From the C-suite to the coaching chair — 30 years of scaling organizations and the leaders who run them.

Executive Coaching · Customer Success · Operations & Growth Strategy

Holly Files

Executive Coach

Challenger · Coach

30+ Years in leadership & coaching
CCO, COO, & GVP Executive-level leadership across tech
4 Corporate board positions held

“Building a solid leadership team is the cornerstone of a successful company.”

Holly Files doesn’t just coach leaders — she’s been one. As a former Chief Customer Officer, COO, and Global VP at companies like Auth0 and New Relic, she’s led through the exact challenges her clients face: hypergrowth, acquisitions, reorganizations, and the leadership gaps that come with scaling fast.

With over 30 years of experience spanning leadership development, operations, M&A integration, change management, and succession planning, Holly helps leaders and organizations bridge the gap between strategic plan and operational execution. She’s worked with companies at every stage — early-stage, high-growth, mid-market, and public — across technology, manufacturing, education, healthcare, and nonprofits.

At Auth0, Holly was responsible for customer retention and expansion, scaling operations, and building leadership capacity during 65% year-over-year growth. At New Relic, she built the digital engagement strategy for 15,000 commercial customers as Global Vice President of Customer Success Strategy. She’s also served as COO for an online education company and VP of Engineering & Technology for a leading marketing agency.

Holly supports clients through 1:1 coaching, team and leadership development, strategic planning facilitation, organizational and operations assessments, change readiness, and acquisition integration.

She has served on the board of directors of Columbia Helicopters and Lightspeed – A Learning Company, and on the board of advisors for Stackery and Airship, both early-stage VC-funded software technology companies.

Why I Coach

I’ve sat in the seat my clients sit in — leading through growth, navigating acquisitions, building teams from scratch. I coach because I know how lonely and complex those challenges can be, and I know how much faster leaders move when they have someone in their corner who’s been through it. That’s the partner I want to be.

Certifications & Expertise

  • CEO & Senior Executive Coaching
  • Leadership Assessment & Development
  • Strategic Planning & Implementation
  • Succession Planning
  • Executive Team Coaching & Development
  • M&A Integration Support & Coaching
  • Leading Through Transition/Change
  • Organizational Development
  • Strengths-Based Leadership Assessment
  • Board Development & Transition
  • Change Management Coaching
  • Business 360 Assessment
  • Leadership Retreat Facilitation

Holly lives in Portland, Oregon, where she enjoys the beauty of nature and photography.

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