Home » Our People » Our Team

Our Team

Our employee-owners value the refreshing ability to think creatively and possess, on average, 30 years of investment or trust-related experience. This exceptional team of trust professionals was attracted to the concepts of independence and empowerment and to the opportunity to design a company that reflects their philosophy.

Meet Our Team Members:

Brattleboro

Angela K. Bowman

Chief Operating Officer

Fiduciary Taxes
Financial Planning
Estate Planning
Trust Administration
IRA Administration
New Business Development

Angela is the Chief Operating Officer at Trust Company of Vermont. She works with clients as a relationship manager and focuses on increasing efficiencies throughout the company. Angela has over 20 years of experience in trust administration and working with clients to ensure their goals are met. She resides in West Chesterfield, NH with her husband and son, and enjoys cheering on her son, house renovations, and spending time with her family.

Western New England College, B.A.
Graduate Cannon Trust School
Trust, estate and tax experience since 2004

Paul Copeland, CFA

Vice President

Portfolio Management
Equity/Fixed Income Analysis
New Business Development

Paul has extensive experience in financial management and is part of our investment management team. He moved from the Boston area in 2006 and is a board member of the International Fellowship House. Paul resides in West Chesterfield, NH with his wife and children. They enjoy playing tennis, biking, basketball, and board games in their free time.

Wheaton College, B.A.
Chartered Financial Analyst (CFA) Charterholder
Portfolio Manager since 2013
Financial Industry experience since 1998
Equity and fixed income research

Lisa Edwards

Trust Officer

Account Administration

Lisa is an essential part of the administrative support team in the Brattleboro office. She joined Trust Company of Vermont with 18 years of experience leading the fee revenue team at TD Wealth Management. Lisa and her husband Joe reside in Vernon, and much of her free time is spent with her grandchildren or cruising on vacation.

Trust banking experience since 1994

Bobi Flynn

Vice President & Founder

Fiduciary Taxes
Trust Administration

Bobi is an enrolled agent who leads the fiduciary tax department at Trust Company of Vermont. With experience in trust taxation and the administration of trusts and estates, she is passionate about her work and is one of the company’s founding members. Bobi is one of the original founders and a resident of Newfane, Vermont. She enjoys outdoor activities like dog agility, kayaking, hiking, and skiing with her beloved Brittney Spaniel, Willow.

William Patterson College, B.A.
Graduate of the Williams College Trust School
Trust, tax and operations experience since 1974
Enrolled Agent (qualified to testify before the IRS)

ANGIE E. Freeman

Vice President & Founder

Operations

Angie is the Operations Department head. She was one of the Founders of Trust Company of Vermont and has worked in operations for her entire career. Angie and her husband Jim reside in Vernon and are working towards visiting every National Park in the United States.

Champlain College
Trust operations experience since 1984

Read Andrea’s personal profile. (2005)

Kelly L. Gagnon, CTFA

Trust Officer

Trust Administration
Trust & Estate Settlement

Kelly is a trust administrator, with expertise in probate matters. With 25 years in financial institutions, including nine in trust operations and administration, Kelly brings a wealth of knowledge to Trust Company of Vermont. When she’s not at work, you can find her cheering on her kids at school events, volunteering in her community, or planning her next Disney vacation.

Greenfield Community College, A.S.
Certified Trust and Fiduciary Advisor (CTFA)
Graduate Cannon Financial Institute
Trust Administration and Retail Banking since 1998

Katie Gardner

Trust Officer

Financial Planning
Trust Administration
IRA Administration

Katie is a trust administrator with a focus on financial planning for her clients. She joined Trust Company of Vermont after gaining experience in financial planning while working for a wealth management company in England. Katie previously worked as a nurse, specializing in Pulmonary and Rheumatology medicine. She lives with her family in Keene, NH, where she enjoys watching her son play soccer and camping in York, Maine.

Kaplan College of Financial Planning
Planning experience since 2018

Ashley Gilbert

Operations Specialist

Trust Operations

Ashley has over 12 years of banking and trust operations experience.

She lives in Massachusetts with her two daughters and enjoys skiing, paddle-boarding, going on hikes and chasing sunsets.

Todd Gray

Vice President

Portfolio Management
Equity/Fixed Income Analysis
Compliance

Todd is a seasoned member of our investment management team. His experience in investment research, strategy, and portfolio management spans a long career that includes two appointments as Chief Investment Officer. Since 1986, Todd has managed money for individuals, corporations, government entities, and non-profit organizations. He and his wife Karen live in Keene, NH.

