Sales Development Representative

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 AI-native platform for the flexible workforce. Our agents run onboarding and verification, manage work and pay, bill and stay compliant, and support workers on one record, across 1099 contractors, international contractors, and flexible W-2 employees.

We’re a Series B startup based in NYC with backing from some of the best VCs and operators around, including Andreessen Horowitz (a16z), Touring Capital, 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!

• As a Sales Development Representative, you’ll play a crucial role in breaking into new accounts across all levels of our target customer segments.
• Collaborate with Account Executives, conduct market research to identify potential customers and leads, and qualify those leads.
• Drive Wingspan’s outbound prospecting motion, generating sales leads that turn into opportunities and closed business.
• Demonstrate your ability to be a tenacious self-starter every day as you advance your career.
• Educate and develop leads through outbound prospecting via phone calls, videos, emails, and events.
• Generate email sequences and make cold calls to map and penetrate accounts.
• Conduct follow-up calls and emails until meetings are set.

• Available to work in our New York City office 3–4 days per week.
• You are an active communicator who collaborates with internal and external stakeholders to consistently improve processes and communication.
• Previous SDR/BDR or sales internship experience is a plus.
• Experience in a fast-growing startup and/or in the HR or payments space is a plus.

• No prior SDR experience is required. Recent college graduates and candidates with sales or similar internships, or entrepreneurial experience, are encouraged to apply.
• You have an entrepreneurial mindset and enjoy building and testing new processes.
• You are adaptable and comfortable in a fast-paced environment.
• You are extremely organized and a diligent note-taker.

Our interview process includes three conversations, with next steps confirmed after each round:

1. Screen with Wade (30 minutes): Discuss your interest in the role, work you have followed through on, and how you have handled feedback or setbacks. Examples from jobs, internships, school, or independent projects are welcome.
2. Live practical with JJ or another Account Executive (30 minutes): Use a short product and buyer brief to prioritize accounts, draft outreach, and try a simulated call. You will receive feedback and have a chance to apply it.
3. Final with Jake (45 minutes): Work through a fresh scenario and discuss how you organize your work, learn, and use coaching.
4. Decision and offer: For finalists, we review interview evidence and coordinate references before a hiring decision and any offer.

There is time for your questions in each interview. No slides or take-home assignment are required. If any assessment or preparation is needed before a later round, we will share instructions in advance.

At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. This role pays a $65,000 annual base salary with $85,000 annual on-target earnings ($65,000 base plus $20,000 variable at target) 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.

• Unlimited vacation
• Competitive stock option package
• Medical, dental, and vision benefits
• Top-of-the-line Mac laptop
• 401(k) matching
• Wellhub gym membership

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 Jake Hansen at [email protected].

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.