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Chief Revenue Officer; Equity- CoFounder

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: The Wilkinson Firm
Full Time position
Listed on 2026-06-03
Job specializations:
  • Business
    Business Management, Business Analyst, Corporate Strategy
  • Management
    Business Management, Business Analyst, Corporate Strategy
Salary/Wage Range or Industry Benchmark: 425000 USD Yearly USD 425000.00 YEAR
Job Description & How to Apply Below
Position: Chief Revenue Officer (Equity-Based CoFounder)

Overview

What s the next ten years of your career worth in real ownership?

The Wilkinson Firm (TWF) is an enterprise workforce strategy and staffing firm with two divisions: HR Advisory for the mental health industry and Premium Hospitality Staffing. A Gov Con vertical is emerging across both. Headquartered in NC and Atlanta. We launched in April 2025 and we are now in Year 2 of operations. Three active staffing contracts in delivery. FY26 trajectory $425-525K.

Zero loans, zero institutional debt. A healthy valuation already on the table. Defined path to $5M+ over the next 24 months. This is a true ground-floor seat for the right CRO who wants to win together and build something great with us.

This is a partnership role, not an employment role. You join as an LLC member with a defined membership interest. Cross-division CRO membership lives either at the holding-co level or pro-rata across division LLCs, negotiable based on revenue allocation. The membership interest tiers are the headline. Tier 3 (3-8%) grants at hire if you clear a 6-month trial against the 5-gate evaluation.

Tier 4 (8-15%, true partner level) progresses at month 18-24 with sustained firm-wide revenue performance. Vesting runs four years with a one-year cliff. Zero institutional debt means no forced dilution from future investor rounds, so your membership stays your membership. Profit distributions flow quarterly, proportional to membership. Direct attribution adds 3-5% override on total firm revenue and 5-10% on revenue you directly sourced.

Role

and responsibilities

You own revenue across all three lines: HR Advisory (mental health industry), Premium Hospitality Staffing, and the emerging Gov Con vertical. You orchestrate the SDR + AE teams in both divisions, manage the VP of Sales (Hospitality) and VP of Business Development (cross-division), partner with division Founding Team leads on go-to-market strategy, and own the firm-wide pipeline + forecast.

What you own
  • Firm-wide revenue motion across HR Advisory, Hospitality Staffing, and Gov Con
  • SDR + AE team orchestration across both divisions
  • Management of VP of Sales (Hospitality) and VP of BD (cross-division)
  • Pipeline architecture and forecast across all three lines
  • Marketing-to-sales handoff orchestration
  • Revenue operations:
    Hub Spot architecture, reporting, attribution
  • Cross-division enterprise account strategy (clients buying from multiple divisions)
What success looks like
  • Day 90:
    Unified pipeline view across all three divisions in Hub Spot, revenue forecast operational
  • Day 180: $750K firm-wide revenue trajectory established, Tier 3 membership grant landed
  • Day 365: $1.5M-$2.5M firm-wide annualized revenue achieved, all three divisions producing
  • Month 18-24: $3M-$5M firm-wide annualized, Tier 4 progression on the table
Who you are
  • 15+ years in revenue leadership at services firms, ideally across multiple divisions or business lines
  • Track record of taking a services firm from $1M to $5M+ in 24-36 months
  • Senior network across HHS, hospitality, or both verticals
  • Familiar with cross-division revenue orchestration and shared-services account strategy
  • You've made enough money to take a member-grade swing, or you're early enough to bet on yourself
  • Comfortable representing the firm at C-suite level
Bonus points
  • Former CRO or VP Revenue at a multi-division services firm
  • Existing senior relationships in hospitality or HHS
  • Hub Spot Sales Hub admin-level fluency
  • Published thought leadership on services revenue strategy
Additional notes

Tax structure is K-1, not W-2. Self-employment tax applies. Talk to your CPA before signing. The founder takes no guaranteed monthly distributions today either. We share the upside as members.

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