University of Maine, B.S., Business Administration
Husson College, M.S., Business Management
Graduate of the ABA National Trust School
Equity & fixed income management & research
Portfolio Manager since 1985

Timberly Grout, CTFA, AEP

Vice President

Estate Planning
Trust Administration
IRA Administration
New Business Development

Timberly is responsible for overseeing all aspects of client relationships, bringing with her over three decades of experience in wealth management. Though she’s still a “Vermonter” at heart, she now lives in Northfield, MA with her husband. When she’s not working, Timberly enjoys baking, golfing, hiking, traveling, and spending time with horses.

Greenfield Community College, A.S.
Certified Trust and Financial Advisor (CTFA)
Graduate Cannon Trust School
Accredited Estate Planner (AEP)
Trust administration and estate planning experience since 1989

Lori Miller

Trust Operations Officer

Operations

Lori is a valuable member of the Operations Department. With over a decade of experience in trust operations, Lori provides essential support to the company. During her free time, she enjoys exploring nearby trails and reading books from her town library.

Wilson College
Community College of Vermont
Trust operations experience since 1990

Kathy Patenaude

Office Manager

Office Management
Audit Clerk

Kathy is the office manager for the Brattleboro location and provides administrative support across the company. She has over 20 years of experience in trust work and has been with the Trust Company of Vermont since its early days. Kathy lives with her husband in Brattleboro and their three daughters are also nearby. In her leisure time, Kathy enjoys reading, watching football games, and spending time with family and friends.

American Institute of Banking
Trust operations experience since 1998
Retail banking experience since 1988

Jennifer Rowe, ESQ.

Vice President 

Fiduciary Taxes
Estate Planning
Trust Administration
IRA Administration
New Business Development

Jenny is an attorney and trust officer at our Brattleboro Office. She has over ten years of private practice experience in estate planning, taxation, and trusts. Before law school, she was an academic and teacher of writing and literature. She lives with her husband in Brattleboro and enjoys their old house and a garden that always has room for one more plant.

Amherst College, B.A.
Columbia University, Ph.D.
Albany Law School, J.D.
Estate planning and taxation experience since 2011

Crystal Winn

Trust Operations Specialist

Operations

Crystal is a valued member of our operations team, using her prior experience in education accounting to ensure that everything runs smoothly. She lives in Chesterfield, NH with her partner and enjoys scrapbooking, crafting, and going to concerts in her free time.

Champlain College B.S.
Accounting and retail banking experience since 2003

Burlington

Jeanne C. Blackmore, Esq.

Vice President

Trust Counsel
Estate Planning
New Business Development

Jeanne provides in-house counsel and loves working with clients and their attorneys to achieve their estate planning goals. Before joining Trust Company of Vermont, Jeanne managed the estate planning practice at a large Burlington law firm for many years and worked in the National Office Tax Practice of Ernst & Young for over a decade. Jeanne resides in Charlotte, VT, and enjoys playing tennis and hiking with her dogs.

New York University School of Law, LL.M. Taxation 1994
University of San Diego School of Law, J.D. 1993 
St. John’s College, B.A. 1989
Admitted to bar in California, Vermont and U.S. Tax Court
ACTEC Fellow

Chris Cassidy, MBA

President & CEO

Portfolio Management
Equity/Fixed Income Analysis
New Business Development

Chris is the President of Trust Company of Vermont and manages client portfolios and provides strategic planning for the company. He first joined as an intern before graduating and joining the company full-time. He now resides in Burlington with his wife Alice, and they enjoy spending as much time as possible with their daughter Callie.

University of Vermont, M.B.A.
Skidmore College, B.A., Economics and Business
Equity research since 2002
Chartered Financial Analyst (CFA) Level II Candidate

Lynette A. Chase, CTFA

Vice President

Trust Administration

Lynette is a seasoned trust administrator and relationship manager at the Burlington Office. She joined Trust Company of Vermont after over two decades of experience in trust administration and investment management. Lynette lives in Jericho with her husband, Chris, and their pet American Foxhound, Vigor.

Certified Trust & Financial Advisor (CTFA)
Graduate of Cannon Trust School
Trust and Investment Experience since 1996

David T. Debellis, CFA

Vice President

Portfolio Management
Equity/Fixed Income Analysis
New Business Development

David is a valued member of our investment management team and serves as the chair of our Trust Investment committee. Prior to joining, he worked at Chittenden Bank for more than 10 years. David and his wife Erica live in Saint Albans with their golden retriever, Rossi. They have two adult sons, whom they enjoy spending time with whenever they can.

St. Michael’s College, B.A.
Chartered Financial Analyst (CFA) designation
Equity and fixed income management and research
Portfolio manager since 1992

View David’s personal profile. (2004)

Livia K. DeMarchis, Esq.

