Ep 42: Why Sales Leaders Fail – And How to Win Instead

Timestamps:

07:16 They Ignore RevOps—and Just “Hope” Deals Happen

15:12 They Chase the Number and Ignore the Game

15:48 If You Haven’t Baseline Rated Your Team, You’re Leading Blind

26:27 Lone Wolves Get Exposed as They Rise

27:13 Your Sales Engineers, CSMs, and Marketing Team Will Save You—Or Bury You

31:06 They Can’t Drive Change (And Get Stuck in the Status Quo)

37:06 You’re Only As Strong As Your Worst Performer

About Bart Fanelli:

Bart Fanelli is a CEO and Co-Founder of Skillibrium and he was CRO at Outsystems and VP of Global Field Success at Splunk. Bart has led teams in scaling up from $65M to $1.7B, and another company scaled from $100M to $300M in three years. Bart is an author the book “The Success Cadence,”  … so get ready to take notes for what he is about to say.

Sales leadership is one of the toughest roles in business. The expectations are sky-high, the pressure is relentless, and the margin for error is razor-thin. Most sales leaders don’t make it past the 18-month mark—not because they aren’t talented, but because they fall into avoidable traps.

They Chase the Number and Ignore the Game

Why This Fails:

Short-term thinking kills long-term success. Leaders focus on immediate results without understanding the system. Sales leaders often fall into this trap because they are focused on immediate results rather than long-term sustainability. The problem is that when leaders push for numbers without fixing the underlying issues, they create a cycle of poor forecasting, low rep engagement, and unsustainable deal pressure. This leads to burnout, poor retention, and ultimately, missed targets.

Do This Instead:

•     Understand what you’ve inherited
•     Fix the fundamentals first
•     Shift from ‘chasing’ to ‘engineering’ revenue

Many leaders make the mistake of thinking they can fix these issues overnight, but effective change requires a strategic and phased approach. Leaders who take the time to understand their team, align with finance and RevOps, and establish a repeatable system see long-term success. Those who ignore these fundamentals end up constantly firefighting instead of leading.

Lone Wolves Get Exposed as They Rise

Why This Fails:

What made you a top rep won’t make you a great leader. Lone-wolf behavior doesn’t scale. Sales leaders often fall into this trap because they are focused on immediate results rather than long-term sustainability. The problem is that when leaders push for numbers without fixing the underlying issues, they create a cycle of poor forecasting, low rep engagement, and unsustainable deal pressure. This leads to burnout, poor retention, and ultimately, missed targets.

Do This Instead:

•     Earn trust before giving orders
•     Shift from ‘star player’ to ‘coach’
•     Build a bench, not just a pipeline

Many leaders make the mistake of thinking they can fix these issues overnight, but effective change requires a strategic and phased approach. Leaders who take the time to understand their team, align with finance and RevOps, and establish a repeatable system see long-term success. Those who ignore these fundamentals end up constantly firefighting instead of leading.

They Ignore RevOps—and Just “Hope” Deals Happen

Why This Fails:

Revenue isn’t magic—it’s math. Ignoring RevOps leads to poor forecasting and inefficiencies. Sales leaders often fall into this trap because they are focused on immediate results rather than long-term sustainability. The problem is that when leaders push for numbers without fixing the underlying issues, they create a cycle of poor forecasting, low rep engagement, and unsustainable deal pressure. This leads to burnout, poor retention, and ultimately, missed targets.

Do This Instead:

•    Master forecasting
•    Invest in process efficiency
•    Make RevOps your superpower

Many leaders make the mistake of thinking they can fix these issues overnight, but effective change requires a strategic and phased approach. Leaders who take the time to understand their team, align with finance and RevOps, and establish a repeatable system see long-term success. Those who ignore these fundamentals end up constantly firefighting instead of leading.

They Can’t Drive Change (And Get Stuck in the Status Quo)

Why This Fails:

Seeing the problem isn’t enough—you have to fix it. Resistance and inaction kill change. Sales leaders often fall into this trap because they are focused on immediate results rather than long-term sustainability. The problem is that when leaders push for numbers without fixing the underlying issues, they create a cycle of poor forecasting, low rep engagement, and unsustainable deal pressure. This leads to burnout, poor retention, and ultimately, missed targets.

Do This Instead:

•    Make change non-negotiable
•    Build alliances internally
•    Execute in phases

Many leaders make the mistake of thinking they can fix these issues overnight, but effective change requires a strategic and phased approach. Leaders who take the time to understand their team, align with finance and RevOps, and establish a repeatable system see long-term success. Those who ignore these fundamentals end up constantly firefighting instead of leading.

Your Sales Engineers, CSMs, and Marketing Team Will Save You—Or Bury You

Why This Fails:

Sales isn’t a solo sport. SEs, CSMs, and marketing teams are critical, but bad leaders neglect them. Sales leaders often fall into this trap because they are focused on immediate results rather than long-term sustainability. The problem is that when leaders push for numbers without fixing the underlying issues, they create a cycle of poor forecasting, low rep engagement, and unsustainable deal pressure. This leads to burnout, poor retention, and ultimately, missed targets.

Do This Instead:

•    SEs: Treat them like partners, not resources
•    CSMs: Align on retention goals
•    Marketing: Demand quality, not just volume

Many leaders make the mistake of thinking they can fix these issues overnight, but effective change requires a strategic and phased approach. Leaders who take the time to understand their team, align with finance and RevOps, and establish a repeatable system see long-term success. Those who ignore these fundamentals end up constantly firefighting instead of leading.

If You Haven’t Baseline Rated Your Team, You’re Leading Blind

Why This Fails:

You don’t actually know who’s good without structured assessment. Guessing leads to poor management decisions. Sales leaders often fall into this trap because they are focused on immediate results rather than long-term sustainability. The problem is that when leaders push for numbers without fixing the underlying issues, they create a cycle of poor forecasting, low rep engagement, and unsustainable deal pressure. This leads to burnout, poor retention, and ultimately, missed targets.

Do This Instead:

•    Use a skill/will matrix
•    Coach the coachable, cut the lost causes
•    Personalize development plans

Many leaders make the mistake of thinking they can fix these issues overnight, but effective change requires a strategic and phased approach. Leaders who take the time to understand their team, align with finance and RevOps, and establish a repeatable system see long-term success. Those who ignore these fundamentals end up constantly firefighting instead of leading.

You’re Only As Strong As Your Worst Performer

Why This Fails:

Your bottom 30% will sink the ship. Weak performers drag down culture and performance. Sales leaders often fall into this trap because they are focused on immediate results rather than long-term sustainability. The problem is that when leaders push for numbers without fixing the underlying issues, they create a cycle of poor forecasting, low rep engagement, and unsustainable deal pressure. This leads to burnout, poor retention, and ultimately, missed targets.

Do This Instead:

•    Coach up or out
•    Set a hard deadline for progress
•    Protect your top and mid-performers

Many leaders make the mistake of thinking they can fix these issues overnight, but effective change requires a strategic and phased approach. Leaders who take the time to understand their team, align with finance and RevOps, and establish a repeatable system see long-term success. Those who ignore these fundamentals end up constantly firefighting instead of leading.

Summary

Sales leadership is brutal. The failure rate is high. But if you understand the game—align with finance, baseline your team, drive change, and stay coachable—you can win. Most leaders don’t fail because they’re bad at selling. They fail because they don’t lead. Get that part right, and everything else follows. 

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