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Director of Employer Partnerships, Stealth Educational Startup (Remote) - $200,000/year USD

Crossover
Chicago, IL Remote Full Time
POSTED ON 8/11/2026
AVAILABLE BEFORE 11/2/2026
You do not wait for a polished category. You create one. This role is designed for an enterprise sales builder capable of entering an undefined market, educating senior HR and Total Rewards executives, and transforming a novel concept into confirmed employer commitments. If you require inbound lead flow, an established budget allocation, or a proven playbook, this position will not align.

We are establishing a new workplace-giving channel designed to support scholarship funding in advance of its January 2027 launch. The structure is distinctive: employers are not required to allocate budget. The program is structured around a federal tax credit, meaning the sale does not compete for HR technology spending. Instead, it centers on helping large organizations recognize a zero-cost opportunity to advance education through payroll giving.

Your workweek will focus on enterprise prospecting, discovery conversations, multi-stakeholder engagement, and deal closure. You will engage with HR, Total Rewards, Benefits, CSR, Finance, and Legal executives. You will articulate tax-credit mechanics with precision, address questions regarding ERISA and state eligibility, and convert buyer insights into a more refined go-to-market strategy. In time, your efforts will serve as the blueprint for a scalable enterprise channel.

This is a remote, US-based position requiring travel. If you have successfully closed complex enterprise transactions, thrive on building demand from the ground up, and seek sales work connected to scholarship funding at scale, we encourage you to apply.

What You Will Be Doing

  • Develop outbound enterprise pipeline targeting HR, Total Rewards, Benefits, CSR, Finance, and Legal executives at large employers
  • Conduct discovery conversations that identify buyer priorities, decision-making pathways, objections, and readiness for launch
  • Navigate complex, multi-stakeholder enterprise sales cycles to sell a federal tax-credit-funded workplace-giving program
  • Address questions concerning tax credits, ERISA, state eligibility, legal review, finance review, and employer approval for launch
  • Collect market insights from buyer interactions to refine ideal customer profiles, messaging, and go-to-market strategy

What You Won’t Be Doing

  • Relying on inbound leads or an established demand engine to generate your pipeline
  • Selling a conventional HR tech solution that competes for existing employer budget allocations
  • Overseeing employee enrollment, payroll implementation, or post-launch account management
  • Executing brand awareness campaigns or transferring leads to another party for closing
  • Leading a sales team rather than personally building and closing enterprise opportunities

Director Of Employer Partnerships 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.

Basic Requirements

  • 7 years of enterprise B2B sales experience
  • Proven track record selling into HR, Total Rewards, Benefits, CSR, or workplace-giving buyers
  • Demonstrated success achieving complex enterprise quotas with multi-stakeholder buying groups
  • Strong outbound prospecting capabilities and a history of generating pipeline from scratch
  • Capability to communicate complex tax-credit-funded programs clearly to executive, legal, and finance audiences
  • 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 Requirements

  • Experience selling workplace giving, employee benefits, HR tech, CSR, or philanthropy programs to large employers
  • Experience building demand for a new category or evangelical sale without an established budget line
  • Familiarity with payroll giving, federal tax credits, ERISA, or state eligibility considerations
  • Progression from quota-carrying SDR or BDR to enterprise AE

About Stealth Educational Startup

We are a stealth educational startup in Austin, TX (center of educational innovation in US). We are building an online community focusing on the most underserved customer base in US education - gifted and talented kids. We are a remote first company who hires globally via Crossover.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5836-US-Chicago-DirectorofEmpl

Salary : $200,000

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