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
You do not refine an established category. You construct it from the ground up. This role is designed for an enterprise sales architect capable of entering an undefined market, educating senior HR and Total Rewards executives, and transforming a novel concept into committed employer partnerships. If you rely on inbound demand, recognized budget categories, or proven sales frameworks, this opportunity will not align.
We are launching a new workplace-giving platform that will fund scholarships ahead of its January 2027 debut. The structure is distinctive: employers are not required to allocate budget. The program is built on a federal tax credit mechanism, meaning the conversation is not about competing for HR technology dollars. It is about guiding large organizations to understand a zero-cost pathway to support education via payroll giving.
Your daily work will center on enterprise outreach, discovery conversations, multi-level stakeholder engagement, and deal closure. You will engage with HR, Total Rewards, Benefits, CSR, Finance, and Legal executives. You will present tax-credit frameworks with precision, address questions regarding ERISA and state-level eligibility, and convert buyer input into a more refined go-to-market strategy. In time, your efforts will establish the blueprint for a repeatable enterprise channel.
This is a remote, US-based position with travel expectations. If you have a history of closing sophisticated enterprise agreements, thrive on generating demand in uncharted territory, and want your sales impact connected to scholarship funding at scale, we would like to connect with you.
What you will be doing
- Develop outbound enterprise pipeline targeting HR, Total Rewards, Benefits, CSR, Finance, and Legal executives at large organizations
- Conduct discovery sessions that reveal buyer motivations, decision-making structures, concerns, and implementation readiness
- Navigate complex, multi-stakeholder enterprise sales cycles for a federal tax-credit-supported workplace-giving initiative
- Address inquiries concerning tax credits, ERISA compliance, state eligibility parameters, legal vetting, finance approval, and employer launch authorization
- Gather market intelligence from buyer interactions to sharpen the ideal customer profile, messaging framework, and go-to-market approach
What you will NOT be doing
- Relying on inbound leads or an established demand generation system to supply your pipeline
- Selling a conventional HR technology product that competes for existing employer budgets
- Overseeing employee enrollment, payroll integration, or post-launch account management
- Executing brand awareness initiatives or transferring leads to another team member for closure
- Leading a sales organization instead of directly generating and closing enterprise deals
Key responsibilities
Build a high-conversion pipeline of large employers committed to launching our payroll-giving program in advance of the January 2027 launch.
Candidate requirements
- 7+ years of enterprise B2B sales experience
- Documented success selling to HR, Total Rewards, Benefits, CSR, or workplace-giving decision-makers
- Verified complex enterprise quota achievement with multi-stakeholder purchasing committees
- Proven outbound prospecting capability and a history of creating pipeline from scratch
- Capacity to communicate complex tax-credit-funded programs clearly to executive, legal, and finance stakeholders
- Executive presence and consultative engagement with senior enterprise leaders
- US work authorization
- Capability to work remotely and travel when required
Nice to have
- Background selling workplace giving, employee benefits, HR tech, CSR, or philanthropy solutions to large organizations
- Experience building demand for an emerging category or evangelical sale without an established budget allocation
- Knowledge of payroll giving, federal tax credits, ERISA, or state eligibility considerations
- Career progression from quota-carrying SDR or BDR to enterprise AE
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