B2B Director Workplace Giving

$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}  ($200 USD/hour)

• Build outbound pipeline with Heads of HR, Total Rewards, Benefits, and CSR at enterprise employers with 10,000+ employees.
• Lead complex, consultative sales cycles across HR, Finance, Legal, Payroll, and executive stakeholders to launch the Workplace Scholarships program.
• Guide employers through questions around payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and program implementation while appropriately directing tax-specific questions to professional advisors.
• Convert signed employers into successful program launches with employees enrolling before the 2027 tax season.
• Capture structured market intelligence from buyer conversations to refine messaging, the ideal customer profile, and the enterprise go-to-market playbook.

• Waiting for inbound leads or relying on an established sales playbook.
• Selling another HR platform competing for an existing employer budget.
• Managing employee support, payroll administration, or post-launch account operations.
• Handing opportunities to another team to close.
• Managing a sales organization instead of personally creating and closing enterprise pipeline.
• Selling incentive travel, "opportunity"/direct-sales programs, or perks with no payroll-deduction or benefits mechanic — this role sells a structured employee benefit to enterprise HR, not a promotion or a lifestyle product.

Build a converting pipeline of enterprise employers that successfully launch the Workplace Scholarships payroll-giving program, creating a scalable employer channel with enrolled employee donors ahead of tax season 2027.

• 7+ years of quota-carrying enterprise B2B sales experience, including at least 3 years in a senior Enterprise AE or Director-level closing role.
• Experience selling into HR, Total Rewards, Benefits, or CSR decision-makers at enterprise employers.
• Personally carried an annual new-business quota of at least $1.5M (ARR, contract value, premium, or equivalent) with a measurable record of quota attainment.
• Personally closed complex, multi-stakeholder deals with employers of 10,000+ employees.
• Personally sold one of the following into HR, Total Rewards, Benefits, or CSR decision-makers at enterprise employers (10,000+ employees): voluntary / employee-elected benefits (education, pet, legal/identity, financial wellness), workplace-giving or CSR platforms, or HCM/PEO/benefits-administration solutions — able to name the specific product, the buyer's title, and the quota carried.
• Proven ability to build enterprise pipeline from zero through outbound prospecting.
• Ability to communicate complex concepts simply, including payroll deduction and federal tax-credit concepts, while appropriately directing tax advice to qualified professionals.
• Legally authorized to work in the United States without sponsorship.
• Able to work remotely with approximately 40% travel.

• Experience selling voluntary or ancillary benefits such as education, financial wellness, pet insurance, legal, or identity protection programs. 
• Experience selling workplace giving or CSR platforms. 
• Existing relationships with enterprise HR, Total Rewards, or CSR leaders. 
• Familiarity with payroll systems, HRIS platforms, and withholding mechanics. 
• Experience creating a new market category or launching a zero-to-one enterprise GTM motion.