Sales Development Representative (HR Advisory) - Raleigh, NC

The Wilkinson Firm; United States; On-site; USD 45,000 - 115,000; Full time

Benefits offered by this job

Equity opportunity

Job summary

The Wilkinson Firm (TWF) is an enterprise workforce strategy and solutions company with two divisions serving behavioral health and HHS clients. You will build the outbound motion to reach $1.2M Y1 ARR and have a path to partnership.

This is a founder-led, equity-bearing role with remote work in the Eastern Time zone. Expect ramp with no base for the first 90 days, then a modest base and commissions on signed engagements, plus bonuses for qualified opportunities and metrics-based milestones.

Qualifications

• 6 months to 3 years in B2B outbound sales (HR consulting, healthcare services, or PEO sales preferred).
• Comfortable selling to mission-driven clinical executives who screen out vendor-feeling outreach.
• Familiar with behavioral health, IDD, or HHS sector, or willing to learn the vertical fast.
• You've worked in a startup or early-stage environment before, or you know that's the environment you want.
• 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.

Responsibilities

• Build the outbound playbook for behavioral health and HHS practice clients.
• Run 30-50 personally-signed cold emails per business day into Executive Directors, Practice Owners, Clinical Directors, CHROs, and CFOs.
• Send 25-40 LinkedIn Sales Navigator connection requests per week with one-line personalized opens.
• Place 8-15 warm-then-cold dials per day to people who opened or accepted.
• Lead with The Workup as the wedge offer in outreach.
• 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.

Skills

B2B outbound sales

CRM logging

HubSpot

Apollo

LinkedIn Sales Navigator

Tools

HubSpot

Apollo

LinkedIn Sales Navigator

Job description

The Wilkinson Firm (TWF) is an enterprise workforce strategy and solutions company with two divisions: HR Advisory (behavioral health and HHS focus) and Hospitality Staffing. Headquartered in NC and Atlanta, Georgia, respectively. The next 24 months are about building and expanding a real book across the HR Advisory practice serving behavioral health and HHS clients.

About this role

TWF's HR Advisory division has product-market fit and a founding-cohort partnership pipeline. The closing motion has been founder-led until now. You're the first SDR. You'll build the outbound motion that refills the pipeline at the cadence the division needs to hit $1.2M Y1 ARR. 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
• HR Advisory engagements are bigger-ticket than Hospitality Staffing. Your commission share compounds faster per signed deal
• The math: 8-15 signed engagements in Y1 at $40,000 to $80,000 average annualized retainer puts the division near its ARR target and puts you in Tier 2 equity range by month 6

The pay

• Base: $0 first 90 days. Modest base ($1,500 to $2,500/month) introduced at month 4 once you've sourced 2-3 signed engagements and cash flow supports it
• Commission: 10% of first-year contract value on every signed HR Advisory engagement you sourced
• Bonus stack: $250 per qualified Discovery Call that converts to a proposal, $2,500 per signed HR Advisory engagement, $1,000 per completed Workup
• Realistic Y1 total comp at target performance: $45,000 to $115,000
• 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, advisory-grade services practice
• Founder-led with hands-on weekly support during ramp
• Equity-bearing with a real path to partner-level ownership
• Built around relationships and trust. We close clinical executives by sitting in their world, not pitching at them

This isn't:

• A mature SDR org with a playbook, dashboards, and an SDR manager above you. You'll help build them
• A high-volume cold-spam motion. HHS executives screen out vendor-feeling outreach in two seconds
• 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 behavioral health and HHS practice clients
• Run 30-50 personally-signed cold emails per business day into Executive Directors, Practice Owners, Clinical Directors, CHROs, and CFOs
• Send 25-40 LinkedIn Sales Navigator connection requests per week with one-line personalized opens
• Place 8-15 warm-then-cold dials per day to people who opened or accepted
• Lead with The Workup as the wedge offer in your outreach
• 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 HR Advisory division has the founder closing, the Director of Community Partnerships sourcing warm relationships, and the partnership pipeline showing strong proof-points. There is no dedicated outbound motion to fill the rest of the funnel. You're it. Without you, the division can't hit its $1.2M Y1 ARR target. With you, it becomes the firm's flagship practice.

What success looks like

• Day 30: outbound stack stood up, first 100 personally-signed emails sent, first 3 Discovery Calls booked, first Workup in flight
• Day 60: 8-12 HR Advisory Discovery Calls booked per month becoming routine
• Day 90: 10% positive reply rate sustained, first 1-2 signed engagements or strong proposal pipeline
• Day 180: Tier 2 equity grant landed if performance sustained
• Day 365: SDR playbook documented, contribution to $1.2M Y1 ARR target traceable in HubSpot, Tier 3 equity progression on the table

Who you are

• 6 months to 3 years in B2B outbound sales (HR consulting, healthcare services, or PEO sales preferred)
• Comfortable selling to mission-driven clinical executives who screen out vendor-feeling outreach
• Familiar with behavioral health, IDD, or HHS sector, or willing to learn the vertical fast
• You've worked in a startup or early-stage environment before, or you know that's the environment you want
• 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 at a behavioral health provider, IDD organization, or HHS-focused consultancy
• Existing relationships with NABH, ABHW, or state-level behavioral health associations
• SHRM credential or HR sector fluency
• 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 Account Executive (HR Advisory) on warm hand-offs and with the Director of Community Partnerships for context on the founding-cohort

What we believe

Trust before revenue. Mission before money. Long game. We treat every clinical executive like a peer, not a target. We build durable relationships, not flashy logos. We pay people in real upside, not in pizza parties.