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VP of Sales, Equity Partner Track - Premium Hospitality Staffing

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: The Wilkinson Firm
Full Time position
Listed on 2026-08-05
Job specializations:
  • Sales
    Business Development
Salary/Wage Range or Industry Benchmark: 425000 USD Yearly USD 425000.00 YEAR
Job Description & How to Apply Below

Join Us at The Wilkinson Firm

Year 2 since launch. Three signed properties. Healthy valuation already on the table. Ground-floor seat to take the hospitality sales engine from $425K to $5M and win together.

The Wilkinson Firm (TWF) is a workforce strategy and staffing firm. Two divisions:
Premium Hospitality Staffing and HR Advisory for the mental health industry. Headquartered in Atlanta and NC. We launched in April 2025 and we are now in Year 2 of operations. Three active hospitality contracts in delivery (Hilton, Convention Center, Holiday Inn). FY26 trajectory $425-525K. Zero loans, zero institutional debt. A healthy valuation already established. Defined path to $5M+ over the next 24 months.

This is a true ground-floor seat for the right partner who wants to win together and build something great with us.

Partnership Structure
  • Membership interest:
    Tier 2 (1-3%) at month 6 if 5-gate evaluation met. Tier 3 (3-8%) at month 18. Tier 4 (8-15%) at month 36 for the right operator.
  • Vesting: 4-year vest, 1-year cliff.
  • LLC split:
    Membership converts to Hospitality Staffing LLC membership if divisions split (planned).
  • Profit distributions:
    Quarterly proportional to membership. Direct attribution: 8% on every signed property account, Y1-3. Recurring revenue share: 1-5% of net profit on staffing fees from accounts you closed.
  • Bonus stack: $5,000 per enterprise hotel chain agreement signed.
  • Guaranteed monthly distributions: $0 Day 1-90. $2-4K/mo Month 3-4. $4-6K/mo Month 6-12 at $300K+ attributable revenue.
  • Y1 OTE at target: $80,000-$180,000 cash + membership vesting + recurring residual.
  • Tax: K-1, not W-2. Self-employment tax applies.
  • Founder's deal:
    Founder takes no guaranteed monthly distributions today either.
This Role

You own the entire sales motion for the Hospitality Staffing division. AE team leadership (Hospitality SDR + AE roles already live), enterprise account strategy (hotel chains: Marriott regional offices, Hilton enterprise, IHG cluster deals), pipeline architecture, sales ops, and the trajectory from three signed properties to fifty.

What's Already Built
  • The hospitality operating system: 35+ documented processes, Five-Lane Command Structure, Traffic Light Exception System, Event Mode Selector, Captain School Pipeline, Gold Shield Certified standards, the TWF Make-It-Right Guarantee
  • Three signed property contracts in delivery as proof of execution
  • hos live
  • MBE-certified, SAM.gov-registered, Hartford-insured, ASA + NAPEO member, TWF Team Portal in production
  • Bench: former EEOC Administrative Law Judge, employment attorneys, Chief Legal & Senior Counsel (hospitality contracts), Director of Operations enforcing standards. 32-year enterprise operations specialist
What You Own
  • The Hospitality Staffing sales motion: SDR + AE team management, pipeline strategy
  • Enterprise account strategy: hotel chains, multi-property contracts, regional clusters
  • Pipeline forecast and sales operations
  • Industry presence: NCRLA, GRA, GHLA, AAHOA chapter relationships and event presence
  • Sales team hiring and management as the division grows
  • Coordination with the Founding Partner of Hospitality Operations on delivery + trial conversion
What Success Looks Like
  • Day 60: SDR + AE motion fully operational, pipeline of 30+ qualified properties in active conversation
  • Day 90: 3-5 new property contracts signed, first enterprise chain conversation advanced
  • Day 180: 10-15 new properties signed cumulatively, Tier 2 membership grant landed
  • Day 365: $1.5M-$2.5M annualized revenue contribution, first enterprise chain deal signed, Tier 3 progression on the table
Who You Are
  • 10-15 years in hospitality staffing sales, hotel BD, or hospitality services sales
  • Track record managing AEs and growing a sales motion from $1M to $5M+ in services revenue
  • Senior network of hotel GMs, Directors of F&B, Catering Directors, regional VPs across the Southeast
  • Familiar with enterprise hotel chain procurement (Marriott, Hilton, IHG, Hyatt regional offices)
  • You've sold hospitality long enough to know the difference between body-shop staffing and trained-team staffing
  • You've made enough money to take a member-grade swing, or you're early enough to bet on yourself
  • Comfortable with up to 25% regional travel
Bonus Points
  • Former VP or Director of Sales at a hospitality staffing firm doing $5M+ revenue
  • Existing relationships with regional VPs at Marriott, Hilton, IHG, Hyatt
  • Active leadership in NCRLA, GRA, GHLA, AAHOA
  • Hub Spot Sales Hub fluency at admin-level
Selection Process
  • Founder conversation (45 min)
  • Strategic exercise: outline the first enterprise hotel chain you'd target and your close strategy
  • Reference checks + work history + background + credit verification (standard for partner-level membership)
  • Membership terms negotiation + LLC operating agreement review
  • What We Believe

    Trust before revenue. Premium under pressure. Ground-floor seat. Real ownership. People deserve to be developed, not discarded. We close because we earn trust, not because we have a slick deck. We win together. We pay people in real…

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