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Navigating the complexities of Professional Employer Organizations (PEOs) is a daunting task for anyone. That’s where I come in. As a PEO Expert and CEO at Dinsmore Steele, I’ve dedicated my career to simplifying this process, saving businesses both time and money. Over the last 16 years, our team has saved over 3,000 companies a staggering $592 million. On average, our clients save $2,016.78 per employee each year—savings that directly impact their bottom line. What sets us apart? I’ve developed the easiest method for comparing the nation's largest PEOs all in one place. With our unbiased expertise and comprehensive approach, we offer unparalleled insights that empower businesses to make informed decisions quickly. Instead of spending over a month researching and negotiating on your own, we streamline the entire process—at no cost to you. Our mission is simple: to make your life easier. We handle the heavy lifting so you can focus on what truly matters—growing your business. As the largest PEO brokerage in the country, we bring unmatched expertise and a commitment to transparency that you won’t find anywhere else. Ready to save time, reduce costs, and optimize your HR strategy? Let’s connect and see how we can make a difference for your company.
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Last year, we switched PEOs. And we went through the exact same process we take our clients through. We compared everything: → Admin fees → Benefits → Workers’ comp and SUTA rates → Plan designs → Technology and support We sat through demos. We negotiated. We asked hard questions. We didn’t shortcut anything—because we don’t let our clients shortcut it either. Why? 1️⃣ Because it makes sense. 2️⃣ Because we eat our own dog food. 3️⃣ Because smart companies compare. But here’s what surprised me: Even we almost forgot to do it. And this is what I realized: No one is immune to inertia. Even the experts. Even the ones who know better. That’s why comparison needs to be built into your business rhythm. Not just when things feel broken—but before they do. ✔️We saved real money. ✔️Got better support. And now we walk the talk—because we’ve been through it ourselves. If it’s been 2+ years since you’ve compared your PEO, you might be missing more than you think.
I’ve always liked animals. Even as a kid, I never understood people who didn’t. The first time I ever got into a fight? Someone was being cruel to a cat. Saw this quote the other day and couldn’t stop thinking about it: “If people don’t like you, that’s fine. But if dogs don’t like you… you might need to take a good, hard look at yourself.” Honestly? It feels true. Hope you're spending your Saturday with people (and pets) who just get you. Agree or disagree?
If you’re struggling to find clients, start by finding your people using your competitors. Too many sales people are chasing cold leads. Or worse—waiting for inbound. Here’s a better play: Target the people already using your competitors. → They’ve already bought into the value of what you do. → They’ve already allocated budget. → They just picked someone else. → You don’t need to educate them. → You just need to prove you’re better. Here’s the move: → List your top 5–10 competitors → Identify who their clients are → Reach out with insight, not a pitch → Build a relationship before you sell I know this works—because I’ve done it. And after working with over 6,100 companies in the last 15 years, I’ve seen the best sales strategies in the world up close. This one? It works. Struggling to find clients? Stop chasing random leads. Start looking where your competitors are already doing the work for you. Try it. Then let me know how it goes.
You don’t own a business. You own a job… …if you’re still doing everything yourself. No system = no freedom. Just higher stress and a bigger headache. When I started Dinsmore Steele, I did everything. 👨💼Sales. Ops. Payroll. Fire drills. All of it. I told myself I didn’t have time to build systems. Then I finally took a vacation. Or tried to. And it hit me—hard: Without systems, I wasn’t a business owner. I was an overworked employee… with no boss. In the past, I didn’t have time to build systems. Now? I don’t have time not to. Once I put real systems in place, the chaos slowed—and the business scaled faster than I expected. That’s when I truly became the owner of a business. Here’s the difference: Owning a job • You chase every lead manually • You send invoices late • You onboard employees in your head • You’re the fire department and the fire • You can’t step away Owning a business • Leads come in on autopilot • Payroll and benefits are handled by systems • New hires follow a clear, repeatable playbook • You work on the company—not in the chaos • You can take a vacation—money still comes in Want to know if you own a business or a job? Ask yourself … “What happens if I step away for 30 days?” Your answer will tell you everything. Struggling with this now? At Dinsmore Steele, we help founders stop running in circles— and start scaling with structure. DM me to learn how.
Your PEO isn’t a set-it-and-forget-it decision. But most companies treat it like one. We recently worked with a national ad agency. They joined a big-name PEO 12 years ago—and never looked back. They didn’t love the service. But figured switching would be too much of a headache. Too much paperwork. Too much hassle. Until they found out we handle everything for them. What we uncovered: → They were overpaying by $175 per employee in admin fees. 🔎Why? Because when they joined, they had 7 people—and $175 per head made sense. But now? They’ve got 82 employees. Same admin fee. Same PEO. Massive gap in value. These often-overlooked decisions can cost your company hundreds of thousands—if not millions—over time. 🚀 Your business grew. 💸 Your costs did too. But your PEO? It stayed the same. If you haven’t audited your PEO in 2+ years, you’re likely overpaying. And there’s a better option waiting. When’s the last time you took a real look under the hood?
