The Sales Leadership Gap in Mid-Market Companies: Why Promoting Your Top Rep Isn't the Answer

I've watched this story play out dozens of times over my career.

A company has a sales rep who's crushing it. Top of the leaderboard. Respected by peers. Hungry for more responsibility. The logical next step? Promote them to sales manager.

It feels right. It rewards performance. It keeps your best person from leaving.

And according to research from Harvard Business School, it's a mistake 82% of the time.

The Data Is Uncomfortable

In 2018, researchers Alan Benson, Danielle Li, and Kelly Shue published a study in Harvard Business Review that finally put hard numbers behind what many executives have suspected for years. They examined promotion decisions at 214 firms covering more than 50,000 salespeople—and the findings were stark.

According to the study, each higher sales performance rank corresponded to a 15% higher probability of being promoted to management. That makes intuitive sense—we promote our top performers.

But here's where it gets interesting: each higher sales rank also correlated with a 7.5% decline in the performance of that manager's subordinates after the promotion.

The researchers didn't mince words. As they put it in Harvard Business Review: "Firms tend to promote top sales workers into management, even though they become the worst managers."

In other words, companies systematically promote their best individual performers into roles where they systematically underperform. The Peter Principle isn't satire—it's data.

Why This Happens

I've spent 25 years building sales organizations at Cisco, Splunk, Cloudflare, and others. I've promoted hundreds of people into leadership roles. And I've learned—sometimes the hard way—that selling and managing require fundamentally different skills.

Top salespeople are often driven by personal achievement, individual recognition, and the thrill of closing. They're competitive, sometimes to a fault. They succeed by being the best person on the team.

Management requires a completely different orientation. Success as a manager means making other people successful. It requires patience, delegation, coaching, and the willingness to step back and let others take credit.

The very traits that make someone exceptional at closing deals often make them a frustrating, micromanaging, or disengaged leader. The superstar closer who motivated themselves through personal competition suddenly has to motivate eight different people with eight different drivers.

The Scope of the Problem

If this were an isolated issue, companies could manage around it. But the research suggests it's systemic.

Most companies get manager selection wrong. According to Gallup's research on managerial talent, organizations fail to choose the candidate with the right talent for the job 82% of the time. Gallup also found that only about one in ten people possess the natural talent required to manage effectively.

First-time managers receive almost no training. Research from the Center for Creative Leadership found that almost 60% of first-time managers never receive any management training when they transition into leadership. They're expected to figure it out on their own—often while still carrying a personal quota.

Sales manager training is an afterthought. A 2025 study by SBI and the Revenue Enablement Society found that nearly 40% of enablement teams have no dedicated sales manager training program whatsoever. Of the companies that do have programs, only 34% actually delivered training to their managers in the preceding twelve months.

The coaching gap drives turnover. According to research cited by Zenger Folkman, up to 60% of salespeople say they're more likely to leave their job if their manager is a poor coach. In a tight labor market, that's not a performance problem—it's a retention crisis.

Employee engagement has collapsed. Gallup's State of the Global Workplace report found that the global percentage of engaged employees fell to just 21% in 2024—a drop that cost the world economy an estimated $438 billion in lost productivity. Manager engagement saw the sharpest decline, falling from 30% to 27%.

And here's the connection that matters most: according to Gallup, managers account for at least 70% of the variance in employee engagement scores across business units. When your managers struggle, everything downstream struggles with them.

What This Costs You

The consequences aren't abstract. They show up in your pipeline, your forecast, and your P&L.

Declining quota attainment. When managers can't coach effectively, reps underperform. The Harvard Business Review research showed measurable declines in subordinate performance under promoted top performers. Multiply that across your team and you're leaving significant revenue on the table.

Forecasting chaos. Untrained managers often lack the discipline to inspect pipeline rigorously or the experience to know when a rep is being optimistic versus realistic. The result is forecasts that consistently miss—making it impossible to plan hiring, inventory, or capacity.

Turnover you can't afford. When your best reps leave because their manager can't develop them, you lose twice: the cost of replacement (recruiting, onboarding, ramp time) and the lost production while the seat sits empty or underperforms.

A leadership vacuum. If you're not developing managers internally, where will your next generation of sales leaders come from? Companies that don't invest in leadership development find themselves perpetually dependent on external hires—expensive, risky, and slow to ramp.

The companies that invest in manager development see the difference. According to the SBI and Revenue Enablement Society study, organizations prioritizing sales manager development achieve 7% higher quota attainment than those that don't. That's not a marginal improvement—for a company doing $50M in revenue, that's potentially $3.5M in additional sales.

