Robertson Ryan Top Workplace- Careers


Thank you for your interest in a career at Robertson Ryan, a Top 100 US Insurance Agency. Our culture is dynamic and focused on people, which is why most employees have worked at Robertson Ryan well over a decade.

We are committed to providing the industry’s best service to our customers, environment for our team and support in our communities. Through agency growth and retirements we may have a variety of openings. However, we might not be actively seeking to fill a position with your background. In this case, we encourage experienced insurance candidates to apply for future openings.

We’re proud to share more about our culture through our guiding principles here, Mission | Vision |  Values

Our Advantages:

  • Flex Schedules
  • Profit Sharing
  • Casual Work Environment
  • Community Involvement/Volunteer Opportunities
  • Generous PTO and Holidays
  • Health/Vision/Dental Insurance
  • Life Insurance
  • 401-k with Match
  • Engagement Committee & Employee Council
  • We support your growth and encourage continuing education and obtaining industry designations
  • And More!


Current Openings

Agent Owner 

Status: Full-time
Location: Remote across US or Flex between Home and Office

We are an agency for agents. Our agents are owners and retain 100% ownership of their book. There are various options for agents, or entire agencies that are looking to scale-up or work toward perpetuation. The best fit for an Agent Owner has many years of experience with a non-captive agency and has an established book.

Read an interview by Insurance Business Magazine with our CEO on being an agent with Robertson Ryan, here


Account Manager | Commercial Lines

Status: Full Time
Location: Burlington, WI

As a Commercial Lines Account Manager you handle the ongoing service needs for clients and help our Agent Owners build long-term relationships. Serving as the client’s sounding board and liaison for insurance needs you will help prepare, deliver and maintain their custom insurance programs. Must have 3-5 years commercial lines experience, attention to detail, be a problem solver and provide excellent customer service.


Account Manager | Personal Lines, Florida

Status: Full-time
Location: Bokeelia, FL / Hybrid

As a Personal Lines Account Manager you handle the ongoing service needs for clients and help our Agent Owners build long-term relationships. Serving as the clients trusted liaison for insurance needs you will help prepare, deliver and maintain the client’s custom insurance programs. We are looking for a self-directing and knowledgeable candidate with at least 3 years experience handling multiple insurance carriers and brokers and have a 220 License in FL. This is an excellent opportunity to make a big impact and be part of a growing team with a top 100 US agency.


Commercial Insurance Account Manager – Towing

Status: Full-time
Location: Remote

As a Commercial Insurance Account Manger you handle the ongoing service needs for clients and help our Agent Owner and Senior Account Manager maintain a book of business. Experience in Towing and/or Trucking is preferred, with Epic Management system and work in the Midwest Region.

Major Responsibilities:

  • Handle daily tasks relating to processing renewals, endorsements, claims, certificates, and accounting/billing items
  • Ability to understand complex exposures
  • Assist in daily tasks and related items for existing and new business
  • Strong organizational skills
  • Ability to quickly change priorities in a fast paced environment and be proactive
  • Strong communication skills with the Senior Account Manager/Producer

Other Requirements:

Minimum of 2 years experience in commercial client service position and experience with the FMSCA Familiar with Federal Motor Carrier Safety Administration (FMCSA) requirements is favorable.

Property and Casualty License


Marketing & Communications Specialist

Status: Full-time
Location: Milwaukee, WI (Potential Hybrid or Remote)

Position Overview:

The Marketing & Communications Specialist will play a crucial role in the growth of our insurance agency by being an important point of contact for marketing activities. The role requires strong communication and writing skills, as well as a solid grasp of both insurance and technology. The candidate will need to excel in crafting compelling written content and effectively conveying complex insurance concepts in an accessible manner.

A key aspect of the role is the ability to work with various teams and individuals within the agency, necessitating strong interpersonal skills and the ability to collaborate effectively in a diverse environment. This team member will need to work independently, taking initiative and driving marketing projects forward in a fast-paced setting.

The candidate should possess a comfortable familiarity with technology, as it will be used to enhance marketing efforts and they will help administer several agency programs. An understanding of how technology can be leveraged to optimize marketing strategies and workflows will be advantageous.

Major Responsibilities:

  • Contribute towards the overall smooth flow of the Marketing Department by handling various operational and administration matters centered around, marketing, communication and public relations
  • Write compelling stories for our blog, trade publications and general marketing materials that position Robertson Ryan as a leader and an industry expert
  • Concept, write and send client email campaigns and administer Client Circle/Rocket Referrals software
  • Collect and analyze data/client lists for agents and agency projects and help source through other internal Applied Epic agency management system resources for list building purposes
  • Serve as Administrator and in-house resource for marketing technology, including Zywave and HR Workplace Services (HRWS). Maintain vendor relationships
  • Demonstrate, train and follow-up with select clients on Zywave and HRWS systems as requested by Agent Owners
  • Serve as a resource for agent sales prospecting (Zywave MiEdge, D&B, other)
  • Take lead on available content for Epic Proposals/Summary’s supplemental pages
  • Administer client mobile app/online portal for Personal Lines
  • Work directly with agents on communication and help advise on effectively communicating with prospects and clients
  • Help on-board new agents with Marketing Department support and serve as an on-going resource to for their questions and growth strategies
  • Be available as a resource for department managers to help manage marketing and communication related projects as needed by their functional areas
  • Coordinate stock promotional materials and event signage
  • Coordinate, promote and host hot-topic prospect and client webinars/videos and track results
  • Partner with Digital Marketing Manager to support digital content creation
  • Collaborate with VP and Digital Marketing Manager on internal and external branding and communication projects
  • Help coordinate annual Community Service Day and ongoing agent/agency community giving efforts
  • Other marketing department tasks and projects as needed


