Regional Director, Healthcare Sales

Proofpoint

Proofpoint sales leader driving Healthcare cybersecurity revenue across Michigan, Illinois, and Wisconsin. Coaching Account Executives through MEDDICC inspection, AI-enabled selling, and enterprise deal execution.

Posted 8/4/2026full-timeIllinois, Missouri, Wisconsin • 🇺🇸 United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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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 LeadershipMEDDICC Opportunity QualificationPipeline ManagementAI-Powered Sales ToolsCoaching and Development of Sales Teams

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales ForecastingBusiness PlanningAccount PlanningNegotiationPerformance AnalysisSales Methodology ExecutionRevenue Target AchievementComplex Sales Cycle ManagementC-Level Stakeholder EngagementSales Technology Utilization

Soft Skills

Exceptional CommunicationExecutive PresenceCoaching SkillsMentorshipCollaboration

Tools & Technologies

Salesforce EinsteinGongMicrosoft CopilotClariOutreach

Certifications & Qualifications

Bachelor’s DegreeMBA or Advanced Business Education

Industry Keywords

CybersecurityCloud SecurityEmail SecurityIdentity SecurityData ProtectionSales EngineeringCustomer SuccessChannel PartnersStrategic AlliancesGeographically Distributed Teams

Tech Stack

Tools & technologies

CloudCyber Security

About the role

Key responsibilities & impact

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

What you’ll need

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

Benefits

Comp & perks

Competitive compensation
Comprehensive benefits
Flexible work environment
Annual wellness and community outreach days
Always on recognition for your contributions
Global collaboration and networking opportunities
Career success on your terms