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