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

The Wilkinson Firm Opportunity

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.

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

Who you are:

• 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)

Bonus points:

• 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

What we believe:

Trust before revenue. Mission before money. We treat every clinical executive like a peer, not a target. We build durable relationships, not flashy logos. We pay people in real upside, not in pizza parties.

Application Tips:

1. Visit hr.thewilkinsonfirm.com. Five minutes. Understand the practice you'd be building with.
2. Find The Wilkinson Firm on LinkedIn. Look around at our social media presence.
3. In your cover note, tell us one thing: which founding-cohort relationship type would you target first as your Year-2 conversion priority, and why?

What to expect from us:

• Reply within 48 hours of application
• First-round screen within 7 days
• Full process: 3 weeks
• We tell you yes or no. We do not ghost.