Sales Director – Healthcare Mid-Market & Enterprise (IT Services & Generative AI)

(US-Based)

Location: United States (Remote, with travel to clients and events)

Department: Sales

Reports to: CEO

About The Role

We are looking for a senior sales leader in the US with a proven track record of selling IT services into mid-market and enterprise healthcare customers.

You will focus on winning and growing customers across key healthcare segments:

• • Providers: IDNs, health systems, hospitals, ambulatory networks
  • Payers: national and regional health plans
  • MedTech: medical device and diagnostics companies
  • HealthTech: digital health, virtual care, health SaaS/platform companies
  • Biotech / Life Sciences: research, clinical trials, and related organizations
    

Your Main Mission

• • Open and grow mid-market and enterprise healthcare accounts across these subsegments.
  • Sell AI-led and accelerator-based IT services (digital transformation, product engineering, data/analytics, and generative AI solutions).
    

You should already understand how enterprise healthcare buyers think—their priorities, internal decision dynamics, procurement processes, security/compliance concerns, and what it takes to move a deal from first meeting to signed MSA/SOW.

Key Responsibilities

• New Business Development (Mid-Market & Enterprise Healthcare)
• • Own and build a go-to-market strategy for a new logo acquisition strategy for mid-market and enterprise healthcare organizations across providers, payers, MedTech, HealthTech, and biotech.
  • Build and manage a strategic territory / account plan focused on high-potential mid-market and enterprise healthcare accounts.
  • Drive full-cycle enterprise sales: prospecting, discovery, solution positioning, demos/POCs, navigating legal/procurement, and closing.
  • Leverage and expand relationships with CXO and VP-level stakeholders (CIO, CDO, CMO, COO, CMIO, CNIO, VP Revenue Cycle, VP Product, etc.).
• Selling IT Services & AI-Led Accelerators
• • Position and sell our IT services offerings, including:
  • Product engineering and platform development
  • Systems integration and interoperability
  • Data platforms, analytics, and reporting
  • Digital transformation and managed services
  • Lead with business problems and outcomes, not just staff augmentation—focus on solutions, accelerators, and generative AI use cases.
  • Collaborate with internal teams to shape AI-powered proposals, such as:
  • LLM-based assistants and copilots for clinicians, ops teams, and revenue cycle
  • RAG (Retrieval-Augmented Generation) solutions on clinical, operational, or payer data
  • Workflow automation around documentation, prior auth, coding, denials, care coordination, and patient engagement
  • Work closely with the Healthcare & Generative AI Solutions Lead (India) and delivery leaders to align offerings to real client needs and craft compelling SOWs.
• Account Growth & Relationship Management
• • Become a trusted advisor across your accounts—understand their multi-year roadmap, regulatory pressures, and digital priorities.
  • Grow accounts via multi-threaded relationships and cross-sell/up-sell across providers, payers, MedTech, HealthTech, and biotech buying centers.
  • Run structured account governance: QBRs, roadmap sessions, executive check-ins, and ongoing relationship development.
• Pipeline, Forecasting & Collaboration
• • Build and maintain a robust, qualified pipeline in CRM with clear next steps and stakeholder maps.
  • Deliver accurate forecasts on pipeline, bookings, and revenue.
  • Partner with Marketing on campaigns, events, and content aimed at mid-market and enterprise healthcare buyers.
  • Collaborate with Pre-Sales and AI/Solutions teams to design relevant demos, PoCs, and tailored proposals.
• Market & Customer Insight
• • Gather and share market intelligence on trends, competitors, and customer priorities across provider, payer, MedTech, HealthTech, and biotech segments.
  • Help refine our positioning, pricing, and offerings based on real-world feedback from enterprise buyers.
  • Represent the company at industry conferences, regional events, and associations to build brand and pipeline.
    

Required Experience & Qualifications

• • 8–15 years of B2B sales experience, with at least 5+ years selling IT services into US mid-market and/or enterprise healthcare customers.
  • Proven track record of closing 6- and 7-figure deals with healthcare organizations such as:
  • Large provider/IDN health systems
  • Regional/national payers
  • MedTech and diagnostics firms
  • Digital health / HealthTech / virtual care platforms
  • Biotech / life sciences organizations
  • Strong understanding of enterprise healthcare buyer needs, including:
  • Clinical and operational workflows
  • Revenue cycle and financial pressures
  • Interoperability (EHR integrations, FHIR/HL7), data platforms, and analytics
  • Security, compliance (HIPAA, PHI), and risk in IT and AI solutions
  • Experience selling IT services and/or managed services (not just pure SaaS) is essential.
  • Demonstrated experience selling or positioning AI, data, or analytics solutions; familiarity with generative AI (LLMs, copilots, RAG, automation) in a business context is strongly preferred.
  • Comfortable working with distributed global teams (India-based delivery and solutions teams).
  • Excellent communication, negotiation, and executive-level presentation skills.
  • Located in the US with ability to travel to clients and events as required.
    

Key Skills & Competencies

• • Hunter mentality – energized by opening new mid-market and enterprise healthcare accounts.
  • Healthcare enterprise fluency – understands how providers, payers, MedTech, HealthTech, and biotech organizations buy and operate.
  • Consultative selling – able to lead outcome-focused conversations vs. commodity rate discussions.
  • AI-aware and forward-looking – comfortable discussing generative AI opportunities, risks, and value with non-technical executives.
  • Deal orchestration – strong at coordinating legal, procurement, security, IT, clinical, and business stakeholders across long sales cycles.
  • Relationship builder – able to develop and sustain multi-level, multi-year relationships.
  • Ownership & accountability – comfortable carrying a bookings target and being measured on revenue and margin.
    

What Success Looks Like In 12–18 Months

• • A strong pipeline of qualified mid-market and enterprise healthcare opportunities across providers, payers, MedTech, HealthTech, and biotech.
  • New logos closed and at least a few strategic accounts progressing from first project to multi-year partnerships.
  • Clear revenue contribution from AI-led solutions and accelerators, not just traditional staff augmentation.
  • Tight internal alignment with delivery, solutions/AI, and marketing around who we serve, what we sell, and how we win in healthcare.