Meet the Mentors Shaping the Future of Insurance: Tony Chimera

In the fast-paced and dynamic world of the insurance industry, recognition is due to those who not only excel but also dedicate their time and knowledge to mentor the next generation of professionals. The Mentor of the Year Finalists represent a group of exceptional individuals who have gone above and beyond in their commitment to nurturing talent and fostering growth within the RISE Community and beyond.

In this exclusive spotlight series, we take a closer look at their journeys, motivations, and the insights they’ve gained throughout their careers. Whether you’re an industry veteran seeking inspiration, a newcomer looking to break into the field, or simply curious about the inner workings of the insurance world, these finalists have a wealth of knowledge to share. Join us as we engage with these luminaries, gain invaluable perspectives, and celebrate their achievements in this exciting and enriching series.

Meet Tony Chimera, Chief Talent Officer at Westfield Specialty and 2022 Mentor of the Year Finalist:

Q: Can you share a memorable success story or a significant achievement from your career in insurance?

A: The startup of Westfield Specialty 2 years ago is what I think of immediately. The president, Jack Kuhn, and I started Employee 1 and 2 and now have almost 400 colleagues in the US and UK together. It was a unique “blank sheet of paper” opportunity with the focus on as talent, relationships and speed to market in the Specialty Insurance space while being part of a 175 year old company with a great reputation. We will be over $1.3 billion in GWP in our 2nd full year and I would rank our talent among the highest in the industry.

Q: If you could have a conversation with one influential figure, living or historical, who would it be and why?

A: Jackie Robinson – courage, grace, skill and commitment. Absolute hero of mine.

Q: How do you handle setbacks or failures in your career, and what have you learned from those experiences?

A: Don’t take yourself too seriously and do not let someone else try to define you. I worked for someone who really had a different approach to managing relationships and the direction of HR as a whole. I leaned into the business and worked to mitigate that, but I think I let that person’s feedback really wear on me.

In summary, we will all have setbacks – you are not taking risks if you do not have setbacks and we are in the business of risk. Grow from them and do not make the same mistakes twice!

Q: In your opinion, what are the key qualities that make a successful leader in the insurance industry?

A: Empathy, transparency, accessibility, and communication

Q: What are your favorite ways to network and build connections within the insurance community?

A: Conferences have maximum impact. Work the room, be curious, be brave as titles are just people. Linked in offers ease of access and the ability to network outside your immediate company and connections. Finally, leverage all the amazing associations in our industry!

Q: What role has mentorship played in your career, and do you have any tips for finding a mentor?

A: The answer is complicated, but yes. I have never defined it as mentorship. I have focused on assembling a board of personal directors who are really mentors. Background. I think the key is it will evolve, and it should be reciprocal. Also, pick people that are different and diverse from you and your background.

Q: Can you share a memorable experience or a valuable lesson you learned through your involvement with RISE?

A: My memorable experience was the leadership gala this year where I looked around the room and saw the industry I envision going forward – energetic, diverse, talented, and engaged.

Q: What steps do you take to promote diversity and inclusion in your workplace and the insurance community?

A: Be intentional, be a sponsor, and make sure it is part of everything you do and truly part of your culture. I think companies make the mistake of trying to accomplish significant things and miss the boat on sustainable engagement around DEIB. I understand how hard it is to track qualitative actions, but in my opinion those activities are often as important and demonstrate to everyone that DEIB is a living and breathing initiative.

Q: How do you approach continuous learning and professional development to enhance your skills and knowledge?

A: Be a voracious learner and use all the tools available to you – reading books and industry briefs, networking, conferences, LinkedIn.