Sales Development Representative (Hospitality Staffing) - Charleston, SC

The Wilkinson Firm (TWF) is an enterprise workforce strategy and solutions company with two divisions: Hospitality Staffing and HR Advisory (behavioral health and HHS focus). Headquartered in Atlanta, Georgia and NC, respectively. Three active staffing contracts today; the next 24 months are about building and expanding a real book across the Hospitality Staffing industry.
About this role
TWF's Hospitality Staffing division is in 0-to-1 mode. You're not running a machine someone else built. You're the first SDR. You'll build the outbound motion with the founder, and if you're the right person, you become a partner in this division long-term.
The partner upside

TWF Earned Equity Ladder: Tier 2 (1-3% equity) eligible at month 6 against the 5-gate evaluation

Tier 3 (3-8% equity) progression by month 18 if you continue performing and take on strategic ownership

Tier 4 (8-15% equity, true partner level) by month 36 for the right person

Recurring revenue share: 1-5% of net profit on staffing revenue from accounts you sourced, paid quarterly, residual for the life of the account

The math: build a book of 20-30 hotel accounts at $50,000 average annualized recurring, your residual stream alone compounds into a meaningful annual income within 24 months independent of base + commission

The pay

Base: $0 first 90 days. Modest base ($1,500 to $2,500/month) introduced at month 4 once you've signed your first 2-3 accounts and cash flow supports it

Commission: 10% of first-year contract value on every signed account you sourced

Recurring revenue share: 1-5% of net profit on recurring staffing revenue from accounts you sourced

Bonus stack: $250 per qualified Discovery Call that converts to a proposal, $1,000 per signed account

Realistic Y1 total comp at target performance: $35,000 to $85,000 plus residual stream that compounds

Equity: see "The partner upside" above

What this is and isn't
This is:

Employee-level-1 on the outbound side of a relationship-led services firm

Founder-led with hands-on weekly support during ramp

Equity-bearing with a real path to partner-level ownership

Relationship and book-of-business work. We close because we earn trust, not because we have a slick demo

This isn't:

A mature SDR org with a playbook, dashboards, and an SDR manager above you. You'll help build them

A volume-spam motion. Every email goes out personally signed

A hand-holding environment. People who need a defined system to operate inside will struggle here

What you'll do

Build the outbound playbook for hospitality property accounts

Run 40-60 personally-signed cold emails per business day into hotel GMs, Directors of F&B, Banquet Directors, and Catering Directors

Send 30-50 LinkedIn Sales Navigator connection requests per week

Place 10-20 warm-then-cold dials per day to people who opened or accepted

Qualify replies, book Discovery Calls on the founder's calendar, log everything in HubSpot

Iterate copy weekly. Document what works so the next SDR has a playbook

Why this role exists
TWF's Hospitality Staffing division has the founder, operational leadership, and three signed contracts in delivery. There is no dedicated outbound motion yet. You're it. If we get the outbound machine right with you, this division becomes the engine of TWF's first $5M in revenue. That's the prize.
What success looks like

Day 30: outbound stack stood up, first 100 personally-signed emails sent, first 5 Discovery Calls booked

Day 60: 12-20 Discovery Calls booked per month becoming routine

Day 90: 8% positive reply rate sustained, first 2-3 accounts signed

Day 180: Tier 2 equity grant landed if performance sustained, residual revenue stream starting to compound

Day 365: SDR playbook documented, next SDR onboarded against your foundation, Tier 3 equity progression on the table

Who you are

6 months to 3 years in B2B outbound sales (services or hospitality staffing preferred)

You've worked in a startup or early-stage environment before, or you know that's the environment you want

Comfortable being employee-level-1 on a function. You build the system, not inherit it

You log every touch in CRM. If it's not logged, it didn't happen

Self-directed. The founder will not check your activity hourly

Eastern Time work hours

Bonus points

Prior experience selling into hotel F&B, banquet, or catering verticals

Existing relationships with regional chambers, NCRLA, GHLA, AAHOA

Experience building an outbound motion from scratch at a prior startup

HubSpot, Apollo, or Sales Navigator fluency

HOW WE WORK:

- Remote, Eastern Time

- Async-friendly inside core hours (9am-1pm ET overlap minimum)
- Weekly 1:1 with founder during ramp
- Tech stack ready on Day 1: HubSpot, Apollo, LinkedIn Sales Navigator, Slack
- You'll partner with the Director of Hospitality Operations on trial conversion follow-through

What we believe
Trust before revenue. Mission before money. Long game. We don't cold-spam. Every email goes out personally signed. We build durable relationships, not flashy logos. We pay people in real upside, not in pizza parties.
Application Tips
1. Visit . Five minutes. Understand the company 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: what's the first bet you'd make in your first 30 days here, and why?
What to expect from us
- Reply within 48 hours of application
- First-round screen within 7 days
- Full process: 2-3 weeks
- We tell you yes or no. We do not ghost.
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