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Account Executive, Mid Market - Wingspan

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Job Title
Account Executive, Mid Market
Job Location
Remote (USA)
Job Description

Who We Are

For the freelancers 57 Million Freelancers in the US the administrative burden of self-employment is a full-time job that doesn't pay. Wingspan is the first one-stop shop for knowledge-based freelancers that streamlines income, benefits, and taxes -- think Justworks for freelancers. We've assembled a world-class team that has the HR, technology, and insurance expertise to execute this vision and build Wingspan into a big business with significant impact. If you’re as excited to champion freelancers as much as we are, you’ll fit right in at Wingspan.

How we show up:

  • We're empathetic to ourselves, each other, and our customers’ needs
  • We look for root causes. When something goes wrong, we commit to solving at the source.
  • We are fast and agile. As an early stage startup we value progress over perfection. Our team is proactive, takes ownership and is comfortable operating in ambiguous, at times chaotic situations.
  • We’re impact obsessed. We don't do things for the sake of doing them -- we are always weighing impact vs. output in everything we do.
  • We are curious: about our clients' unique needs, about the changing nature of work, and about how we can build tangible tools to support freelancers.

What you'll do:


  • Prospect new clients and communicate with clients
  • Articulate Wingspan’s relevance to prospective clients
  • Discover and match use cases effectively to the Wingspan platform
  • Document account details like: main use case, deal time frame, and drive next steps via our CRM.
  • Product demos.
  • Build relationships in the industry and with prospective clients
  • Travel as needed for client meetings

Who You Are:

You Are:

  • Team player eager to collaborate with a small team.
  • You have a growth mindset
  • You have empathy for yourself, your team and your customers
  • You are comfortable with ambiguity
  • You are results focused and accountable
  • You like to be competitive
  • You are curious about everything: From the changing nature of work to the problem Wingspan is hoping to solve for it’s clients
  • You are detailed and action oriented, with ability to manage multiple requests, respond quickly and with high quality, and problem solve on the fly.


  • You have experience building a pipeline from scratch and working with a CRM
  • You have strong written and verbal communication skills
  • You can breakdown complicated matters and communicate them clearly
  • Experience in a full-cycle sales role, ideally in SaaS
  • Track record of forecast accuracy and revenue deliverables
  • Consistent overachievement against sales targets in past experience


  • At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. The annual total compensation (this includes base and incentive pay) for this role ranges is $170,000 OTE + 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.

Benefits & Perks

    • Unlimited vacation
    • Competitive stock option package
    • $300 one-time WFH stipend
    • Medical, dental, and vision benefits
    • Top of the line Mac laptop
    • 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.**

To all recruitment firms we do not work with: Wingspan does not permit the submission of agency-provided resumes. Kindly refrain from sending resumes to our job-related email addresses and Wingspan staff members. Wingspan will not be held accountable for any charges associated with unsought resumes.

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].

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 success and innovation.

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Wingspan Headquarters Location

New York, NY

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Wingspan Company Size

Between 20 - 100 employees

Wingspan Founded Year


Wingspan Total Amount Raised


Wingspan Funding Rounds

View funding details
  • Series A

    $14,000,000 USD

  • Seed

    $3,500,000 USD