What does it take to make the list of the best insurance companies to work for in the USA? Not the same thing twice, according to Insurance Business America’s Top Insurance Employers 2026 report: this year’s winners span a 4,000-person national wholesale brokerage headquartered outside Chicago and a 67-person retail agency in Springfield, MO, founded in 1885. One is owned by a publicly traded global broker. The other is owned, in part, by its own frontline staff.

To qualify for recognition, organizations first completed an employer form detailing their offerings, then their own employees anonymously rated the workplace on compensation, benefits, culture, and development. Organizations needed a 75 percent or greater average satisfaction rating to make the list. What separates this year’s winners from the rest of the market is not size, ownership structure, or even the specific benefits on offer. It is a discipline: finding out what employees actually want, then building around it.

Insurance employers are not short on things to worry about right now: tight labor markets for underwriting and claims talent, wage pressure from outside the industry, and a workforce that increasingly expects flexibility as a baseline rather than a perk. IBA’s 2026 winner data shows how differently individual firms have responded. Across this year’s winning organizations, average employee satisfaction scores ranged from roughly 4.02 to 4.58 on a five-point scale, and the highest scores did not cluster among the largest firms. A smaller agency with a few dozen staff scored competitively against firms with thousands of employees, and vice versa.

Multiyear data from the same survey program shows employees have consistently ranked retirement plans and medical coverage among the benefits that matter most to them every year since 2021, with vacation leave close behind since the survey began tracking it in 2023. The importance placed on flexible work options has held steady in a narrow band rather than fading as pandemic-era habits normalized. That consistency matters for employers deciding where to spend limited benefits budgets: the data suggests employees are not chasing the newest perk. They are asking for a stable, well-communicated set of fundamentals, delivered by an employer that keeps asking whether it is getting them right.

That employer discipline matters more now than it has in years. US insurers are heading into a tightening labor market, with job openings falling to a decade low in early 2026 even as an aging workforce continues to shrink the talent pool, according to Marsh’s 2026 People Risk report, covered by Insurance Business America. Limited career advancement, technology skills gaps, and rising labor costs from competition for talent were the top concerns Marsh identified among HR and risk professionals surveyed for that report.

Broader workforce research points to the same pattern from a different angle. Perceptyx’s fifth annual State of Employee Listening study, based on more than 750 senior HR leaders at large organizations, found that companies running what it calls “continuous listening” programs, meaning they act on employee feedback at every level rather than running a single annual survey, are 11 times more likely to report high workforce engagement and retention than companies at the most basic, one-off listening stage. That same research found mature listening organizations are nearly twice as likely to run effective coaching and development programs, almost exactly the pairing Risk Placement Services describes in how it built out its Producer Development Program.

The same research also points to a stubborn gap between hearing feedback and acting on it. Across the organizations Perceptyx studied, 71 percent of employees say their employer shares survey results, but only 51 percent say those results led to an actual improvement (Perceptyx, State of Employee Listening 2026). Closing exactly that gap, between hearing something and visibly changing something, is what separates this year’s two Top Insurance Employers 2026 winners from an organization that runs a survey and simply files it away.

Two of this year’s winners, Risk Placement Services and Ollis/Akers/Arney Insurance & Business Advisors, arrived at that discipline from very different starting points.

RPS, a Gallagher company headquartered in Rolling Meadows, IL, employs roughly 4,000 people across its wholesale brokerage and underwriting operations. For HR director Tasha Smith, the starting point for employee experience is straightforward: find out what people actually want, rather than assuming leadership already knows.

“I think that oftentimes companies just kind of create out of thinking that they know best,” Smith says. “What kind of sets us apart is that we actually ask: What are you interested in? Where are we lacking? Where do we need to improve?”

Those questions are not rhetorical at RPS. The company collects the answers through engagement surveys and periodic third-party culture audits, including a recent Culture of Impact survey conducted with Orange Leaf Consulting that reached about 150 employees across the business. Coaching emerged as a clear gap. RPS already ran a Producer Development Program (PDP) for early-career sales talent, built around a year of hands-on training paired with a production team. What the survey identified was missing: dedicated coaching, separate from an employee’s direct manager.

RPS added that layer, pairing PDP participants with coaches drawn from branch managers and regional presidents outside their own office. The change gives early-career employees direct access to senior leaders they would not otherwise work with day to day. Smith says the company is now tracking its third cohort of PDP participants and coaches, and the group has already driven approximately $1 million in revenue.

