For Execs by Execs

Oak Bluffs Executive Coaching is a premier global executive coaching firm dedicated to empowering Fortune 500 executives with transformative leadership development and training solutions. With a commitment to fostering execution-oriented leadership, our coaching and training programs elevate C-suite executives, emerging leaders, and high-potential individuals. We serve as our client’s strategic partners, helping them navigate the complex challenges of today’s business landscape and inspire transformational change within their organizations.

An Accomplished Team

Our team is led by Shawn O’Connor, a graduate of Harvard Business School (MBA, Highest Honors) and Harvard Law School (JD, Honors), who returned to teach at Harvard in 2017. Shawn is the recipient of Harvard’s 2023 Joanne Fussa Award for Excellence in Management Education. Shawn has nearly 25 years of managerial experience at McKinsey, Mercer Management Consulting and Lehman Brothers, along with numerous entrepreneurial successes. Shawn previously founded Stratus Prep, a global educational consultancy that he sold to a private equity firm in 2014.

As CEO, Shawn leads a team of executive coaches and consultants comprised of industry-leading experts in leadership, organizational behavior, strategy, human resources, marketing, and operations. All of our consultants and coaches who work with senior executives have 20+ years of experience with proven and transparent track records.

Our Clients Come From…

The Secret to Executive Success

Key Services

Executive Coaching: Our coaches are accomplished consultants, former executives, and thought leaders who work one-on-one with executives to hone their leadership skills, enhance their strategic decision-making, and foster highly effective internal and external communications.

Leadership Development: We offer tailored leadership development programs that focus on cultivating the next generation of high-achieving corporate leaders.

Skills Training for Aspiring Leaders: At Oak Bluffs, we offer customized training programs for high-potential individuals in disciplines including but not limited to strategy, marketing, innovation, human resources, operations, and finance.

Diversity and Inclusion Training: Oak Bluffs is a pioneer in diversity, equity, inclusion, and belonging. We offer specialized training programs that help organizations leverage the power of diverse leadership and build more inclusive cultures. We have specialized expertise in LGBTQ+ leadership development

Why Choose Oak Bluffs

Proven Results: We deliver tangible results for multinational companies and Fortune 500 executives. To ensure your success, we collaboratively develop and track the most relevant KPIs to ensure we are providing a demonstrable return on investment.

Tailored Solutions: We understand that each organization and individual has unique needs. Through a robust intake and proposal process, Oak Bluffs provides customized programs that align with each client’s distinct goals and needs.

Fortune 500 Experience: We understand the intricacies of effective leadership within Fortune 500 companies and provide solutions tailored to your complex environment.

Diversity and Inclusion: Many of our clients are increasingly focused on supplier diversity; Oak Bluffs is proud to be an LGBTQ+ led and majority-owned firm.

Join us!
Executive Leadership and Values Program

New Cohort Starts in June