Senior Account Executive, Stealth Educational Startup (Remote) - $200,000/year USD at Crossover

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 Won’t 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

Senior Account Executive Key Responsibilities

Establish a qualified 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 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 Requirements

• 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

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-SandySpr-SeniorAccountE