Operations Manager in Milwaukee, Wisconsin at Steffens Insurance Group

OPERATIONS MANAGER

Steffens Insurance Group — Waterford, WI

Steffens Insurance Group has been in the same market, serving the same families, for almost 40 years. Now leadership is building the infrastructure to run the firm without the founder in every seat - and this hire is the person who builds it.

You'd report to the Director of Operations. Your job is to keep compliance clean, payroll accurate, hiring moving, and the systems running underneath all of it. This isn't a support role. Take it away, and the firm feels it immediately.

Who Belongs Here

You act without asking permission. If something's clearly yours to handle, you handle it and report back - you don't email to check first.

You'd rather simplify a process than add another step to it. The systems you build need to survive you taking a day off.

You understand that every internal decision eventually touches a client relationship. How you handle a vendor dispute says something about the firm.

You hold yourself to a high bar without being told to. You don't coast, and you don't blame the system when something goes wrong.

Why Steffens Insurance Group

• You'll work directly with the Director of Operations and always know why your work matters

• Small firm, real visibility - your contributions won't get lost in a hierarchy

• Growth path built in - as the operations function grows, so does this seat

• Family-run leadership - Derik, Jake, and Katie Steffens are building this business, and you'd be part of that

• Starting salary based on experience, with a 90-day review

Full benefits:

• Health insurance

• Dental insurance

• Vision insurance

• Short-term disability insurance

• Life insurance

$40,000 - $55,000 yearly

What you'll do

• Compliance and documentation are yours. Carrier requirements, licensing renewals, regulatory deadlines - none of it slips because you forgot to track it.

• Payroll and the accounting workflows are yours too. That means catching a problem before it becomes someone else's.

• You run hiring and onboarding start to finish - posting the role, screening applicants, scheduling interviews, getting new hires productive on day one. Leadership makes the final call on who gets hired. Everything before that is your pipeline.

• The firm's vendor and technology relationships run through you. You're not writing code - you're managing access, coordinating vendors, and making sure the agency management system helps the firm instead of slowing it down.

• You keep the operational calendar - meetings, renewal deadlines, follow-ups - so nothing gets missed because nobody was watching.

• You own how the firm runs, day to day. If a process is clunky, you fix it. You don't work around a bad system for two years because nobody assigned you to rebuild it.

• There's no team under you yet. This is a small firm, and priorities can shift mid-morning. Confidential information runs through this seat constantly - the discretion required here is absolute. If you need someone telling you what to do next, this job will feel wrong fast.

• Track and manage compliance deadlines, including carrier requirements, licensing renewals, and regulatory filings, so nothing expires without warning.

• Support payroll processing and accounting workflows, catching discrepancies before they reach the owners.

• Run hiring and onboarding start to finish: postings, screening, scheduling, and first-day coordination.

• Coordinate IT troubleshooting and vendor relationships, and keep the agency management system running.

• Manage the firm's operational calendar: meetings, deadlines, and follow-ups on the radar before they're due.

• Handle confidential employee and business information with discretion, always.

• Support special projects and initiatives as they come up.

• 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 at once.

• Professional discretion with confidential information.

• US work authorization.

• Ability to work onsite in Waterford, WI.
  

What you don't need:

• Insurance or financial services experience. We train on the specifics.

• A specific degree.

• Prior payroll or accounting certification.

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.