“It’s not just helping them,” Smith says. “It’s helping the business as well.”

The same responsiveness shows up in smaller decisions. RPS initially ran its career-empowerment development sessions monthly, then moved to a quarterly schedule after employees said the pace felt overwhelming and created a fear of missing out if they could not attend every session. Mental health support followed a similar path: Smith, a certified yoga nidra facilitator, has hosted bimonthly meditation sessions for about two years, drawing roughly 100 employees per session. When participants asked for the sessions in other languages, RPS added Spanish and French options.
 

“What kind of sets us apart is that we actually ask: What are you interested in? Where are we lacking? Where do we need to improve?”
Tasha SmithRPS

A: “I think, for me, the first thing that comes to mind is just to be seen and to feel supported. I want to make sure that we create a space where not only do we create really great programs, but those programs are created because of the feedback from the teammates.”

A: “I think for our leaders in general, that has been tricky. It’s like, ‘How do you engage someone when we’re not really here’? I definitely feel more connected when we’re utilizing video, which I would say the majority of us do. We still try to have flexibility within teams, but we do see higher retention rates and collaboration in the offices that choose to go in a little bit more than be virtual.”

A: “We try to educate on the resources that we have and let them know: this is for you to be able to get more time back for you. This is for you to be able to manage and navigate work that used to take you hours, and now maybe you can do it in a shorter period of time. If there is some sector that’s going away, then we would communicate on that.”

RPS’s own employer submission for the 2026 report backs up Smith’s account with specifics: a 401(k) plan with a five-year vesting match, participation in Gallagher’s Employee Stock Purchase Plan at below-market pricing, up to 61 days of maternity leave and 28 days of paternity leave, and a wellness budget of $150 per employee each quarter.

That level of investment tracks with research from RPS’s own parent company. Gallagher’s 2025 US Benefits Benchmarks Report, based on survey responses from more than 4,000 US organizations, found employers increasingly building benefits strategies around physical, emotional, career, and financial health together, rather than treating them as separate line items. John Tournet, US CEO of Gallagher’s Benefits & HR Consulting Division, framed the shift in the report’s release as a chance for employers to rethink employee care holistically rather than as a set of disconnected line items.

That parent-company investment is one piece of a broader growth story. Insurance Business America’s earlier coverage of Gallagher’s brokerage growth strategy outlines how the firm has climbed to become the world’s third-largest insurance brokerage through acquisitions and international expansion, providing the financial backbone behind subsidiaries like RPS.

Ollis/Akers/Arney Insurance & Business Advisors (OAA) has operated in Springfield, MO, since 1885. Today it employs 67 people, and unlike RPS’s global parent structure, OAA’s ownership sits with the people who work there. The agency runs on an Employee Stock Ownership Plan (ESOP) that distributes agency stock annually based on company earnings, vesting over six years.

For Myleah Shrimpton, OAA’s vice president of claims and a nearly 16-year employee, that ownership structure is inseparable from how the agency listens to its own staff. “When you talk to frontline to the very top, you’re talking with an owner,” Shrimpton says. “That brings a whole different feel to it, to make change.” She is careful to note that ownership does not guarantee every idea gets adopted. “Like any company, not every idea is adopted,” she says. “But there is an ability here to have a seat at the table.”

That account lines up with broader research on employee ownership. In an NCEO survey of ESOP companies published in July 2026, the average voluntary quit rate among employee-owned businesses was 11 percent, compared with a 26 percent average across all US companies tracked by the Bureau of Labor Statistics’ Job Openings and Labor Turnover Survey. Eighty-five percent of the ESOP companies NCEO surveyed said employee ownership had a positive effect on recruitment and retention, and when asked what drives that retention, respondents most often reached for one word: culture.

Shrimpton describes OAA’s culture, after almost 16 years watching it evolve, as being at its healthiest point. She credits the people the agency hires rather than any single program. “Our culture is our people at the end of the day,” she says. “I feel like we have some of the very best, who do their work with excellence and also care beyond the job. They really care about the people, the clients we serve, and one another.”

That care extends to how the agency manages people through different seasons of their lives, rather than applying blanket policy. Shrimpton points to OAA’s approach to flexibility and hybrid work as an example: rather than mandating a fixed number of remote or in-office days across the board, supervisors work with individual employees based on their circumstances. OAA’s own employer submission for the report describes staff using flexible and remote arrangements to care for ailing family members and to manage foster care and adoption placements, while still meeting work commitments.

