Enterprise 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
Category creation is not given. You create it. This role is designed for an enterprise sales professional who can enter an undefined market, guide senior HR and Total Rewards executives through new concepts, and convert education into committed employer partnerships. If you depend on inbound pipelines, recognized budget categories, or established sales frameworks, this opportunity will not align.
We are building a new workplace-giving channel designed to support scholarship funding in advance of a January 2027 launch. The structure is unconventional: employers are not required to allocate existing budget. Instead, the program leverages a federal tax credit, meaning the conversation is not about competing for HR technology dollars. It is about demonstrating how large organizations can enable education support through payroll giving at zero cost.
Your time will center on enterprise outreach, discovery conversations, multi-stakeholder engagement, and deal closure. You will engage with leaders across HR, Total Rewards, Benefits, CSR, Finance, and Legal functions. You will present tax-credit mechanics with precision, address concerns related to ERISA and state-level eligibility, and use buyer insights to strengthen the go-to-market strategy. In time, your efforts will establish the groundwork for a repeatable enterprise sales motion.
This is a remote position based in the US, with travel requirements. If you have a history of closing sophisticated enterprise agreements, thrive in demand-generation environments, and want your sales contribution connected to scholarship access at scale, we encourage you to apply.
What you will be doing
- Develop outbound enterprise pipelines targeting HR, Total Rewards, Benefits, CSR, Finance, and Legal stakeholders at large organizations
- Lead discovery sessions that identify buyer priorities, internal decision workflows, potential objections, and implementation readiness
- Navigate complex, multi-stakeholder enterprise sales cycles to sell a federal tax-credit-backed workplace-giving solution
- Address inquiries concerning tax credits, ERISA compliance, state eligibility parameters, legal due diligence, finance approval, and employer launch authorization
- Collect and synthesize market intelligence from buyer interactions to sharpen ideal customer profiles, messaging frameworks, and go-to-market execution
What you will NOT be doing
- Relying on inbound lead generation or an established demand engine to populate your pipeline
- Selling conventional HR technology solutions that vie for pre-allocated employer budgets
- Overseeing employee enrollment processes, payroll integration, or post-launch account management
- Executing brand awareness initiatives or transferring qualified leads to others for closing
- Leading a sales organization rather than directly generating and closing enterprise deals yourself
Key responsibilities
Build a pipeline of signed large employers committed to launching our payroll-giving program ahead of the January 2027 go-live date.
Candidate requirements
- 7+ years of enterprise B2B sales experience
- Proven success selling into HR, Total Rewards, Benefits, CSR, or workplace-giving buyers
- Demonstrated complex enterprise quota attainment with multi-stakeholder buying groups
- Strong outbound prospecting skills and a track record of building pipeline from zero
- Ability to explain complex tax-credit-funded programs accurately to executive, legal, and finance audiences
- Executive presence and consultative communication with senior enterprise decision-makers
- US work authorization
- Ability to work remotely and travel as needed
Nice to have
- Background selling workplace giving, employee benefits, HR tech, CSR, or philanthropy solutions to large employers
- Experience building demand for emerging categories or evangelical selling without established budget allocations
- Knowledge of payroll giving, federal tax credits, ERISA regulations, or state eligibility frameworks
- Career progression from quota-carrying SDR or BDR roles to enterprise AE positions
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