ShareWillow Raises $8.5 Million to Help Trades Businesses Pay Technicians for Performance

NEW YORK — Most of the artificial intelligence pitched to small businesses lives in the office: chatbots that answer the phone, tools that write marketing emails, software that chases invoices. ShareWillow, a New York startup, is betting on a different spot in the business, the technician in the van.

The company announced an $8.5 million seed round last week, with participation from Lerer Hippeau, Circadian Ventures, Twelve Below, Charge Ventures, Notation Capital, Scott Belsky, Austin Rief, Expa and others. Founder and CEO Ryan Shank told Very Frontier that the financing brings ShareWillow’s total funding to $12.3 million.

What the Software Does

ShareWillow builds what it calls a performance pay platform for home service businesses: HVAC, plumbing, electrical, drain cleaning, roofing, restoration, pest control and similar trades. It connects to the field service software many contractors already run, including ServiceTitan, Housecall Pro and Jobber, and turns their job records into incentive plans.

According to the company, its AI agents pull job data, calculate every payout and flag missing information before payroll runs. Technicians see what each job paid them in real time in the ShareWillow app. Owners set the rules, tying bonuses to measures such as profitability and productivity.

That replaces something many shops still do by hand. As Very Frontier put it, the platform stands in for processes that businesses manage “through spreadsheets, manual calculations and complicated bonus schemes.”

The Business Case

The pitch rests on a labor problem every trades owner knows. In its AlleyWatch interview, ShareWillow cites a Jobs for the Future projection of about 1.7 million skilled trades openings a year through 2035, and says formal training programs prepare only about 55 people for every 100 workers needed. More than 3 million Americans work as technicians in home service trades, the company says, citing the Bureau of Labor Statistics.

When skilled people are that scarce, owners who can’t show their best technicians a clear path to higher pay tend to lose them. ShareWillow’s argument is that making pay visible job by job, while the work is happening, does more for retention than a bonus that shows up at the end of a pay period with little explanation.

The Numbers, With a Caveat

The company has shared several traction figures. It says hundreds of businesses run their pay on the platform, revenue has grown eightfold over the past 18 months, and technicians received more than 14,000 payouts in the past 12 months. Technicians earned $2 million in performance pay through ShareWillow in September 2026 alone, and the company says the average technician on a plan takes home $1,334 more a month than before the plan started.

Those are company-reported figures. As both Very Frontier and Unite.AI noted, they have not been independently audited, and a higher average paycheck doesn’t by itself prove the software caused the increase. A business that adopts a performance plan may also be changing prices, staffing or the jobs it takes.

What Comes Next

ShareWillow says it will use the money to expand the platform, hire, extend its integrations and build relationships with franchise brands and private equity groups that own home service companies, according to The SaaS News.

The bigger product bet is Willow, a more agentic tool the company is building on top of its pay engine. Willow is meant to brief technicians before each call, coach them through the week, and let owners test changes to a pay plan against real jobs before rolling them out. ShareWillow told AlleyWatch that its first customers will get access in early 2027.

On pricing, the company told AlleyWatch it charges a monthly subscription for each technician on a plan, with office users free. Most customers start with a “Plan Design & Launch” package, in which ShareWillow’s team builds the plan with the owner and rolls it out. Larger businesses and franchise and private equity groups get custom plans.

Why It Matters for New York Owners

New York City has no shortage of plumbing, heating and electrical contractors, and many of them are small, family-run shops competing for the same licensed technicians. For those owners, the ShareWillow round is a signal worth reading in two ways.

First, investors are now funding AI aimed at frontline workers, not only at the front desk. Second, the underlying idea doesn’t require any particular vendor. A contractor can start by asking a simple question: can each technician see, in plain numbers, how the work they did this week turned into their pay? If the honest answer is no, that gap may be costing more in turnover than any software subscription.

Before adopting any pay-for-performance plan, owners should check it against New York wage-and-hour rules and talk to an accountant or employment lawyer, since bonus structures can affect overtime calculations and payroll taxes.

Lerer Hippeau, the New York venture firm, framed its investment in a portfolio post around the size of the market, calling home services “a large and growing market.” Whether ShareWillow wins it will depend on whether owners believe the paychecks are fairer, and whether technicians do too.