Mid Market Account Executive - Healthcare

Overview

You sell AI-powered automation software to mid-market healthcare organizations—hospitals, clinics, and specialty practices with 50-500 beds or multiple locations. The product automates patient communication, scheduling, and operational workflows. You're part of the team building out the healthcare vertical after the company proved the model in property management.

Role Snapshot

Company Context

Stage: Later-stage (537 employees, expanding into new verticals)

Size: 537 employees

Growth: Actively hiring across GTM, proven PMF in property management, now scaling healthcare vertical

Market Position: Category leader in property management AI, challenger in healthcare where established players exist

GTM Reality

Pipeline Sources:

• 30% Inbound - website demos, industry conference leads, referrals from property management customers who know healthcare operators
• 60% Outbound - you're calling COOs, Directors of Operations, Patient Experience leads at regional hospital systems and multi-location clinics
• 10% Partners - some healthcare tech consultants and EHR implementation partners

SDR/AE Structure: Likely shared SDR pool or self-sourcing—healthcare vertical is being built so you won't have dedicated SDR coverage initially

SE Support: Shared SE pool for technical demos and integration discussions with IT teams

Competitive Landscape

Main Competitors: Healthcare-specific patient engagement platforms, contact center solutions, legacy call center tech, incumbent vendors already integrated with EHR systems

How They Differentiate: AI that actually works vs. basic chatbots, proven automation ROI from property management use cases, modern interface vs. legacy healthcare software

Common Objections:

• "We already have patient communication tools through our EHR"
• "Healthcare is too regulated/complex for AI"
• "We need HIPAA compliance proof and security reviews"
• Integration concerns with existing Epic/Cerner systems

Win Themes: Staff shortage relief, patient satisfaction scores, operational efficiency gains, modern patient experience expectations

What You'll Actually Do

Time Breakdown

Prospecting (35%) | Active Deals (40%) | Internal (25%)

Key Activities

• Outbound Prospecting: You're building lists of regional health systems, urgent care chains, specialty practice groups (orthopedics, oncology, etc.). Cold calling Directors of Operations and Patient Experience VPs. Most don't pick up. You're targeting 20-30 connects per week to book 4-5 discovery calls.

• Discovery & Demo: Walking healthcare ops leaders through how AI handles appointment scheduling, patient intake, follow-up reminders, and basic triage questions. You're translating property management success stories to healthcare language. Demos require SE support for integration questions.

• Multi-Stakeholder Coordination: Healthcare deals involve Operations, IT/Security (for HIPAA compliance), Finance (for ROI justification), and sometimes clinical leadership. You're scheduling separate calls with each group, then trying to get them all in the same room for a decision.

• Proof of Concept Management: Larger deals require 30-60 day pilots. You're coordinating implementation timelines, setting success metrics, checking in weekly on progress, and troubleshooting issues with the product team. Many POCs extend because healthcare moves slowly.

The Honest Reality

What's Hard

• Healthcare buying is slow: Even mid-market deals involve legal reviews, security assessments, and committee approvals. Deals that should close in Q2 slip to Q4 regularly. You'll spend a lot of time waiting on procurement.

• You're explaining AI to skeptics: Many healthcare operators have been burned by "AI" that was just basic automation. You're constantly proving the tech actually works and isn't just buzzwords. Clinical staff can be particularly skeptical.

• Integration complexity: Every hospital uses different EHR systems (Epic, Cerner, Meditech). IT teams want detailed integration specs. You're leaning heavily on SEs and implementation teams, but you need to understand enough to navigate these conversations.

• New vertical means less proof: You don't have 50 healthcare case studies yet. You're adapting property management ROI stories and relying on early healthcare customer references. Some prospects want to wait and see.

What Success Looks Like

• Closing 8-12 new logos per year at $50K-250K ACV
• Maintaining 3-4x pipeline coverage (if you have $700K quota, you need $2M+ in realistic pipeline)
• Getting 2-3 deals into POC stage per quarter
• Building repeatable outbound playbooks that the next AE hires can use

Who You're Selling To

Primary Buyers:

• VP/Director of Operations at regional health systems (3-10 hospitals)
• COO or Administrator at multi-location clinic groups
• VP of Patient Experience at hospital systems
• Practice Administrators at large specialty practices (50+ providers)

What They Care About:

• Staff shortage relief: They can't hire enough front desk staff or call center agents. Can AI actually reduce headcount needs or allow redeployment?
• Patient satisfaction scores: HCAHPS scores and patient experience metrics affect reimbursement. Does this improve wait times and responsiveness?
• Cost per patient interaction: What's the ROI vs. hiring more staff or outsourcing to a call center?
• Integration and compliance: Will this work with their EHR? Is it HIPAA compliant? What's the implementation timeline and disruption?

Requirements

• 3-5+ years selling B2B software, preferably in healthcare tech, workflow automation, or similar complex solutions
• Experience managing 3-6 month sales cycles with multiple stakeholders
• Comfortable with consultative selling—you're diagnosing operational problems, not pushing features
• Self-starter mentality—this is a new vertical so there's less structure and you'll be building playbooks
• Healthcare domain knowledge helpful but not required (you can learn)
• Based in NYC with ability to travel to healthcare systems in Northeast/Mid-Atlantic region
• Quota-carrying experience at $500K+ annual number