Gayle has served a variety of organizations as internal and external consultant, coach, and teacher for over 20 years. She has also held senior management positions in strategic planning, organizational development, operations, and communications with organizations in the financial services sector, and has served on the boards of several not-for-profit organizations.

Her current work revolves around the themes of coaching and supporting leaders in developing and increasing organizational and team effectiveness: leading, managing, and supporting organizational change initiatives, and identifying and embracing individual development opportunities for both themselves and those with whom they work. She is also committed to supporting adult students seeking advanced degrees through her teaching roles with Babson College and Endicott College.

She has worked with the Markel Corporation, and predecessor companies in a strategic planning role supporting several corporate initiatives. Before the merger of Max Capital and Harbor Point in May 2010, Gayle served as Senior Vice President, Operations, and Deputy Chief Risk Officer at Harbor Point, having joined the company at inception.

Prior to joining Harbor Point, she was a director, shareholder, and president of The Sherwood Group, an independent consulting firm. From 1996 – 2003, she held various senior management positions with Centre Solutions, and served as President and Chief Executive Officer of eVenture Centre, both subsidiaries of Zurich Financial Services. From its inception in 1987 through 1996, she served as Senior Vice President and General Manager of School, College, and University Underwriters, Ltd. (SCUUL). Before joining SCUUL, Gayle held various positions in higher education.

Gayle currently serves on the Management Department faculty at Babson College, and also on the faculty of The Van Loan School of Graduate and Professional Studies, Endicott College. She splits her time between Bermuda, where she has lived for 30 years with her husband, and Boston.


  • BA – College of William and Mary
  • MBA – University of Pennsylvania, The Wharton School
  • MS – Organizational Dynamics, concentration in Executive Coaching, University of Pennsylvania

Certifications & Further Training

  • Immunity to Change Facilitator Training; Deliberately Developmental Organizations Workshop; BetterUp Coach training and qualification process


Communities of which I am a member, seeing the ocean every day from my windows, and working with adult learners to discover meaning, possibility, and transformation in both small moments and great experiences



Mary is an organization effectiveness expert with an unwavering belief that by building on strength, teams/ leaders/ organizations can overcome thorny issues, imagine and create vibrant futures, deal with tough situations, and be stronger for the process.


Katie is passionate about building effective teams and helping individuals become purposeful, high-functioning leaders. For more than 20 years, she has worked with boards, leadership, and staff to develop strategic plans, to assess programs and to implement initiatives.


Chris founded True Change Associates in 2015 after 20 years of working with academic institutions, corporations, and nonprofit organizations focusing on diversity and inclusion, equity and social justice, leadership development, and team building.


Janice holds a PhD in Psychoeducational Processes with a focus in organization development. She has been a professor and student of leadership for thirty years. Her career reflects her purpose: the holistic development of employees and the organizations they serve.