Location: Remote, Chicago-preferred | Type: Full-Time | Compensation: $80k - $100k base, $120k - $150k OTE, + equity
About Grapefruit Health
Grapefruit Health is a healthcare tech-enabled services company that is addressing the massive staffing shortage in healthcare. We do this by training and managing clinical students to perform remote, telephonic interactions with patients using our web application. By doing this, we can close gaps in care at half the cost and twice the speed. Patients get the care they need, healthcare organizations can do much more, and you get to learn while you earn. It is a win-win-win!
Role Overview
We are looking for a driven, entrepreneurial Business Development Lead to own and accelerate our growth engine. This is a high-impact, high-visibility role reporting directly to the CEO. You will own the full top-of-funnel — generating pipeline, running outbound campaigns, deploying automations, managing our CRM, and representing Grapefruit Health at industry conferences. Our CEO will remain the primary closer, and you will work in close partnership to take deals far down the field before handing off.
This is the right role if you thrive in an autonomous environment, have deep healthcare industry knowledge, and want to be a key architect of a company's growth story — not a cog in a large sales machine. The expectation is that you grow with us: year one you build the engine, year two you run it and own revenue, and as we scale, you build the team around you.
Your First 90 Days
This role is several jobs in one — outbound, RevOps, and early-stage discovery. We want to be honest about that. Here's how we think about the priority order out of the gate:
Days 1–30: Learn + Audit
Understand our ICP deeply
Audit and clean the CRM
Shadow the CEO on active deals
Map our current outbound gaps
Days 31–60: Launch Outbound
First sequences live
LinkedIn outreach running
First qualified meetings booked
CRM pipeline stages defined
Days 61–90: Build the Engine
Consistent weekly meeting volume
Conference strategy for next event
Reporting dashboard live for CEO
Playbook documented
Where You're Headed
We built this role with a clear growth track in mind, not just a job description:
Year 1 — Build the pipeline engine. Own top-of-funnel and mid-funnel. Hit activity KPIs. Get the CRM humming. Represent us at 4–6 conferences. Success is measured in meetings booked, opportunities created, and pipeline built — not closed revenue.
Year 2 — Own closed revenue from deals you sourced. Begin closing smaller deals independently. Take on more of the sales cycle from the CEO. Compensation grows with results.
Year 3+ — Build and lead a BD team. Path to Director or VP of Sales for the right person. This is the goal — we want to promote from within.
What You'll Do — And Much More
Lead Generation & Outbound
Own and execute outbound campaigns from strategy to send — copy, sequencing, A/B testing, and optimization
Build and work targeted prospect lists using LinkedIn Sales Navigator, conference attendee lists, other internal tools, and industry databases
Identify, research, and prioritize net-new accounts within our ICP — payers, providers, vendors, and value-based care organizations
Qualify inbound leads and convert them into sales opportunities
Guess, test, iterate! Try a ton of tools, use AI, experiment on what is out there and find ways to hack for efficiency and effect!
CRM & Revenue Operations
Own Grapefruit Health's CRM (we use Attio) — data hygiene, pipeline visibility, stage definitions, and reporting. It currently needs lots of love!
Build and maintain dashboards that give leadership real-time visibility into pipeline health and activity metrics
Create and document outbound processes, playbooks, and templates that can scale as we grow
Track and report on KPIs weekly: meetings booked, opportunities created, pipeline value, and activity volume
Conference & Event Coverage
Represent Grapefruit Health at healthcare industry conferences — HLTH, ViVE, AHIP, Becker's, and others
Plan conference strategy in advance: pre-book meetings, identify targets in attendance, and follow up with pipeline discipline within 48 hours
Build relationships at events that translate into pipeline, not just business cards
Sales Execution
Run initial discovery calls and advance deals through the first 2–3 stages of the sales cycle independently
Build compelling business cases and tailor outreach to specific buyer personas: VP/SVP Quality, CMO, Chief Medical Officer, VP Operations
Partner closely with the CEO as the primary closer — prepare briefings, join calls as needed, and ensure seamless handoffs
Manage 6–18 month sales cycles with persistence, creativity, and organized follow-through
What We Are Looking For
Required
Deep healthcare industry knowledge with 3+ years selling into payers, health systems, ACOs, or value-based care organizations
Demonstrated success booking meetings and generating pipeline through outbound — cold email, LinkedIn, and phone
Experience managing a CRM (HubSpot, Salesforce, Attio, or similar) with strong data hygiene habits
Ability to sell complex solutions with deal sizes ranging from $100K to $1M annually
Comfortable operating independently with a high degree of ownership and accountability
Exceptional written communication — you write messages that actually get responses
Willing and able to travel to 4–8 conferences per year
Strongly Preferred
Experience with LinkedIn Sales Navigator and outbound sequencing tools (Outreach, Apollo, Salesloft, or similar)
Familiarity with HEDIS, Stars ratings, value-based contracts, or care gap closure
Background selling to VP and C-suite stakeholders in regulated industries
Prior experience at a healthcare startup or growth-stage company
Track record of sourcing and progressing deals, not just managing inbound or expanding existing accounts
Compensation & Benefits
Base Salary $80,000 – $100,000 depending on experience
On-Target Earnings $120,000 – $150,000 total OTE — Year 1 OTE is achievable through activity alone, without closed revenue
Activity Bonus $$$ per qualified opportunity created — this is the variable comp you fully control in Year 1
Revenue Commission 2% of closed revenue on deals sourced and progressed by you (Year 2+ primary upside)
Equity Details discussed during process
Benefits Health, dental, vision, 401k — details provided during interviews
Travel Conference travel expenses fully covered
How We'll Measure Success
Year 1 — Activity & Pipeline
Qualified opportunities created per month
Meetings booked with VP+ decision makers
Outbound sequences launched and response rates
CRM data completeness and pipeline accuracy
Conference meeting-to-opportunity conversion
Year 2+ — Revenue
Pipeline sourced and progressed to CEO for closing
Closed revenue from deals you originated
Average deal size and sales cycle length
Net-new logos vs. expansion
Who Thrives in This Role
Green Flags ✅
You've built pipeline from scratch before
Comfortable being patient through 12–18 month cycles
You like owning the process end-to-end
Can name the HEDIS measures your last buyer cared about
You write outbound emails that actually get replies
You want a path to building and leading a team
Red Flags 🚩
All your wins came from inbound or renewals
You need a large team around you to operate
You want to close deals yourself immediately
You've only sold to provider groups, not payers or ACOs
CRM admin feels beneath you
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