Senior Director, Head of Enterprise Sales (Health & Benefits)

Location: Home-based remote role in the United States; office location listed in Oak Brook, Illinois. Travel required 25–40% for broker and consulting firm visits, executive briefings, and industry events. Relocation is not provided.

Salary: $175,800–$225,000 per year, with possible incentive and bonus opportunities.

Company

hirify.global provides health and wealth solutions, including automatic rollover services, health savings accounts, emergency savings, and custody services, serving employers, plan sponsors, recordkeepers, TPAs, and institutional partners.

What you will do

• Lead enterprise new-business growth strategy and deliver annual revenue, sales, and growth targets for large employers.
• Build go-to-market strategy, prioritize market opportunities, and evaluate buyer needs, competition, pricing, and emerging opportunities.
• Lead, coach, performance-manage, and develop four Enterprise Sales Executives while establishing territories, account strategies, and performance goals.
• Drive pipeline creation, qualification, forecasting, opportunity reviews, and disciplined sales execution.
• Build consultant, broker, distribution, and executive employer relationships and represent Inspira in major prospect meetings, finalist presentations, and industry events.
• Partner with Marketing, Product, Solutions, Operations, Finance, Legal, and Client Management to win complex enterprise pursuits and monitor growth KPIs.

Requirements

• 12+ years of progressive sales experience in health insurance, managed care, employee benefits, or consumer-directed health, with significant new-business responsibility.
• 4+ years leading and developing sales teams, including hiring and performance management.
• Proven success closing large, complex employer-group business through consultant-led RFPs and formal procurement processes.
• Experience structuring enterprise pursuits across product, operations, finance, and legal functions.
• Bachelor’s degree in Health Care Management, Business Administration, Marketing, or a related field, or equivalent education and experience.
• Fluency with Salesforce, sales analytics, and AI-powered productivity tools; ability to travel 25–40% and provide personal transportation when needed.

Nice to have

• Experience selling to jumbo or national multi-site and multi-state employer groups.
• Experience with HSA, FSA, HRA, and COBRA products and enterprise benefits procurement.
• Established relationships with national benefits consulting firms.

Culture & Benefits

• Values include compassion, integrity, accountability, continuous improvement, and collaboration.
• Healthcare benefits, 401(k) savings plan, company holidays, paid time off, parental leave, and employee assistance program.
• Monday–Friday schedule with flexibility for evenings or weekends when supporting broker leadership engagements and industry events.
• Home-based work arrangement with occasional travel and prolonged periods of sitting and standard office-equipment use.