B2B Director Workplace Giving
$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

B2B Director Workplace Giving   $200,000 USD/year

Description

You do not need a polished category. You build one. This is for an enterprise sales builder who can walk into a blank market, educate senior HR and Total Rewards leaders, and turn a new idea into signed employer launches. If you need inbound leads, a known budget line, or a mature playbook, this will feel wrong.

We are creating a new workplace-giving channel that helps fund scholarships ahead of its January 2027 launch. The model is unusual: employers do not need to find budget. The program is designed around a federal tax credit, so the sale is not about taking share from HR tech spend. It is about helping large employers understand a zero-cost way to support education through payroll giving.

Your week will be built around enterprise prospecting, discovery, multi-stakeholder selling, and closing. You will speak with HR, Total Rewards, Benefits, CSR, Finance, and Legal leaders. You will explain tax-credit concepts with care, handle questions around ERISA and state eligibility, and turn buyer feedback into a sharper go-to-market playbook. Over time, your work becomes the foundation for a scalable enterprise channel.

This is a remote, US-based role with travel. If you have closed complex enterprise deals, enjoy creating demand from zero, and want your sales work tied to scholarship funding at scale, we want to hear from you.

What you will be doing

  • Build outbound enterprise pipeline with HR, Total Rewards, Benefits, CSR, Finance, and Legal leaders at large employers
  • Run discovery calls that uncover buyer priorities, decision paths, objections, and launch readiness
  • Sell a federal tax-credit-funded workplace-giving program through complex, multi-stakeholder enterprise cycles
  • Resolve questions around tax credits, ERISA, state eligibility, legal review, finance review, and employer launch approval
  • Capture market feedback from buyer conversations to refine the ideal customer profile, messaging, and go-to-market playbook

What you will NOT be doing

  • Waiting for inbound leads or a mature demand engine to feed your pipeline
  • Selling a standard HR tech tool that competes for an existing employer budget
  • Managing employee enrollment, payroll implementation, or post-launch account operations
  • Running brand awareness campaigns or handing leads off to someone else to close
  • Managing a sales team instead of personally creating and closing enterprise opportunities

Key responsibilities

Create a converting pipeline of large employers signed to launch the our payroll-giving program before the January 2027 launch.

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

  • Experience selling workplace giving, employee benefits, HR tech, CSR, or philanthropy programs to large employers
  • Experience creating demand for a new category or evangelical sale with no established budget line
  • Familiarity with payroll giving, federal tax credits, ERISA, or state eligibility issues
  • Quota-carrying SDR or BDR to enterprise AE progression

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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