Enterprise AE: Launching Payroll-Driven Scholarships

Texas Sports Academy Main; United States; Remote; USD 340,000 - 460,000; Full time

Benefits offered by this job

Remote work

40% travel

Impactful mission

Job summary

Workplace Scholarships is building a new employer channel to fund K-12 scholarships through payroll giving, nationwide, with a federal tax-credit program starting in 2027. You’ll educate senior HR, Total Rewards, and CSR leaders, build confidence in a brand-new model, and launch enterprise partnerships from the ground up.

You will lead outbound pipelines at Fortune-scale employers, navigating HR, Finance, Legal, Payroll, and CSR stakeholders to close multi-million-dollar deals and enable program

Qualifications

• 7+ years of quota-carrying enterprise B2B sales experience.
• At least 3 years in a senior Enterprise AE or Director-level closing role.
• Experience selling to HR, Total Rewards, Benefits, or CSR leaders at enterprise employers.
• Personally carried an annual new-business quota of at least $1.5M ARR or equivalent.
• Proven ability to close complex, multi-stakeholder deals with large employers.
• Ability to build enterprise pipelines from zero through outbound prospecting.
• Legally authorized to work in the United States without sponsorship.
• Remote-friendly with approximately 40% travel.

Responsibilities

• Build outbound pipeline at enterprise employers with 10,000+ employees.
• Lead complex, consultative sales cycles across HR, Finance, Legal, Payroll, and CSR stakeholders.
• Guide employers through payroll deduction and ERISA mechanics.
• Convert signed employers into successful program launches before the 2027 tax season.
• Capture market intelligence to refine messaging and ICP.

Skills

Enterprise B2B sales

New-business quota

Stakeholder management

Payroll-deducted benefits

Remote-friendly

Complex concepts communication

Zero-to-one market building

Job description

Workplace Scholarships is building a new employer channel to fund K-12 scholarships through payroll giving, nationwide, with a federal tax-credit program starting in 2027. You’ll educate senior HR, Total Rewards, and CSR leaders, build confidence in a brand-new model, and launch enterprise partnerships from the ground up.

You will lead outbound pipelines at Fortune-scale employers, navigating HR, Finance, Legal, Payroll, and CSR stakeholders to close multi-million-dollar deals and enable program