Administrative Operations Assistant

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 be working directly with the Director of Operations — not running errands, but holding the operational infrastructure that keeps compliance clean, systems running, people paid correctly, and the hiring pipeline moving. That's a different job than most "admin" postings.

What the Work Actually Looks Like

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

You’ll support payroll processing and accounting workflows. That means accuracy under pressure and knowing when to flag something before it lands on Katie’s desk as a problem.

You’ll run the hiring and onboarding process. That means posting roles, screening applications, scheduling interviews, and getting people set up on Day 1 — Katie touches it when there’s a decision to make, not before.

You'll troubleshoot IT and technology issues — not fix code, but coordinate with vendors, manage access, and keep agency management systems from becoming bottlenecks.

You’ll manage the operational calendar for the firm. Meetings, renewal deadlines, internal follow-ups — on radar before they’re due.

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

Who Belongs Here

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

Clarity over complexity means 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 that only you understand.

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

A-players only means 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

• Direct working relationship with the Director of Operations — you’ll know exactly what your work is moving and why it matters
• Small-firm environment where your contributions are visible, and ownership is real
• Clear growth path as the firm builds out its operational infrastructure
• Family-run culture — Derek, Jake, and Katie Steffens are the leadership team, and this is their business to build
• $40,000–$48,000 starting salary based on experience, with a 90-day review built into the process
• Benefits package

$40,000 - $48,000 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.