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Case Study /

Scaling Leadership for the Future


The founder of a very successful, established company retired and had promoted senior management into new roles prior to leaving. An insulated culture left the next generation of company leadership vulnerable at a crucial time. The Creative Executive worked with the new President and CEO and 40 manager-level executives to help them align, gain more accountability and individual ownership, and embrace change as an engine for innovation.


Insurance Company


1:1 Coaching
NextGen Leaders


In-Depth Work
with President + CEO


Although the incoming president had been with the company for more than 10 years, she was new to her role. Her leadership would be essential for cultivating the NextGen executives tasked to lead the organization into the future.


  • Assert purposeful leadership to encourage the culture shift necessary for innovation and change.
  • Delegate more responsibilities and accountability to senior management. 

  • Create and support leadership development to create buy-in and a road forward for executives and middle management.
  • Bridge the experience and expertise gaps between senior managers and directors. 

  • Be a confident and dynamic steward of the company’s vision through public speaking and presentations. 


  • The new president defined what her role looked like for her.
  • She became a driver of new initiatives and growth (training, mentoring, leadership development, communications coaching, corporate social responsibility, DEI, etc.)
  • Learned a process for public speaking that allowed for her to gain more confidence. Now when she speaks in front of company groups, she is often acknowledged by her audience for her authentic messaging.
  • Director-level management is taking more ownership, senior management is more flexible with sharing responsibilities, and the executive leadership team is thriving and aligned in their vision and results.


A technical expert who had been with the company since the beginning moved into the
CEO role. He would need to evolve from a technical mindset to one that considered the broader implications of his role across the entire organization.


  • Develop his leadership style as the CEO
  • Exude more presence and confidence whenspeaking publicly
  • Build a network of peers in similar roles for continued support, mentorship, and idea-sharing
  • Create a space that enables others to step in and offer up innovative ideas that complement his expertise and experience.


  • Gained clarity around his strengths and opportunities for growth through a 360-leadership assessment
  • Acquired new storytelling and messaging techniques for enrolling audiences
  • Utilized feedback to shift his leadership style in a way that enhanced and complemented his strengths, goals, and impact objectives
  • Increased his exposure to new ideas and his network to include executives from diverse industries, with varying levels of experience

General Company Effort

Leadership + Culture Development During a Strategically Important Transition


A leading underwriter with more than 20 years in business was dealing with a sea change in leadership. Legacy leaders were retiring, and a new generation of leadership was on its way in. Five key partners would also be moving on over the course of three years.

Coinciding with this leadership shift, low morale was an epidemic that affected a third of their people. With one particularly admired and beloved leader transitioning out, there was the potential for a leadership vacuum
at a strategically important time for the company.


Our approach centered around first fostering regular strategic conversations with NextGen leaders. We focused on leadership development on multiple levels; 360-Leadership Assessments for senior executives and team managers and 1:1 coaching for 40 managers.

In addition to comprehensive executive coaching and consulting with newly appointed executives, we also facilitated biannual meetings with senior leaders and team managers.


  • Team managers have thrived under new autonomy and taken more ownership
  • NextGen leaders have new domains
  • Creation of a leadership team that is committed tothe company and its employees’ long-term success
  • Ongoing leadership development and action plans for each executive
  • Boosted morale and productivity through a transitional time

*We also worked with 40 of their leaders in management to assess, define strengths and opportunities, and create a personalized development plan with clear actions.

Company Feedback


Jen and her Creative Executive team have not only helped us grow as a management team, but also as individuals. Collaboration and awareness amongst the management team is at a very high level due to C/E involvement. The experience has been enlightening to our entire company and it is exciting to see real results from the efforts.