Director of Business Development
$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 

United States
Fully-remote
full-time (40 hrs/week)
Flexible schedule
Long-term role

Director of Business Development   $200,000 USD/year

Description

You do not polish an existing category. You create it. This role is for an enterprise sales professional who can enter an undefined market, educate senior Total Rewards and HR executives, and convert a novel concept into confirmed employer commitments. If you require established inbound pipelines, recognized budget allocations, or proven go-to-market frameworks, this opportunity will not align.

We are establishing a new workplace-giving channel designed to fund scholarships in advance of a January 2027 launch date. The approach 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 focuses on helping large organizations recognize a zero-cost pathway to support education through payroll giving.

Your time will center on enterprise prospecting, discovery, multi-stakeholder engagement, and deal closure. You will engage HR, Benefits, Total Rewards, Legal, Finance, and CSR executives. You will articulate tax-credit mechanics with precision, address concerns related to state eligibility and ERISA, and translate buyer input into an increasingly refined go-to-market strategy. Over time, your contributions will establish the foundation for a scalable enterprise sales channel.

This is a remote position based in the US with travel expectations. If you have successfully closed complex enterprise transactions, thrive on generating demand from the ground up, and want your sales efforts connected to scholarship funding at scale, we encourage you to apply.

What you will be doing

  • Develop outbound enterprise pipelines targeting HR, Benefits, Total Rewards, Legal, Finance, and CSR leaders at large organizations
  • Conduct discovery conversations that identify buyer priorities, approval processes, objections, and readiness to launch
  • Lead the sale of a federal tax-credit-funded workplace-giving program through multi-stakeholder, complex enterprise sales cycles
  • Address questions concerning tax credits, state eligibility, ERISA compliance, legal review, finance approval, and employer launch authorization
  • Gather market intelligence from buyer interactions to refine ideal customer profiles, messaging frameworks, and go-to-market strategies

What you will NOT be doing

  • Relying on inbound leads or an established demand generation engine to populate your pipeline
  • Selling a conventional HR technology solution that competes for existing employer budgets
  • Overseeing employee enrollment, payroll integration, or post-launch account management operations
  • Executing brand awareness initiatives or transferring leads to others for closing
  • Leading a sales team rather than directly generating and closing enterprise deals yourself

Key responsibilities

Build a pipeline of large employers committed to launching our payroll-giving program that converts into signed agreements before the January 2027 launch date.

Candidate requirements

  • 7+ years of enterprise B2B sales experience
  • Demonstrated success selling to HR, Benefits, Total Rewards, CSR, or workplace-giving decision-makers
  • Proven track record of complex enterprise quota achievement with multi-stakeholder buying groups
  • Strong outbound prospecting capabilities and a history of building pipeline from scratch
  • Capability to explain complex tax-credit-funded programs with accuracy to executive, legal, and finance stakeholders
  • Executive presence and consultative communication skills with senior enterprise buyers
  • US work authorization
  • Ability to work remotely and travel as required

Nice to have

  • Background selling workplace giving, employee benefits, HR technology, CSR programs, or philanthropy solutions to large employers
  • Experience generating demand for a new category or evangelical sale without an established budget line
  • Knowledge of payroll giving, federal tax credits, ERISA regulations, or state eligibility considerations
  • Career progression from quota-carrying SDR or BDR to enterprise AE

Meet a successful candidate

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Andrew Allen
Andrew  |  VP of Content Marketing
New Zealand

Andrew had thought he had already lived his life's dream working on Broadway. His life is even better now he found a role with Crossover.

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