Regional Director, Named Healthcare Sales-MI/WI

About Us:

Proofpoint is a global leader in human- and agent-centric cybersecurity. We protect how people, data, and AI agents connect across email, cloud, and collaboration tools. Over 80 of the Fortune 100, 10,000 large enterprises, and millions of smaller organizations trust Proofpoint to stop threats, prevent data loss, and build resilience across their people and AI workflows. Our mission is simple: safeguard the digital world and empower people to work securely and confidently. Join us in our pursuit to defend data and protect people.

How We Work:

At Proofpoint you'll be part of a global team that breaks barriers to redefine cybersecurity guided by our BRAVE core values:

Bold in how we dream and innovate

Responsive to feedback, challenges and opportunities

Accountable for results and best in class outcomes

Visionary in future focused problem-solving

Exceptional in execution and impact

First-Line Sales Leader (Regional Sales Manager)

About the Role

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.

Key Responsibilities

Revenue Leadership

• 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.

MEDDICC Inspection Excellence

• 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.

AI-Enabled Sales Coaching & Productivity

• 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.

Coaching & Talent Development

• 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.

Sales Execution

• 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.

Business Planning & Operational Excellence

• 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.

Leadership & Culture

• 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.

Required Qualifications

• 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.

Preferred Qualifications

• 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.

Success Measures

Within the first 12 months, successful leaders will:

• Consistently achieve or exceed team quota.
• Improve forecast accuracy and pipeline quality.
• Increase MEDDICC adoption and opportunity quality across the team.
• Demonstrate measurable improvements in win rates, sales cycle efficiency, and average deal size.
• Increase seller productivity through effective AI adoption and coaching.
• Recruit, develop, and retain top-performing talent.
• Build a culture of accountability, collaboration, and continuous improvement.

Leadership Competencies

The successful candidate demonstrates:

• Customer Obsession
• Coaching Excellence
• MEDDICC Inspection Mastery
• AI-Enabled Leadership
• Data-Driven Decision Making
• Strategic Thinking
• Operational Excellence
• Executive Presence
• Talent Development
• Cross-Functional Collaboration
• Innovation & Continuous Improvement
• Inclusive Leadership

Why Proofpoint

At Proofpoint, you'll help protect organizations and people from today's most critical cybersecurity threats while leading a team that makes a measurable impact on customers around the world. As a sales leader, you'll shape the next generation of enterprise sellers by combining world-class coaching, disciplined execution, and AI-enabled innovation to drive extraordinary customer outcomes and business growth.

Why Proofpoint?

At Proofpoint, we believe that an exceptional career experience includes a comprehensive compensation and benefits package. Here are just a few reasons you'll love working with us:

• Competitive compensation

• Comprehensive benefits

• Career success on your terms

• Flexible work environment

• Annual wellness and community outreach days

• Always on recognition for your contributions

• Global collaboration and networking opportunities

Our Culture:

Our culture is rooted in values that inspire belonging, empower purpose and drive success-every day, for everyone.

We encourage applications from individuals of all backgrounds, experiences, and perspectives. If you need accommodation during the application or interview process, please reach out to accessibility@proofpoint.com.

How to Apply

Interested? Submit your application along with any supporting information- we can't wait to hear from you!