The Payroll Career Arc: Entry Level to Executive — What No One Tells You

Jim O'Connor's Playbook for Fixing America's Broken Benefits System

In this explosive episode of It's About Payroll, we sit down with Jim O'Connor, President & Founder of Premier Health USA, to expose the hidden truths behind America's healthcare benefits crisis — and what employers, employees, and payroll professionals can do RIGHT NOW to fight back. 💥 What you'll learn in this episode: ✅ Why America's benefits system gets a D (and what it would take to earn an A) ✅ The "Insurance Hamster Wheel" trapping employers with the Big Four carriers ✅ How level funded & partially self-insured plans can get your money BACK at the end of the year ✅ The #1 mistake employers make when selecting benefits (hint: they never ask their employees) ✅ Why the paycheck is the most powerful benefits communication tool you're not using ✅ How payroll and benefits teams can team up for a home run ✅ What employee benefits will look like by 2030 ✅ Jim's surprising take on what employees STILL want — same as they did 40 years ago 💡 Whether you're a payroll professional, HR leader, small business owner, or benefits consultant — this episode will change how you think about healthcare, compensation strategy, and the future of work. 🔗 Connect with Jim O'Connor & Premier Health USA: 🌐 Website: www.premierhealth-usa.com 📧 Email: joconnor@ph-usa.com 🌐LinkedIn: https://www.linkedin.com/in/joconnorpremierhealthusa/ 📲 Enjoyed this episode? Do us a favor: 👍 LIKE this video 🔔 SUBSCRIBE & hit the bell so you never miss an episode 📤 SHARE with a payroll pro, HR leader, or business owner who needs to hear this https://wrkdefined.com/podcast/its-about-payroll, itsaboutpayroll.io https://youtu.be/RkVPNtuyAbg 💬 Drop your thoughts in the COMMENTS — what grade would YOU give America's benefits system? 🎙️ It's About Payroll — the podcast where payroll professionals, business leaders, and HR innovators come together to make sense of the workforce landscape. Quote of the Day 💬 "Every meaningful breakthrough in life begins with a long season of unnoticed work." — Robin Sharma #employeebenefits #payroll #healthinsurance #hrstrategy #smallbusiness #LevelFundedPlans #healthcarecosts #payrollpodcast #BenefitsStrategy #humanresources #workplacebenefits #JimOConnor #PremierHealthUSA #ItsAboutPayroll #openenrollment #affordablecareact #employeeretention #hrleadership #businessgrowth #healthcarebenefits

Payroll: The Past, Present & Future

Is payroll still just a back-office function? Not anymore. In this episode, Walt and Brian break down how payroll has transformed from a purely administrative role into a strategic, compliance-driven, employee-experience powerhouse — and where it's headed next. 🔑 What We Cover: How payroll evolved from processing checks to influencing company strategy The real story behind payroll cutoffs (and why we need to stop using the term loosely) Earned wage access: perk or expectation? Is biweekly pay becoming obsolete? AI in payroll — error detection, anomaly flags, and what AI still can't replace The payroll "offensive lineman" analogy that hits different Lightning round: Payroll hot takes — will paper checks disappear? Should payroll have a C-suite seat? 💡 Key Takeaways: Payroll professionals are increasingly being pulled into executive-level conversations around compliance, data governance, and employee experience Nearly 80% of Americans live paycheck to paycheck — pay speed is now a strategic priority AI will enhance payroll, but human oversight and compliance expertise remain irreplaceable Bad data = bad results, no matter how smart the AI 📚 Mentioned in This Episode: Andy Valentine (previous episode) Max van der Glees Bussink & "The Payroll Pivot" by Nick Day Celery (AI payroll error detection), Paycom, iSolve, Career Learning, Nerd Outfitters (Troy) CPT (Certified Payroll Technician) Course — first cohort launching June 1st! & more! 🎓 CPT Course Now Open! Learn to process payroll inside a real payroll system before you ever get a job. Cohort 1 starts June 1st. On-demand version coming soon. Free Payroll Nerd T-shirt or hoodie included! 📖 Get the Book: Digital version on sale for just $2.99! https://www.amazon.com/-/es/About-Payroll-Your-Blueprint-Start/dp/B0GPK85YYM itsaboutpayroll.io https://youtu.be/rSFw18ZZqQo https://wrkdefined.com/podcast/its-about-payroll 🎙️ It's About Payroll is the podcast for payroll professionals at every stage — from first job to C-suite conversations. Subscribe, share, and tell a friend to tell a friend. #Payroll #PayrollProfessional #HumanResources #EarnedWageAccess #AIinPayroll #PayrollTech #FinancialWellness #PayrollCertification #HRTech #ItsAboutPayroll #PayrollNerd #CPT #PayrollCompliance #FutureOfWork #PayrollLeadership

