Job Details

Overview

We are seeking a seasoned Enterprise Account Executive to sell employee benefit plans and workforce solutions to staffing and workforce management firms. This role focuses on complex, consultative sales cycles with senior decision-makers, including owners, CFOs, CHROs, and HR leadership.

The ideal candidate has a strong background selling into staffing organizations and understands benefits administration, compliance, and multi-state workforce models.

Key Responsibilities

• Own and manage the full sales cycle for staffing and workforce organizations
• Develop and execute strategic account plans for mid-large market and enterprise staffing firms
• Build trusted relationships with executive-level stakeholders across HR, Finance, and Leadership
• Sell employee benefit plans including health, ancillary, and voluntary benefits aligned to staffing workforce models
• Conduct consultative discovery to understand client workforce structures, compliance needs, cost drivers, and growth plans
• Navigate complex buying committees and long sales cycles
• Partner closely with underwriting, implementation, and client success teams to ensure smooth onboarding and long-term retention
• Accurately forecast pipeline activity, manage HubSpot CRM data, and consistently meet or exceed revenue targets

Required Qualifications

• Previous proven experience as with B2B sales, with a strong preference for mid-market or strategic accounts
• Proven success selling employee benefits, insurance, HR solutions, or workforce-related services
• Experience managing complex, consultative sales cycles with executive buyers
• Strong executive presence, negotiation skills, and business acumen
• Working knowledge of benefits brokerage, carrier sales, or benefits technology
• Familiarity with staffing firm business models and employee benefit programs
• Demonstrated ability to build and grow a high-value enterprise pipeline within the staffing industry

Compensation & Earnings Potential

• Base salary + uncapped commission structure
• Realistic first-year on-target earnings: $115,000+
• High performers have the opportunity to exceed OTE significantly
• Compensation aligned with activity, pipeline ownership, and closed revenue

What Success Looks Like

• Becoming a trusted advisor to executive buyers within staffing organizations
• Driving long-term, high-value benefit partnerships
• Consistently growing revenue through strategic account expansion and retention