Full-service coaching for executive leadership teams

The Climb isn’t coaching, it’s a full-contact rebuild for executive teams who are done playing small.

You’ll get Jess in your corner - no filters. Just systems that scale, execution that sticks, and the accountability you’ve been avoiding. Monthly owner calls, direct access, and zero room for excuses.

This is where chaos dies and growth takes over. Space is limited.

I don’t cheerlead, I challenge. If you can’t handle real accountability, this isn’t your climb.

This program is for you if…

You’re running a $15M+ machine and it’s starting to wobble. Sloppy team. Slower moves. Execution’s suffering and you’re sick of playing operational whack-a-mole. You’re a growth-obsessed CEO ready to lock your crew in, kill the chaos, and eliminate bottlenecks—fast.

The Climb delivers results in 90 days. No frills. No guesswork. Just you, your team, and a system that wins.

What Will You Get Out of The Climb?

When you commit to The Climb, you don’t just get coaching - you get systems that stick, language that aligns, and a new level of performance that doesn’t fade after the program ends.

  • Clearer org chart, cleaner accountability. No more fuzzy roles or finger-pointing. Everyone knows what they own and how to win.

  • A leadership team that actually leads. Key players will step up, speak the language, and drive the strategy needed.

  • Faster, better decisions. You’ll spend less time in meetings and more time executing. Alignment gets tighter. Efficiency increases.

  • Scalable systems that stick. From meeting rhythms to scorecards - you’ll build infrastructure that works at $15M and scales to $100M+.

  • Cultural reset. Low standards get exposed. High standards get installed. Leaders start acting like owners, not employees.

  • Operational traction. You’ll stop putting out fires and start making moves. Projects close. Revenue climbs. Bottlenecks break.

  • A CEO who’s out of the weeds. CEOs will delegate with confidence and lead with clarity - without being the fixer for every problem.

Proof The Program Delivers

Still wondering what The Climb with Jess Stewart is all about?

Why Risk Climbing?

  • Elevate your organization and build the legacy you deserve.

  • Create something unparalleled in your industry.

  • Thinking about selling your company? Build your organization and your systems for optimal valuation.

  • Regain control of the most important 3 Ps of your organization - your people, process, and profit.

  • Eliminate a lack of operational efficiency, accountability, & standardization.

  • Reignite innovation, creativity, and inspiration within your executive leadership team and your organization.

  • Stay dynamic and sustainable - avoiding the common traps of "How the Mighty Fall."

Ready to Climb?

Fill out the form below to get details and pricing for your team.