Recruit · Retrain · Retain

Build a sales team you trust.

We help you find the right salesperson, retrain them for your business, and help you retain them with the systems, coaching, and accountability they need to perform — so you can finally get sales off your plate.

Build My Sales Team → See How It Works

No long-term contracts  ·  Results in 90 days

40+ Founders helped
10+ yrs Sales experience
1 system From hire to handoff
Sound familiar?

Your sales team shouldn’t need you to hold it together.

The real problem

A sales team is only as good as the system around it.

Good people still need a clear process, strong scripts, coaching, management, and accountability. Wingman helps you improve the team you have and add the right people when you need them.

🎯

Recruit

Bring the right people onto the team when you need more capacity, a stronger fit, or a different skill set.

📈

Retrain

Improve the people you already have with better process, scripts, coaching, call feedback, and a clearer way to sell.

🤝

Retain

Give the team the management, coaching, scorecards, and accountability they need to keep performing — without turning you into a full-time sales manager.

What has to go right

Three obstacles stand between you and a sales team you trust.

Whether you’re improving the people you already have or bringing in someone new, the same three things have to go right.

Obstacle 01 · Recruit

How do you add the right people when the team needs to grow?

When you need another salesperson, the goal isn’t simply to fill a seat. It’s to bring in someone who fits the role, the process, and the team you’re building.

01

Define Who You Actually Need

We build a role scorecard around the outcomes, experience, behaviors, and coachability that matter for your business.

02

Support the Search

When hiring is part of the plan, we help source, screen, and narrow the field so your time is spent with strong candidates instead of sorting through noise.

03

Select for the System

We evaluate candidates for how they think, sell, learn, and respond to coaching — so the person you add can succeed inside the system you’re building.

Obstacle 02 · Retrain

How do you make the salespeople you already have better?

Most teams don’t need more motivation. They need a clearer process, better messaging, useful coaching, and consistent feedback on what is actually happening in the calls.

04

Build the Sales Playbook

We turn the sales knowledge spread across your calls, CRM, scripts, follow-up, and head into a repeatable process your rep can follow.

05

Train With Structure

Your team learns the offer, buyer, process, and expectations through a deliberate training system instead of everyone inventing their own version of sales.

06

Coach the Real Calls

Call review, role-play, and feedback turn training into actual improvement — so good reps get better and weak spots become obvious before they become expensive.

Obstacle 03 · Retain

How do you manage a good rep without becoming their full-time sales manager?

Hiring and training a rep is not the end of the job. They still need clear expectations, pipeline management, coaching, accountability, and performance conversations. Without a management system, founders either micromanage everything or ignore sales until something breaks.

07

Manage the Numbers

We put simple scorecards and pipeline visibility in place so you can manage activity, conversion, follow-up, and forecast without sitting in every call.

08

Run the Management Rhythm

We help establish the weekly one-on-ones, pipeline reviews, coaching conversations, expectations, and accountability that keep the rep focused and problems visible.

09

Coach Performance — Not Every Deal

Ongoing call review and feedback help the rep improve while giving you a practical way to lead sales without jumping back in as the closer.

How it works

Build the team. Improve the team. Manage the team.

One system for making sales less dependent on the founder.

1
Recruit

Add the Right People

If you need another salesperson, we help define the role, support the search, evaluate candidates, and bring the right person into the system.

2
Retrain

Improve the Team You Have

We tighten the process, scripts, playbook, training, and call coaching so your current team gets better — not just busier.

3
Retain

Manage Without Micromanaging

We put the scorecards, pipeline reviews, coaching cadence, one-on-ones, and accountability in place so you can lead sales without becoming the salesperson again.

Why Wingman?

Hiring is only one part of the handoff.

Finding the right person matters. But so does what happens after they join the team: onboarding, sales training, coaching, management, and accountability.

Wingman is built around the whole sales system — not just the hire.

Already have a salesperson? Great. We can start with training and management. Need another one? We can help with that too.

What founders are saying

★★★★★
"Before Wingman, I was on every single sales call. Within 6 weeks, my rep was closing deals on her own. I got my Friday afternoons back."
MR
Marcus R. Founder, Digital Agency ($2.4M ARR)
★★★★★
"We'd tried to document our sales process twice before — it never stuck. Jeff actually got in the weeds with us and built something the team could actually use."
SK
Sarah K. CEO, B2B Consulting Firm
★★★★★
"Our close rate went from 22% to 38% in the first month just from fixing our pitch. I wish I'd done this two years ago."
DL
David L. Owner, Marketing Agency
Jeff Pecaro
About Jeff

Sales should not depend on the founder forever.

After 10+ years in sales and direct response marketing, I kept seeing the same pattern: founders could generate demand and close business themselves, but the moment they tried to hand sales off, things got messy.

I created Wingman to solve the whole handoff — not just the hire. The goal is simple: put the right salesperson in the seat, help them become successful, and give you enough visibility and confidence to finally step back.

40+ Founders helped
10+ yrs Sales experience
$1–5M Sweet spot revenue
Need a different starting point?

Only need part of this?

Maybe you already have the team and need better training. Maybe management is the problem. Maybe you need help adding one more rep. Or maybe the sales process needs work before anything else. We can build a custom plan around the piece that is actually holding you back.

Schedule a Call →

Build a sales team that works without you holding it together.

Book a free strategy call and we’ll look at your current team, process, management, and hiring needs — then identify the fastest path to a sales function you can trust.

Build My Sales Team → No pressure. Just a practical conversation about getting sales off your plate.
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