General Manager, Benefits & Insurance

Miami, FL, United States

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

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.

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