Saved $200K+. Helped a pro sports team. Solved messy HR across 5 industries. Here’s what we tackled recently: 🏥 A medical device company stuck with a 37% benefits renewal → We got them out fast. New PEO, $92,000 saved. 🍽️ A food service brand ready to ditch their PEO → We transitioned them to an ASO, replicated every service, and cut overhead. ⚖️ A litigation finance firm needed options → CFO didn’t know they were overpaying. Found a better fit and saved them $54,000. 🏡 A mortgage brokerage wanted to offer health coverage to 1099s → We set up an AHP plan that made them look Fortune 500. 🏟️ A Major League team needed help covering front office staff and players → We moved them to a PEO that could scale with their needs. Total savings across these teams? Over $200,000. All by asking one simple question: 👉 Is this still the best setup for us? If you're growing—and your PEO, benefits, or HR systems haven’t been reviewed in the last 12 months…Let’s talk. 📞 Book a Strategy chat DM me "PEO" and I'll send you the link.
Staying with the wrong PEO is like driving with the parking brake on. 🏃♂️ You might still be moving. 💰 Revenue is growing. Headcount’s up. Business feels good. But under the surface… → You’re overpaying on admin fees → Your benefits are getting worse each year → Your team’s support tickets are going unanswered → Your workers’ comp and SUTA rates keep climbing And you think: “Well, it’s not that bad. Switching sounds like a pain.” But here’s the reality: The cost of switching is almost always less than the compounding cost of staying stuck. In the last 15 years, I’ve worked with over 6,100 companies. And I’ve only seen one that wasn’t overpaying for their PEO— us. Why? → Because we compare. → We audit. → We make sure the PEO still fits the business. Most companies never do. And it costs them hundreds of thousands. Your business has evolved. But your PEO hasn’t. If you haven’t reviewed your PEO in the last 2 years, you’re likely overpaying—and possibly partnered with the wrong one altogether. We help companies quietly compare, with no disruption. Ready to see how your PEO stacks up? DM me.
This week, my best friend turns 11. He’s never closed a deal. Never built a business. Never posted on LinkedIn. But he’s taught me more about leadership, loyalty, and life… …than most people I’ve worked with. His name is Jefe. And here are 11 things he’s taught me that made me a better man: 1. Show up the same every day. Good mood. Bad mood. Jefe’s at the door—tail wagging. That kind of emotional consistency? It’s a superpower in business and life. 2. Presence > Productivity. He doesn’t care what’s on the calendar—he just wants my full attention. Clients and teams? They want the same thing. 3. Protect your pack. Jefe is chill—until someone threatens his people. Loyalty over charm. Always. 4. Celebrate the little things. A walk. A treat. A nap in the sun. Business wins feel better when you know how to celebrate the small stuff, too. 5. Listen more than you speak. He picks up on energy—not words. Good leaders do the same. 6. Rest like it’s your job. When he’s off, he’s off. No guilt. No grind. Just rest. There’s a lesson in that. 7. Trust is earned, not assumed. Jefe doesn’t give his trust away easily. But when he does? It’s rock solid. The same should be true in leadership. 8. Forgive fast. I’ve stepped on his tail more than once. He’s over it in seconds. People hold grudges. Dogs move on. 9. Energy doesn’t lie. Jefe has never misjudged a person. Neither have I—when I trust my gut. 10. Love without conditions. He’s never cared about what I do. Just who I am. If only we led people that way. 11. You don’t need words to lead. He doesn’t talk. But everyone around him knows how he makes them feel. That’s leadership. So here’s to Jefe—my silent mentor. 11 years of wisdom, wrapped in fur and loyalty. I love you, buddy. You’ve made my life better. What have your pets taught you about life or leadership?
The worst time to find out you chose the wrong PEO? - When compliance breaks. - When your renewal spikes. - Or when your CFO says, “What exactly are we paying for?” If you’re exploring a PEO, you’ve got 3 options: 1. DIY You fill out forms. You talk to reps. You hope the provider you choose works out. - No benchmarks. - No insight. - And no leverage. 2. PEO Sales Rep They know their platform inside and out. - But if their solution isn’t a perfect fit? - They can’t help you compare. - They’re paid to sell their product — not find your best option. 3. Dinsmore Steele We’re PEO brokers — but more importantly, we’re strategic partners. - We don’t quote every provider. - We quote the right ones — based on your headcount, risk profile, benefits needs, and long-term growth. We also: • Explore medical options (fully, level, self-funded) • Compare ASO vs. PEO • Deliver a strategy, not a sales pitch So you choose with clarity, not guesswork. If you’re considering a change or just want to validate your current setup: DM me “PEO Options.” Cassandra Anderson Barbara Pailley Alicia Mole Jessica Bertram Dinsmore Steele
I love trends - well some of them. Here's one that seems to be getting better and better. Not sure if anyone would buy these, but I'd sure love to give them away. Which one is your favorite?
