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Remote Jobs

Head of Employer Sales (Hybrid)

Remote Jobs, Boston, Massachusetts, us, 02298

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Why consider this job opportunity Opportunity to lead and own the enterprise sales market for an established company

Excellent compensation package with strong benefits

Direct partnership with the CEO and access to a deep advisor network for strategic support

Real infrastructure and support from Product, Marketing, and Client Success teams

Potential for career growth into sales leadership as the company scales

What to Expect (Job Responsibilities)

Own full‑cycle enterprise sales to CHROs and Total Rewards leaders at mid‑to‑large employers, from prospecting through close

Manage and build on an existing pipeline while developing targeted prospecting strategies

Close multi‑million‑dollar annual contract value (ACV) deals with typical sales cycles of 6‑9 months

Partner directly with the CEO and Senior Commercial Advisors on high‑stakes enterprise opportunities

Refine and scale the employer sales playbook by identifying effective strategies and making them repeatable

What is Required (Qualifications)

5-7+ years of experience selling HR tech, digital health, or workforce solutions to senior HR buyers

Proven track record of closing complex enterprise deals with CHROs and Total Rewards leaders

Experience in pivot or expansion mode, building early traction into consistent revenue

Ability to operate independently as the sole sales hire without constant direction

Strong credibility with HR executives and the ability to communicate effectively in their language

How to Stand Out (Preferred Qualifications)

Experience shaping a sales motion rather than just executing an existing playbook

Willingness to travel as needed to meet client demands

We prioritize candidate privacy and champion equal‑opportunity employment. Central to our mission is our partnership with companies that share this commitment. We aim to foster a fair, transparent, and secure hiring environment for all. If you encounter any employer not adhering to these principles, please bring it to our attention immediately.

We are not the EOR (Employer of Record) for this position. Our role in this specific opportunity is to connect outstanding candidates with a top‑tier employer.

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