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FRACTIONAL VP OF SALES

Senior sales leadership embedded in your business without

the full-time hire.

WHO THIS IS FOR

You're running a B2B company with real revenue pressure and a sales function that isn't performing at the level the business needs.

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Maybe you're a Series A or Series B founder who's been the primary closer and knows that can't scale. Maybe you're a PE-backed operator with a team that's working hard but missing its number. Maybe you've tried hiring your way out of it and it hasn't worked.

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What you need isn't another advisor.

 

You need an operator someone who steps in, takes ownership, and builds a sales motion that holds.

That's this engagement.

THE PROBLEM

Most companies don't have a talent problem. They have a structure problem.


Deals stall because there's no shared qualification discipline. Pipeline is unreliable because stages aren't tied to buyer behavior. Forecasts are wrong because no one has agreed on what "late stage" actually means. Reps are working hard without a system that makes their effort repeatable.


And in the middle of all of it, the founder or operator is still the one closing deals because no one else has the context, the authority, or the process to do it without them.


That's not a hiring problem. That's a leadership and infrastructure problem.

 

And it compounds every quarter you leave it unaddressed.

THE SOLUTION

I embed as your Fractional VP of Sales with a seat at the table, accountability to your revenue number, and direct involvement in the team, the pipeline, and the deals.


This is not a weekly check-in. This is operational sales leadership on a fractional basis.


Depending on where you are and what's most urgent, we typically work through:

Sales Infrastructure

  • Discovery Call framework what your team asks, listens for, and does with what they learn

  • Pipeline stages tied to real buyer behavior, not internal wishful thinking

  • Qualification discipline so your forecast reflects reality

  • Proof of concept structure when it accelerates a deal and when it's a stall tactic

Team & Execution

  • Weekly deal reviews with live pipeline strategy

  • Call coaching grounded in what's actually happening in your market

  • Objection handling built into a shared playbook, not improvised every time

  • Hiring and role timing when to add headcount and when not to

GTM & Revenue Strategy

  • ICP clarity and messaging alignment

  • Competitive positioning in active deals

  • Revenue architecture how your segments, channels, and motions work together

  • Sales and marketing alignment so pipeline quality improves upstream

OUTCOMES

Companies that go through this engagement come out the other side with:

  • A sales process the team actually runs not a deck that lives in Google Drive

  • A pipeline your leadership team can trust and act on

  • Reps who know how to qualify, advance, and close without constant founder involvement

  • A forecast that gets more accurate each week

  • A sales function built to scale with or without you in every deal

 

The goal is not dependency. It's a revenue engine that outlasts the engagement.
 

WHO THIS IS FOR

This is a 12-month fractional engagement designed to install, run, and stabilize your sales function.

 

Month 1–2: Diagnose & Design Full audit of pipeline health, team performance, process gaps, and GTM alignment. We identify the highest-leverage fixes and build the foundational infrastructure.

 

Month 3–6: Build & Install Playbook development, stage redesign, discovery framework, weekly operating cadence, and live deal strategy. The system goes in while the team runs on it.

 

Month 7–12: Run & OptimizeOngoing sales leadership team coaching, pipeline reviews, forecast accountability, hiring support, and continuous refinement. The motion stabilizes and performance compounds.

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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.

If your sales function needs senior leadership; not another framework, not another workshop let's have a direct conversation about whether this engagement is the right fit.

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No pitch. No pressure. Just clarity.

LET'S TALK

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

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No pitch.

No pressure.

Just a clear conversation.

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978-804-0453

©2025 BY LESTER SYDNEY 

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