The agency’s weekly all-staff communication, Plan of the Week, gives every employee-owner a turn in the spotlight, alongside birthdays, work anniversaries, and a rotating wellness article. Quarterly State of the Agency meetings bring in an outside guest presenter and keep every employee current on the business. OAA also runs an in-house claims department covering both property and casualty and health benefits claims, a service Shrimpton considers a defining differentiator. 

“Claims are why people buy insurance,” she says. Rather than referring clients back to their carrier, OAA’s claims staff help navigate the process directly, including complex situations like pre-authorization disputes and denied claims.
 

“When you talk to frontline to the very top, you’re talking with an owner. That brings a whole different feel to it, to make change”
Myleah ShrimptonOllis/Akers/Arney Insurance & Business Advisors

A: “As a whole, I’ve been here almost 16 years, so I’ve seen different iterations of staff and culture. I feel like, obviously, no place is perfect. I don’t want to paint an unrealistic picture, but personally I feel in many ways it’s the healthiest we’ve been.”

A: “We have an in-house claims department, which is uncommon for an agency our size. Claims are why people buy insurance, and rather than telling clients to go call their carrier, we have dedicated people to help them navigate the process, including things like pre-authorization and denied claims.”

A: “The company provides tuition reimbursement for graduate work and full payment for designation work. I actually started my own master’s work in risk management, focusing on public policy, and the company supported that.”

OAA’s employer submission adds further texture to Shrimpton’s account: a fully paid wellness program built around a national platform called WellSteps, a 24-hour on-site fitness center, up to eight paid hours of volunteer time off, and a 50 percent 401(k) match up to two percent of pay.

OAA is far from being the only agency to use employee ownership as a perpetuation strategy. Insurance Business America’s case study on employee stock ownership plans in insurance agencies profiles a 150-year-old agency that has run on an ESOP since 1975 and credits the structure with a 97 percent employee retention rate.

Both RPS and Ollis/Akers/Arney are watching the same technology shift reshape how employers listen to their own people. Smith describes RPS’s approach to AI tools like Copilot as a matter of transparency: giving every employee access to the same resources, and framing automation as a way to reclaim time rather than eliminate roles. Shrimpton describes a similar dynamic at OAA, where staff are trained on AI as the industry’s pace of change accelerates, alongside continuing education support for designations and graduate study.

Neither agency treats AI as a listening mechanism in itself; both still rely on surveys, culture audits, all-staff meetings, and direct manager conversations to find out what their people need. But as engagement data becomes easier to collect and analyze at scale, insurance employers of every size are likely to face growing pressure to act on what they learn faster, and more visibly, than a once-a-year survey cycle allows. The employers best positioned for the next 12 to 24 months are not necessarily the ones with the biggest benefits budgets. They are the ones that have already built a habit of asking, and a track record of changing something because of the answer.

Workforce composition adds another layer to that pressure: survey data shows parental-leave benefits matter most to staff with under three years of tenure, while priorities shift toward long-term financial and health security, and loyalty programs, once tenure passes the 10-year mark.

Set RPS and Ollis/Akers/Arney side by side and the differences are the point. Different ownership models, different employee bases, different benefits budgets. What both organizations share is less a program than a posture: a willingness to ask employees what matters to them, and a track record of changing something in response, whether that means adjusting the cadence of a development series, adding a coaching layer to an existing program, or building a weekly communication that puts an employee-owner in the spotlight. That posture, more than any single benefit or perk, is what separates this year’s winners on the list of the best insurance companies to work for in the USA from employers that assume they already know what their people want.

Best Insurance Companies to Work for in the USA | Top Insurance Employers

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  Orion180
   
  
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  RPS
   
  
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  Balavant Insurance Group
   
  
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  Brown & Riding
   
  
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  Ryan Specialty
   
  
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  USG Insurance Services, Inc.
   
  
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  USI Insurance Services
   
  
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  Utica National Insurance Group
   
  

• ARU
• C3 Risk & Insurance
• Commercial Insurance Associates
• Converge
• DUAL North America
• Elpha Secure
• Great Lakes General Agency
• HawkSoft
• HomeServices Insurance
• Insureon
• Jimcor Agency
• MountainOne Insurance Agency
• Ollis/Akers/Arney Insurance & Business Advisors
• Philadelphia Insurance Companies
• PolicySaver
• Post Insurance & Financial
• RightSure
• RPR Insurance
• RWR WV
• Shepherd Insurance
• The Liberty Company Insurance Brokers
• Wye River Insurance
• XS Brokers