Wingspan · 1 month ago
Senior Product Manager, Contractor Experience
Wingspan is a Series B startup based in NYC that is building a payroll platform specifically for independent contractors. The Senior Product Manager for Contractor Experience will own the vision and roadmap for a suite of consumer FinTech products, focusing on enhancing the financial lives of contractors through innovative solutions.
Financial ServicesFinTechInformation TechnologyPayments
Responsibilities
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
Qualification
Required
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
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
Preferred
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
Benefits
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
Company
Wingspan
Wingspan is the first payroll platform for contingent work—automating onboarding, payments, 1099s, and contractor benefits
Funding
Current Stage
Growth StageTotal Funding
$41.5MKey Investors
Touring CapitalGrand Central Tech
2025-05-09Series B· $24M
2023-03-16Series A· $14M
2021-01-01Seed
Leadership Team
Recent News
Company Ventures
2025-08-13
Beinsure - Insurance, Reinsurance, InsurTech Insights
2025-08-04
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