General Manager Insurance

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

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.

• 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

• 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

• 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

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.