Senior Account Executive
$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

Senior Account Executive   $200,000 USD/year

Description

You will not enter a polished market. You will construct one. This role is designed for an enterprise sales professional capable of entering an undefined space, informing senior HR and Total Rewards executives, and converting a novel concept into executed employer agreements. If your process depends on inbound pipeline, established budget categories, or proven frameworks, this opportunity is not aligned with your approach.

We are establishing a workplace-giving channel designed to fund scholarships in advance of a January 2027 launch. The structure is distinctive: employers are not required to locate budget. The offering is structured around a federal tax credit, meaning the sales motion does not compete for HR technology spending. Instead, it centers on guiding large employers through a zero-cost method to support education via payroll giving.

Your daily focus will include enterprise-level prospecting, discovery engagement, multi-stakeholder navigation, and deal closure. You will engage HR, Total Rewards, Benefits, CSR, Finance, and Legal executives. You will present tax-credit mechanics with precision, address inquiries related to ERISA and state eligibility requirements, and translate buyer input into a more refined market entry strategy. In time, your contributions will establish the groundwork for a repeatable enterprise channel.

This is a remote position based in the US and includes travel requirements. If you have successfully closed sophisticated enterprise transactions, thrive on generating demand from nothing, and seek sales work connected to scholarship funding at scale, we encourage your application.

What you will be doing

  • Develop an outbound enterprise pipeline targeting HR, Total Rewards, Benefits, CSR, Finance, and Legal stakeholders at large employers
  • Conduct discovery conversations that identify buyer concerns, approval pathways, resistance points, and implementation readiness
  • Execute the sale of a federal tax-credit-enabled workplace-giving solution across complex, multi-party enterprise sales cycles
  • Address inquiries concerning tax credits, ERISA compliance, state eligibility criteria, legal scrutiny, finance approval, and employer launch authorization
  • Collect buyer insights from sales conversations to sharpen the ideal customer profile, value messaging, and go-to-market approach

What you will NOT be doing

  • Relying on inbound demand or an established lead generation system to populate your pipeline
  • Offering a conventional HR technology product that competes for existing employer budgets
  • Overseeing employee participation, payroll integration, or post-deployment account management
  • Executing brand marketing initiatives or transferring qualified leads to others for closure
  • Leading a sales organization rather than directly generating and closing enterprise deals

Key responsibilities

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

Candidate 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 buying committees
  • Robust outbound prospecting capabilities and proven ability to generate pipeline from scratch
  • Capacity to articulate complex tax-credit-funded offerings with precision to executive, legal, and finance stakeholders
  • Executive-level presence and consultative engagement with senior enterprise buyers
  • US work authorization
  • Capability to work remotely and travel as required

Nice to have

  • Background selling workplace giving, employee benefits, HR tech, CSR, or philanthropy solutions to large employers
  • Track record of building demand for an emerging category or missionary sale without a recognized budget line
  • Knowledge of payroll giving, federal tax credits, ERISA, 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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