Senior Product Manager, Contractor Experience

In today’s economy, an increasing number of workers are choosing to freelance. By 2027, half the U.S. workforce will be independent contractors. Yet there is no system of record for this vast self-employed community and the legions of businesses that increasingly rely on it. A new paradigm is needed to accommodate the future of work that is suddenly no longer in the future. That is what Wingspan is building.

Wingspan is the first payroll platform designed specifically for independent contractors and their businesses. We make onboarding, payments, and compliance easy for flexible workforces of all sizes. Whether you’re a one-person business or a large enterprise, Wingspan has you covered.

We’re a Series B startup based in NYC with backing from some of the best VCs and operators around, including Andreessen Horowitz (a16z) and the CEOs and founders of Warby Parker, Harry’s, Allbirds, Invision, and Flatiron Health.

Now we're hiring for you: an ambitious individual ready to help build, design, and take us to the next level.

Are you ready to be part of a team redefining the future of work? Apply now!

This isn't your typical product management role. You will evolve our key business line: the Contractor Experience.

You will have the opportunity to build a new suite of consumer FinTech products, with the backing of an established, high-growth platform. You will own the vision, roadmap, and core business metrics for a product suite designed to capture a contractor's entire financial life—from income and banking to taxes and savings. If you are a builder with deep B2C FinTech experience who thrives on 0-to-1 challenges, this is the role for you.

This role is based in our New York City office, and we operate on a hybrid model requiring in-person collaboration four days a week. We believe this approach fosters a strong team environment, enhances communication, and accelerates innovation.

• Own the Vision & Roadmap: You will own, define, and execute the product strategy for the entire contractor experience.
• Be a FinTech GM: Define and own the monetization and attachment rate targets for our FinTech suite, including our debit card, instant payouts, and Tax Withholding.
• Master the User: Conduct deep user research to intimately understand the financial pain points and goals of our diverse contractor segments.
• Drive Growth & Engagement: Your roadmap will focus on capturing a contractor's complete income graph through features like a guided deposit switch tool and off-platform income ingestion, making Wingspan the default destination for all their earnings.

• Deep B2C FinTech Expertise: You have direct, hands-on experience building and scaling consumer-facing financial products (e.g., neobanking, payments, tax software, personal financial management, lending, or investing).
• A True 0-to-1 Builder: You thrive in ambiguity and have a demonstrated history of taking ideas from a whiteboard sketch to a successful product in the market. You are comfortable building business cases and creating a roadmap from scratch.
• Startup DNA: You are scrappy, biased for action, and have experience working in fast-paced, high-growth startup environments.
• Metrics-Driven & Commercially Minded: You are obsessed with the "why" behind the data and have experience owning and driving commercial outcomes (revenue, monetization, adoption) in addition to core product metrics.
• User Empathy: You are passionate about talking to users and translating their needs into a compelling product vision.
• Bonus points if you are:
• A former startup founder or a very early-stage employee.
• Experienced in building AI/ML-driven products that act on a user's behalf, not just advise them.
• Personally familiar with the challenges of being an independent contractor or freelancer.

• 5+ years of Product Management experience, with a proven track record of shipping products from concept to launch and scale.
• Must be authorized to work in the United States. At this time we are unable to transfer or sponsor visas

Compensation

• At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. The annual base salary for this role ranges from $180k - $220k, and is accompanied by a target equity package and an extensive suite of benefits, including medical, dental, and vision insurance. All figures cited are in USD and pertain to workers located in the United States.
• We understand that each candidate brings a unique combination of skills, experience, and qualifications to the table, which is why we tailor our compensation packages based on factors such as expertise, years of experience, certifications, and other factors.
• Join us in our mission to innovate and excel, knowing that you will be valued and recognized for your job-related knowledge, skills, and experience. Our comprehensive benefits and rewards are designed to help you thrive both professionally and personally, as we work together to shape the future of our industry.

• Unlimited vacation
• Competitive stock option package
• $300 one-time WFH stipend
• Medical, dental, and vision benefits
• Top of the line 14" Macbook Pro
• Travel stipend for team off-sites
• 401k Matching
• Wellhub, fitness benefit

**We appreciate candidates who are open and honest about what they’re looking for so we can ensure it’s a fit on both sides.**

Wingspan does not accept agency-provided resumes from recruitment firms we do not partner with, and any unsolicited resumes sent to our job-related emails or staff will not result in charges to Wingspan.

At Wingspan, we are an equal opportunity employer passionately dedicated to fostering a diverse and inclusive workplace. We wholeheartedly believe that embracing diversity of perspectives and backgrounds is essential to building the best products and providing delightful experiences for our users and team members. We are proud to maintain an environment free from discrimination, retaliation, and harassment.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, ancestry, ethnicity, marital status, pregnancy, disability, genetic information, protected veteran status, or any other characteristic protected by law or ordinance. As we strive for excellence, we are committed to ensuring fair employment practices and business dealings and rejecting any form of discrimination or retaliation.  These protections and commitments extend to all management practices and decisions, including recruitment and hiring, appraisal systems, promotions, training, and career development programs. Consistent with these obligations, Wingspan also provides reasonable accommodations to employees and applicants with disabilities and for sincerely held religious beliefs, observances, and practices.

If you would like to request an accommodation as part of the application process, please let us know in your submission.

Join us in our mission to create a company and products we love, as we celebrate our diverse workforce and promote an inclusive work environment that drives innovation and success.