Employee Benefits Sales Director $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
In most enterprise sales roles, you compete for budget within an established category. In this one, you will create the category itself.
Workplace Scholarships is establishing a new employer distribution channel that allows employees to support K-12 scholarships via payroll giving, leveraging a new federal tax credit. Employers are not required to allocate new benefits budget or displace a current vendor. Your role is to educate senior leaders in HR, Total Rewards, and CSR, establish confidence in an entirely new model, and convert enterprise employers into launch partners ahead of the 2027 tax season.
You will serve as the first enterprise seller dedicated to this channel. This involves generating pipeline from the ground up, accessing Fortune-scale employers, and managing complex buying groups that span HR, Finance, Legal, Payroll, and CSR. Each conversation will influence not only your own pipeline but also the messaging, ideal customer profile, and go-to-market strategy for the broader organization.
This role is designed for someone who thrives in environments where structure does not yet exist. You will not inherit inbound demand or an established sales process. You will create it. If you have successfully sold voluntary benefits, workplace giving, or payroll-integrated programs to enterprise employers and are looking to build something with significant social impact, we would like to speak with you.
What you will be doing
- Develop outbound pipeline targeting Heads of HR, Total Rewards, Benefits, and CSR at enterprise employers with 10,000+ employees.
- Manage complex, consultative sales cycles involving HR, Finance, Legal, Payroll, and executive stakeholders to implement the Workplace Scholarships program.
- Address employer questions related to payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and program rollout while directing tax-specific inquiries to professional advisors where appropriate.
- Transform signed employers into successful program launches with employees enrolling ahead of the 2027 tax season.
- Collect structured market intelligence from buyer interactions to improve messaging, refine the ideal customer profile, and strengthen the enterprise go-to-market playbook.
What you will NOT be doing
- Relying on inbound leads or working from a pre-built sales playbook.
- Selling yet another HR platform that competes for existing employer budget.
- Overseeing employee support, payroll administration, or post-launch account operations.
- Transferring opportunities to another team for closure.
- Managing a sales organization rather than personally building and closing enterprise pipeline.
Key responsibilities
Establish a converting pipeline of enterprise employers that successfully implement the Workplace Scholarships payroll-giving program, building a scalable employer channel with enrolled employee donors in advance of the 2027 tax season.
Candidate requirements
- 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 to 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.
- Experience selling employee-elected, payroll-deducted benefits, workplace-giving programs, or similar enterprise HR offerings.
- 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.
Nice to have
- 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.
Applying for a role? Here’s what to expect.
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