The sales expert founders call when they're ready to stop doing it all themselves

After 10+ years in sales and direct response marketing, I've helped dozens of agency owners and consultants build sales systems they can actually hand off — without losing the personal touch that got them this far.

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Jeff Pecaro
40+ Founders helped
10+ yrs Sales experience
90 days Avg. time to handoff
$1–5M Sweet spot revenue
My story

I didn't set out to be a sales consultant. I just kept solving the same problem.

Early in my career, I worked in sales and direct response marketing — and what I noticed was that the best founders I worked with were always trapped by the same thing: their sales process only worked when they were on the call.

It's not a skill problem. It's a systems problem. The pitch, the objection handling, the follow-up cadence — all of it lives in the founder's head, and there's no way to hand it off without torching close rates and client relationships.

"Most founders don't need to be better at sales. They need to build a process that works without them."

That realization is what led me to create Wingman. I work hands-on with founders to extract their sales process, rebuild it into something teachable, and train their team to run it — so the founder can finally get off the front lines.

When I'm not helping founders delegate their sales, you'll find me nerding out on cold brew, visiting national parks, or coaching entrepreneurs on how to tell better stories about their companies.

How I work

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Diagnose before prescribing

I spend the first weeks listening and reviewing before making any recommendations. Every business is different — cookie-cutter playbooks don't work here.

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In the trenches with you

I ride along on calls, review real recordings, and work directly with your team — not just send over a slide deck and call it consulting.

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Results you can measure

We track close rates, pipeline velocity, and rep performance from week one. You'll always know if it's working.

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Built to make myself redundant

The goal is a self-running sales system, not a dependency on me forever. When we're done, your team owns the process.

Background

What I bring to the table

10+ years in sales & direct response marketing

From cold outreach to high-ticket consulting sales, I've worked across the full spectrum of B2B sales environments.

Fractional sales leadership for $1–5M service businesses

I specialize in the exact growth stage where founder-led sales becomes a bottleneck — and where a full-time VP of Sales isn't yet justified.

Sales process design & documentation

Building repeatable playbooks, ICP documents, objection libraries, and CRM workflows that new reps can actually follow.

Rep hiring, onboarding & training

I help you find salespeople who fit your culture, onboard them with the playbook we build together, and coach them to hit quota.

Want to see if we'd be a good fit?

Book a free 30-minute call. No pitch — just an honest conversation about where your sales process is and what it would take to delegate it.

Book a Free Call → Send a picture of your dog and I'll bump you to the top of the list 🐶