PEO Playbook

Running a business across multiple states comes with one big challenge: workers’ comp. Rates vary, rules change, and claims can spiral out of control. In this episode, Chad Philly and Marty Gray dive into how PEOs leverage buying power, manage claims, and protect business owners across state lines. Learn how proper documentation, proactive claims handling, and nationwide coverage can save your bus...

Compliance can feel like alphabet soup—FMLA, ADA, ACA, HIPAA, EEO…the list goes on. For small business owners, keeping up with these laws is overwhelming and costly if done wrong. That’s why having the right PEO partner is a game-changer. In this episode of The PEO Playbook , host Chad Philly and Staff Brokers CEO Marty Gray break down how PEOs protect businesses by handling the complex world of c...

In this episode of the PEO Playbook, host Chad Philly and CEO Marty Gray unpack how Staff Brokers built its national network of insurance agents and PEO partnerships. Discover how Staff Brokers: Helps agents place “hard-to-insure” clients Shares lifetime recurring commissions Protects agent relationships while solving client comp problems Delivers creative solutions like rebates and % of payroll m...

Benefits are no longer optional; they're essential to attracting and retaining great talent. In this episode of The PEO Playbook, Chad Philly and Marty Gray reveal how PEOs simplify benefits, cut costs, and give small businesses access to healthcare, dental, vision, disability, and even perks like pet insurance. Whether you’re a business owner looking to streamline your HR or an entrepreneur t...

In this episode of the PEO Playbook, host Chad Philly and CEO Marty Gray unpack how Staff Brokers built its national network of insurance agents and PEO partnerships. Discover how Staff Brokers: Helps agents place “hard-to-insure” clients Shares lifetime recurring commissions Protects agent relationships while solving client comp problems Delivers creative solutions like rebates and % of payroll m...

HR mistakes can cost your business time, money, and even lawsuits. In this episode of The PEO Playbook , Chad Philly and Marty Gray reveal how PEOs take the HR burden off your shoulders. From employee handbooks and workplace policies to unlimited HR support, discover how a PEO keeps your business compliant while saving you time and stress. Learn more and book a call: www.peoplaybook.com/booknow

When disaster strikes — hurricanes, pandemics, or economic shutdowns — small businesses are often the hardest hit. In this episode of The PEO Playbook , Chad Philly and Marty Gray reveal how PEOs act as a lifeline during crises. From payroll continuity and government relief applications to employee assistance and records recovery, discover why having a PEO partner can be the difference between sur...

Compliance – From I-9s to W-4s, PEOs help employers stay compliant and avoid costly mistakes. Employee Portals – Digital systems give employees access to pay stubs, tax forms, and benefits at their fingertips. Employer Benefits – Save time, reduce paperwork, and focus on running your business while PEOs handle the details. Discover how outsourcing onboarding to a PEO not only protects your busines...

Wrongful termination. Sexual harassment. Discrimination claims. Most small business owners think, “That’ll never happen to me”—until it does. In this episode of The PEO Playbook , Chad Philly and Staff Brokers CEO Marty Gray break down how PEOs protect employers through EPLI (Employment Practices Liability Insurance) and EAPs (Employee Assistance Programs) . Learn how PEOs provide affordable acces...

In this episode of The PEO Playbook , Chad Philly and Marty Gray from Staff Brokers dive into how PEOs simplify workers’ comp with a pay-as-you-go system that eliminates surprises and streamlines your job costing. They discuss multi-code job roles, multi-state payroll compliance, audit risk, and how to avoid bidding jobs with blind labor costs. Whether you're a contractor scaling into new stat...

In this episode of The PEO Playbook , Chad Philly and Marty Gray from Staff Brokers break down how PEOs simplify the chaos of operating in multiple states. From payroll tax compliance to state unemployment complexities, they discuss how a good PEO partner helps business owners avoid costly mistakes, stay compliant, and scale confidently—even when crossing state lines. If you're bidding jobs in...

