Enterprise 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
Building a polished category is not your starting point. You create it. This role is designed for an enterprise sales professional who can enter an undefined market, educate senior leaders across HR and Total Rewards, and convert a novel concept into committed employer partnerships. If you rely on inbound leads, established budget categories, or proven playbooks, this position will not align with your approach.
We are establishing a workplace-giving channel designed to fund scholarships in advance of a January 2027 launch. The structure is distinct: employers are not required to allocate budget. The offering is built on a federal tax credit framework, meaning the sale does not compete for existing HR technology spend. Instead, it focuses on guiding large employers through a zero-cost method to support education via payroll giving.
Your time will center on enterprise prospecting, discovery conversations, multi-stakeholder sales cycles, and deal closure. You will engage with leaders across HR, Total Rewards, Benefits, CSR, Finance, and Legal functions. You will articulate tax-credit mechanics clearly, address concerns related to ERISA and state eligibility, and use buyer insights to refine the go-to-market approach. Over time, your efforts will establish the groundwork for a repeatable enterprise channel.
This is a remote, US-based position that includes travel. If you have a history of closing complex enterprise agreements, thrive on generating demand from the ground up, and want your sales achievements connected to scholarship funding at scale, we encourage you to apply.
What you will be doing
- Develop outbound enterprise pipeline by engaging HR, Total Rewards, Benefits, CSR, Finance, and Legal executives at large employers
- Conduct discovery sessions that identify buyer motivations, decision structures, concerns, and readiness to launch
- Sell a federal tax-credit-enabled workplace-giving solution through multi-stakeholder, complex enterprise sales cycles
- Address questions involving tax credits, ERISA compliance, state eligibility criteria, legal vetting, financial review, and employer approval processes
- Gather market intelligence from buyer interactions to sharpen the ideal customer profile, refine messaging, and enhance the go-to-market playbook
What you will NOT be doing
- Relying on inbound leads or an established demand generation system to populate your pipeline
- Selling a conventional HR technology product that draws from an existing employer budget category
- Overseeing employee enrollment, payroll integration, or post-launch account management activities
- Executing brand awareness initiatives or transferring leads to another person for closure
- Leading a sales team rather than personally generating and closing enterprise deals
Key responsibilities
Build a high-conversion pipeline of large employers committed to launching our payroll-giving program prior to the January 2027 launch date.
Candidate requirements
- 7+ years of enterprise B2B sales experience
- Proven track record selling to HR, Total Rewards, Benefits, CSR, or workplace-giving decision-makers
- Documented enterprise quota achievement with multi-stakeholder buying committees
- Strong outbound prospecting abilities and a history of generating pipeline from scratch
- Capacity to clearly explain complex tax-credit-funded programs to executive, legal, and finance stakeholders
- Executive presence and consultative communication skills with senior enterprise leaders
- 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 sale without an established budget allocation
- Knowledge of payroll giving, federal tax credits, ERISA, or state eligibility frameworks
- Career path from quota-carrying SDR or BDR to enterprise AE
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