Holly Files

Executive Coach

Holly Files has extensive experience as a Coach and an Operations Executive in building organizations and leaders to attain the next level of revenue growth and expansion successfully. She brings over 30 years of experience in leadership development, operations, Mergers & Acquisitions (M&A) integration, change management, and succession planning. She has worked with companies in various stages, such as early-stage, high-growth, mid-market, and public organizations. She believes building a solid leadership team is the cornerstone of a successful company.

Most recently, Holly was the Chief Customer Officer at Auth0, a leader in identity and authentication software technology. Her responsibilities included ensuring customer retention and expansion, scaling operations, and building leadership capacity during significant high growth (65% YoY). Her prior operational experience includes serving as the Global Vice President (GVP) of Customer Success Strategy at New Relic. As GVP, she was responsible for building a digital engagement approach for the company’s 15,000 commercial customers. Additionally, she has experience as Chief Operating Officer for an online education company and VP of Engineering & Technology for a leading marketing agency. She has been in various executive leadership roles in customer operations for several high-growth technology companies.

As a consultant, Holly has worked with companies going through significant growth or change events to help them bridge the gap between their strategic plan and operational execution. Holly has worked in industries such as technology, manufacturing firms, education, healthcare, and non-profits. She supports her clients by providing 1:1 coaching, developing teams and leaders through coaching and teaching, facilitating strategic planning work, leveraging organizational & operations assessments, preparing for change, and aiding acquisition integration.

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

Skills and Expertise

  • Leadership Assessment and Development
  • CEO & Senior Executive Coaching
  • Strategic Planning Facilitation & Implementation Support
  • Succession Planning
  • Executive Team Coaching and Development
  • Acquisition Integration Support & Coaching
  • Leading through Transition/Change
  • Organizational Development
  • Re-organization Facilitation & Implementation
  • Strengths Based Leadership Assessment
  • Board Development & Transition Support
  • Change Management Coaching & Leadership
  • Business 360 Assessment
  • Coaching & Consultation
  • Retreat Facilitation