Chief of Staff - Product

Workforce Intelligence: The People-First Playbook for Leading Your Company Through AI Transformation. Mike Sullivan, Co-Founder & Chief Growth Officer at OneDigital and Vinay Gidwaney, Chief Product Officer also at OneDigital joins Enterprise Radio. They are co-authors of the new book "Workforce intelligence: The People-First Playbook for Leading Your Company Through AI Transformation". This episode of Enterprise Radio is in association with the Author Channel. * Mike, you open the book by saying AI scares you. How does a CEO leading a $1.5 billion company turn that fear into a strategy rather than a liability? * Vinay, most AI books argue that technology teams should lead digital transformation. You argue the opposite - that it belongs to HR. Make the case. * You refer to AI at OneDigital as coworkers, and go on to give them names - Dex, Amy, and others. Why does that framing matter, and what does it actually change about how people show up to work alongside them? * What is "the humanity test" - and what does your answer to it reveal about the kind of company you're building? * You describe a 'blended workforce' of humans and AI. What does managing that look like in practice - day to day? Michael Sullivan is the co-founder of OneDigital, an insurance advisory and financial services firm he has built over 26 years into a $1.5 billion business with 6,000 colleagues, 100,000 employer clients, and more than 10 million Americans and Canadians depending on the quality of its advice. A history major with no coding background, Michael became the unlikeliest of advocates for AI transformation - spending an all-nighter building a working software tool that changed the direction of his company. He has led OneDigital through four existential crises: the dot-com collapse, the Affordable Care Act, a global pandemic, and now the AI revolution. Mike's voice carries the narrative chapters of the book - the honest account of a business leader who was scared, got moving, and chose to share the playbook. Vinay Gidwaney joined OneDigital as Chief Product Officer after three decades building software companies. His background includes helping run the mass COVID-19 vaccination sites at Fenway Park and Gillette Stadium - logistics operations moving 10,000 people per day under real-world pressure. His gift, as OneDigital's CEO describes it, is his clarity about what actually drives successful transformation: not the technology itself, but how people evolve alongside it. That insight is the operating system behind the Workforce Intelligence framework. Vinay takes over the methodology chapters, providing the quantitative framework, the WI Score formula, the Coworker deployment methodology, and the operational tools that make the book actionable on Monday morning.

OneDigital grows Chicago footprint, adds trucking specialty with Midwest Insurance agency deal. Buying spree continues as major group benefits agency adds more P&C. Group benefits broker OneDigital has added another agency to its growing national property and casualty business. This time it's in the Chicago suburbs, and the deal leans heavily into trucking. The Atlanta-based insurance, financial services and HR consulting firm announced on August 18 that it has brought on Midwest Insurance Agency, a 30-year-old commercial brokerage based in Elk Grove Village, Illinois. The agency gives OneDigital a bigger presence in a market it already serves, along with a specialty that's hard to build from scratch: insuring trucking fleets, owner-operators and the contractors who move freight around the Midwest. Midwest Insurance Agency's 20-person team supports more than 1,000 clients. Its book is weighted toward commercial transportation, cargo and logistics coverage, owner-operator and independent contractor programs, contractor's insurance, and a smaller niche in home health and medical professional liability. Founder and president Tom Hammond will stay on to run the agency, which keeps its Elk Grove Village office under the OneDigital name. Transportation risk is one of the tougher lines to underwrite well, and agencies with decades of carrier relationships in that space don't come up for sale often. Todd Belden, OneDigital's president for the Central region, credited Hammond's team with mastering "one of the most complex and specialized segments" in the P&C market. Hammond described the deal as a way to give clients access to a bigger platform without losing the "hands-on, relationship-driven service" his agency was built on. The deal follows a pattern OneDigital has used across its Central region before, including its earlier acquisition of Watko Benefit Group under Belden. What sets this one apart is the trucking focus, arriving at a time when commercial auto risk is still one of the hardest lines in the market. Insurance Business has covered the volatility facing trucking firms heading into 2026, as tariff swings, soft freight rates and rising repair and litigation costs squeeze carriers' margins, and brokers have described how fleets are adjusting to survive the hard commercial auto market through better data, safety technology and faster claims reporting. Buying an agency with established carrier relationships in that niche gives a national broker underwriting credibility it would otherwise take years to build. OneDigital's P&C division now serves more than 19,000 clients across all 50 states. The firm has made more than 31 acquisitions in that practice since 2021, nine of them in the Central region. Across all its practice lines - P&C, employee benefits, retirement plan services, wealth management and HR consulting - OneDigital says it has around 450 professionals working out of 35 offices in the Central US. Dowling Hales advised on the transaction, with Managing Director Harshal Gorde credited for his role in getting the deal done. Terms were not disclosed. The deal also comes as insurance distribution keeps consolidating. OneDigital took on a new ownership structure last year when Stone Point Capital and a Canadian pension investor took a majority stake in the firm at a valuation above $7 billion, capital that helps fund exactly this kind of tuck-in deal. Private capital-backed buyers accounted for more than 70% of announced insurance brokerage M&A transactions through the first half of 2026, according to M&A advisory firm MarshBerry, even as overall deal volume has cooled a little from recent years' pace. For Midwest Insurance Agency's clients, the practical change is likely to be small at first: same team, same relationships, now backed by a national carrier network and OneDigital's benefits, retirement and HR consulting arms.

