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 combination of onsite (3 days per week) and remote work expectations. This model is designed to provide our employees with an optimal balance between in-person collaboration and the convenience of remote work. We believe this approach fosters a more productive and engaging work environment while supporting our commitment to employee well-being and work-life balance.
Please note that the specific onsite and remote work schedule will be established based on the requirements of the role and the needs of the organization, and remain subject to Company discretion. The Company reserves the right to modify its in-person and remote work policies and expectations.

Benefits & Perks

Flexible PTO
Savings and Investments - 401(k) with company match
Competitive stock option package
$300 one-time WFH stipend
Medical, dental, and vision benefits
Top of the line 14" Macbook Pro
Wellness stipend
Travel stipend for team off-sites

**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 the Wingspan People Team, people-team@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.