Hospitality Sales Leader — Ground-Floor to $5M Growth

The Wilkinson Firm; Chicago (IL); On-site; USD 80,000 - 180,000; Full time

Benefits offered by this job

Bonus per signed property

Quarterly profit distributions

Guaranteed monthly distributions based on milestones

Job summary

The Wilkinson Firm is seeking an experienced leader for the Hospitality Staffing division, responsible for the entire sales motion including SDR and AE team management.

You will develop enterprise account strategies, manage a pipeline of opportunities, and contribute to significant revenue growth. Ideal candidates have a robust background in hospitality staffing sales and relationships within major hotel chains like Hilton and Marriott.

This role offers the chance to be part of a dynamic firm with significant growth potential.

Qualifications

• 10-15 years in hospitality staffing sales or related field.
• Track record of growing services revenue from $1M to $5M+.
• Familiar with staffing standards and enterprise procurement.

Responsibilities

• Own the entire sales motion for the Hospitality Staffing division.
• Lead the AE team to secure contracts with major hotel chains.
• Manage pipeline strategy and forecast revenue contributions.

Skills

Hospitality staffing sales experience

Sales team management

Networking with hotel GMs

Pipeline strategy

Enterprise hotel chain knowledge

Job description

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 (LLC member with profit distributions)

• 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
• hospitality.thewilkinsonfirm.com 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
• HubSpot Sales Hub fluency at admin-level

Selection process

4 steps. We move at the pace of the right partner.

1. Founder conversation (45 min)
2. Strategic exercise: outline the first enterprise hotel chain you'd target and your close strategy
3. Reference checks + work history + background + credit verification (standard for partner-level membership)
4. 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 upside, not in pizza parties. We are building something great and we want partners who feel the same way.

Application Tips

1. Visit hospitality.thewilkinsonfirm.com. Five minutes.
2. Find The Wilkinson Firm on LinkedIn.
3. Cover note: (1) which hotel chain enterprise account would you target first and how, and (2) why you're ready to take a member-grade swing instead of a traditional VP Sales base.

What to expect from us

• Reply within 48 hours of application
• First-round founder conversation within 7 days of qualification
• Full process: 4-6 weeks
• We tell you yes or no. We do not ghost.