Rebecka Kilkenny

CIO at K2 Insurance Services

Can you please provide a little introduction about yourself

Currently, I am the Chief Information Officer for K2 Insurance Services. Based in San Diego, I joined K2 about 10 years ago as it was getting off the ground as a newly formed MGA/Program Administrator.  K2 operates within niche segments of the property and casualty insurance industry.  

I live in San Diego with my husband and two amazing kids.  I enjoy watching and playing all kinds of sports!    

What has your journey to your position been like? What path have you taken?

After graduating from college, I moved to San Diego, where I found a job that was in no way related to my degree.  Given the student loans I was about to start paying, I remained determined to find a job where I could actually put my degree to good use.  A few months later, I landed a job as a Business Analyst, and with that, my career in the insurance industry took off. 

For just shy of two years, I worked as a BA, soaking up as much insurance product, operations, and insurance knowledge as I could.  About a year into the role, I also started taking additional classes related to project management and began preparing for my PMP certification.  At the time, together with my managers and mentors, we were noticing a growing need for our company to add additional structure to how we were approaching tech-related projects.  I knew I wanted to be the one to help define and execute that mission.  I was promoted to Project Manager and later Project Director, where I started the first official PMO for the company.

Fast forward to the beginning of my journey with K2, I was initially working with K2 as a consultant to vet new M&A opportunities as well as identify possible issues and solutions for already acquired programs and organic startups. I was quickly selected for the CIO role and began formally laying the groundwork for what is now an amazing K2 IT team that is responsible for supporting over 500 employees and 24 different program units.

Has it always been your vision to reach the position you’re at? Was your current role part of your vision to become a tech leader?

Reflecting on my career so far, I can say yes, being a CIO was always part of my vision. I believe that experience as a CIO is such a powerful stepping stone to any other executive role because CIOs have an excellent awareness and understanding of multiple facets of a business. I believe this makes CIOs some of the most well-rounded leaders, with a striking ability to lead through change and truly understand a business from the inside out.

Have you had a role model or mentor that has helped you on your journey?

I am extremely grateful to say that I have had numerous amazing mentors throughout my journey.  One quality they all shared was their ability to help me realize my strengths, even in times of failure.  This type of mentorship and support is incredibly valuable and I always strive to pay it forward.

How do you see the role of the technology leader evolving over the next 5 years?

I see the role of the technology leader evolving to normalize combining technology and business leadership into one cohesive package versus keeping them separate as though leaders can only possess one skill or the other.

What skills do you think leaders of the future will need in order to thrive?

Leaders of the future will need to possess strong emotional intelligence and social awareness skills.  These skills allow a leader to stay authentically in tune with the human element of every decision and interaction which fuels the correlation between happy employees, happy customers, and successful companies.

How do you keep current with new skills, technologies and personal development?

I read as much as I can.  I also enjoy finding webinars, conferences, or courses where I can dive into topics I am eager to explore.

What do you see as the next leap in technology that will impact your business or industry in particular?

The utilization of Adaptive AI to drive real-time product, service, and claim handling enhancements. 

“Don’t let a fear of failing keep you from trying.”

If you were mentoring a leader of the future, what advice or guidance would you give to help them on their way?

Be kind and patient with yourself and others, and don’t let a fear of failing keep you from trying.

Is there anything in particular that you would still like to achieve in your career or what is the next step on your journey?

I still have a lot to achieve in my career, including a goal to expand into other roles or industries. 

If you could change one thing in the world, what would it be?

That people would always treat each other respectfully.

A big thank you to Rebecka Kilkenny from K2 Insurance Services for sharing her journey to date.