Regional Director, Named Healthcare Sales-Central

Proofpoint•Carapichaima, IL

11d•Hybrid

About The Position

Proofpoint is seeking a high-impact First-Line Sales Leader to lead, coach, and develop a team of Account Executives responsible for acquiring new customers and expanding strategic relationships within a defined territory. This leader will be accountable for delivering predictable revenue growth while fostering a culture of accountability, collaboration, and continuous development. The ideal candidate is a modern sales leader who combines exceptional coaching skills, operational rigor, and data-driven decision making with a passion for developing talent. They embrace AI-enabled selling, leverage inspection to improve execution, and consistently raise the performance of their team through disciplined coaching and customer-centric leadership.

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 to improve sales execution.
Exceptional communication, executive presence, and coaching skills.
Bachelor’s degree or equivalent professional experience.

Nice To Haves

Experience selling cybersecurity, cloud security, email security, identity security, or data protection solutions.
Experience leading geographically distributed enterprise sales teams.
Familiarity with AI-powered sales platforms such as Gong, Salesforce Einstein, Microsoft Copilot, Clari, Outreach, or similar technologies.
Experience working with channel partners and strategic alliances.
MBA or advanced business education is a plus.

Responsibilities

Lead a team of Account Executives to consistently achieve and exceed quarterly and annual revenue targets in the Healthcare vertical.
Drive predictable revenue through rigorous pipeline management, forecast accuracy, and disciplined business reviews.
Develop and execute territory and account strategies that maximize new logo acquisition and expansion opportunities.
Inspect leading performance indicators to proactively identify risks, accelerate deal progression, and improve conversion rates.
Establish a culture of inspection over inspection for compliance, ensuring MEDDICC is used as a strategic coaching framework rather than a qualification checklist.
Conduct regular opportunity inspections focused on Metrics, Economic Buyer engagement, Decision Criteria, Decision Process, Identify Pain, Champion strength, and Competition.
Coach sellers to improve deal quality, eliminate blind spots, and increase forecast confidence through disciplined MEDDICC execution.
Drive consistent opportunity reviews that improve win rates, shorten sales cycles, and increase average deal value.
Partner with Sales Engineering and executive leadership on strategic deal coaching for the organization’s most critical opportunities.
Champion the adoption of AI-powered sales tools to improve seller productivity, coaching effectiveness, and customer engagement.
Leverage AI-generated insights to identify coaching opportunities, analyze customer interactions, improve pipeline health, and accelerate seller development.
Utilize conversational intelligence, account insights, and productivity platforms to deliver personalized coaching at scale.
Encourage responsible experimentation with AI to automate administrative work, improve account planning, enhance executive communications, and maximize customer-facing time.
Foster a culture of continuous learning where technology amplifies human coaching rather than replaces it.
Recruit, onboard, develop, and retain top-performing sales talent.
Conduct structured weekly coaching focused on pipeline creation, opportunity progression, MEDDICC execution, executive engagement, negotiation strategy, and account planning.
Build individualized development plans aligned with career growth and performance objectives.
Develop future leaders by providing stretch opportunities, mentorship, and regular performance feedback.
Create an environment of accountability, collaboration, and continuous improvement.
Partner with Sales Engineering, Customer Success, Marketing, Channel, SDR, and Customer Advocacy teams to deliver exceptional customer outcomes.
Participate in executive customer meetings and strategic deal reviews.
Guide complex enterprise sales cycles involving multiple stakeholders and executive sponsors.
Ensure consistent execution of Proofpoint’s sales methodology, sales process, and operating cadence.
Develop quarterly business plans aligned with corporate objectives.
Maintain high forecast accuracy through disciplined inspection and data-driven decision making.
Analyze territory performance, competitive dynamics, whitespace opportunities, and pipeline health.
Use dashboards, analytics, and AI-driven insights to improve operational efficiency and sales execution.
Establish an operating rhythm that balances accountability, coaching, and execution excellence.
Lead by example with integrity, humility, customer obsession, and operational excellence.
Foster an inclusive, high-performance culture where accountability and collaboration thrive.
Champion innovation by encouraging adoption of modern selling techniques, digital engagement, and AI-enabled workflows.
Reinforce Proofpoint’s values through consistent leadership behaviors and decision making.