Inside the AI Hiring Pipeline: Interns, Apprentices, and Full-Time Coworkers | Vinay Gidwaney & Mike Sullivan, OneDigital

Vinay Gidwaney is Chief Product Officer and Mike Sullivan is Co-Founder and Chief Growth Officer of OneDigital, a 6,000-person, PE-backed benefits, HR, and wealth consultancy serving roughly 100,000 employers. Their contrarian bet: AI transformation has almost nothing to do with technology and everything to do with treating AI as talent. Instead of automating tasks, OneDigital built an internal hiring pipeline for AI, complete with job descriptions, an intern-to-apprentice-to-full-time promotion path, and performance improvement plans, and used it to avoid the layoffs most "AI transformation" playbooks assume are inevitable.

Liam sits down with both of them to unpack the night Mike built a "disruption calculator" that showed OneDigital was on track to cut 1,800 of its 6,000 jobs, and how that all-nighter became the catalyst for a different strategy. They get into Ben, the AI coworker now handling daily conversations with 1,600 benefit consultants, why Vinay cites a claim from Lemonade's CEO that AI agents scored higher on customer empathy than human call center staff, the risk of companies "renting back" their own intelligence after gutting their workforce, and the thinking behind their upcoming book, Workforce Intelligence, releasing August 25th.

Key Topics Covered

Why treating AI adoption like rolling out a new CRM guarantees failure

The failed early bet on automating RFPs, and why augmenting human thinking won instead

The stat that proves AI adoption is personal: a manager's own AI use doubles their team's usage

Building an AI "disruption calculator" overnight, and the 1,800-job number it produced

OneDigital's three-part AI framework: coworkers, builders, and agents

How OneDigital literally hires its AI: job descriptions, interns, apprenticeships, and performance improvement plans

Meet Ben, the AI coworker fielding daily conversations with 1,600 benefits consultants

Why they stay LLM-agnostic and separate the intelligence layer from the model and the harness

The real risk behind AI cost metering: losing access to the intelligence your company now depends on