  • Demonstrate 5+ years of corporate communications / writing experience
  • Attention to detail for copy writing/editing and overall corporate branding
  • Strong written and verbal communication skills
  • Experience working with complex software programs including email platforms
  • Strong customer service focus for internal-clients with a commitment to building long-term relationships
  • Growth mindset with dedication to professional development and continual learning
  • Self-driven and proactive approach for going the extra-mile
  • Insurance experience preferred, but not required
  • Willing to consider Hybrid or Remote candidates with the right experience


VP of Finance

Status: Full-time
Location: Milwaukee, WI

Position Overview:

Reporting directly to the CEO, the VP of Finance manages a group of finance/admin staff that are responsible for all aspects of financial reporting, internal controls over financial reporting, regulatory compliance for Robertson Ryan & Associates.

S/he will have a “roll-up sleeves” mentality capable of working in a dynamic, fast-paced environment. RRA is experiencing rapid growth, so the VP, Finance will be a hands-on, operational leader with strong communication skills. S/he will serve as a partner to the CEO and leadership team balancing strategic and tactical leadership in growing and building the company.

Scope of Responsibilities:

  • Oversee the management of the month-end close process and related accounting processes for RRA
  • Oversee the preparation of quarterly and annual financial statements and audited financial statements, related footnote disclosures and Management’s Discussion and Analysis (MD&A)
  • Ensure conformity with all applicable statutory insurance accounting principles
  • Manage the company’s relationship with the external auditors and lead the interim review and annual year-end audit process.
  • Manage the company’s relationship with financial regulators.
  • Establish, implement, and monitor appropriate internal controls and policies to ensure conformance and compliance with statutory accounting principles and other regulatory requirements
  • Manage the company’s various tax requirements; federal income tax, state and local income tax, real and personal property, franchise, value-added taxes, and sales and use taxes
  • Oversee the preparation and delivery of all internal management reports including delivery to the company’s leadership team, board of directors and shareholders
  • Manage the Finance/admin team
  • Oversee the payroll function
  • Manage the accounts receivable and accounts payable function
  • Manage the finance information systems and general ledger computer applications necessary to maintain proper records and adequate internal controls.
  • Present information to and work with the leadership team, board of directors and shareholders in a timely, transparent and professional manner.
  • Analyze, consolidate and direct all accounting procedures together with other routine reports.
  • Acts as a trusted business partner to direct and analyze studies of expenditures and general economic, business and financial conditions as well as their impact on the organization’s policies and operations.
  • Ensuring strong cash flow management of the company
  • Analyzes operational issues affecting the company and determines their financial impact.

Leadership Responsibilities:

Carry out leadership responsibilities in accordance with the organization’s policies and applicable laws. Responsibilities include: training employees; planning, assigning, and directing work; appraising performance; rewarding and disciplining employees; addressing complaints and resolving problems.


To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

  • Proven track record in leading a successful financial reporting team and success as a motivational team-builder; a developer of staff, coach and mentor.
  • Collaborative style; believes in partnering, shares information and resources, and operates collaboratively across functions.
  • Must be a working manager, capable of operating in a fast-paced and environment, able to handle pressure well, be self-motivated and detail- oriented.
  • Brings a high energy level to the role and the team. Knows when to “roll up the sleeves” and lead by example and when to delegate effectively. Approaches the role and the organization with an innovative and results-driven mindset.
  • Brings superior project management ability and demonstrates high standards regarding the quality and thoroughness of business and technical analysis.
  • Results-driven versus process-driven. Demonstrates the ability to manage upward and downward; present facts and ideas to leadership, board of directors, shareholders in a respectful manner yet with a willingness to challenge when appropriate.
  • Demonstrates a strong character with a high level of integrity and strong ethical standards in a manner that builds trust and confidence.
  • Represents well as a company and community ambassador. Participate actively in professional and insurance industry-related organizations, conferences, etc. to stay up to date on the latest guidance and project a positive image.

Education and/or Experience:

Bachelor’s degree in accounting from a four-year college or university required. Along with 7 to 8 years of related experience required in professional services and financial reporting experience required.

Desired Skills:

  • Property/casualty insurance background
  • Statutory Accounting
  • Public accounting
  • Reinsurance accounting
  • Broader financial services accounting