Enterprise Account Executive – Workplace Scholarships

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop an outbound pipeline targeting Heads of HR, Total Rewards, Benefits, and CSR at large employers with over 10,000 employees.

• Oversee intricate, consultative sales processes involving HR, Finance, Legal, Payroll, and executive stakeholders to initiate the Workplace Scholarships program.

• Assist employers in understanding payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and implementation while directing tax-related inquiries to qualified professional advisors.

• Transform signed employers into successful program launches, ensuring employee enrollment before the 2027 tax season.

• Gather structured market intelligence from buyer interactions to enhance messaging, refine the ideal customer profile, and develop the enterprise go-to-market strategy.

• Establish a robust pipeline of enterprise employers that effectively implement the Workplace Scholarships payroll-giving program, fostering a scalable employer channel with enrolled employee donors in advance of the 2027 tax season.

• Personally generate and secure enterprise pipelines instead of managing a sales team.

⛳️ Requirements

• 7+ years of quota-carrying enterprise B2B sales experience, including a minimum of 3 years in a senior Enterprise AE or Director-level closing role.

• Proven experience selling to HR, Total Rewards, Benefits, or CSR decision-makers within enterprise organizations.

• Personally managed an annual new-business quota of at least $1.5M (ARR, contract value, premium, or equivalent), with a documented history of achievement.

• Successfully closed complex, multi-stakeholder deals with employers that have over 10,000 employees.

• Experience in selling employee-elected, payroll-deducted benefits, workplace-giving programs, or similar enterprise HR solutions.

• Demonstrated capability to build enterprise pipelines from the ground up through outbound prospecting.

• Ability to convey complex ideas in a simple manner — including payroll deduction and federal tax credit mechanics — while directing tax advice to qualified professionals as needed.

• Legally permitted to work in the United States without the need for sponsorship.

• Capable of working remotely with approximately 40% travel.

• Nice to have: Experience in selling voluntary or ancillary benefits such as education, financial wellness, pet insurance, legal, or identity-protection programs.

• Nice to have: Experience in selling workplace-giving or CSR platforms.

• Nice to have: Established relationships with enterprise HR, Total Rewards, or CSR leaders.

• Nice to have: Familiarity with payroll systems, HRIS platforms, and withholding mechanics.

• Nice to have: Experience in creating a new market category or implementing a zero-to-one enterprise go-to-market strategy.

🏝️ Benefits

• Remote position based in the U.S., with approximately 40% travel required.

• Start date: as soon as possible.