Sales Account Executive

Experience: 4-7 years of mid-market B2B sales experience

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.

• 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 Hub Spot CRM data, and consistently meet or exceed revenue targets

• 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

• Becoming a trusted advisor to executive buyers within staffing organizations
• Consistently growing revenue through strategic account expansion and retention