Your healthcare benefits benchmark may be wrong: Here's what to measure instead. Share: Healthcare benefits benchmarking compares an employer's health plan costs and performance against relevant peer groups. Effective benchmarking goes beyond total cost per member by accounting for factors such as geography, plan design, population health risk, unit costs, utilization, and high-cost claimants. Every insurance organization and benefits consultant knows the annual benchmarking ritual. The report arrives. The numbers get reviewed. A conclusion gets reached. And most of the time, that conclusion is wrong. At Summit 2026, Nauman Shaikh, VP of Actuarial and Analytics at OneDigital, made a case that most employer health benefit benchmarks are not just incomplete, they are actively misleading. The problem is not a lack of data. It is the way comparisons are built, the assumptions baked into peer cohorts, and the metrics that never make it into the analysis at all. The stakes are significant. Healthcare is the second-largest operating expense for most US employers, behind wages only. It represents roughly 65 to 70 percent of total employee benefits cost and approximately 10 percent of total wages. And right now, it is trending in a direction that most organizations have not accounted for. The budget gap no one is talking about. In 2026, healthcare costs are trending at nine to ten percent annually. Historical norms ran closer to five to six percent. Most employers are budgeting four percent. The gap between what organizations plan for and what they actually pay is not a rounding error. It is a structural problem, and benchmarking done poorly is one of the reasons it keeps widening. Shaikh walked through the five forces driving the current trend. Specialty pharmacy costs, including GLP-1s, gene therapies, and cell therapies, now represent 50 percent of total pharmacy spend. A post-pandemic rise in chronic conditions, including obesity and behavioral health, is compounding the problem. Delayed-care rebound from COVID continues to add claims volume. Provider consolidation has reduced plan sponsor leverage in contract negotiations. And baseline medical inflation has not moderated the way many expected. Each of these is measurable. None of them surface correctly in a raw benchmark comparison. Why the wrong healthcare benchmark can lead to the wrong decision. Shaikh opened with a story that illustrated the risk clearly. A CFO at a 3,000-employee manufacturing company had walked into a meeting convinced his plan had a problem. His benchmark report showed healthcare costs running 22 percent above benchmark on a per-member, per-month basis. His instruction was straightforward: fix it. What followed was a risk adjustment analysis that accounted for the company's geography, plan design, healthcare morbidity scores, and chronic condition prevalence. Once those factors were normalized, the company was actually performing four percent better than benchmark. The CFO had been on the verge of cutting health benefits for 3,000 employees based on a comparison that was never apples to apples. That is not an edge case. It is a pattern. What the comparison actually needs to include. The core problem with most benchmarking is peer cohort selection. Comparing a manufacturing employer with an aged, high-morbidity workforce to a general market average produces a distorted picture in both directions. A meaningful benchmark has to reflect what the plan would cost among employers with genuinely similar populations, accounting for geography, plan design, member risk scores, and clinical complexity. Beyond cohort selection, Shaikh identified unit cost as the dominant driver of healthcare expense growth right now. Understanding what a plan is paying for inpatient, outpatient, and professional services, measured against Medicare prices, cash prices, and carrier contract rates, is more critical than ever. Utilization patterns and the shift in mix toward higher-acuity services compound the problem. Tracking all three together produces a significantly more accurate performance story than total cost per member alone. The third gap is tail risk. Two rules define the reality of self-funded plan exposure: five percent of members drive 50 percent of plan cost, and 20 percent drive 80 percent. Plans that track high-cost claimant cohorts and build intervention protocols around them operate differently than those that wait for the annual renewal to surface the problem. Benchmarking only works if it drives decisions. Shaikh was direct about where the process most often breaks down. Benchmarking becomes a reporting exercise rather than a decision-making tool. The report lands, gets reviewed, and sits. Three decisions should follow a rigorous benchmarking process. The first is funding strategy. "If you're an employer in the US, you are in the business of healthcare, like it or not," Shaikh told the Summit audience. The structure of how a plan is funded determines how much operational control the employer retains. The market continues to move toward self-funding precisely because it creates leverage that fully insured arrangements cannot match. Vendor and network strategy is the second. When benchmarking exposes unit cost variances by service category, the next step is evaluating whether current network contracts are producing competitive pricing. Transparency data and reference-based pricing analyses become essential inputs to that conversation. Pharmacy strategy is the third, and it is increasingly urgent. Given that specialty pharmacy is trending faster than medical, GLP-1 exposure, biosimilar adoption rates, and specialty penetration are metrics that every plan sponsor should be tracking by name, not buried in aggregate pharmacy cost numbers. The shift from retrospective to predictive. The annual benchmark review is an outdated model. Shaikh described the capabilities that forward-thinking benefit consultants are already building into their practices: real-time dashboards replacing static reports, AI-flagged high-cost claimant alerts that identify exposure weeks before claims materialize, micro-cohort analytics tracking specific high-cost conditions, and anomaly detection that surfaces billing irregularities and clinical outliers automatically. The shift is from explaining the past to anticipating the future. Shaikh's closing challenge was direct: are you benchmarking metrics that tell the future story, or only the past? Are you separating what a plan has inherited from what it can actually control? Employers who are asking those questions are already asking them. The question is whether their consultants are equipped to answer. Solutions. * Business services * Process * Strategy