Who We Are

Wingspan serves independent contractors and the businesses that hire them. Our customers are the backbone of the modern economy and are radically underserved by legacy payroll platforms. Our job is to make working with them effortless.

Wingspan is the first payroll platform built specifically for the independent workforce. We're different because of our end-to-end contractor management: seamless onboarding, automated payments, and built-in compliance, all in one place, for flexible workforces of any size. That's why the businesses that rely on contractors trust Wingspan to handle the complexity so they don't have to.

This market is massive and ours to define. By 2027, half the U.S. workforce will be independent contractors, and we're the system of record they've never had. We're a Series B company backed by Andreessen Horowitz (a16z) and the founders and CEOs of Warby Parker, Harry's, Allbirds, Invision, and Flatiron Health.

Strategic Enterprise Account Executive

This is a 0-to-1 role for someone who's spent years close to a complex enterprise product and knows how to translate that depth into customer trust. As our first enterprise hire on the commercial side, you’ll shape how we go to market and work shoulder-to-shoulder with the CEO, Product, and Engineering to make sure what we're building actually delivers. There's no inherited playbook, you'll help write it. If you'd rather be the expert in the room than the rep in the room, this role is for you.

What you'll do:

• Own the full customer lifecycle for enterprise accounts, from identifying the right prospects to navigating complex buying processes
• Guide finance and accounting leaders and their teams through evaluating and adopting a genuinely technical product, translating complexity into clarity
• Lead multi-threaded discovery and executive-level conversations across long sales cycles with multiple stakeholders
• Partner closely with the CEO to build our enterprise go-to-market approach from the ground up
• Collaborate with Product and Engineering as a direct conduit from customers, your field insights should shape what we build
• Drive targeted, strategic outreach to the right customer profiles
• Work with marketing to develop materials and messaging that reflect how enterprise buyers actually think about this problem
• Travel roughly once a month to build relationships with customers and prospects in person
• Be the face of our brand with enterprise buyers: technically credible, deeply empathetic, and sharp on the business problems we solve

Who you are:

• You have 5+ years of experience in enterprise SaaS in a role that requires deep product and technical fluency. This could be solutions engineering, product management, or enterprise sales with a highly technical product
• You've worked on or alongside a complex B2B product and can hold your own in conversations with both technical teams and finance/operations leaders
• You are a self-starter and thrive in and are excited by an ambiguous environment where you can build something from 0-1
• You become an expert in your domain, always seeking to deepen your understanding of the industry and prospects you sell to 
• You are based in NYC or willing to relocate and value the collaboration of building something great together in person
• You think commercially: you understand how to move enterprise deals forward, build consensus across stakeholders, and create durable customer relationships that grow over time.

Compensation:

• At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. The on target earnings for this role ranges $250,000-$300,000 with uncapped commission, 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.

Location:

• This role will be based in New York City and will have a hybrid work model that consists of a combinati