Positioning & GTM for Founder-Led B2B Service Firms Selling Upmarket

Help your buyer make the internal case for choosing you
When "they do great work" is not enough to win the deal

A four-week positioning and messaging sprint to beat out the better known name.

Start with the Logo-Swap Test A 48-hour diagnostic and recommendations →
Where I did this work
IBM | eBay | Amex | FlyByAds | GF | Sorium | Citi | And More... | 3× Effie Award Winner

"We'll discuss internally." Then, silence

Playing it safe can feel less risky. But when every B2B agency and services firm sounds like an interchangeable "full-service strategic partner," deals go to whoever is most familiar / least risky.

B2B is also business-to-individual. The person choosing you has to sell your firm internally -- to their boss, their boss' boss, finance, procurement, and others. If things go bad, they're on the hook.

Your positioning is not only competing against other vendors, but also against the risk of being wrong.

Each stakeholder is judging on different criteria. If your champion doesn't have the proof points, the deal stalls and you'll never hear the real why.

While they may want the best firm for the job, they really want a choice they won't regret.

"Swap the logos. Would anyone notice?"

If you can swap your firm's logo onto a competitor's website and it basically works, you've uncovered a very expensive B2B positioning problem.

Do you have a positioning and messaging problem?

(Check all that apply)
A promising deal went quiet right after "we'll run it internally"
You lost a pitch last quarter to a bigger or better-known firm
Procurement negotiated you down before you signed
Your homepage would still work with a competitor's logo on it
Your best pitch lives in your head and your team can't repeat it
You're pitching mid-market and enterprise clients with the same story that wins small ones
Checked any of these? A Sprint can help.

No-Regrets Positioning

A No-Regrets Position matters because B2B buyers don't just evaluate solutions. They evaluate risk. Your champion has to sell your firm internally. If things go wrong, they're accountable. Your positioning has to make it easy to say yes and hard for anyone else to say no.

We get there by starting with your goals and working backward: who you serve best, what problem they urgently need solved, and what only you deliver in a way that makes buyers feel safe, smart, and certain.

The Strategic Staircase ensures change is visible, realistic, and sticky.

The Strategic Staircase
1
Positioning Diagnostic Identify where you blend in and where you stand out so we solve the right problems.
2
ICP & Offers Define who you serve best, what job they're hiring you to do, and how to package and price your work for healthy margins.
3
Messaging & Narrative Build language that answers both questions: "Is this better?" and "Will I look smart choosing this?"
4
GTM System Align your sales, marketing, and operations to the 80/20 of what actually moves non-vanity metrics (aka revenue, cash flow, profit). No more random acts of marketing.

Positioning problems solved.

Agency Repositioning

From discounts and scope creap to 40% higher avarage deal size

The Situation

An agency producing millions of views for clients kept getting asked for discounts and uncompensated add-ons. Great at delivering for others. Invisible at telling their own story.

We sharpened their ICP, point of view, and offer structure. Validated that their pricing and margins supported growth. Organized social proof around the story the right buyers needed to hear. They stopped discounting and started attracting clients who valued what they did.

GTM Strategy

From best-kept secret to a full pipeline

The Situation

A services firm with marquee clients felt like the world's best-kept secret. New business depended entirely on getting in front of the right decision maker and whether that person happened to be in market right now.

We pivoted their messaging and GTM so gatekeepers became advocates instead of walls. We shifted their focus toward longer-term retainers. And their marketing started working for the 95% of out-of-market buyers, warming them into pre-sold prospects.

Direct. Analytical.

I've been on both sides of the table.

I've led strategy, marketing, and brand at IBM and eBay, directing hundred-million dollar budgets. From decades spent selling and approving the contracts you're trying to win, I know what B2B buyers need to hear to sign five, six, and seven-figure contracts.

What works at a large enterprise doesn't always fit a founder-led business. The key is adapting those principles to focus on the highest-impact work and avoiding what is simply nice to have. Fortune 100 rigor, right-sized for founder-led B2B businesses.

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Stop making buyers connect the dots themselves

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