Account Executive, HR Advisory (HHS Focus) - Chicago, IL at The Wilkinson Firm in Chicago, Illinois, United States

Job description

• 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.
• 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.
• 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.

Responsibilities

• 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
• 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 annualized ARR contribution traceable, Tier 3 equity progression on the table

Requirements

• 5-10 years in B2B services sales (HR consulting, healthcare consulting, or PEO sales preferred)
• Familiar with behavioral health, IDD, or HHS sector, or willing to learn the vertical fast
• Sells to clinical executives as a peer, not a vendor
• Comfortable being employee-level-1 on a function
• Self-directed
• Eastern Time work hours
• Located in a market with HHS density (Southeast preferred)
• Prior role at a behavioral health provider, IDD organization, or HHS-focused consultancy
• Existing relationships with NABH, ABHW, or state-level behavioral health associations
• SHRM credential
• HubSpot fluency

Skills

Required

• B2B services sales
• HR consulting
• healthcare consulting
• PEO sales
• selling to clinical executives
• self-directed
• HubSpot (forecasting pipeline)

Preferred

• SHRM credential
• HubSpot fluency

Benefits

• 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