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.

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.

Michael Christian has served as Board President of Someone Else’s Child, Inc. (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 (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 and Education Modified 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, Boston Explorers, Rwanda Youth Partners, Yiya Solutions, The Folk/Americana/Roots Hall of Fame, and the Council of Insurance Agents and Brokers. 

Mike is also the Chairman and Founder of Risk Strategies, 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 radio show on WBZ (iHeartRadio) in Boston. 

Mike majored in Philosophy at the University of California in Santa Barbara.

Phillip Eng is the General Manager and CEO of the Massachusetts Bay Transportation Authority (MBTA). A Civil Engineer with nearly 40 years of transportation experience, including President of the Metropolitan Transportation Authority’s (MTA) Long Island Rail Road and Interim President of New York City Transit, Mr. Eng brings his abilities to spearhead challenging initiatives, modernize aging systems and prioritize safety to bear for the MBTA.

Mr. Eng joined the MTA in 2017 as the Chief Operating Officer, where he drove initiatives and focused on updating transportation systems through the use of innovative technologies, including developing new fare payment applications and piloting new signaling systems. As Acting President for New York City Transit, Mr. Eng led the early efforts of the Subway Action Plan – a comprehensive stabilization and modernization effort to address the challenges facing the New York City subway. During his tenure at the Long Island Rail Road, he initiated the Forward program – a set of strategic initiatives aimed at improving service reliability and enhancing rider experience.

Mr. Eng began his career in public service in 1983 as a Junior Engineer at the New York State Department of Transportation (NYSDOT) where he gained expertise in Structures, Bridge Inspection, Maintenance, and Design and Construction. During his tenure at NYSDOT, Mr. Eng held positions of increasing leadership culminating as Executive Deputy Commissioner, throughout which he played a vital role improving project delivery for significant projects such as the I-81 Environmental Impact Study, the Rochester Train Station, and the construction of the new Kosciuszko and Mario M. Cuomo bridges.

Phillip Eng earned his Bachelor of Engineering at Cooper Union and is a member of the American Society of Civil Engineers. In 2021 the American Society of Civil Engineers, Long Island Branch honored Mr. Eng with the Government Engineer of the Year award.

Terry Andre has led AmCoat as its CEO since 2010. With more than twenty years of contract manufacturing experience, he is uniquely qualified to help dealers develop their businesses and keep the supply chain moving. Terry and his wife Kathy, reside in Destin, Florida and have three adult children.

Jenny Holaday brings her extensive background in the casino industry to her role of President of Encore Boston Harbor, which she assumed in August 2021. Previously the executive vice president of operations, Jenny oversees all aspects of the $2.6B resort’s operations and leads a team of nearly 3,000 employees.

Jenny has lived and worked in gaming regions from the East Coast to Nevada and many places in between. She has held executive positions for companies including Harrah’s, Caesars Entertainment and Mandalay Resort Group and has successfully launched two enterprise-wide casino player programs.

When she isn’t at the resort, Jenny loves to spend time cooking, golfing, or catching up with her two adult children. She lives in Melrose with her dogs, Snoopy and Beans.

With one foot firmly in Reno and the other across the pond at our Bristol, UK office, Jarrod’s globetrotting nature has led him to make meaningful connections with people all over the world. His attention to listening first let’s him learn what makes people tick and, admittedly, helps him harness the insights to propel Noble’s success.

Over the last two decades Jarrod has grown our creative digital performance marketing agency from a single-laptop endeavor to an international company. To date, Noble partnered with brands like Visit Lake Tahoe, Santa Monica, Autodesk, The Islands of Tahiti, Niantic Inc., Adobe, Disney, Visa, Google and more. His passion for creating beautiful human experiences (and his architectural background) have helped Noble translate the best of the real world into virtual architecture.

Jarrod seeks inspiration from the world around him. An avid photographer and outdoorsman, he’s our original Wild Bear—hungry to see the world and always searching for a way to be better. On any given day that could mean sharing his experiences at national conferences, swapping stories with a client or hiking Patagonia with Season, his wife. (Everest is up next. Be better every day, right?)

A mentor, father, husband and visionary, Jarrod has held leadership roles with several non-profit and public-private initiatives in Nevada. He previously served as Co-Executive Director of the San Francisco/Silicon Valley Inc. Magazine’s Business Owners Council, was a board member for Northern Nevada Development Authority (NNDA) and an advisory board member for the Nevada Center for Entrepreneurship & Technology (NCET). He’s taken the stage around the world at Destinations International’s Annual Convention, Social Media Week Bristol, eTourism, DMA West, University of Nevada – Reno, University of Nevada – Las Vegas and Truckee Meadows Community College, just to name a few.

Outside of his office in Reno, Nevada, Jarrod likes to keep his hands busy. He prides himself on being an early adopter, trying any interesting technology that comes on the scene and attending CES in Vegas just for the fun of seeing into the future (and how it can be applied to digital marketing, of course). His passion for photography has led him to new horizons–Iceland, in the near future–and led him to form a group for agency photogs throughout the country.

Want to know more about Jarrod? Pull up a handmade chair, grab a glass of homemade beer, wine or mead, and come prepared to share a story of your own.

Paul is the founder of Boston Venture Studio. Paul has previously co-founded and successfully sold six startups – Kayak, Lola, Moonbeam, GetHuman, Boston Light and Intermute.

Paul is also the founder of four nonprofits – Summits Education in Haiti, Embrace Boston, The Winter Walk for Homelessness, and the Bipolar Social Club.

Paul is the subject of Tracy Kidder’s book “A Truck Full of Money”. You can hear an interview with Paul on “How I Built This” with Guy Raz, and you can see his video from TEDxBoston in 2022.

Paul grew up in Boston (as did his parents), his father was a pipefitter at Boston Gas Company, Paul’s first job was delivering the Boston Globe, and he went to Boston public schools until he studied music and computer science at UMASS Boston. (As you can guess, Paul is a Boston Red Sox fan, and his accent gets worse in bahs.)

Ancient History

Paul was briefly an entrepreneur-in-residence at Greylock, VP of Engineering at NetCentric, SVP of Engineering and Product Management at Interleaf. He also did contract programming for the US Air Force, operations research programming for Data General, programming for a medical device company, and even some video game software and sound-effect development.

Paul received a BS and MS in computer science from the University of Massachusetts, and was awarded an honorary doctorate in 2019. Paul was named Chief Technology Officer of the year by Mass Technology Leadership Council in 2009.