Chief Revenue Officer (Equity-Based Cofounder)

The Wilkinson Firm; Chicago (IL); On-site; USD 100,000 - 250,000; Full time

Job summary

The Wilkinson Firm is seeking a Chief Revenue Officer (CRO) to lead the revenue efforts across their HR Advisory, Premium Hospitality Staffing, and GovCon divisions. This partnership position involves owning revenue operations, orchestrating sales teams, and managing division performance.

Ideal candidates will have over 15 years in revenue leadership within services firms with a track record of significant growth. This is a unique opportunity in a dynamic startup environment with profit distributions and clear membership progressions.

Qualifications

• 15+ years in revenue leadership at services firms.
• Experience taking a firm from $1M to $5M+ revenue.
• Comfortable representing at C-suite level.

Responsibilities

• Own revenue generation across three divisions.
• Manage SDR and AE teams.
• Develop and manage sales pipelines.

Skills

Revenue leadership experience

Track record in services firms

Networking in HHS and hospitality

Cross-division orchestration

Tools

HubSpot

Job description

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. Two divisions today: HR Advisory for the mental health industry and Premium Hospitality Staffing. A GovCon 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.

Partnership structure (LLC member with profit distributions)

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. Bonus stack: $25,000 at first $1M ARR milestone, $50,000 at $2.5M ARR, $100,000 at $5M ARR.

Guaranteed monthly distributions are the honest read on cash. We’re a startup. Day 1‑90 is $0 while you ramp on revenue attribution + membership vesting. Months 3‑4, $3,000‑$5,000/month activates once first division‑wide revenue uplift is measurable. Months 6‑12, $5,000‑$10,000/month at $750K+ firm‑wide attributable revenue. Year 1 OTE at target performance: $100,000‑$250,000 cash + membership vesting.

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.

About this role

You own revenue across all three lines: HR Advisory (mental health industry), Premium Hospitality Staffing, and the emerging GovCon 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 GovCon
• 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: HubSpot 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 HubSpot, 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
• HubSpot Sales Hub admin‑level fluency
• Published thought leadership on services revenue strategy

Partnership due diligence (the selection process)

• Initial founder conversation (45 minutes)
• Strategic exercise: outline the 90‑day revenue acceleration plan across all three divisions
• Reference checks with 3+ professional references
• Work history verification
• Background check
• Credit verification (standard for partner‑level membership)
• Membership terms negotiation + LLC operating agreement review

4‑6 weeks first conversation to signed membership agreement.