Demo

Enterprise Account Executive

Proven Sales
Chicago, IL Full Time
POSTED ON 12/20/2025
AVAILABLE BEFORE 1/18/2026

Are you a strategic hunter who thrives closing large, complex deals? We’re looking for an Enterprise Account Executive to lead new logo acquisition in the benefits / HR tech space.


What you’ll do

  • Hunt and close enterprise deals (1000 employees) with HR, benefits, and finance leadership
  • Lead full sales cycles: prospecting, discovery, executive engagement, RFPs, contract negotiation, and implementation
  • Position a next‑gen AI platform that is proven to boost utilization and reduce costs
  • Work cross‑functionally with marketing, product, customer success to tailor solutions for complex organizations


What you bring

  • Proven track record selling enterprise SaaS / HR tech / benefits platforms (not just SMB)
  • Experience navigating multi‑stakeholder decision processes (HR, finance, legal, IT)
  • Ability to articulate value in cost savings, ROI, employee experience, adoption
  • Hunger, resilience, creativity in breaking into new accounts


What you’ll get

  • Base salary $160,000–$185,000, plus uncapped commission (true double OTE potential)
  • Ground-floor influence in scale stage: your voice will help shape GTM, product, go‑to‑market motion
  • Work with a cutting-edge AI benefits platform - you’re not selling features, but transforming how employees use their health benefits
  • Autonomy, leadership exposure, and a mission-driven domain


If you believe enterprise benefits sales is not just about selling software, but enabling a paradigm shift in employee health & benefits - let’s talk.

Salary : $160,000 - $185,000

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