Account Executive, HR Advisory (HHS Focus) - Chicago, IL

The Wilkinson Firm (TWF) is an enterprise workforce strategy and solutions company with two divisions: HR Advisory (behavioral health and HHS focus) and Hospitality Staffing. Headquartered in NC and Atlanta, Georgia, respectively. Three active staffing contracts today; the next 24 months are about building and expanding a real book across the HR Advisory practice serving behavioral health and HHS clients. ## What's already built Three active staffing contracts in delivery. Two division sites live (hr.thewilkinsonfirm.com, hospitality.thewilkinsonfirm.com). MBE-certified, SAM.gov-registered, Hartford-insured. TWF Team Portal in production. 16+ trademarked frameworks: The Workup (8-dimension workforce diagnostic), PlacementCare (18-month placement guarantee, monitored by the Workforce Emotional Index), the SCAN. BUILD. STAY. operating system, the Earned Equity Ladder, and our six TWF Signature Programs. The bench: former EEOC Administrative Law Judge, employment attorneys (JD, MBA), clinical advisors (LCMHCS, LCMHC, former UnitedHealth Group), PHR-certified Managing Partner, 32-year enterprise operations specialist. 47 combined years HHS experience. 150+ HHS organizations served across 12 states. You're betting on revenue acceleration. The foundation is built. ## About this role The HR Advisory division has product-market fit, a founding-cohort partnership pipeline already warm, and proof-points that close in the room. The dedicated closer hasn't been hired. You're it. You'll convert warm founding-cohort relationships into recurring HR retainers, lead with The Workup as the wedge, and anchor the practice that fuels the firm's $1.2M Y1 ARR target. TWF is mission-led and builder-grade. This is a ground-floor seat. You're joining a company being built, not one already running. Base pay is contribution-based, not entitlement-based, and grows as the company grows. The real long-term play is equity ownership in something you helped create from the ground up. If you want a paycheck without a stake in the outcome, you'll be miserable here. If you want to own what you build, you'll thrive. ## The pay and partner upside - Base: $1,500/month during first 90 days, scales with performance - Commission: 15% of first-year contract value, 10% Y2+ on same account - Bonus stack: $5,000 per signed PlacementCare engagement, $1,000 per completed Workup - Y1 OTE at target performance: $65,000 to $150,000 - Equity: Earned Equity Ladder Tier 2 (1-3%) at month 6 if 5-gate evaluation met. Tier 3 (3-8%) at month 18 with sustained performance + strategic ownership. Tier 4 (8-15%, true partner level) at month 36 for the right person. 4-year vest, 1-year cliff. - The math: 6-10 signed engagements in Y1 at $40,000-$80,000 average annualized retainer + Workup conversion volume puts you in Tier 2 equity range by month 6 and on path to Tier 3 by month 18 ## What this is and isn't **This is:** advisory-grade closing, founder-led ramp, ground-floor seat with real partner path, sitting with clinical CEOs as a peer. **This isn't:** closing against an inherited book (the warm pipeline is yours to convert, the rest is yours to build), transactional services sales, a hand-holding environment. ## What you'll do - Run Discovery Calls with Executive Directors, Practice Owners, Clinical Directors, CHROs, and CFOs at behavioral health and HHS organizations - Lead with The Workup as the wedge offer - Build PlacementCare proposals with the 18-month placement guarantee structure - Convert warm founding-cohort partnership relationships into Year-2 paying engagements - Expand accounts into multi-site, multi-state, and additional service modules - Forecast pipeline weekly in HubSpot ## What success looks like - Day 30: pipeline of 6-10 qualified Discovery Calls, 2-4 completed Workups - Day 60: first signed HR Advisory engagement - Day 90: 2-4 signed contracts, 60% Workup-to-engagement conversion sustained - Day 180: Tier 2 equity grant landed - Day 365: $400,000 to $800,000 annu…