After 15 years in the PEO space, I’ve heard just about every question imaginable. But some come up again and again. Here are a few of the most common — and my honest answers: 1. Does this PEO also do payroll? Yes — all PEOs process payroll. It’s table stakes. 2. Is this the same Aetna we already have? Yes. There’s only one Aetna insurance company. Same goes for Cigna, UHC, and Blue Cross. 3. Who handles HR, benefits, and workers’ comp in the PEO? The PEO does — that’s the core of the co-employment model. 4. Are Aetna, Blue Cross, Cigna, and UHC good networks? Yes. These are the best networks available nationally. 5. Why use a broker instead of going direct? Because we do this every day. You may do it once or twice in your entire career. And here’s the truth … PEOs compete harder when you work with us. 6. Who’s the best carrier? The one that gets your claims paid. Full stop. These are just a few — but they come up constantly. Want our full list of the Top 25 Most Common PEO Questions (and smart, no-BS answers)? Drop “PEO Qs” in the comments or DM me, and I’ll send it over. Cassandra Anderson Barbara Pailley Alicia Mole Jessica Bertram
“We think it’s time to leave the PEO.” That’s what the COO told me when the PE firm brought us into one of their 172-employee portfolio companies. 🚀 HR costs were spiking. 🐌 Support was slow. 🤦♂️ And the team had no visibility into what they were actually paying for. But here’s what most teams miss: Leaving your PEO isn’t always the right move. So we ran a full market analysis: • Multiple PEO quotes • Medical options (fully insured, level-funded, self-funded) • ASO comparisons And after 2 weeks of slow-moving carrier responses… the answer was clear: They shouldn’t leave the PEO. They just needed a better one. 💰 Lower cost. 🎰 Better alignment. ✅ Less complexity. That’s the power of strategy — not guesswork. At Dinsmore Steele, this is how we operate. No pressure. No pitching. Just clarity. If you’re evaluating your PEO — don’t do it alone. DM me “PEO Review” and I’ll send you our 3-part PEO Evaluation Framework. Cassandra Anderson Barbara Pailley Alicia Mole Jessica Bertram
Your calendar is full. But your business is stuck. About 10 years ago, I was drowning in admin work. Every day was packed. But nothing was moving the needle. So I hired an assistant. Finally—relief, right? Not exactly. → I struggled to “find” tasks to delegate → Explaining things took forever → The results weren’t quite right → I’d get frustrated… and just do it myself It wasn’t their fault. I hadn’t built the system. I was trying to hand off chaos and call it delegation. That was my wake-up call. You don’t scale by offloading tasks. You scale by building systems—and making your people part of them. A full calendar might feel like control. But it’s actually the clearest sign you have none. Want to grow? Stop being the glue. Start being the architect. Where are you still winging it—and expecting someone else to clean it up?
You can’t create a new level of growth with the old version of yourself. There was a time I thought being a good leader meant doing more. More oversight. More involvement. More weight on my shoulders. But real growth forced me to face a hard truth: I was the one in the way. What changed everything? → Learning to hand things off → Hiring the best people I could afford → Trusting them to carry out the vision Because being overly involved doesn’t just slow you down— It drives away talented people. They don’t want to be babysat. They want ownership. They want to build alongside you. The old version of me couldn’t do that. The new version had to show up. Every new level of growth requires a new level of leadership. And that starts with letting go. What’s one thing the old you keeps doing that the next-level you needs to stop?
I made a bet 15 years ago. That companies deserved better PEO advice. - Not sales reps. - Not comparison websites. - But real strategic guidance built on outcomes, not incentives. In the early days, Dinsmore Steele worked exclusively with brokers. They brought us volume — a lot of it. But over time, I realized. Volume doesn’t mean revenue. And it doesn’t build long-term relationships. So I made a tough call: We shifted away from brokers — and started working directly with companies. It upset people. Our pipeline dropped overnight. But we refocused on what mattered. Helping leadership teams and PE firms make better, more informed PEO decisions. The result? • Better clients • More profitable deals • Deeper strategic impact That decision changed the business — and it’s one of the reasons we’re still here today. Short-term would’ve been easier. But in my world, if you’re going to do it — it should be built for the long-term. Otherwise, why bother, am I right?
