CEOs You Should Know Boston

About CEOs You Should Know Boston

CEOs You Should Know is iHeartMedia Boston's showcase of businesses that drive New England's regional economy. Hear from key business leaders who contribute to the vibrant and growing community.

Publisher

iHeartMedia Boston

Category

business

Language

en

Explicit

No

First episode

1 Apr 2021

Latest episode

12 May 2025

Latest episodes

1 of 67 episodes have a transcript.

1. 

   12 May 2025

   Bill Martin, President and CEO, Plymouth Rock Assurance

   Bill joined Plymouth Rock in 2016 and is in charge of our property insurance business and reinsurance programs. Bill has over 30 years of experience in the insurance industry. Bill was formerly President of Bankers Insurance, winning a Celent Model Insurer award in 2014 for simplifying homeowners insurance shopping. He also founded a startup with a new approach to flood insurance and has held senior positions at Farmers Insurance, Progressive and Travelers. Bill is a graduate of Stanford University, with a degree in Survey Data Research. He is a frequent speaker and author on insurance issues and has served on the Institute for Business and Home Safety and other safety organizations. He is an active board member of nonprofits that combat poverty and aid those with intellectual and developmental disabilities. He is an avid sailor, skier and trombone player.

2. 

   18 Nov 2024

   Ryan Bailey, President and CEO, Cambridge Savings Bank

   Over the span of his 20+ year career in financial services, Ryan Bailey has focused on enhancing customer experiences and supporting communities at every turn. Prior to becoming President and CEO of CSB, Ryan held leadership positions at some of the country’s most respected financial institutions, including TD Bank, Bank of the West, JP Morgan Chase, Fifth Third Bank, and Bank of America. His most recent role was as the Head of Retail Banking at USAA, where he led a team of nearly 2,000 customer-focused employees and spearheaded initiatives to deliver world-class products and services to the military community and their families, setting a benchmark for excellence. Ryan holds a Master of Business Administration and a Bachelor’s degree in Business Administration with a focus on Finance from Western Michigan University. Additionally, his active engagement in the Consumer Bankers Association, notably as the former Chair of the Board, underscores his significant contributions and commitment to advancing the industry. Ryan and his wife, Melissa, are proud parents of their three children, Taylor, Duncan, and Griffin. The Baileys also have a passion for sports, with Ryan taking an active role in coaching his children's football teams.

3. 

   11 Nov 2024

   Michael Christian, Board President, Someone Else’s Child, Inc.

   Michael Christian has served as Board President of Someone Else’s Child, Inc. (http://www.someoneelseschild.org/) (SEC) for nearly 25 years. The foundation supports youth causes throughout the U.S., Africa, and Central America with areas of emphasis including education, the arts, youth living with disabilities, economic justice, and collective action efforts. SEC addresses disparities by investing in opportunities for young people to live, learn, grow and engage as contributing members of their communities. Mike is the Managing Partner for Community Impact Ventures (https://communityimpact-ventures.com/) (CIV), a venture capital impact fund that provides financial support to social entrepreneurs and for-profit companies that have missions similar to that of Someone Else’s Child. CIV invests in early-stage firms creating meaningful social impact. He also serves on the boards of MathTalk (https://math-talk.com/) and Education Modified (https://educationmodified.com/) and acts as an advisor to many of the CIV portfolio companies and other start-up organizations. He currently serves on several non-profit boards including the Boch Center/Wang Theater (https://www.bochcenter.org/), Boston Explorers (http://www.bostonexplorers.org/), Rwanda Youth Partners (https://www.rwandayouth.org/), Yiya Solutions (https://www.yiyasolutions.org/), The Folk/Americana/Roots Hall of Fame (https://www.folkamericanarootshalloffame.org/), and the Council of Insurance Agents and Brokers (https://www.ciab.com/). Mike is also the Chairman and Founder of Risk Strategies (https://www.risk-strategies.com/), a leading national insurance brokerage firm. In his role as Chairman, Mike works with Risk Strategies' senior team, private equity partner, and the board of directors on strategic and client value initiatives. He was the Chief Executive Officer of Risk Strategies from 1997 to 2019. He led the private equity-backed company from its start-up beginnings into a top national risk advisor/broker with revenues of over $1.5 billion. Prior to Risk Strategies, Mike held leadership positions with Jardine Insurance Brokers, including serving on the U.S. Board of Directors, AON and Alexander & Alexander. He hosts the What’s @ Risk (https://wbznewsradio.iheart.com/featured/whats-risk/about/) radio show on WBZ (iHeartRadio) in Boston. Mike majored in Philosophy at the University of California in Santa Barbara.

Inside a recent episode

Jarrod Lopiccolo, CEO & Founder, Noble Studios

Published 9 Sept 2024 · Transcript excerpt

[…] I would say that we effectively put the brands of our companies in the hands of their customers. And we create loyalty between the two of them. And so that could be in the form of web development. And there's a great experience of, you know, you're on a website. It could be in the form of campaign ad developments, but they're relevant to you, right? I think that's the real most distinctive point, is that you're not getting ads or you're not getting served information that's not relevant. […]

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

419,297,183

Score snapshot 15 Sept 2025

Podcast Authority Score: 50 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

63

Social presence

0

YouTube

93

Engagement

0

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.