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 existing budget in an established category. In this one, you build the category itself.
Workplace Scholarships is creating an employer distribution channel that allows employees to contribute to K-12 scholarships via payroll deductions backed by a new federal tax credit. Employers are not asked to allocate fresh benefits funding or switch from a current vendor. Your role centers on educating senior leaders in HR, Total Rewards, and CSR, establishing trust in an entirely novel approach, and converting enterprise organizations into launch partners ahead of the 2027 tax season.
You will serve as the first enterprise seller dedicated to this channel. That involves generating pipeline without prior precedent, securing access to Fortune-tier employers, and coordinating with multifaceted buying committees spanning HR, Finance, Legal, Payroll, and CSR functions. Each interaction you conduct will influence not just your own pipeline, but also the positioning, target customer definition, and market-entry framework for the broader organization.
This role suits someone who thrives in greenfield environments. You will not step into existing inbound interest or a proven sales methodology. You will create it. If you have a track record of selling voluntary benefits, workplace giving platforms, or payroll-integrated solutions to enterprise employers and are motivated by work with genuine social purpose, we would welcome your application.
What you will be doing
- Develop outbound sales pipeline targeting Heads of HR, Total Rewards, Benefits, and CSR at enterprise organizations employing 10,000 or more people.
- Manage complex, consultative deal cycles involving stakeholders across HR, Finance, Legal, Payroll, and executive leadership to secure adoption of the Workplace Scholarships program.
- Support employers through operational inquiries related to payroll deduction structures, withholding processes, ERISA compliance, multi-state program eligibility, and implementation logistics, while steering tax-specific matters to qualified advisors.
- Transition signed employer agreements into live program deployments with employee enrollment occurring before the 2027 tax season.
- Document actionable buyer insights from sales engagements to continuously improve messaging, customer segmentation, and the enterprise market strategy.
What you will NOT be doing
- Relying on inbound demand or working within a prebuilt sales framework.
- Promoting another HR technology competing for allocated employer budgets.
- Overseeing employee service functions, payroll processing, or operational account management after launch.
- Passing qualified opportunities to a separate closing team.
- Leading a sales team rather than directly sourcing and closing your own enterprise deals.
Key responsibilities
Establish a high-conversion pipeline of enterprise employers that successfully deploy the Workplace Scholarships payroll-giving program, building a scalable employer distribution channel with active employee donors ahead of the 2027 tax season.
Candidate requirements
- 7+ years carrying quota in enterprise B2B sales, with at least 3 years in a senior Enterprise Account Executive or Director-level closing capacity.
- Proven experience selling to HR, Total Rewards, Benefits, or CSR executives at enterprise-scale employers.
- Demonstrated personal ownership of an annual new-business quota of at least $1.5M (measured in ARR, contract value, premium, or comparable metrics) with verifiable quota achievement.
- Direct experience closing complex, multi-stakeholder agreements with employers of 10,000+ employees.
- Background selling employee-elected, payroll-deducted benefits, workplace-giving solutions, or similar enterprise HR programs.
- Documented success in building enterprise pipeline from the ground up using outbound prospecting methods.
- Skill in explaining sophisticated topics clearly, such as payroll deduction mechanics and federal tax-credit frameworks, while appropriately deferring tax guidance to licensed professionals.
- Legal authorization to work in the United States without requiring sponsorship.
- Capacity to operate remotely with travel expectations of approximately 40%.
Nice to have
- Sales experience with voluntary or ancillary benefits including education benefits, financial wellness tools, pet insurance, legal services, or identity protection offerings.
- Track record selling workplace giving platforms or CSR technology.
- Established professional relationships with enterprise HR, Total Rewards, or CSR decision-makers.
- Working knowledge of payroll systems, HRIS platforms, and tax withholding processes.
- Background in category creation or launching zero-to-one enterprise go-to-market initiatives.
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