If you don’t compare the leader you are… to the leader your business needs…you stay stuck. I’ve noticed something in myself. About every five years, I go through a shift. → The first five? Survival. Everything was about staying alive. Hustle. Grit. Doing it all. → The next five? Refinement. I focused on building better systems, stronger relationships, and tightening the process. → Now? It’s about expansion. Scaling what works. Stepping into growth. Building something bigger than me. And I know the next five will demand something different again. Each stage demanded a different version of me. And each one started with this question. “What have I been doing? What needs to change?” Because no one jumps from $1M to $5M overnight. You grow by shedding what used to work—and becoming who your business needs next. Every new level of business requires a new level of leadership. If you haven’t compared the way you lead today with where you want to go tomorrow— you’re probably in your own way. What stage are you in right now?
Some weeks, you sprint. Some weeks, you reflect. This one was both. I’ve been thinking a lot about the seasons of business—and how each one demands a different version of you. This past week, I shared stories and strategies around one core idea: If you don’t compare where you are to where you want to go, you’ll never grow. I’ve learned that firsthand over 15+ years, working with thousands of companies. And also just by living it. From: → Running on survival instinct → To refining how I lead → To building systems that scale → And now… expanding beyond what I thought was possible And here’s something I’ve come to believe: I’ve heard that “comparison is the thief of joy.” And in life, I agree. But in business—when you’re making decisions, leading a team, and building your future? Comparison is vital. You can’t grow if you’re afraid to look honestly at what’s working… and what’s not. Wherever you are right now—grinding, scaling, rebuilding…take a second to look back. You’ve already evolved. And the next version of you? It’s already taking shape. Have a great weekend. You’ve earned it.
In my 30s, I rarely went on vacations. Worked most weekends. Didn’t take real time off. Nothing was more important to me than building Dinsmore Steele. So I poured everything into it. ⏳More hours. 🗜️More pressure. 🏋️More weight on my shoulders. And it worked—until it started to wear me out more than it was building me up. I wasn’t lazy. I was just always on. Too buried in work to actually lead. Eventually I learned: Growth doesn’t come from working more. It comes from building better. And building better starts when you step back—so others can step up. Now? I don’t work every weekend. Not because I care less… But because I care enough to play the long game. You can’t create your next level from a place of burnout. And your team won’t rise if you never give them room. What’s one thing you wish you had prioritized more in your 30s? Tag a founder who needs this reminder #Entrepreneurship #WorkLifeBalance #FounderLife
5 years in business. And in 5 days, everything changed. In 2015, things at Dinsmore Steele hit a wall. A major PEO partner stopped paying us. My entire team walked away to chase “bigger dreams.” And suddenly, it was just me. 💰We still had revenue. 🚴♂️But the momentum? Gone. ⚙️The machine that built it? Broken. I was frustrated. Embarrassed.🙈 Mostly at myself—for letting it get to that point. Maybe you’re there right now. If so—keep reading. Because I knew two things: 1. I was going to rebuild. 2. I had let too many unqualified people work on things that didn’t work. So I sat down and made a list. What’s working. What’s not. Then I cut everything that wasn’t. No more fluff. No more passengers. Just focus. 🧘 I picked up the phone and got to work. And that energy? It spread. I rebuilt Dinsmore Steele with people aligned in direction and drive. People who wanted to build—not just talk about building. Looking back now? It was worth every scar. That PEO? Their execs started another one. And now? They can’t even get a call with us. The dream-chasers? Turns out those dreams were fever dreams. They’re selling HSA cards now. Here’s the truth. No matter where you are in your journey—you can start over. And if you do, start with what’s working. 💥 Cut the noise. 🛜 Keep the signal. 💪 And move. What’s one thing you cut that changed everything?
I lost my career in the 2008 crash. Discovered PEOs while working at a startup. Fascinated by the model. Spent the next 15 years building Dinsmore Steele—brick by brick. Some years were lean. Some were brutal. But every one taught me something worth sharing. Here’s what I’ve learned: • Flash doesn’t scale. Clarity does. ✨➜🔍 • The best operators ask questions—not just for answers, but for understanding. ❓ • Simple beats complex—especially when you’re trying to grow. ⚙️ • You don’t need to be the loudest—you just need to be right. ✅ • Most decisions don’t need more time. They need better information. ⏳➜🧠 When I started, PEOs were barely on the radar. Now they’re powering some of the fastest-growing companies in the country. 🚀 But the fundamentals haven’t changed: • Solve real problems. ✔️ • Do what you say you’re going to do. 🤝 • Make complex things simple for the people you serve. 🧩 No shortcuts. No noise. Just the work. What’s the hardest lesson you’ve learned in business? Drop it in the comments—I’d love to hear it.
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