Why Mid-Market Companies Get This Wrong

If the data is this clear, why do so many mid-market companies keep making the same mistake?

Promotion is the only reward lever. In many organizations, the only way to recognize and retain top performers is to promote them. There's no senior individual contributor track, no way to increase compensation without adding management responsibility. So the best sellers get pushed into management whether they're suited for it or not.

Training feels like a luxury. When you're running lean—and every mid-market company is running lean—investing in manager development feels like a nice-to-have. There's always a more urgent priority: a quarter to close, a territory to cover, a deal to save.

Nobody models what good looks like. If your own path to leadership didn't include structured development, you may not realize what's missing. Many sales leaders assume that figuring it out on your own is just how it works.

The feedback loop is slow. Unlike a missed quota, which shows up immediately, the damage from poor management unfolds over months. By the time engagement scores drop and turnover spikes, the root cause is obscured.

What Good Looks Like

I've been fortunate to build teams at companies that treat leadership development as a competitive advantage. The difference between organizations that develop leaders and those that don't is stark.

They separate rewards from roles. The best organizations create career paths that allow top performers to advance without becoming managers. Senior account executive roles, strategic account positions, and specialist tracks let people grow their compensation and influence while staying in roles that match their strengths.

They select for management potential, not just sales performance. The Harvard Business Review research found one telling predictor of management success: collaboration. Salespeople who worked complex deals with multiple stakeholders—and shared credit across teams—became significantly better managers. They'd already practiced the skills management requires.

They invest before the promotion. Organizations that develop leaders don't wait until someone is struggling in a new role. They identify high-potential future leaders early and begin developing coaching, communication, and strategic thinking skills while those people are still individual contributors.

They provide real training, not check-the-box programs. A two-day management seminar doesn't create capable leaders. The companies that get this right invest in ongoing development: coaching from experienced leaders, regular feedback loops, structured skill-building over months and years.

They hold managers accountable for development, not just numbers. In high-performing organizations, managers are evaluated on the growth of their people, not just the growth of their pipeline. Promotion to senior management requires demonstrated ability to develop talent.

Over my career, I've developed more than 100 sales professionals to President's Club recognition. That didn't happen by accident—it happened because the organizations I worked for invested in giving managers the tools, training, and accountability to develop their people.

The Path Forward

If you recognize your company in these patterns, the path forward isn't complicated—but it does require intention.

Audit your current state. How did your current managers get their roles? What training did they receive? How do you measure their effectiveness beyond quota attainment? Be honest about the gaps.

Create alternative career paths. If promotion to management is the only way to reward top performers, you're forcing people into roles they may not want and won't excel in. Build tracks that let great sellers stay great sellers.

Invest in development before promotion. Identify the people with genuine leadership potential—not just top sales numbers—and begin developing them now. Mentorship, stretch assignments, and coaching should precede the promotion, not follow it.

Provide real support for new managers. The transition from seller to manager is one of the hardest in any career. Don't expect people to figure it out alone. Pair new managers with experienced mentors, provide structured training, and create safe spaces for them to learn.

Measure what matters. Track manager effectiveness through subordinate performance, engagement scores, and retention rates—not just team quota attainment. What gets measured gets managed.

The leadership gap in mid-market sales organizations is real, expensive, and fixable. The companies that close it will build sustainable competitive advantage. The ones that don't will keep wondering why quota attainment is declining, why their best people keep leaving, and why growth feels harder every year.

Andrew Devlin is a Fractional VP of Sales who helps CEOs of $10M-$100M companies build predictable revenue through sales infrastructure and leadership development. Over his 25-year career at Cisco, Splunk, Cloudflare, and other high-growth organizations, he has developed more than 100 sales professionals to President's Club recognition.

Ready to develop your sales leaders?

Sources

• Benson, Li, and Shue, "Promotions and the Peter Principle," The Quarterly Journal of Economics (2019); Harvard Business Review (March 2018). Study of 214 firms and 53,035 sales employees.

• Gallup, "State of the American Manager: Analytics and Advice for Leaders." Findings on manager selection and engagement variance.

• Gallup, "State of the Global Workplace: 2025 Report." Global engagement fell to 21% in 2024.

• SBI and Revenue Enablement Society, "Closing the Training Gap for Frontline Sales Managers" (March 2025).

• Center for Creative Leadership, "Common Challenges Faced by New Managers."

• Zenger Folkman research on sales coaching and turnover.