General Manager, Benefits & Insurance

GM Benefits & Insurance - Worklio

Worklio · HCM Platform Now Hiring · Leadership Role General Manager, Benefits & Insurance Build and own our benefits brokerage practice from the ground up - with a warm existing book, a profitable platform behind you, and uncapped upside. 🌐 Remote 👤 Reports to CEO 💼 Full-Time 📈 Equity Available

$120–150K Base Salary

$200–250K OTE at Plan

Uncapped Commission

$5–10M+ Revenue Potential Yr 3–4

The Opportunity Worklio is a profitable, founder-led HCM platform delivering embedded payroll, HR, and benefits administration to thousands of US employers. We're growing fast across construction, healthcare, and professional services - and we need a leader to build the benefits and insurance practice on top of our existing payroll network.

This is a P&L ownership role, not a sales role. You'll build the infrastructure, the team, the carrier relationships, and the revenue - with a warm book of payroll clients already in place from day one. This role reports directly to the CEO.

What You'll Own 📋 Licensing & Compliance Entity setup, state licensing, carrier appointments, ERISA and ACA compliance framework

🤝 Carrier Relationships Medical, dental, vision, life, disability, and workers' comp carrier negotiations

📈 Benefits Sales Group health, ancillary, and workers' comp to employers with 50–500 employees

👥 Team Building Hire and manage licensed benefits advisors and account managers as volume scales

🏗️ Partner Channel Roll out benefits across our embedded partner network in construction and accounting

🔧 Workers' Comp Program Build a pay-as-you-go workers' comp program tied to payroll, starting with construction

Who You Are

• →Licensed - active Life & Health license required; P&C a strong plus
• →Experienced - 7+ years in group benefits brokerage, administration, or employee benefits consulting
• →A builder - you've grown a book of business or built a team from scratch, not just managed an inherited one
• →Operationally strong - comfortable with benefits tech, carrier portals, ACA, ERISA, and Section 125
• →Commercial - you understand revenue, margin, and what it takes to grow a profitable brokerage practice
• →Entrepreneurial - energized by ambiguity, ownership, and the upside that comes with building something real

Bonus Points

• ⭐Construction or healthcare employer experience
• ⭐Embedded benefits or benefits-as-a-service background
• ⭐PEO, ASO, or HCM technology experience
• ⭐Tax-advantage benefits plan administration
• ⭐Existing carrier relationships and appointments
• ⭐Workers' comp MGA or captive experience

Why This Role You're not walking into a cold start. Our payroll platform already serves employers across the US - every one of them a warm opportunity. The book exists. It just needs a leader to activate it. Direct CEO access, no bureaucracy, equity participation in a business targeting a significant exit. Commission is uncapped. This role has the potential to generate $5–10M+ in annual revenue within 3–4 years. We understand payroll and compliance deeply. You won't be explaining what a W-2 is.

Ready to build something? Send your resume and a brief note on what you've built to careers@worklio.com

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