Payroll Operations Manager Jobs in Racine, WI (NOW HIRING)

OPERATIONS MANAGER

Steffens Insurance Group — Waterford, WI

Steffens Insurance Group is a family-run financial and insurance firm in Waterford, WI. Nearly four decades in business, same market, same families... and now the leadership team is building the internal infrastructure to run without the founder in every seat.

This hire is part of that plan. You'd report to the Director of Operations and own the infrastructure that keeps compliance clean, systems running, people paid correctly, and the hiring pipeline moving. In a firm this size, that's not a support seat. It's the seat that holds the place together.

What the Work Actually Looks Like

You own the compliance and documentation calendar... carrier requirements, licensing renewals, regulatory deadlines. Nothing gets tracked loosely, and nothing expires because it was forgotten.

You own payroll accuracy and the accounting workflows. That means precision under pressure, and catching the problem before it lands on Katie's desk as one.

You run hiring and onboarding end-to-end. Posting roles, screening applications, scheduling interviews, getting people productive on Day 1. Katie weighs in on the final hire, not the pipeline.

You own the firm's technology relationships. Not fixing code... coordinating vendors, managing access, and keeping the agency management system from turning into a bottleneck.

You run the operational calendar. Meetings, renewal deadlines, internal follow-ups, all of it on radar before it's due.

And you own how the firm runs day to day. The systems you build are the reason it can operate without the founder in every seat. When a process is clunky, you rebuild it... you don't work around it for two years.

This is a small firm. There isn't a team under you yet. When something needs doing and it's in your lane, you figure it out. Priorities shift... sometimes mid-morning. Confidential information moves through this role constantly, and the standard for discretion is absolute. If you need a supervisor to tell you what's next, this seat will be uncomfortable fast.

Who Belongs Here

Ownership without permission. You see what needs doing and you do it. You don't send an email asking whether to handle something you can clearly handle. You take care of it and report back.

Clarity over complexity. You question a process before adding steps to it. You build simple systems that hold up when you're out of the office, not elaborate ones only you understand.

Relationships before revenue. In a firm like this, every internal interaction touches the client relationship eventually. How you handle a vendor dispute or a deadline change reflects on the firm. You take that seriously.

A-players only. You hold yourself to the standard that the rest of the team holds each other to. You don't coast. You don't blame the system. You find a way.

Why Steffens Insurance Group

• A direct working relationship with the Director of Operations... you'll know exactly what your work is moving and why it matters
• A small-firm environment where your contributions are visible and your ownership is real
• A clear growth path as the firm builds out its operations... this seat grows as the function does
• Family-run culture... Derek, Jake, and Katie Steffens are the leadership team, and this is their business to build
• Starting salary based on experience, with a 90-day review built in
• Full benefits: health, dental, vision, STD, life

$40,000 - $55,000 yearly

• Track and manage compliance deadlines — carrier requirements, licensing renewals, regulatory filings — so nothing expires without warning.
• Support payroll processing and accounting workflows, catching discrepancies before they reach Katie.
• Run the hiring and onboarding process end-to-end — postings, screening, scheduling, and first-day coordination.
• Coordinate IT troubleshooting and technology vendor relationships; keep agency management systems operational.
• Manage the firm’s operational calendar — meetings, deadlines, and internal follow-ups on radar before they’re due.
• Handle confidential employee and business information with professional discretion at all times.
• Support Katie on operational projects and special initiatives when they arise.

Required:

• At least 2 years of experience in administrative, operations, or executive support.
• Proficiency with Microsoft Office and comfort learning new software platforms.
• Demonstrated ability to manage multiple priorities and deadlines simultaneously.
• Professional discretion with confidential information.
• US work authorization.
• Ability to work onsite in Waterford, WI.

You do NOT need:

• No insurance or financial services experience required — we train on the specifics.
• No specific degree required.
• No prior payroll or accounting certification required.

Steffens Insurance Group is a family-owned independent agency in Waterford, WI. Mike Steffens spent 44 years building it. Derik, Jake, and Katie are running it now. We handle the complexity most small-market agencies hand off — full commercial and personal lines P&C through SIG, combined with sophisticated financial planning through V3 Financial, for clients who’ve been with us long enough to refer their kids. They’re not shopping for the cheapest policy. They’re paying for continuity with people who know them. We hire A-players because one wrong hire in a firm this size affects everyone, and because the people here hold a standard they’re not willing to lower.