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Head of Support



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See open jobs at Wingspan.
IT, Customer Service
United States · Remote
Posted on Monday, January 8, 2024

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 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!

Impact of the Role:

The Head of Support will play a pivotal role in defining and executing our customer support strategy. This individual will be responsible for leading a high-performing team, ensuring exceptional customer experiences, and driving continuous improvements in our support processes. Their work will significantly impact customer satisfaction and loyalty, directly influencing Wingspan’s reputation and success.

What You'll Do:

  • Design a balanced support framework, integrating dedicated staff, outsourced resources, and leveraging self-service strategies and AI enhancements.
  • Lead, mentor, and expand a team of support professionals, fostering a culture of excellence, accountability, and continuous learning.
  • Analyze support metrics and KPIs to identify trends, address areas of concern, and implement improvements.
  • Collaborate closely with cross-functional teams, including Product, Engineering, and Customer Success, to enhance product offerings and customer experience.
  • Ensure the support team is equipped with the necessary tools and training to provide top-notch service.
  • Strategically identify, select, and implement a Support Tooling to facilitate the rapid scaling and efficient management of Wingspan's support platform


  • Proven experience in leading and scaling customer support or customer success teams in a dynamic environment.
  • Strong track record in improving customer satisfaction and support metrics within a software company, preferably with a payments component
  • Excellent leadership and people management skills, with the ability to inspire and develop high-performing teams.
  • Strategic thinker with a customer-first mindset and a knack for problem-solving.
  • Experience with customer support technologies and platforms (e.g., Zendesk)


  • Minimum of 5 years in a leadership role within customer support or a related field.
  • Demonstrated experience in managing technical support teams, especially in a SaaS or payments environment.
  • Ability to work in a fast-paced, high-growth environment, with flexibility to adapt to changing priorities.
  • Strong analytical skills with a data-driven approach to decision-making.
  • Excellent communication and interpersonal skills, with the ability to engage effectively with both internal teams and customers.
  • Experience at a Seed - Series B company building support teams from the ground up


  • At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. The annual base salary for this role ranges from $165,000- $190,000, 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.

Benefits & Perks

  • 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

**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 [Clifton Jadoo at cliffj@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.

This job is no longer accepting applications

See open jobs at Wingspan.