What Every Payroll Leader Must Know About Global Payments

In this episode of It’s About Payroll, Brian and Walt sit down with Andy Valentine, Key Account Director at Ebury, to talk about the often-overlooked side of payroll: making sure people actually receive their money. Andy explains that payroll accuracy is only half the battle. Once gross-to-net is calculated, companies still have to manage payment timing, banking data, foreign exchange, local payment rails, compliance checks, and global banking relationships. The conversation covers why global payments fail, including incorrect beneficiary data, correspondent banking delays, country-specific payment requirements, and anti-money laundering compliance reviews. Andy also explains the importance of penny testing, payroll calendars, finance approvals, and working backward from payday to avoid missed payments. Listeners will also hear about FX risk, dormant cash sitting in local accounts, payroll leakage, stablecoin, AI, fraud risks, and the growing need for payroll, finance, and treasury to work as one team. The big takeaway: payroll is not complete until employees are actually paid.

Season 16 in Review

Brian and Walt are back with a (much-anticipated) Season 16 review! In this episode, the hosts reflect on what made this season groundbreaking — from game-changing guests to major milestones for the Payroll Universe brand. In this episode: Word of the season: "Groundbreaking" vs. "Impactful" — and why both fit The biggest surprise: just how many payroll-adjacent businesses are shaping the industry The episode that changed everything: Trent from CotaPay and the death of payroll cutoff times Melissa Walker (Sounder Benefits) and how employers can actually save money on benefits Brian Smith (Top to Bottom Solutions) and the myth that benefits only cost you money Behind the scenes: what goes into prepping each season that listeners never see How the podcast has personally changed both hosts Book updates: It's About Payroll has a new cover and formatting, and Walt's Bruised But Not Broken is a must-read The Certified Payroll Technician (CPT) course launch on iSolved This or That: Hip-Hop Edition 🎤 Resources mentioned: It's About Payroll (book) – digital copy on sale for $2.99 Bruised But Not Broken by Walt CotaPay | Sounder Benefits | Top to Bottom Solutions | Payroll Like a Boss Certified Payroll Technician (CPT) course – payrolluniverse.com 🔔 Subscribe, like, and share with a payroll pro who needs this! https://wrkdefined.com/podcast/its-about-payroll itsaboutpayroll.io https://youtu.be/kkZ1a4uSx1g #itsaboutpayroll #payrollpodcast #payrollprofessional #season16 #PayrollUniverse #cpt #payrolltips #HRPayroll #smallbusiness #PayrollNerd

The Payroll Career Arc: Entry Level to Executive — What No One Tells You

🔥 Is your payroll career stuck on autopilot? In this episode of It's About Payroll, Brian and Walt break down the real payroll career arc — from entry-level grind to strategic leadership — and the stage nobody talks about: the waiting period. Whether you're just starting out, feeling stagnant, or ready to level up, this episode is your roadmap. In this episode, we cover: ✅ The 4 stages of the payroll career journey ✅ Entry-level mistakes that hold payroll pros back ✅ How to move from "task-heavy" to strategic payroll leadership ✅ The dangerous waiting period — and how to survive it ✅ Why more money doesn't always mean less stress at the top ✅ The difference between being a payroll manager vs. a payroll LEADER ✅ AI layoffs in 2026: What 100,000+ tech job cuts mean for payroll pros ✅ Why 53% of employees would leave over ONE payroll mistake ✅ "I Should Have Known Better" — payroll war stories you'll relate to 💡 Key Insight: Payroll accuracy isn't just an operational issue — it's a retention strategy. One mistake can trigger turnover. 🎓 New Course dropping soon! Learn payroll inside a live payroll system. Perfect for career changers and new grads. 🔔 Subscribe for weekly payroll industry insights, career tips, and real talk from payroll professionals who've been in the trenches. 👍 Like | 💬 Comment | 📤 Share with a payroll pro who needs to hear this https://youtu.be/oTALfUt0KVo itsaboutpayroll.io #Payroll #PayrollCareers #HumanResources #HR #PayrollManager #CareerGrowth #PayrollProfessional #AILayoffs #PayrollTips #ItIsAboutPayroll #PayrollLeadership #CareerDevelopment #WorkplaceStrategy