Corey Penn, executive coach, in a gray blazer on an urban street

Executive Coaching & Advisory

Lead from
30,000 feet

I coach executives at critical inflection points — as they step into bigger roles, prepare for succession, or lead through complex transitions. An ICF-certified executive coach with 20+ years of senior leadership at Fortune 500 companies, I bring a rare blend of lived corporate experience and coaching expertise to leaders navigating change.

Connect
  • ESPN
  • Comcast
  • Staples
  • Wayfair

What does it mean to lead from 30,000 feet?

Corporate leadership is both invigorating and overwhelming. Under the pressure of daily demands, it's easy to get caught in the weeds and lose sight of the bigger picture — and the bold decisions that drive real growth.

My work helps executives elevate their thinking, gain fresh perspective, and simplify their strategic focus — building the mental resilience to thrive in high-pressure environments and lead their teams more effectively.

Step back from the chaos and reflect from a higher vantage point — and lead with renewed conviction and intentionality.

I work with…

01

Organizations

My approach sharpens corporate executives' ability to elevate and simplify their leadership — optimizing their overall impact.

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02

Individuals

A deeper sense of clarity for senior leaders navigating career transition.

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Corey Penn, studio portrait, arms crossed in a black top

About Corey Penn

I'm an ICF Certified Executive Coach helping corporate executives and senior leaders navigate career growth and transitions. As former Chief of Staff to C-level executives at Fortune 500 companies including Comcast, Staples, and Wayfair, I bring deep expertise in corporate strategy, talent management, and M&A integration — and have coached executives across tech, biotech, consumer products, financial services, management consulting, logistics, and philanthropy.

At the core of my work: helping clients sharpen their strategic vision while building the mental resilience to thrive and make an impact under pressure.

Clients value my broad business experience as a foundation for trust and connection. My warmth, calm, and unwavering commitment help them unlock fresh perspectives with clarity and purpose.

Corey's Expertise & Credentials

  • ICF Certified Executive Coach
  • Certified in Leadership Circle Profile (LCP) 360 Assessment
  • 20+ years of corporate leadership (ESPN, Comcast, Staples, Wayfair)
  • Chief of staff to CEO, CTO, CCO at Fortune 500 companies
  • Certified Project Management Professional (PMP)
  • Guest Lecturer: Boston College, Syracuse University
  • Bachelor of Arts – Journalism (Syracuse University Newhouse School)

My Approach

People-centered, results-driven, and rooted in deepening clarity, perspective, and impact.

Connection

Trust built through a calm, grounded commitment to clients — accelerating the unlock of new perspectives.

Actionable Strategies

Self-awareness tools and frameworks that build a tailored roadmap to elevate leadership impact.

Sustainable Momentum

Coach and client co-create a customized plan for long-lasting, durable momentum.

What Clients Are Saying

Ready to elevate your leadership?

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Let's discuss how we can work together. I offer complimentary 30-min chemistry sessions.

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Contact Me

Have questions or need more information? Feel free to send me a message.

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