Vice President

Trust Counsel
Estate Planning
New Business Development

Livia is in-house trust counsel and enjoys collaborating with clients and their outside counsel to construct and fine tune estate plans. Previously, she worked as a partner in the estate planning group at a renowned Burlington law firm. With experience as a clerk for the Hon. John A. Dooley at the Vermont Supreme Court and as an associate at a well-known Boston law firm, Livia brings a wealth of knowledge to her role. She currently lives in Burlington with her husband and three children.

Yale Law School, J.D. 2010
Yale School of Forestry & Environmental Studies, M.E.M. 2005
Yale College, B.A. 2004
Admitted to the bar in Vermont and Massachusetts

Jill R. Dolan

Vice President

Financial Planning
Estate Planning
Trust Administration
IRA Administration
New Business Development

Jill is a relationship manager specializing in estate and financial planning. She has over ten years of experience and is a graduate of American University. Jill and her husband, Patrick, live in Essex Junction with their two rescue dogs, Pearl, and Sage.

American University B.A.
Trust experience since 2014

Sarah Ennis

Trust Administrator

Trust Administration
IRA Administration

Sarah serves as a Trust Administrator in our Burlington office, bringing over 18 years of banking experience from a local institution where she held various roles focused on client relationships, ensuring personalized support and expertise. A native Vermonter, Sarah resides in Burlington with her husband and cherishes time with family. In her free time, she embraces the outdoors through kayaking, cycling, and snowshoeing, appreciating Vermont’s natural beauty. 

Vermont Technical College, B.S.
Retail Banking since 2005

Daniela Fortier, MBA

Trust Administrator

Trust Administration
IRA Administration

Daniela is a Trust Administrator and collaborates by assisting clients and other members of the administration team. She joined Trust Company of Vermont after moving from Rapid City, South Dakota. Her previous role as Trust Specialist and Corporate Analyst brings a wealth of fiduciary experience to her role. Daniela enjoys traveling and currently lives in Colchester with her husband and three pugs: Maggie, Gracie and Ruby. 

National American University, M.B.A.
Clarkson University, B.S.

Tanner Freeman, CFA

Portfolio Manager

Portfolio Management
Equity/Fixed Income Analysis
New Business Development

Tanner is a committed member of our investment management team. Tanner interned with Trust Company of Vermont and was later hired after graduating from the University of Vermont. Tanner lives in Burlington, enjoys staying active, and often takes his dog, Benny, along for the ride.

University of Vermont, B.S.
Business Administration & Finance

Chris Lafayette, CFA

Chief Investment Officer

Portfolio Management
Equity/Fixed Income Analysis
New Business Development

Chris brings a wide rage of experience to the investment team, having spent 12 years managing assets at a family office in NYC, as well as an interlude helping build electric aviation company BETA Technologies. Chris currently resides in South Burlington with his wife and spends his free time coaching his children in various sports.

Stonehill College, B.S.
Chartered Financial Analyst (CFA)®
Equity and fixed income research since 2005
Portfolio manager since 2007

Cynthia McGregor

Vice President

Estate Planning
Trust Administration
IRA Administration

Cynthia’s vast experience in trust and estate administration makes her a valuable member of the Trust Company of Vermont team. As a relationship manager, she is committed to providing top-notch support to her clients in trust administration and estate settlement. Cynthia lives in Colchester and cherishes spending time with her loved ones.

Certified Trust & Financial Advisor
Graduate of Cannon Trust School
Trust and retail banking experience since 1982

Nancy mongeon

Office Manager

Office Management

Nancy is an office manager for our Burlington office. Prior to joining TCV, Nancy worked as a legal assistant for 40+ years. She lives in Milton with her husband, Ken, and enjoys spending time with their 5 grandchildren.

41 years of law firm experience

Kate Murphy

Trust Officer

Trust Administration
Probate and Estate Administration

Kate supports her clients in trust administration. Kate came to TCV with nearly two decades of legal experience, most recently as a legal assistant in probate and estate at one of Burlington’s largest law firms. Kate resides in Essex Junction with her four young children. When she is not at her children’s extracurricular events, she can usually be found knitting – often in the company of the family cat, Cousy.

University of Vermont, B.A.
Probate and estate planning paralegal since 2012

Ashley Neary, CISP

Vice President

Trust Administration
IRA Administration

Ashley is a trust administrator who collaborates with clients and their attorneys to manage estate plans. After 8 years of experience providing legal support to a busy law firm specializing in real estate, Ashley joined the Trust Company of Vermont. She currently resides in Essex Junction with her husband Ryan and their three young children who keep them especially busy.

Champlain College, B.S.
Paralegal and registered law clerk experience since 2009

Michelle L. Paracka

Trust Officer