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

You do not polish an existing category. You create it. 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 committed employer partnerships. If you rely on inbound pipeline, established budget categories, or proven playbooks, this opportunity is not for you.

We are building a new workplace-giving channel to fund scholarships in advance of a January 2027 launch. The model is distinct: employers are not asked to allocate budget. The program leverages a federal tax credit, so the conversation is not about competing for HR technology dollars. It is about demonstrating how large employers can enable education support through payroll giving at no cost.

Your day-to-day will center on enterprise prospecting, discovery conversations, multi-stakeholder sales cycles, and deal closure. You will engage HR, Total Rewards, Benefits, CSR, Finance, and Legal executives. You will articulate tax-credit mechanics with precision, address concerns involving ERISA and state-level eligibility, and translate buyer input into a more refined go-to-market strategy. In time, your contributions will form the basis of a scalable enterprise channel.

This is a remote, US-based position requiring travel. If you have successfully closed complex enterprise transactions, thrive on generating demand from scratch, and seek sales work connected to scholarship funding at scale, we would like to speak 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 conversations that reveal buyer priorities, internal approval paths, objections, and implementation readiness
• Advance sales of a federal tax-credit-supported workplace-giving program through intricate, multi-stakeholder enterprise buying cycles
• Address inquiries related to tax credits, ERISA compliance, state eligibility parameters, legal vetting, finance approval, and employer launch authorization
• Collect market intelligence from buyer interactions to sharpen the ideal customer profile, value messaging, and go-to-market approach

What You Won’t Be Doing

• Relying on inbound interest or a fully developed demand generation system to populate your pipeline
• Selling a conventional HR technology product that vies for existing employer budget allocation
• Overseeing employee enrollment processes, payroll integration, or post-launch account management
• Executing brand marketing initiatives or transferring qualified leads to another closer
• Leading a sales organization rather than personally generating and closing enterprise deals

Director Of Business Development Key Responsibilities

Build a converting pipeline of large employers committed to launching our payroll-giving program ahead of the January 2027 launch date.

Basic Requirements

• 7+ years of enterprise B2B sales experience
• Documented success selling to HR, Total Rewards, Benefits, CSR, or workplace-giving decision-makers
• Verified track record of complex enterprise quota achievement with multi-stakeholder buyer groups
• Proficient outbound prospecting capabilities and history of creating pipeline from the ground up
• Capacity to explain complex tax-credit-supported programs with accuracy 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 Requirements

• 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 established budget designation
• Knowledge of payroll giving, federal tax credits, ERISA frameworks, or state eligibility considerations
• Career 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-Clevelan-DirectorofBusi