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GTM Planning Working Session for Leadership Teams

A facilitated executive working session designed to isolate where growth is breaking and define the next 90 days with precision.

The Pattern

Growth rarely breaks all at once.

It drifts.

Market clarity softens.
Messaging fragments.
Execution gets heavier.


Revenue becomes harder to predict.

This is not a marketing problem.
It’s structural.

Let’s architect what comes next.

When this pattern shows up, the solution is not another initiative.It is clarity.

Leadership teams need space to surface misalignment, agree on what truly matters next, and define the next 90 days with discipline.

That is the purpose of the GTM Planning Working Session.

Trusted by Teams from Startup to Enterprise

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From Startup to Scale

Real Impact, Real Results

 Newgistics
Partnered with the CEO to reposition the business and scale from early growth to acqusition by Pitney Bowes. $5M to $250M.
 ESO
Led go-to-market-strategy as the company grew from $10M to $248M expanding into new buyer segments and accelerating enterprise adoption
RetailMeNot

Helped scale marketing from

$125M to over $435M by clarifying positioning, aligning GTM prorities, and building a repeatable demand engine.

Across these companies, the pattern was consistent: growth accelerated when the GTM engine was rebuilt to match the stage and complexity of the business.

What This Engagement Delivers

The GTM Planning Working Session helps the executive team make explicit, shared decisions about how the company will grow and where it will not invest  over the next 90 days.

This is not about polished decks or theoretical frameworks.

 

It is about:

• Surfacing misalignment across leadership
• Creating shared language around growth priorities
• Identifying where growth is breaking
• Translating strategy into a focused 90-day roadmap

 

You leave with:

• Clear agreement on the 1–3 priorities shaping the next quarter
• Explicit decisions about what to stop
• A realistic GTM execution roadmap
• Leadership alignment around what matters now

The outcome is decision clarity, not analysis depth.

Apply for an Executive Planning Session

© 2025 by  Jonathan Dampier

                   Fractional CMO & GTM  Advisor

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