In this episode, Chad Philly and Marty Gray of Staff Brokers pull back the curtain on what really makes a PEO partnership thrive. From vetting ownership and work comp structures to ensuring consistent service and crisis readiness, they break down the key factors that separate average providers from great ones. Learn how the right PEO can simplify operations, reduce risk, and improve your employee...

Operating across state lines? You’re not alone—and you’re definitely not crazy for feeling overwhelmed. In Episode 11 of The PEO Playbook , Chad Philly and Marty Gray break down how PEOs help businesses stay compliant with tax laws, workers’ comp rules, and HR regulations when managing teams in multiple states. Whether you're expanding into new territories or just have crews traveling between...

What if you could eliminate payroll headaches, skip the year-end workers' comp audit, and consolidate all your HR, benefits, and compliance tasks into one weekly transaction? In this episode of The PEO Playbook , Chad Philly shares how PEOs help business owners buy back their time—replacing multiple vendor meetings, tax filings, and admin redundancies with one seamless system. If you’re spendi...

If you’ve ever used the phrase “1099 employee,” this episode is for you. In Episode 9 of The PEO Playbook , Chad Philly breaks down the real differences between independent contractors and W-2 employees—and what happens when business owners get it wrong. Learn about behavioral and financial control, relationship-based tests, and the legal consequences of misclassification. This episode walks you t...

In this episode of the PEO Playbook, Chad Philly of Staff Brokers breaks down one of the most misunderstood areas of employee classification: who qualifies for overtime and who doesn’t. From the legal definitions of exempt vs. non-exempt to the five major exemption categories (executive, administrative, professional, outside sales, and computer programming), Chad explains exactly how business owne...

After a costly workers’ comp incident and juggling multiple disconnected HR systems, Loco Graphics turned to a PEO—and everything changed. In this episode, Chad Philly sits down with Greg Winters to uncover how outsourcing HR, payroll, and compliance gave his team peace of mind, reduced admin overwhelm, and brought real cost savings. Hear how a sign company found simplicity and support through Sta...

When you’re a small business working on rooftops, good luck finding affordable workers’ comp. That’s exactly how Joshua Brosich from Always a Sweep got introduced to the world of PEOs. In this episode of The PEO Playbook , host Chad Filley interviews Joshua about his journey from struggling to get coverage to saving $40,000 in his first year after switching PEOs. Hear how payroll outsourcing, risk...

In this episode of The PEO Playbook , host Chad Filley explains how PEOs take the guesswork—and the legal risk—out of employee handbooks. Learn how the right partner helps you build clear, compliant, and customized policies that protect your business without tying your hands. From handling new marijuana laws to avoiding discrimination claims, this is everything you didn’t know you needed to know a...

In this episode of The PEO Playbook , Chad Filley walks through what really happens when a work comp claim hits—and how PEOs take the headache off your plate. Learn why PEOs are incentivized to close claims fast, how they manage fraudulent injuries, and how their claims teams keep your business focused on revenue—not red tape. Whether you're new to PEOs or facing your first employee injury, th...

Thinking about partnering with a PEO but not sure how it works? In this episode of The PEO Playbook , Chad Filley walks through the full onboarding process—from data collection and underwriting to choosing the right PEO and setting up payroll. Learn what documents you’ll need, what mistakes to avoid, and why social media can make or break your approval. If you're considering outsourcing your H...

In this episode of The PEO Playbook , Chad Filley and Marty Gray tackle one of the biggest misconceptions about PEOs: that outsourcing payroll and HR means losing control. Spoiler alert—it’s the opposite. Learn how leveraging a PEO gives business owners more time, better compliance, and deeper control over finances, growth, and employee benefits. From real-world success stories to how PEOs handle...

In the debut episode of The PEO Playbook , host Chad Filley sits down with Marty Gray, CEO of Staff Brokers, to break down what a Professional Employer Organization (PEO) really is—and how it can transform your business. From reducing workers’ comp costs to simplifying payroll, healthcare, and HR headaches, Marty explains how PEOs bring the power of corporate-level infrastructure to small and grow...

Intro