Knowing when to switch PEOs isn’t a matter of preference. It’s a strategic inflection point, one that can either protect millions in margin or quietly erode enterprise value.
Early on, a PEO can be the right choice: bundled benefits, simplified compliance, consolidated payroll. But as the business matures, the cracks start to show. Costs creep up. Responsiveness fades. Complexity increases. And suddenly, what once supported scale is now limiting it.
This guide breaks down how to know when to switch PEOs, and how to do it without disruption.
Before the problems are obvious, they’re usually subtle. Smart CFOs and operators track these signs early:
Creeping Costs: Are benefit rates rising annually without market justification or transparency?
Service Drift: Do support tickets linger, compliance advice feel canned, or account managers rotate frequently?
Compliance Gaps: Is your PEO keeping you ahead of federal, state, and local employment law, or just reacting when issues arise?
System Friction: Can your PEO’s tech actually integrate with your broader finance, HR, and reporting stack?
No single flag demands action. But together, they tell a clear story: your PEO is no longer aligned with your Strategic PEO Advisory needs.
Beyond subtle drift, there are moments that demand a hard look at whether your current model still fits:
Contract Renewals: Most PEOs operate on annual cycles. Renewal is a strategic moment, your chance to renegotiate, benchmark, or exit.
Carrier Changes: When your PEO switches insurance carriers, it can upend employee satisfaction and increase cost exposure.
Expansion: Whether it’s new states, new capital, or new headcount, growth requires infrastructure that can scale, not just “get by.”
In these moments, the cost of staying put often outweighs the lift of switching. That’s why we built this simple tool to help you compare PEOs before you commit.
Handled strategically, transitioning from one PEO to another can be smooth, fast, and value-positive. Here’s how:
Benchmark Everything: Use market data to compare benefits, admin fees, risk pools, and tax treatment.
Audit for Compliance: Clean up classifications, wage bases, and state-by-state exposure.
Simplify Your Stack: Use the switch to consolidate platforms and remove friction from payroll to reporting.
Get Strategic Guidance: Don’t ask a vendor what to do. Work with an independent advisor whose only incentive is your outcome.
Knowing when to switch PEOs is a strategic decision, not a reactive one.
The companies that move early don’t just save money. They gain visibility, control, and a foundation built for scale.
If your current PEO is starting to show its limits, don’t wait for a breaking point. Evaluate now. Move intentionally. And build the future on your terms.
Strategic PEO Advisory™. Designed to scale.
Senior PEO Consultant
Alicia helps businesses navigate the world of PEOs—whether they’re evaluating options, switching providers, or simply looking to get more value from renewals. At Dinsmore Steele, she manages the RFP process from start to finish, gathers competitive quotes, and delivers detailed analyses that give clients clarity and confidence. Acting as a bridge between companies and PEOs, Alicia makes sure onboarding, compliance, and benefit transitions are smooth and stress-free.
With a strong background in PEO brokerage, consulting, and customer service, Alicia brings both industry expertise and a client-first mindset. Her style is strategic and detail-oriented—she’s known for keeping projects organized, proposals accurate, and communications clear. Over the years, she’s successfully negotiated lower fees, secured stronger service agreements, and uncovered hidden savings that translate into measurable ROI. Clients trust her not just for her knowledge, but for her ability to listen, advocate, and deliver solutions that make a real difference.
Alicia’s passion for helping others extends beyond the office. She’s a dedicated animal rescue advocate, actively volunteering with dog rescues and adoption efforts—and a proud dog mom of three herself. She also loves staying active through strength training, hot yoga, and pickleball. Whether with clients, colleagues, or in her community, Alicia thrives on building strong connections and supporting others in reaching their goals.
Peo Consultant
Ethan helps clients make sense of the complex PEO landscape, guiding them through evaluations to find the right long-term solution. Before joining Dinsmore Steele, he spent several years at ADP—starting in small business and later selling TotalSource—working closely with companies in blue collar industries, professional services, and tech. A consistent top performer, Ethan has built a reputation for listening closely, cutting through the noise, and finding solutions that actually solve the problems clients are facing.
His strengths lie in navigating the overwhelming number of PEO options to identify the best fit for each company’s goals. Ethan’s approach works because it’s rooted in problem-solving—he focuses on what matters most to clients and ensures every recommendation aligns with their specific needs. What he enjoys most is the trust clients place in him and the satisfaction of delivering solutions that truly fit.
Operations Director
Pat is the glue that keeps operations running smoothly at Dinsmore Steele. As Operations Director, Pat focuses on processes, workflows, and accounts—making sure nothing falls through the cracks and every system works the way it should.
With a career that spans industries and countries, Pat brings a truly global perspective to the team. Prior to joining Dinsmore Steele, Pat served as a Marketing Manager for a restaurant chain in the Philippines, a Regional Sales Director for a tech start-up in Vietnam, an Accounts Manager for the Central Bank of the Philippines, and an Operations Manager for an HR firm in Australia. This diverse background has given Pat the ability to see both the big picture and the finer details, spotting inefficiencies, improving workflows, and bridging gaps between teams to create systems that actually scale. Known for being strategic yet execution-focused, Pat makes sure every plan is not only effective but also executable.
Pat’s early career as an international model with Elite Model Management developed a sharp eye for branding, visual storytelling, and creative direction. That creative perspective still shows up in their work today, blending operational precision with design-minded detail. Outside the office, Pat enjoys exploring new ways to merge structure with creativity, bringing balance to both professional and personal pursuits.
Chief Human Resources and Client Experience Officer
Bobbi Jo is a seasoned HR leader who believes people strategy should always push the business forward—not just keep it running. With more than two decades of experience, she’s helped companies tackle big challenges like turnover, scaling through acquisitions, and building systems that make HR less reactive and more proactive.
