General Manager, Benefits & Insurance

Job Description

Job Description

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 View email address on us.fitly.work

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