S4 EP69: Making a company an even greater place to work - Allison Keavey Luther, Deputy Chief of Human Resources, Plymouth Rock Assurance

The Insurance Coffee House

On the Insurance Coffee House Podcast this week, we welcome Allison Keavey Luther, Deputy Chief of Human Resources at Boston-based Plymouth Rock Assurance

Allison talks about her career journey from TV producer at CNBC to catching the start-up bug, working as General Manager for early-stage businesses.

From there she rode a massive wave of growth at Wayfair, where she was ‘pulled’ in to HR.

She joined Plymouth Rock in 2023 to work alongside CHRO, Mary Strong, and support the next phase of business growth.

Allison gives an insight in to Plymouth Rock’s 40-year history, with the business now managing over $2 billion in auto and home insurance premiums, across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania.

She highlights the top-down culture, embodied by founder Jim Stone and the desire to create an environment where employees are happier than they would be anywhere else

Allison discusses some of the initiatives in place to drive culture forward, including being intentional about how they work together in the physical environment.

On-site gym facilities, drop-in meditation sessions, online recognition program all contribute to creating a culture of friendliness, good citizenship, integrity, loyalty, hard work, and the pursuit of excellence.

She shares her one recommendation for insurance leaders coming to interview there at Plymouth Rock.

“Let us see who you are. When we are making a hire, particularly at the senior level, culture matters just as much as technical qualifications.

Our culture statement is such a critical part of our success that we need to have folks who can advance our culture in the right ways.”

Allison urges her HR peers to set the bar high and not to make short-term trade-offs when looking to fill roles.

She shares some of the tools and technology Plymouth Rock are using to support talent and help people do their jobs better.

As for the one lesson her job has taught her, she wants everyone to learn, Allison emphasizes the power of active listening.

“Whether it's a talent or a business challenge, taking the time to really get the full picture. Hear whatever sides of the story are there to make the best decision for the business and the people in it.”

And for anyone considering an insurance career move, Allison concludes by advising people to consider how they feel at work every day.

“Sometimes we don't check in regularly enough with are we feeling valued? Are we feeling respected? Do, do we feel like there is growth for us ahead? At Plymouth Rock, those are the standards for our people and for our leaders.”

Connect with Allison Keavey Luther on LinkedIn or find out more about Plymouth Rock Assurance

The Insurance Coffee House Podcast is brought to you by Insurance Search.

We are a global Insurance Executive Search Consultancy, supporting Insurance and Insurtech businesses to attract and retain the very best insurance talent.

Find out more about showcasing your employer brand as a guest on the Insurance Coffee House Podcast or sign up to our News and Insights.

Or follow us on LinkedIn, Twitter or Instagram

Insurance Executive Search Consultants in USA, London and Bermuda.

Copyright Insurance Search 2025 – All Rights Reserved.