Head of Outplacement Services

Executive Career Upgrades | Remote → Nashville, TN (Early 2027) | Reports to CEOWhy This Role ExistsWe've placed over thousands of Directors, VPs, and Execs into roles they love. Two time Inc. 5000 honoree. 48th fastest Veteran owned organization in America. Featured in major business publications. Our candidate side engine is the strongest in the market and it's powered by AI we've built into every layer of our process.Now corporate America is asking us to bring that same firepower to the other side of the table.We're launching an Outplacement Services division to serve mid-market companies (500–5,000 employees) navigating restructurings, RIFs, and transitions. The category is dominated by tired incumbents LHH, RiseSmart, INTOO, Right Management running 1990s playbooks dressed up with light technology. We're going to take their lunch.We need someone to lead it.  This position will start as remote then relocate to our Nashville, TN location in early 2027.What You'll OwnYou'll build and run the entire Outplacement Services division as a P&L owner, sitting on the executive team and reporting directly to the CEO. This is not a "manage what's already here" role. There is no team yet, no playbook yet, no client list yet only a ferocious brand, real AI infrastructure, and a CEO who's all in on this becoming a major revenue line.You will:Set the go-to-market strategy: ICP definition, pricing architecture, packaging, deal structurePersonally close the first wave of enterprise deals (25-50% of your time in Year 1 is direct selling)Build the team underneath you BDRs, AEs, and Customer Success with hire #2 funded after the first $100K bookedArchitect the channel strategy across PE portfolio HR teams, Am Law 200 employment practices, benefits brokers (Marsh, Lockton, NFP, Gallagher), M&A advisors, and Vistage adjacent CEO networksOwn RFP capability, procurement navigation, and contract negotiationCross-sell into our existing database of thousands of already placed executives many of whom are now CHROs, CPOs, and VPs of HR at your target accountsRepresent ECU at SHRM, Talent Acquisition Week, Workhuman, HR Tech, and other industry eventsWho You Are5–15 years selling outplacement, talent management, or adjacent enterprise HR services. This is non-negotiable. You know how CHROs buy, what procurement asks for, and how to navigate a 6–9 month enterprise sales cycle.You've personally closed deals in the $100K–$1M+ range and led teams that closed multi-million-dollar booksYou've built or significantly scaled a division, region, or vertical from a near-clean startYou have a real network of CHROs, CPOs, VPs of HR, and HR partners at PE firms and benefits brokeragesYou're a builder, not a maintainer. You're frustrated by the pace at incumbents and want to build something betterCompensationBase salary: $175,000–$275,000Variable / commission: $100,000–$400,000+ at targetOTE: $375,000–$675,000+ Executive team seat with direct CEO accessFull benefits, relocation package, conference and T&E budget (SHRM, Workhuman, HR Tech, Talent Acquisition Week, Vistage events)Tech stack already in place: HubSpot, ZoomInfo, AI-powered research and intelligence layer, Avoma, full CRM and outreach infrastructureWhy NowThe outplacement category is being disrupted in real time. AI is reshaping how candidates job-search, how employers transition exiting employees, and what "good" looks like in a separation experience. The incumbents are too slow to adapt. We're not.If you've spent the last decade selling outplacement and watching your company drag its feet on technology, brand, and innovation this is the seat you've been waiting for.At Executive Career Upgrades you’ll join a high-performing team that genuinely cares and is building toward becoming one of the largest career services organizations in the country. We’re seeking a seasoned professional to help scale the business during a major growth phase. For the right person with the right skill set, this represents an exceptional career opportunity with significant long-term upside.