If you're a roofing company in need of employees, SkillBridge has you covered. This program helps active military service men and women transition out of the military and into jobs. Plus, the military pays their wages for up to six months as their service comes to an end.
Dan Cherry from PE Assist joined Pete McKendrick on The Roofr Report to share some details about how the program works, and how roofing companies can set up a program to onboard skilled military veterans.
Here are the takeaways from their conversation:
Veterans bring the stability crews are short on
Stable, long-term hires are getting rarer, and veterans tend to bring that with them. Most have spent years in one organization, taking direction and building a career there. They're used to working on a team, being outside, and carrying real responsibility at a young age.
"These guys getting out of the military have spent 4 to 25 years at the same company," Dan says.
Sales adds another pull. The more a rep closes, the more they earn, and for a lot of people leaving the service, that's more than they've ever seen.
SkillBridge is a paid-by-the-military trial run
SkillBridge lets service members in their last 12 months of service ask their command to leave early for an internship with a civilian company. The military keeps paying them. You get to see how they work before anyone signs anything.
"There was a period in 2009 to 2010 where 30% of these people getting out of the military could not find a job."
The program grew out of the post-2008 slump, when jobs were scarce for people leaving the service. A 2011 pilot project led to about 5,000 participants in 2014.
Today, Dan says, 22,000 to 24,000 people go through it every year.
Want to register your business for the program?
Reach out to Dan Cherry and he'll help you get set up.
Email: dan@PE-Assist.com
Phone: 612-548-4912
What businesses need to qualify
Dan says the process isn't hard, just daunting. To qualify, you need:
- A business that's been operating for at least three years
- A W-2 position you can offer when the internship ends
- Tools and required gear for the intern — like shirts, an iPad, or a ladder (if the job calls for it)
Internships run from about two to six months. You can't pay the intern a dime, but you also don't have to hire them. If it's not a fit, you part ways.
For sales roles, that unpaid window is a big deal. New reps in insurance work can take two to three months to build a pipeline. An intern can spend that stretch shadowing your top closers, then start day one as an employee with deals already in motion.
"It really gives them the opportunity to get out, go do a job for a while, get to know a company, and the company can get to know them."
You can fill more than sales seats
Sales gets the spotlight, but SkillBridge works for any W-2 role. Dan sees veterans landing in:
- Exterior sales
- Estimating, which can be done 100% virtually
- Production and production coordination
- Operations
- Leadership
Military logistics backgrounds map well to coordination work. Think tracking what's needed, where it's coming from, and whether the paperwork is right.
Leadership is a smart angle, too. Dan suggests giving a sales leader who's already on your team three interns and one regular rep to manage.
"If I've got somebody next to me I'm teaching, I do it even better."
They get real practice training and guiding, and you keep the payroll that would've gone to extra reps. A production manager with an intern assistant works the same way.
Hiring vets can set you apart with homeowners
Dan's take: homeowners warm up to veterans. And if your company supports the military through programs like SkillBridge or Hiring Our Heroes, say so on your website and marketing. When five roofers look the same on Google, that's an extra reason to pick up the phone.
It lines up with what homeowners told us. In the Roofr 2026 Homeowner Survey, 65% were willing to pay more for a roofer they felt a stronger personal connection with. Connection starts at the door.
The bigger opportunity is that almost nobody is doing this. Fewer than 100 companies per state offer SkillBridge internships, Dan says.
About 200,000 people leave the military each year, and only 10% to 12% get a shot at the program, mostly because there aren't enough employers. Contractors love the idea of hiring vets. They're just busy building roofs and making payroll.
"They want to support a veteran."
How to get started (and when)
The clock matters here. Per Dan, you have until Dec. 1 to sign up for next year, and he wants to hear from interested contractors ASAP so approval is done by the end of November.
- Book a 20-minute virtual call with Dan at pe-assist.com to see if it's a fit.
- Get approved by the military so commanders know your internship exists (that's the step that feels daunting).
- Get your internship posted on skillbridge.mil.
- Start matching with candidates.
PE Assist asks for a sponsorship to help with that process. Dan says they currently track more than 1,000 people leaving the service, with their resumes, past jobs, and where they want to live. That's a candidate pool you won't find on a job board.
"It feels daunting. But it's actually not the most difficult thing in the world."
Ready to get started?
Reach out to Dan Cherry and he'll help you get your business set up with the program.
Email: dan@PE-Assist.com
Phone: 612-548-4912
FAQ
What is SkillBridge, and can my roofing company use it?
SkillBridge lets service members in their last 12 months of service do an internship with a civilian employer while the military keeps paying them. Your company can use it if you've been in business at least three years and have a W-2 position to offer at the end. You also need to get approved by the military first.
Can I pay a SkillBridge intern?
No. The military covers their pay during the internship, and employers aren't allowed to pay them. You can supply gear like shirts, an iPad, or a ladder.
Do I have to hire the intern when the internship ends?
No. Internships last about two to six months, and either side can walk away if it's not a fit. If it is a fit, you've already trained the person you're hiring.
What roofing jobs can SkillBridge interns fill?
Any W-2 role. Dan sees exterior sales, estimating, production, coordination, operations, and leadership roles. Estimating internships can even be done virtually.
What's the deadline to join SkillBridge for next year?
Per Dan, the sign-up deadline this year is Dec. 1. But it takes time to process the application, so start ASAP. Dan recommends contacting PE Assist by Nov. 11 so your approval paperwork can wrap up by the end of November.