Who We Are

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 A 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 were 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!

Impact of the Role

• To analyze and optimize Wingspans product performance, drive data-informed decisions, and contribute to the development of enterprise-grade software tailored for independent contractors and their businesses over the next 12-18 months.
• Create, maintain, and update product documentation, user guides, FAQs, and training materials.
• Coordinate with departments for smooth product releases and change management.
• Manage customer feedback channels and analyze insights to inform product decisions.
• Collaborate with Customer Success to address user pain points.
• Conduct post-launch reviews using FullStory and other methods to identify issues.
• Document areas for improvement and provide actionable insights for product iterations.

Qualifications 

• Bachelor’s degree in Business, Computer Science, Information Systems, or a related field.
• Preferred: Master’s degree in Business Administration, Product Management, or a related field.

Experience

• 3+ years in product management, product operations, or a similar role within a SaaS or fintech environment.
• Preferred: Experience with financial products and services, and relevant regulatory requirements.
• Strong analytical skills with experience in data analysis and interpretation.
• Proficiency in project management and collaboration tools (e.g., Jira, Confluence, Asana).
• Experience with SQL and data visualization tools (e.g., Tableau, Power BI).
• Familiarity with AI tools such as ChatGPT, Claude, or similar platforms.
• Sufficient understanding of software development to gauge engineering complexity, costs, and considerations.

Requirements

• Excellent written and verbal communication skills in English, conveying complex information clearly.
• Experience creating and maintaining product documentation and training materials.
• Strong analytical and problem-solving skills, with data analysis and interpretation experience.
• Proficiency in project management, collaboration tools (e.g., Jira, Confluence, Asana), SQL, and data visualization (e.g., Tableau, Power BI).
• Familiarity with AI tools (e.g., ChatGPT, Claude) and UX principles.
• Understanding of software development processes and engineering considerations.
• Demonstrated ability to work cross-functionally and manage multiple stakeholders.
• Experience with customer feedback tools, usability testing, and A/B testing methodologies.
• Knowledge of market research techniques and competitive analysis.
• Certification in product management or related field (e.g., Pragmatic Marketing) preferred.
• Ability to work during Eastern Standard Time (EST) business hours (7am-3pm) for at least 2 business days per week.

Benefits & Perks

• Unlimited vacation
• Competitive stock option package
• $300 one-time WFH stipend
• Top of the line 14" Macbook Pro
• Travel stipend for team off-sites
• 401k Matching 

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 contact [Ariel Sachtjen at ariels@wingspan.app

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.