Before partnering with a PEO brokerage, businesses must evaluate services, costs, compliance support, scalability, communication practices, and technology to ensure the partnership truly enhances HR efficiency and employee experience. Asking the right questions upfront helps uncover hidden fees, service limitations, or weak support structures that could hinder growth. A thorough, transparent assessment ensures you choose a PEO broker that protects your business, supports long-term scaling, and delivers real value.
Before partnering with anyone, knowing the right questions to ask a PEO broker can help you avoid hidden fees, compliance risks, and operational challenges.
Committing to a PEO brokerage is a significant decision for any business. Knowing the right questions to ask a PEO broker can help you evaluate services, costs, compliance, and support before committing. It can streamline operations, manage human resources, and even assist with compliance. However, to ensure you make the most informed choice, it’s essential to ask the right questions. Here are crucial inquiries to consider before entering into an agreement with a PEO brokerage.
Understanding the range of services offered by a PEO brokerage is crucial. Ensure they provide essential HR management, payroll processing, employee benefits, and compliance consulting tailored to your business needs. Often, PEOs operate under a co-employment arrangement, where they manage crucial HR functions while you retain control over your business operations, such as hiring and culture Why Use a PEO Broker to Find the Right PEO.
Some PEOs offer more extensive services like risk mitigation and regulatory guidance, which can be advantageous for businesses in highly regulated industries. It’s important to clarify whether these services are included in the base package or come at an additional cost. Other innovative services that might be on offer include time and labor management tools, which can greatly enhance productivity by automating everyday tasks.
Evaluating the service quality is as important as the service range. Seeking feedback from current or past clients can provide insights into the reliability and efficiency of the services rendered by the PEO. If possible, request demonstrations or trials to determine if their systems and processes align with your expectations and needs.
Evaluate the employee benefits packages available through the PEO. Consider whether they offer competitive health insurance, retirement plans, and additional perks that can attract and retain top talent. A PEO often provides access to benefits typically reserved for larger organizations, such as comprehensive health care and wellness programs, due to their ability to negotiate collectively for better rates and coverage.
Attractive well-being initiatives, including mental health services, fitness memberships, or even childcare assistance, can significantly bolster employee loyalty and satisfaction. It’s worth asking how these benefits are managed, whether there’s flexibility in tailoring them to meet specific employee needs, and how they are communicated to ensure high participation rates.
When reviewing fees, these questions to ask a PEO broker will ensure you uncover any hidden charges and understand total financial commitment.
Understanding the fee structure is vital. Ask about startup fees, ongoing costs, and any hidden charges. Knowing the financial commitment upfront helps in budgeting effectively. The common pricing models include a percentage of the total payroll or a fixed fee per employee per month, each with its own merits depending on your financial strategy and organizational size.
Beyond the upfront fees, consider the potential for additional costs that might arise. Some PEOs charge extra for specialized services such as extended HR support or legal consulting. It’s critical to weigh these costs against the value these services bring to your operation, ensuring a balanced approach to PEO investment.
Compliance with regulations is key. Inquire about how the PEO keeps up with legal changes, handles compliance issues, and supports your company’s adherence to laws and regulations. A reliable PEO should have mechanisms for keeping abreast with ever-evolving employment laws and best practices, offering guidance to help your business navigate these complex requirements smoothly.
Regular training sessions on topics like harassment prevention and updates on labor laws are essential services a reliable PEO should offer. Additionally, a PEO’s ability to conduct regular audits or compliance checks can provide further reassurances of adhering strictly to statutory requirements.
As your business grows, so too should your PEO’s capacity to support you. Ensure they can handle an increasing workforce and expanded operations seamlessly. A scalable PEO model provides the agility necessary to adjust to various business phases, from startups expanding rapidly to established companies diversifying their services or increasing their geographical footprint.
An effective PEO should be capable of rapid adaptation to your company’s evolving needs, allowing for smooth transition periods without downtime or interruptions in service levels. This extends to the ability to integrate new technological solutions that can facilitate streamlined onboarding and workforce data management as your business continues to expand.
