Chair Case Study

Today in our Chair case study, we speak with Karen Rolleston. Karen brings deep experience as a CEO, entrepreneur, and governance leader, with a strong focus on emerging technologies and AI. After co-founding and scaling EdTech businesses across Australasia, she led technology companies through complex transformation, while continuing to advise boards on navigating innovation. As Chair of Syndicate 143, Karen brings a grounded, future-focused perspective to every session, fostering clarity, connection, and capability among the CEOs she mentors.

Can you share a brief overview of your professional background and what led you to become a Chair for the CEO Syndicate?

After completing an MBA in my mid-30s, I co-founded and scaled a group of EdTech companies across New Zealand and Australia, before moving into CEO roles leading technology businesses through growth and transformation. More recently, I completed a Master of Technological Futures focused on AI governance and served as a subject matter expert for the Institute of Directors, co-developing their online AI course for boards. My current portfolio includes governance and advisory roles, with a focus on helping boards navigate emerging technologies and build AI capability.

What motivated you to work with The CEO Institute, and how does the role of Chair align with your personal and professional values?

I deeply value the importance of having a supportive group of peers who understand the unique challenges and pressures of the top job and the concept of ako - where everyone is both teacher and learner in a shared journey of growth and support.

In my experience, the core qualities of a successful business leader lie at the intersection of vision, empathy, and accountability. Vision provides direction and purpose, empathy builds trust and connection, and accountability ensures follow-through and results. In syndicate sessions, we foster these qualities by encouraging open, honest conversations, challenging assumptions, and creating space for reflection

In what ways do you see the CEO Syndicate positively impacting the personal and professional lives of its members?

The syndicate offers a trusted and confidential space where members can tap into the collective experience of others who’ve walked similar paths. Whether you're facing a tough decision, navigating growth, or dealing with leadership challenges, you can almost always count on someone having been there before. It’s a place where practical advice, fresh perspectives, and genuine support are readily shared - helping you move forward with confidence and clarity.

How do you stay informed on current business trends and issues, and how do you integrate this knowledge into your sessions?

I read widely and draw on my experience across a variety of industries. Recently, I’ve introduced scenario-based discussions—exploring how emerging trends might play out and what the potential impact could be on their business.

How do you balance providing guidance with encouraging CEOs to find their own solutions to business challenges?

The focus is on fostering a trusted environment where members feel comfortable asking questions, digging deeper, and drawing on the collective knowledge and experience of the group. Sometimes, the greatest value comes simply from listening and reflecting.

What lasting impact do you hope to leave on the CEOs you work with through The CEO Institute?

Each member feels fortunate to be part of a group where they’re surrounded by peers who genuinely understand them and the challenges they face. Having a trusted support network and sounding board offers empathy, fresh perspective, and the clarity needed to navigate decisions and stay focused.