As a former CHRO, Bobbi Jo knows what it takes to lead a high-performing HR team and get results in fast-changing environments. She’s streamlined processes, redesigned job structures, and rolled out performance tools that stick—all with a focus on creating efficiency without losing sight of the people behind the work. Having been both a sole contributor and a leader of large teams, she gets what HR professionals at every level are up against, and she knows how to help them shine.
Bobbi Jo is the person you call when HR needs to be more than just a support function. She guides businesses through PEO transitions, benefit renewals, and M&A integrations, while also digging into the nuts and bolts like compensation benchmarking, pay equity, recruiting strategies, and turnover action plans. She’s skilled at building or reworking HR systems, creating policies that actually work in practice, and setting up engagement programs that inspire real results. Whether it’s payroll, performance reviews, or planning the next generation of leaders, Bobbi Jo brings clarity, structure, and energy to every project.
Marketing Director
Rachel leads all things marketing at Dinsmore Steele, where she’s known for turning big business goals into smart, data-driven strategies that actually connect with people. Her superpower? Blending creativity with analytics to build marketing programs that not only look good but also drive real, measurable growth.
Rachel has worn just about every marketing hat: go-to-market planning, brand positioning, demand generation, team leadership, and more. She’s built marketing programs from the ground up, partnered with product, design, sales, and growth teams, and helped transform complex ideas into stories that resonate with customers. From launching new ad formats and running multi-channel campaigns to refining customer journeys with data insights, Rachel brings a mix of strategic thinking, collaboration, and a results-driven mindset.
When she’s not leading marketing initiatives, Rachel’s likely off exploring. She’s traveled extensively (including bungee jumping in Greece!) and loves experiencing new places and cultures. Rachel’s love for travel fuels her curiosity and creativity—she’s always drawing inspiration from new experiences. At home, she finds joy in music—she’s an accomplished pianist and never misses a chance to sit down at the keys.
Chief of Staff
Josh is an operations and marketing strategist who helps businesses scale by combining automation, CRM strategy, and airtight systems that eliminate chaos. With more than a decade of experience supporting executives and business owners, he’s built a reputation for translating big ideas into workflows that actually work.
At Dinsmore Steele, Josh manages client lifecycle campaigns, builds CRM automation in HubSpot, leads outreach strategies, and makes sure marketing vision translates into measurable results. Known for being proactive, precise, and systems-obsessed, Josh is the trusted behind-the-scenes operator who keeps both the DS team and their clients running smoothly.
Josh specializes in creating end-to-end systems that drive growth and efficiency. He builds CRM automation and marketing funnels, designs HubSpot workflows and sequences, and develops follow-up strategies for both active and lost deals. He also supports PEO lead nurturing and client retention efforts, while running survey campaigns, email drips, and slybroadcast voicemail outreach. Beyond campaign execution, Josh strengthens team communication systems, ensures content and campaign quality, and continuously optimizes processes to keep businesses running at peak performance.
SVP/Sales & Revenue
Cassandra joined Dinsmore Steele in 2023, bringing more than a decade of experience and a reputation as one of the top 1% of performers in the PEO industry—earning her the nickname “The PEO Queen.” Few, if any, know more about the inner workings of PEOs than Cassandra, and she uses that expertise to help clients navigate their options with clarity and confidence.
Her role focuses on guiding businesses to the PEO that best fits their needs and budget, then ensuring a smooth transition through the DS platform. With deep experience across PEO, ASO, EOR, HRIS, benefits, payroll, workers’ compensation, compliance, and risk mitigation, Cassandra brings both breadth and depth to every engagement. She combines market knowledge with high-volume productivity and strategic insights to help organizations achieve true scalability. Known for her compassion, professionalism, and dedication, Cassandra always chooses client success above everything else—even when that means losing profit.
Managing Partner
Barbara has been part of Dinsmore Steele since 2016, bringing with her a wealth of industry experience and a knack for building high-performing teams. An industry veteran, she quickly streamlined operations and helped shape a world-class team to better support clients, partners, and providers. What makes Barbara’s perspective especially unique is her background as a former partner in a successful PEO—giving her firsthand experience on both sides of the table and a deep understanding of what it takes to deliver real value.
Today, Barbara focuses on developing cost-effective PEO solutions for organizations of all sizes. She believes the key is understanding each company’s needs and vision, then researching and analyzing the best options to deliver the right fit. Beyond advising clients, Barbara also leverages her deep PEO expertise to work directly with both PEO and ASO providers, helping them expand their marketing engines and strengthen their reach.
Founder and CEO
In 2010, Rodney founded Dinsmore Steele with a clear vision: to give business owners an unbiased, efficient way to shop, compare, and negotiate with Professional Employer Organizations (PEOs). As CEO, he has spent the last 16 years redefining how companies build HR infrastructure—not by selling vendors, but by engineering smarter PEO strategies that protect margins and fuel growth.
Rodney often says most companies don’t pick the “wrong” PEO—they pick without a strategy. That lack of strategy costs businesses time, leverage, and profitability. Through Dinsmore Steele’s Strategic PEO Advisory™, Rodney and his team compress what would normally take months of research into a few days of outcome-driven analysis. The results speak for themselves: over 6,000 companies advised, more than $592M in savings delivered, and an average of $2,016.78 saved per employee, per year. Trusted by growth-stage founders, PE operators, and portfolio teams, Rodney has built an independent, strategic, and proven model that helps businesses design infrastructure that scales—because the right PEO strategy doesn’t just save money, it powers the next stage of growth.
