Brian Kwa

Enterprise SDR

Healthcare AI Startup (YC-backed)

SDROutbound HeavyEnterpriseOn-site📍 San Francisco or New York
Deal Size: $100K-500K+ ACV
Sales Cycle: 6-18 months
Posted by Brian Kwa

Overview

You're prospecting into healthcare organizations to book qualified demos for Account Executives selling an AI product. Your targets are likely VPs of Operations, Clinical Directors, CTOs, or Innovation teams at hospitals, health systems, insurance companies, or life sciences firms. You'll spend most of your day making cold calls, sending emails, and doing LinkedIn outreach.


Role Snapshot

AspectDetails
Role TypeEnterprise SDR (outbound-focused)
Sales MotionOutbound-heavy (healthcare is conservative, minimal inbound)
Deal ComplexityEnterprise (navigating healthcare bureaucracy)
Sales Cycle6-18 months (healthcare moves slowly)
Deal SizeLikely $100K-500K+ ACV (enterprise healthcare contracts)
Quota (est.)10-15 qualified meetings/month

Company Context

Stage: Likely Series A or B (YC-backed, 192 employees, hiring enterprise SDRs)

Size: 192 employees

Growth: Active hiring for multiple SDR roles across two major markets suggests they're scaling GTM

Market Position: Healthcare AI is crowded - competing against established players like Olive AI (now defunct), other AI startups, and internal IT teams at large health systems


GTM Reality

Pipeline Sources:

  • 80-90% Outbound - cold calling, email sequences, LinkedIn (healthcare doesn't generate much inbound)
  • 10-20% Inbound - likely conference leads, content downloads, maybe some product-led signups if they have a demo/trial
  • Referrals/Partners - possible but not primary at this stage

SDR/AE Structure: Dedicated SDR team feeding AEs (that's why they're hiring multiple SDRs)

SE Support: Likely have technical pre-sales support given AI product complexity and healthcare technical requirements


Competitive Landscape

Main Competitors: Depends on their specific AI use case - could be Epic's internal AI tools, other healthcare AI vendors, consulting firms, or "build it ourselves" internal teams

How They Differentiate: Likely claiming better AI models, faster implementation, or specific clinical/operational outcomes

Common Objections: "We already have Epic," "Our IT team is building this," "We need to see clinical validation," "Regulatory concerns," "Budget already allocated," "Call me next fiscal year"

Win Themes: Probably ROI case studies, clinical outcome data, ease of integration, or unique AI capability their competitors don't have


What You'll Actually Do

Time Breakdown

Prospecting/Research (50%) | Outreach Execution (35%) | Internal Meetings (15%)

Key Activities

  • Cold calling: 60-80 calls per day to directors, VPs, and C-suite at health systems. Most go to voicemail. When you get someone live, you have 30 seconds to explain why AI matters before they hang up or say "send me something."
  • Email sequences: Writing and sending personalized emails referencing specific hospital initiatives, recent news, or pain points. Open rates are low because healthcare inboxes are flooded. You're testing subject lines constantly.
  • LinkedIn outreach: Connecting with prospects, engaging with their content, sending InMails. Healthcare folks are less active on LinkedIn than tech buyers, so response rates are lower.
  • Research: Looking up hospital systems, recent news about staffing shortages or operational challenges, finding the right person (not always clear who owns AI purchasing), prepping talk tracks around their specific problems.
  • Meeting handoffs: When you finally book a demo, you qualify the opportunity (budget, timeline, authority, need), brief the AE, and join the first call to make the intro.
  • Internal syncs: Daily standups, weekly pipeline reviews, training on new healthcare messaging, roleplays on handling objections about HIPAA/compliance.

The Honest Reality

What's Hard

  • Healthcare buyers are extremely risk-averse and move slowly. You'll hear "we're interested but need to table this until Q3" constantly. Deals that seem hot go dark for months.
  • Getting past gatekeepers is brutal. Hospital phone systems are mazes. You'll get bounced around departments trying to find who owns AI/innovation initiatives.
  • "Enterprise" means navigating procurement, legal, compliance, IT security, clinical validation teams. Even if someone wants your product, there are 6 other stakeholders who need to approve it.
  • Your meeting quota might be 10-15/month but converting cold calls to booked meetings in healthcare is a grind. Expect 0.5-1% connect-to-meeting rates.
  • Being on-site in SF or NYC means commuting and less flexibility, though you'll have face-time with leadership and AEs.
  • Healthcare has specific jargon (EHR, HL7, FHIR, value-based care, etc.) - you need to learn it fast or you'll sound like an outsider.

What Success Looks Like

  • Hitting 10-15 qualified meetings per month consistently (qualified = budget, authority, need, timeline)
  • 30-40% of your meetings convert to opportunities that AEs work (the rest are tire-kickers or too early)
  • Building a pipeline of warm prospects who aren't ready now but will be in 6-12 months
  • Learning healthcare deeply enough that you can have credible conversations with clinical or ops leaders

Who You're Selling To

Primary Buyers:

  • VP/Director of Clinical Operations, Innovation, or Quality
  • CTO, CIO, CMIO (Chief Medical Information Officer) at health systems
  • VP of Operations or Analytics at payers/insurance companies
  • Heads of Data Science or AI at pharma/life sciences (depending on product)

What They Care About:

  • Clinical outcomes and patient safety (can you prove this works without harming patients?)
  • ROI and cost savings (healthcare margins are thin, need clear financial case)
  • Regulatory compliance (HIPAA, FDA if applicable, state regulations)
  • Integration with existing EHR systems (Epic, Cerner, etc.)
  • Implementation time (they don't have resources for 18-month rollouts)
  • Vendor stability (are you going to be around in 3 years?)

Requirements

  • 1+ years of SDR experience (they want someone who already knows cold calling and email sequencing)
  • Must be in SF or NYC and willing to work on-site (no remote flexibility)
  • Comfortable with enterprise sales cycles (need patience for 6-18 month cycles)
  • Ability to learn healthcare industry terminology and buyer personas quickly
  • Resilience for high rejection rates and slow-moving prospects
  • Strong written communication (emails need to be crisp and relevant to healthcare pain points)