A PEO’s reputation can say a lot about their reliability. Ask for references and case studies to understand their history, client satisfaction, and success stories. Do they have experience with businesses similar to yours in terms of industry and size? Requesting detailed case studies can offer insight into how their services specifically benefitted other businesses.
Refer to testimonials from current clients. These can reveal not only how they managed previous client needs but also the PEO’s responsiveness to new challenges. A PEO with a solid track record often indicates a certain level of trust and reliability, which ensures peace of mind as you enter into a partnership.
Open communication is critical for a successful partnership. Inquire about their communication practices, including how often they provide updates and address your inquiries. Regular communication ensures that any changes in service, compliance updates, or critical business concerns are swiftly and efficiently dealt with, fostering a strong, transparent relationship.
Determine if they offer dedicated account management, providing a single point of contact who understands your unique business needs. This personalized touch can enhance communication efficiency, making it easier to solve issues and make well-informed business decisions.
Technology is integral to efficient operations. Determine what platforms and tools the PEO uses and whether they integrate with your systems to streamline workflows. It’s crucial to understand how technology can reduce inefficiencies, minimize errors, and improve the overall employee experience.
Ask about their data security measures, as this could be pivotal in safeguarding your business’s sensitive information. Given the rise of cyber threats, comprehensive cybersecurity protocols are non-negotiable to protect both your business and employees.
Assess the level of support available to you and your employees. Understand the availability of customer support, account managers, and the resources provided for issue resolution. The best brokers offer a robust support system, ensuring any problems that arise are addressed promptly and adequately.
Explore the details of their post-sale assistance. Reliable PEOBs will not just sign you up and disappear; they should provide ongoing support, helping you maximize the value of their services throughout the lifecycle of your engagement.
Dinsmore Steele’s Strategic PEO Advisory™ benchmarks your PEO or self-funded plan against national averages — so you can see, in hard numbers, whether you’re buying savings or subsidizing risk.
Chief Operating Officer
Stephen Clemente serves as Chief Operating Officer at Dinsmore Steele, where he leads operations, finance, administration, sales enablement, and marketing in support of the firm’s PEO advisory mission. He focuses on strengthening how organizations evaluate, structure, and optimize their PEO relationships — helping clients improve cost, performance, and long-term outcomes through objective, data-driven guidance.
Throughout his career, Stephen has led global, cross-functional teams across a range of industries, including technology, eCommerce, and professional services. He has successfully raised venture capital for startup organizations, guided companies through growth and transformation, and helped maximize enterprise value during business sale and exit processes. His leadership approach emphasizes process discipline, organizational alignment, and building high-performing, collaborative teams.
Known for his commitment to delivering exceptional client outcomes, Stephen works to ensure every engagement results in a high-quality advisory experience and long-term partnership. At Dinsmore Steele, he collaborates closely with the advisory and client service teams to enhance benchmarking, negotiation support, implementation oversight, and ongoing performance management — always with the goal of ensuring clients are fully supported and genuinely delighted with their results.
Director of Broker Sales & Strategy
Chad serves as the Director of Broker Sales & Strategy at Dinsmore Steele, where he leads the broker channel with a clear focus: delivering unmatched support, strategy, and results for our partners and their clients. With a strong commitment to responsiveness and transparency, Chad ensures every broker partner has the guidance, tools, and insights needed to navigate the PEO landscape with confidence. He excels at simplifying complex decisions, strengthening relationships, and aligning solutions that put the client’s best interest at the center.
Whether he’s shaping growth strategy, optimizing partner workflows, or advising on PEO fit, Chad brings both strategic clarity and hands-on follow-through — always grounded in his belief that great brokerage relationships are earned through consistency, honesty, and meaningful impact.
Outside of work, Chad’s world revolves around his family. He takes pride in being a dedicated husband and father, and one of his greatest joys has been coaching his kids throughout the years—from their early seasons to where they are today. Whether on the field or in business, Chad brings the same energy, patience, and commitment to helping people succeed.
Senior PEO Advisor
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 Advisor
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.
