Why Some GTM Leaders Scale—and Others Stall

Building a high-performance GTM (Go-To-Market) team isn’t about having the perfect strategy—it’s about knowing when to be hands-on, when to step back, and how to empower your team to execute at the highest level.

Most GTM leaders start in execution mode—selling, strategizing, hiring, and optimizing—all at once. But the biggest mistake they make? Not evolving their leadership style as the company scales.

The best leaders don’t just push harder; they build systems, develop talent, and create scalable revenue engines.

Let’s dive in.

The Player-Coach Balance: Knowing When to Lead from the Front vs. the Sidelines

In the early days of a startup, the GTM leader is the sales team. They make calls, refine messaging, and figure out what works. But as the company scales, the role needs to evolve—otherwise, they become the bottleneck.

How the Balance Shifts as You Scale

$0 - $10M ARR (80% Player, 20% Coach)

• Closing deals, testing pricing, and refining the GTM motion.
• Leadership means hands-on execution, not just strategy.

$10M - $25M ARR (50% Player, 50% Coach)

• Still working key deals but shifting focus to systematizing what works.
• Building sales playbooks and scaling repeatable processes.
• Hiring and onboarding become as critical as selling.

$25M - $50M ARR (20% Player, 80% Coach)

• Direct selling is now the exception, not the rule.
• The focus shifts to team performance and revenue process optimization.
• The leader is solving bottlenecks, not running deals.

$50M+ ARR (100% Coach, 0% Player)

• The team runs the GTM motion without leadership in the trenches.
• The leader focuses on org-wide revenue strategy and long-term growth.

When Staying Hands-On Becomes a Bottleneck

This transition from player to coach isn’t always smooth. Many GTM leaders struggle to step back, fearing that if they aren’t directly involved in deals, revenue will suffer.

But the reality? Holding onto execution for too long doesn’t drive more revenue—it slows it down.

The best leaders know when to shift their focus from closing deals to building a scalable system that others can execute.

Let’s look at real-world examples of leaders who got this right—and those who didn’t.

The VP Who Scaled by Letting Go

This makes me think about one of my friends who was a first-time VP of Sales at a high-growth SaaS company and was the top seller early on. But as the company approached $15M ARR, they were still involved in every major deal.

The problem? Their team wasn’t developing the skills to close on their own.

The turning point came when they:

• Shifted from selling to coaching.
• Standardized messaging and built training playbooks.
• Empowered reps to own their pipeline without interference.

The result? Revenue doubled in two years, and reps outperformed the VP’s personal closing rates.

Staying Hands-On Without Micromanaging

Letting go is hard for many leaders. They fear losing control, so they insert themselves into every decision, which slows everything down.

The key? Stay engaged without micromanaging.

How to Strike the Balance

Build Autonomy Through Clear Expectations

• Define success, but let the team determine the execution.
• Move from chasing updates to creating a culture of proactive reporting.

Use Data to Track Progress—Not Gut Feel

• Set up dashboards to monitor pipeline health, conversion rates, and sales cycle trends.
• Step in when data flags an issue, not because you feel uneasy.

Encourage Innovation While Guiding Outcomes

• Give reps space to test and iterate.
• Coach through results, not by controlling every move.

The Common Mistake: The Micromanager Who Killed Morale

At another startup, a VP of Sales required daily check-ins where reps had to justify every deal. Instead of coaching, they:

• Overrode rep decisions.
• Rewrote prospect emails.
• Created an environment of fear instead of trust.

The result? 50% of the team quit within a year.

Takeaway: There’s a difference between tracking performance and distrusting your team. Leaders should guide, not suffocate.

The Three Leadership Traits Every GTM Team Needs in 2025

The best leaders in 2025 won’t be the ones who push the hardest. They’ll be the ones who adapt the fastest.

1. Empathy as a Driver for Team Trust

I joined a company once that had some pretty high turnover, which was understandable given they shifted their strategy, which lead to a lot of change, but I dug a little deeper to understand what was the driver or the turnover in the sales org....Burnout.

I could have chalked it up to "things will get better", but Instead of ignoring it, I:

• Created a mentorship program for new reps.
• Held monthly one-on-one check-ins that focused on personal development.
• Gave top reps autonomy to structure their workflows.

The result? Turnover dropped by 40%, and sales productivity increased.

2. Adaptability in a Rapidly Changing Market

A SaaS company targeting startups saw a sudden slowdown in buying. Instead of waiting it out, they:

? Expanded ICP targeting to include mid-market companies.

? Adjusted pricing models to offer flexible payment terms.

? Trained reps on a new outbound strategy tailored to enterprise buyers.

The result? Revenue grew 15% year over year despite market downturns.

3. Data-Driven Decision Making

A CRO at a $50M ARR company didn’t just track revenue. They:

• Monitored pipeline health to spot risk early.
• Used win/loss data to refine sales messaging.
• Optimized sales cycle velocity, cutting 18 days off the buying process.

The result? More accurate forecasting and improved close rates.

Final Takeaways: Scaling GTM Leadership the Right Way

The best GTM leaders aren’t just great sellers—they are great builders.

1. Know when to step back. If you’re still closing deals at $20M ARR, you’re slowing the team down.
2. Trust your team, but track the right data. Data should inform decisions, not create over-surveillance.
3. Adapt fast. What worked last year won’t work next year.

The real test of a GTM leader isn’t how well they sell—it’s how well their team sells without them.

Which leadership shift has been the hardest for you?