Employee Benefits Sales Director $200,000 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 wait for a ready-made category. You create it. This role is built for an enterprise sales professional who can enter an undefined market, engage senior HR and Total Rewards executives, and convert a novel concept into confirmed employer partnerships. If you depend on inbound interest, established budget allocations, or proven sales frameworks, this opportunity will not align.
We are building a new workplace-giving channel designed to fund scholarships in advance of its January 2027 launch. The approach is distinctive: employers are not asked to allocate budget. The program operates through a federal tax credit, which means the sale does not compete against existing HR technology spending. Instead, it involves guiding large employers to understand a no-cost method for supporting education via payroll giving.
Your time will center on enterprise outreach, discovery conversations, multi-stakeholder deal progression, and deal closure. You will engage HR, Total Rewards, Benefits, CSR, Finance, and Legal executives. You will communicate tax-credit mechanics with precision, address concerns involving ERISA and state eligibility, and translate buyer input into a more effective go-to-market approach. In time, your efforts will establish the groundwork for a scalable enterprise sales channel.
This is a remote position based in the US, with travel expectations. If you have a history of closing intricate enterprise transactions, thrive on generating demand from scratch, and seek sales work connected to scholarship funding at scale, we would like to connect with you.
What you will be doing
- Develop outbound enterprise pipelines by engaging HR, Total Rewards, Benefits, CSR, Finance, and Legal executives at large employers
- Conduct discovery sessions that identify buyer needs, approval pathways, resistance points, and implementation readiness
- Navigate complex, multi-stakeholder enterprise sales cycles to sell a federal tax-credit-funded workplace-giving program
- Address inquiries related to tax credits, ERISA, state eligibility, legal scrutiny, finance approval, and employer launch authorization
- Gather marketplace intelligence from buyer interactions to sharpen the ideal customer profile, positioning, and go-to-market strategy
What you will NOT be doing
- Relying on inbound traffic or an established demand generation system to populate your pipeline
- Offering a conventional HR technology solution that draws from existing employer budgets
- Overseeing employee registration, payroll integration, or post-launch account management
- Executing brand visibility initiatives or transferring leads to others for close
- Leading a sales organization rather than personally sourcing and closing enterprise deals
Key responsibilities
Build a pipeline of large employers committed to launching our payroll-giving program, with signed agreements secured before the January 2027 launch date.
Candidate requirements
- 7+ years of enterprise B2B sales experience
- Documented success selling to HR, Total Rewards, Benefits, CSR, or workplace-giving decision-makers
- Proven enterprise quota achievement managing multi-stakeholder buying groups
- Strong outbound prospecting capabilities with a history of generating pipeline from the ground up
- Capability to clearly explain complex tax-credit-funded programs to executive, legal, and finance stakeholders
- Executive presence and consultative communication style with senior enterprise decision-makers
- US work authorization
- Ability to work remotely and travel as required
Nice to have
- Background selling workplace giving, employee benefits, HR technology, CSR, or philanthropy solutions to large employers
- Experience building demand for a new category or evangelical offering without an existing budget allocation
- Knowledge of payroll giving, federal tax credits, ERISA, or state eligibility regulations
- Career progression from quota-carrying SDR or BDR to enterprise AE
Applying for a role? Here’s what to expect.
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