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Open role · Product

Head of Product

ShareWillow is the money app for the 4 million technicians who keep America running. We start with performance pay: every technician sees exactly what they've earned and how to earn more, job by job, in real time, and companies reward performance instead of hours worked. The average technician on a ShareWillow plan takes home $1,334 more a month. Next comes Willow, our AI agent that lives in every tech's text messages, and the payments, cards, and payroll their money runs through.

We're hiring a Head of Product to own what ShareWillow builds next, and why. You'll own the product roadmap, go deep on our customers and their pain points, and turn the outcomes we care about (technicians earning more, owners growing profit, companies keeping their best people) into the requirements, specs, and features that get us there. You'll report directly to our founder and CEO, Ryan Shank, and work closely with engineering and design.

This is a builder seat, not a process seat. Performance pay is working, and now it's time to scale it. At the same time, we're building what comes next: Willow, our AI teammate in every technician's text messages, plus the payouts, cards, and payroll that make ShareWillow the technician's financial home. You've taken a product from 0 to 1 and scaled it before, and you'll do it again here: define the product, write the specs the team builds from, and own the full lifecycle from discovery to launch to scale.

Must be okay with getting pinged on Slack in the evenings and weekends. We are not constrained by a typical 9-to-5 schedule. We want to win.

Who you are

You've taken a product from 0 to 1, then scaled it.

  • 7+ years in product management, including leading product at an early-stage or high-growth B2B SaaS company
  • You must have 0 to 1 experience at a previous startup: you found the problem, shipped the first version, and got real customers using and paying for it
  • Proven experience scaling that product from early adopters to broad adoption, with the metrics to show for it
  • You work backward from outcomes. Hand you "technicians earn 15% more" and you can turn it into the problem, the requirements, the features, and the metric that proves it worked
  • You write specs clear enough that an engineer or designer can build the right thing without a meeting
  • Deep customer empathy, earned through hundreds of customer conversations. You'd rather do a ride-along with a tech than read a survey
  • You've owned the full product lifecycle: discovery, prioritization, spec, build, launch, adoption, and iteration
  • Strong technical fluency in data models, APIs, and integrations
  • You use AI tools in your own work and understand how AI features behave in production
  • Data-driven but decisive. You know when the evidence is good enough to make the call
  • Bonus: experience with SMBs, the trades (HVAC, plumbing, electrical), field service software like ServiceTitan or Housecall Pro, payroll, payments, or shipping AI products

What you’ll do

Own the product, end to end.

  • Own the product vision, strategy, and roadmap, and make the hard calls on what we build and what we don't
  • Scale our core performance-pay product as we grow into new companies, larger customers, and enterprise roll-ups
  • Lead the build of what comes next: Willow, our AI teammate for technicians, and the payouts, cards, and payroll behind it
  • Spend real time with owners, office managers, and technicians through calls, ride-alongs, and usage data, until you understand their pain better than they can describe it
  • Work backward from the outcomes we want to the product requirements, features, and acceptance criteria
  • Write the specs the team builds from, and verify that what ships matches the spec
  • Run the full product lifecycle: discovery, prototyping, spec, launch, adoption, and iteration
  • Set product metrics, instrument them, and report on what moved
  • Partner with the CEO, engineering, design, sales, and customer success, and turn customer and sales signal into the roadmap

You might not be a fit if…

An honest filter. We’d rather you know now.

  • You haven't built a product from 0 to 1 at a startup
  • You want to hire a team of PMs and build a product org before you build product
  • Your product practice is mostly decks, roadmap reviews, and alignment meetings
  • You're skeptical of using AI tools in your day-to-day work
  • You need a large engineering and design team to make progress
  • You're uncomfortable making decisions with incomplete data
  • You are looking for a low-intensity role
  • You want a strong work-life balance and to be offline after 5pm and on weekends

Why join

Get in early. Win big.

This is the product seat at an early-stage company with proven product-market fit: 8× revenue growth in 18 months, and $24M a year now flowing to technicians through ShareWillow. You'll work directly with the founder and lead engineer, talk to customers constantly, and define the product that becomes the money app for 4 million technicians. You'll work on a small, talented team building a $10 billion company.

Unusually high upside: $150K–$230K base, meaningful early-stage equity, 100% medical and dental benefits, and a 401k with employer match.

We're proud to be an equal opportunity employer open to all qualified applicants regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital or familial status, disability, pregnancy, gender identity or expression, veteran status, genetic information, or any other legally protected status.