Assistant Controller (Milwaukee, WI)

Recognized nationally as a Top Workplace and Top 100 US Insurance Agency!

Since 1960, Robertson Ryan Insurance has provided comprehensive solutions across Business, Benefits, and Personal Insurance. We proudly serve over 70,000 clients, from small businesses to major national accounts across various industries. With a team of more than 526 professionals and partnerships with over 150 insurance companies, we are the 44th largest Property & Casualty Insurance Agency according to the Insurance Journal. Our dynamic and enjoyable culture is a cornerstone of our success, with many team members having been with us for over a decade. It’s an exciting time to join our growing firm!

Position Summary

The Assistant Controller is a key member of the finance team responsible for supporting the Controller in managing the company’s accounting operations and financial reporting. This role will play a critical part in ensuring accuracy, compliance, and efficiency of accounting processes within a large, complex insurance brokerage. The Assistant Controller will also lead initiatives to document and enhance accounting policies, processes, and procedures to ensure consistency and scalability across the organization.

Essential Duties And Responsibilities

This list of duties and responsibilities is not all inclusive and may be expanded to include other duties and responsibilities, as management may deem necessary from time to time.

• Support the Controller in overseeing daily accounting operations including cash reconciliations, accounts payable, accounts receivable, general ledger accounting, fixed assets, and expense management.
• Assist in preparation of monthly and annual financial statements in compliance with GAAP.
• Manage, reconcile and review general ledger accounts, ensuring accuracy and timely reporting.
• Support audits (internal and external) by preparing required documentation and responding to inquiries.
• Develop, document, and maintain accounting policies, procedures, and internal controls to strengthen compliance and operational efficiency.
• Identify and implement process improvements to enhance accuracy, timeliness, and scalability of financial reporting.
• Assist in budget preparation, forecasting, and variance analysis to support management decision-making.
• Collaborate with cross-functional teams (operations, HR, and independent agent producers) to ensure accurate financial data and reporting, delivering exceptional customer service.
• Provide supervision, guidance, and mentoring to accounting staff.
• Ensure compliance with regulatory requirements specific to the insurance industry.
• Perform special projects, financial analysis, and ad-hoc reporting as assigned.
  
  
  

Preferred Qualifications

• Bachelor’s degree in Accounting, Finance, or related field (CPA or progress toward CPA preferred).
• 5+ years of progressive accounting experience, preferably in the insurance, financial services, or related industry.
• Experience in Public Accounting is highly preferred.
• Strong knowledge of GAAP, internal controls, and financial reporting.
• Experience with insurance accounting systems and large ERP platforms strongly preferred.
• Demonstrated ability to document and improve processes and procedures.
• Self-starter with excellent organizational skills, a can-do attitude, and the ability to work independently as well as collaboratively.
• Strong customer service mindset with the ability to support internal teams and external partners effectively.
• Proficiency with Microsoft Excel and other financial reporting tools.
• Strong communication skills with ability to collaborate across multiple departments.
• Supervisory or team lead experience a plus.
• Must be willing to work onsite, M-F at our downtown corporate headquarters in Milwaukee, WI.
  
  
  

Work Environment

• Fast-paced, high-volume insurance brokerage environment.
• Role may require occasional extended hours during month-end and year-end closes.
  
  
  

Certificates, Licenses, Registrations:

• CPA Preferred
  
  
  

Other Skills and Abilities:

• Sets priorities and manages workflow to ensure efficient, timely and accurate processing of transactions and other responsibilities.
• Maintain a cordial and effective relationship with carriers, co-workers, vendors and other business contacts. Ability to work in a team environment.
• Keep informed regarding industry information, new product information, legislation, coverages and technology to continuously improve knowledge and performance.
  
  
  

EEO/AA Statement: Robertson Ryan provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Attention to all Recruiting Agencies: Recruitment at RRI works on a direct sourcing model. We will contact agencies directly if needed. RRI is not responsible for any related fees for resumes submitted to job postings, our employees or any other part of our company.