer than 10 people, a Director or even a Sales Manager might be a better fit than a VP.


 

Compensation Considerations

Another pitfall is overpaying for a role that doesn’t require an executive-level salary. Here are some general guidelines:

  • For a Director of Sales overseeing a team of 10-20 people, total compensation should generally not exceed $300,000. Anything beyond this may indicate you’re overpaying or hiring someone misaligned with your current stage.

  • For smaller teams (fewer than 10 people), consider hiring a Sales Manager with 5-7 years of strong sales experience. Their compensation should range between $200,000 and $250,000, depending on their leadership skills and track record.

If your budget is tight, consider offering equity instead of high cash compensation to attract talent who is invested in your long-term success.


 

Matching Leadership to Team Size and Deal Complexity

Your choice of sales leader should also align with the complexity of your sales process. For example:

  • If your average deal size is less than $250,000 and falls in the $5,000 to $75,000 range, you don’t need a VP of Sales. A Director or Sales Manager can effectively handle the responsibilities while staying connected to the details.

  • Leaders of small teams need to be willing to get into the weeds—whether that’s helping BDRs craft sequences or assisting AEs in closing deals.

High-level strategy is important, but for small teams, execution and operational leadership matter more.


 

Avoiding the "Revolving Door"

In some regions, particularly in startup hubs, we’ve seen companies cycle through CROs, VPs, and Directors every 6 to 18 months. This churn often stems from misaligned expectations and overhiring for the stage of the company. Such turnover can be devastating, leading to layoffs, loss of team morale, and even the departure of key team members who were loyal to the outgoing leader.

To avoid this, focus on finding a leader who:

  • Has the right level of experience for your team size and stage.

  • Is excited to grow with your company, rather than seeking a purely executive role.

  • Aligns with your company’s culture and values.


 

Conclusion

The right sales leader can drive tremendous growth, but only if their skills and approach align with your team’s size, structure, and goals. Avoid the temptation to hire based solely on titles or pedigree. Instead, focus on finding someone who can roll up their sleeves, build processes, and lead by example.


At DataBased, we specialize in helping companies make these critical decisions. If you’re navigating the tricky waters of hiring a sales leader, let’s talk—we’d love to help you find the perfect fit for your team.


Ready to take your sales team to the next level?
Contact us for more insights and personalized support.


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