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Regional Director, Healthcare Sales

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Jobtailor
Full Time position
Listed on 2026-08-16
Job specializations:
  • Sales
    SaaS Sales, Account Manager, Director of Sales
Salary/Wage Range or Industry Benchmark: 180000 - 280000 USD Yearly USD 180000.00 280000.00 YEAR
Job Description & How to Apply Below
  • Lead and coach a team of Account Executives responsible for acquiring new customers and expanding strategic Healthcare relationships.
  • Deliver predictable revenue growth through pipeline management, forecast accuracy, and disciplined business reviews.
  • Develop territory and account strategies to maximize new-logo acquisition and expansion opportunities.
  • Inspect performance indicators and conduct MEDDICC-based opportunity reviews to improve deal quality, win rates, sales cycles, and deal value.
  • Partner with Sales Engineering and executive leadership on strategic deal coaching.
  • Champion AI-powered sales tools and use AI insights, conversational intelligence, account insights, and productivity platforms to improve seller productivity and development.
  • Recruit, onboard, develop, and retain top-performing sales talent.
  • Conduct weekly coaching on pipeline creation, opportunity progression, MEDDICC execution, executive engagement, negotiation, and account planning.
  • Build individualized development plans and develop future leaders through mentorship, stretch opportunities, and feedback.
  • Partner with Sales Engineering, Customer Success, Marketing, Channel, SDR, and Customer Advocacy teams.
  • Participate in executive customer meetings and strategic deal reviews.
  • Guide complex enterprise sales cycles involving multiple stakeholders and executive sponsors.
  • Ensure execution of Proofpoint’s sales methodology, sales process, and operating cadence.
  • Develop quarterly business plans aligned with corporate objectives.
  • Analyze territory performance, competitive dynamics, whitespace opportunities, and pipeline health.
  • Use dashboards, analytics, and AI-driven insights to improve operational efficiency and sales execution.
  • Foster an inclusive, accountable, collaborative, and high-performance culture.
Requirements
  • 5+ years of frontline sales leadership experience in enterprise SaaS or cybersecurity
  • Demonstrated success leading teams that consistently exceed revenue targets
  • Proven experience hiring, coaching, and developing high-performing Account Executives
  • Deep expertise in MEDDICC or MEDDPICC opportunity qualification and inspection
  • Experience leading complex enterprise sales cycles involving C-level stakeholders
  • Strong forecasting, pipeline inspection, and business planning capabilities
  • Experience leveraging CRM analytics, sales technology, and AI-powered productivity tools
  • Exceptional communication, executive presence, and coaching skills
  • Bachelor’s degree or equivalent professional experience
  • Experience selling cybersecurity, cloud security, email security, identity security, or data protection solutions preferred
  • Experience leading geographically distributed enterprise sales teams preferred
  • Familiarity with Gong, Salesforce Einstein, Microsoft Copilot, Clari, Outreach, or similar platforms preferred
  • Experience working with channel partners and strategic alliances preferred
  • MBA or advanced business education is a plus
Core Competencies

Demonstrates strong leadership in enterprise sales, focusing on pipeline management, MEDDICC execution, and team development. Proficient in leveraging AI-powered sales tools and analytics to drive revenue growth and improve sales processes.

Highest-signal resume keywords
  • Enterprise SaaS Sales Leadership
  • MEDDICC Opportunity Qualification
  • Pipeline Management
  • AI-Powered Sales Tools
  • Coaching and Development of Sales Teams
ATS Optimization Keywords
Hard Skills
  • Sales Forecasting
  • Business Planning
  • Account Planning
  • Negotiation
  • Performance Analysis
  • Sales Methodology Execution
  • Revenue Target Achievement
  • Complex Sales Cycle Management
  • C-Level Stakeholder Engagement
  • Sales Technology Utilization
Soft Skills
  • Exceptional Communication
  • Executive Presence
  • Coaching Skills
  • Mentorship
  • Collaboration
Certifications & Qualifications
  • Bachelor’s Degree
  • MBA or Advanced Business Education
Industry Keywords
  • Cybersecurity
  • Cloud Security
  • Email Security
  • Identity Security
  • Data Protection
  • Sales Engineering
  • Customer Success
  • Channel Partners
  • Strategic Alliances
  • Geographically Distributed Teams
Tools & Technologies
  • Salesforce Einstein
  • Gong
  • Microsoft Copilot
  • Clari
  • Outreach
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