About Gridwise
Gridwise is building the operating system for the modern flex workforce.
More than 400 million people globally now earn income through flexible, app-based work across rideshare, delivery, hourly labor, and rapidly expanding on-demand categories. This is no longer a niche segment of the labor market. It represents one of the most significant structural shifts in how work gets done. As AI, automation, and cost pressures reshape industries, companies are increasingly turning to flexible labor models, and the flex workforce is becoming foundational to how services are delivered and how cities function.
Yet while platforms have become more sophisticated, the tools available to workers have not kept pace. Flex workers are managing multi-platform income streams in a dynamic, algorithm-driven environment with limited visibility and fragmented data.
Gridwise exists to change that.
Our B2C flex worker app helps independent workers maximize earnings, optimize time, and make smarter decisions across platforms. We unify fragmented marketplace data and turn it into actionable insight: when to work, where to work, who to work for, and how to maximize income per hour and per mile. As incentives shift and AI-driven systems increasingly shape opportunity, workers need an intelligent copilot to help them operate at their best, not manual tracking and guesswork.
Today, Gridwise has:
- Empowered 1M+ flex workers
- Tracked 1B+ trips across major platforms
- Achieved 100% year over year revenue growth to date
- Reached profitability as of October 2025
Our business model is powered by a multi-pronged revenue flywheel:
- Subscriptions from flex workers who pay for premium optimization tools
- Aggregated, anonymized labor and mobility data products sold to enterprise customers
As our B2C user base grows, our data becomes more powerful. As our data business scales, we reinvest into building better tools for workers. The result is a reinforcing ecosystem connecting workers, platforms, and the broader flexible work economy.
The role
The Head of Product for the Flex Worker App will lead the evolution of Gridwise's core consumer experience. This is not a feature factory role. It is an opportunity to shape the primary interface between independent workers and the future of work.
You will shape product strategy and own execution for a product used daily by workers whose income depends on the quality of our insights. You will operate at the intersection of marketplace dynamics, labor economics, data intelligence, and behavioral design. You will help define how AI-driven decision support transforms gig work.
You will also sit at the center of our flywheel. The Flex Worker App drives subscription revenue and generates the data that powers Gridwise Analytics, our enterprise data business, so the decisions you make on the consumer side compound across the company.
Gridwise is at an inflection point: scaling rapidly, profitable, and positioned to become the indispensable application for flex workers globally. The next phase of growth will be driven by product leadership that combines analytical rigor, deep empathy for users, and bold thinking about the future of flexible work.
Scope and team
- Reports directly to Ryan Green, co-founder and CEO
- Starts with two direct reports, with the mandate and support to build and grow a global product team over time
- Owns the roadmap, metrics, and outcomes for the Flex Worker App end-to-end
- Partners closely with Engineering, Design, Data Science, and Business Development, and works directly with both co-founders on company strategy
What you're responsible for
- Drive the full product lifecycle for the Flex Worker App, from research, design, specification, metrics definition, development, launch, and beyond.
- Own subscription growth for the app, including activation, conversion, retention, and pricing and packaging decisions.
- Identify clear, measurable metrics to track the success of the product, and the hypotheses that need to be proven along the way.
- Understand the competitive landscape for flex work and gig economy products, and use customer feedback to identify new market opportunities and develop strategies for capturing them.
- Build, coach, and grow the product team. Continually refine how the team works while empowering team members to feel heard and respected.
- Work closely with Design, User Research, Engineering, Data Science, Business Development, and other cross-functional teams to prioritize features and ship product.
- Be the company's go-to expert and internal evangelist for the Flex Worker App.
What we're looking for
Must have
- Experience leading product for a consumer application at a meaningful scale, delivered in native mobile apps.
- Track record of growing subscription or recurring consumer revenue, including work on conversion, retention, and pricing and packaging.
- Experience building or managing a product team, including hiring, coaching, and setting how the team operates.
- Uses data and insights to drive product decisions and identify opportunities, paired with strong business sense and the intellectual curiosity to become a subject matter expert in a complex ecosystem.
- High degree of user empathy and the ability to advocate for the user while advancing the needs of the business.
- Exceptional written and presentation skills, with the ability to distill complex problems into simple documentation tailored to the audience.
- Passion for making flex work a better pursuit for our users, and the patience to solve hard problems and work around operational roadblocks.
- Strong proficiency in using modern AI tools to drive optimal productivity
Preferred, but not required
- AI native way of working. You use AI tools daily to research, prototype, analyze, and ship faster, and you have opinions about where AI belongs in a product and where it does not.
- Avid user of gig economy services across rideshare, delivery, and other types of marketplaces
- Experience shipping AI or ML-driven features in a consumer product
- Gig economy, marketplace, or flex work experience.
Culture
Gridwise is a 25-person, remote-first team led by co-founders Ryan Green (CEO) and Brian Finamore (CTO). We operate with high ownership and high accountability. Everyone is expected to think like a builder, not a bystander.
Our culture is collaborative and entrepreneurial. We move quickly, make decisions with imperfect information, and focus on measurable impact. Titles matter less than outcomes. The best data-driven ideas win, regardless of where they come from.
Because our product directly impacts workers' livelihoods, we take user empathy seriously. We balance speed with responsibility, and ambition with discipline.
Professional growth is a priority. Team members are given real ownership, meaningful scope, and the opportunity to shape product and company direction. We value intellectual rigor, curiosity, and resilience, along with the ability to work hard, support teammates, and enjoy the process of building something that matters.
Compensation and perks
We believe in compensating builders fairly, giving them ownership in what they create, and providing the flexibility and support to do their best work.
- Annual cash compensation of $190,000 to $230,000, depending on experience and location
- Meaningful equity participation in a profitable, growing company
- Remote-first culture. This role is open to candidates based anywhere in the US, working on US hours
- Comprehensive medical, dental, and vision coverage, with an HSA option
- 401(k) plan
- Flexible PTO, with a two-week minimum encouraged, plus parental leave
- Monthly rideshare and delivery credits to stay close to the product
- Coffee subscription and home office stipend
Equal opportunity
Gridwise is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law. If you need an accommodation at any point in the process, let us know and we will work with you.
Interested in joining the team?
Fill out the application form. We review every submission and will reach out if there's a fit. If you would rather reach us directly, email careers@gridwise.io.