Trades businesses can’t hire technicians fast enough. Jobs for the Future projects about 1.7 million skilled trades openings a year through 2035, yet formal training programs prepare only about 55 people for every 100 workers needed. Most AI built for the trades targets the office, but no call runs without a technician, and owners who can’t show their best people a clear path to higher pay lose them to competitors. ShareWillow builds the performance pay platform that closes that gap for HVAC, plumbing, electrical, roofing, and other home service businesses by connecting to field service software like ServiceTitan, Housecall Pro, and Jobber, where its AI agents calculate every payout and flag missing data before payroll runs. Technicians see what each job paid them in real time in the ShareWillow app, and the average technician on a plan now takes home $1,334 more a month than before. The company’s revenue has grown 8x in the past 18 months, hundreds of businesses run their pay on the platform, and technicians earned $2M in performance pay in September 2026 alone. Next, the company is expanding those agents into Willow, which will brief technicians before each call, coach them through the week, and let owners test pay plan changes against real jobs before rollout, with first customers getting access in early 2027.
AlleyWatch sat down with ShareWillow Founder and CEO Ryan Shank to learn more about the business, its future plans, and recent funding that brings the company’s total funding to $12.3M, and much, much more…
Who were your investors and how much did you raise?
We raised an $8.5M seed round with participation from Lerer Hippeau, Circadian Ventures, Twelve Below, Charge Ventures, Notation Capital, Scott Belsky, Austin Rief, Expa, and others.
Tell us about the product or service that ShareWillow offers.
ShareWillow is the performance pay platform for home service businesses: HVAC, plumbing, electrical, drain cleaning, roofing and more. We connect to the field service software owners already run, like ServiceTitan, Housecall Pro and Jobber, and turn their job data into performance pay plans. Our AI agents calculate every payout and flag missing data before payroll runs, and techs see what they earn in real time, job by job, in the ShareWillow app.
Next, we’re expanding those agents into a more agentic product called Willow. Willow will brief techs before each call, coach them through the week and help owners test changes to their pay plan against real jobs before they roll them out.
What inspired the start of ShareWillow?
I’ve spent my career building products for the trades. Across all of it, pay was the problem every owner brought up. Owners wanted to share the upside with their best people and didn’t know how to do it fairly. Techs wanted to know what it took to make more.
We started by helping small businesses share profit with their teams. The trades got the most out of it, so we built for them, and that grew into performance pay.
How is ShareWillow different?
Most AI in the trades is built for the office: phones, scheduling, dispatch. We build for the tech. Techs make the revenue in these businesses, and there aren’t enough of them to go around.
We’re also built for the trades from the ground up. We plug into the software owners already use, our team designs each pay plan with the owner, and every tech can see what each job paid them. That visibility is what changes behavior. When a tech can pull out their phone and see what that last job paid, they start running the call like an owner.
What market does ShareWillow target and how big is it?
We serve home service businesses: HVAC, plumbing, electrical, drain cleaning, restoration, roofing, pest control and more. More than 3 million Americans work as techs in those trades, according to the Bureau of Labor Statistics, out of more than 18 million in the skilled trades overall. Jobs for the Future projects about 1.7 million trades openings a year through 2035, so every owner is competing for the same people. Hundreds of businesses run their pay on ShareWillow today and in September 2026 we paid out over $2m to techs on our platform.
What’s your business model?
We charge a monthly subscription per tech on a plan, and office users are free. Most customers also start with our Plan Design & Launch package, where our team builds the plan with the owner and rolls it out to the team. Larger businesses and franchise and private equity groups are on a custom plan.
How are you preparing for a potential economic slowdown?
Performance pay is built for a slowdown. When pay is tied to the work, labor costs move with revenue, so owners get a predictable labor rate on every job instead of a fixed payroll that stays the same when calls drop off. In a tight market, that’s a reason to switch, not to cut.
What was the funding process like?
There’s more capital out there than the headlines suggest. You hear a lot of doom about how hard it is to raise, but funds have money to deploy, and most of them aren’t getting into the handful of AI companies everyone is chasing. We had no shortage of investors to talk to.
The hard part is the story. Every investor asks some version of “why can’t someone build this with Claude?” You can build almost anything now, so your story has to be very tight and you need something unique that the big AI players can’t easily replicate.
What are the biggest challenges that you faced while raising capital?
Getting someone to step up and lead. The lead does the diligence, the legal work and most of the heavy lifting, and a lot of investors would rather follow. Everyone wants there to be a lead. Writing a check is easy. Finding someone willing to do the work of leading the round is the hard part.
What factors about your business led your investors to write the check?
Growth and pull from customers. Our revenue is up 8x in the last 18 months. Techs received more than 14,000 payouts through ShareWillow in the past 12 months, and in September alone they earned $2 million in performance pay through the platform. The average tech on a ShareWillow plan takes home $1,334 more a month than before their plan started.
What are the milestones you plan to achieve in the next six months?
- Roll out Willow to our first customers in early 2027
- Bring performance pay to more home service businesses
- Grow the team
- Expand integrations across field service, payroll and accounting software
- Build partnerships with private equity platforms and franchise brands in home services
What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?
Stay close to your customers and charge for the value you deliver. We grew because owners could see the result in their own numbers: techs earning more and labor costs they could predict. If customers can measure what you do for them, they’ll pay for it and tell other owners. That’s worth more than any amount of funding.
Where do you see the company going now over the near term?
ShareWillow started as performance pay. Now we’re building a team of AI agents that helps every tech win on every job, and helps every owner build a business their best people never want to leave. Over the next year, that means getting Willow into the hands of our customers and putting a real-time view of their pay in front of more techs across the trades.
What’s your favorite fall destination in and around the city?
The West Side Highway.
