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FOUNDER & CEO ADVISORY

Make the right GTM & Sales decisions faster, with less second-guessing.

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WHO THIS IS FOR

PROBLEM

SOLUTION

A weekly operating rhythm with a trusted partner to clarify decisions, translate strategy into execution, and keep sales focused on what actually moves revenue.

  • ​​Sales process refinement 

         (discovery call, deal flow, execution)​

  • Confidence in forecast & pipeline reality—no more guessing​​

  • Messaging & positioning clarity that aligns to your ICP​​​​​​​

  • ​​Pressure-test assumptions before they cost time or credibility​

  • Translate strategy into actions you can execute this week​

  • Hiring and role timing (when not to hire matters just as much)​​​

OUTCOMES

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Founders and CEOs who carry sales responsibility without a formal sales backgroundand find themselves repeatedly pulled into sales challenges that consume time and distract from running the broader business.

Founders face new sales challenges every day pricing decisions, deal stalls, unclear pipeline, and hiring calls they’ve never had to make before.​​

WHAT WE FOCUS ON

Depending on what’s most urgent, we typically work through:

​

  • What to say (and what to stop saying) in discovery calls​

  • Whether a deal is real, or just noise​

  • What your pipeline is actually telling you​

  • When a proof of concept makes sense and when it’s a stall tactic​​

  • How to tighten your stages so forecasting becomes predictable​

  • When to hire your first rep, your first leader, or neither yet​

  • How to create consistency without slowing momentum

Clear decisions. Less second-guessing.

Stronger execution. You leave each week with:

  • ​A smaller set of priorities​

  • Cleaner calls on what matters now​

  • A plan you can execute immediately​

  • A pipeline you can trust more each week

Portrait James Geyer, Co-Founder & COO AccountAim

James Geyer
Co-Founder & COO

AccountAim

Lester played a key role in shaping AccountAim’s go-to-market strategy. His ability to combine hands-on sales coaching with a clear understanding of early-stage execution had a measurable impact on our traction and momentum.

Portrait Sean Woods, CEO CGM Sports

Sean Woods
CEO 

CGM Sports

Lester brought structure and momentum at a pivotal stage of our business. His guidance in a high-stakes negotiation was decisive, helping us focus on what mattered and avoid costly missteps. He moves conversations to decisions.

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LET'S TALK

If you’re a founder or CEO leading sales without a sales background and want grounded, experienced support we should speak.

​

No pitch.

No pressure.

Just a clear conversation.

  • Email
  • LinkedIn
  • Instagram

978-804-0453

©2025 BY LESTER SYDNEY 

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