Senior Account Executive $400,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Description
Unlike most enterprise sales roles that ask you to capture share within an established category, this position requires you to define and build a new one.
Workplace Scholarships is establishing a novel employer channel that allows employees to contribute to K-12 scholarships via payroll giving, leveraging a new federal tax credit. Employers are not required to allocate new benefits budgets or displace current vendors. Your role centers on educating senior leaders in HR, Total Rewards, and CSR, establishing trust in an entirely new framework, and securing enterprise employers as launch partners ahead of the 2027 tax season.
As the inaugural enterprise seller dedicated to this channel, you will construct pipeline from the ground up, establish access to Fortune-scale employers, and manage intricate buying committees spanning HR, Finance, Legal, Payroll, and CSR functions. Each engagement will influence not only your own pipeline but also organizational messaging, customer profiling, and the foundational go-to-market strategy.
This position suits someone energized by creation in uncharted territory. There is no inherited demand flow or polished sales methodology to follow. You will author it. If you have a track record selling voluntary benefits, workplace giving platforms, or payroll-integrated solutions into enterprise employers and seek to contribute to something with substantial social value, we should connect.
What you will be doing
- Develop outbound pipeline targeting Heads of HR, Total Rewards, Benefits, and CSR at enterprise employers with 10,000+ employees.
- Own and advance complex, consultative sales cycles involving HR, Finance, Legal, Payroll, and executive decision-makers to enable Workplace Scholarships program adoption.
- Support employers through inquiries related to payroll deduction, withholding mechanics, ERISA compliance, multi-state eligibility, and implementation logistics, while appropriately referring tax-specific matters to professional advisors.
- Drive signed employer commitments through to successful program launches, ensuring employee enrollment occurs prior to the 2027 tax season.
- Document and synthesize market intelligence from buyer interactions to improve messaging, sharpen the ideal customer profile, and advance the enterprise go-to-market framework.
What you will NOT be doing
- Depending on inbound lead generation or working from a mature sales playbook.
- Competing for existing employer budgets by selling another HR technology platform.
- Overseeing employee support functions, payroll administration tasks, or post-launch account management.
- Transferring qualified opportunities to a separate closing team.
- Leading a sales organization rather than directly sourcing and closing enterprise deals.
Key responsibilities
Construct a pipeline of enterprise employers that converts into successful Workplace Scholarships payroll-giving program launches, establishing a repeatable employer channel with active employee donor enrollment in advance of the 2027 tax season.
Candidate requirements
- 7+ years of quota-carrying B2B enterprise sales experience, with a minimum of 3 years in a senior Enterprise AE or Director-level closing capacity.
- Direct selling experience into HR, Total Rewards, Benefits, or CSR decision-makers at enterprise employers.
- Track record of carrying an annual new-business quota of at least $1.5M (ARR, contract value, premium, or equivalent) with documented quota attainment.
- Proven success personally closing complex, multi-stakeholder agreements with employers of 10,000+ employees.
- Background selling employee-elected, payroll-deducted benefits, workplace-giving solutions, or comparable enterprise HR programs.
- Demonstrated capability to generate enterprise pipeline from zero through outbound prospecting efforts.
- Skill in explaining complex topics clearly, including payroll deduction and federal tax-credit structures, while directing tax advice to qualified professionals when appropriate.
- Legal authorization to work in the United States without sponsorship.
- Capacity to work remotely with approximately 40% travel.
Nice to have
- Background selling voluntary or ancillary benefits including education, financial wellness, pet insurance, legal, or identity protection offerings.
- Experience with workplace giving or CSR platform sales.
- Established relationships with enterprise HR, Total Rewards, or CSR executives.
- Knowledge of payroll systems, HRIS platforms, and withholding procedures.
- History building a new market category or launching a zero-to-one enterprise go-to-market initiative.
Applying for a role? Here’s what to expect.
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Chat-style screening interview.
Cognitive aptitude test.
Prove real-world job skills.
Interview with the hiring manager.
Pass proctored test.
Accept job offer.
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