Our
Team

Our founders and second and third generation family members work with an expert team of professionals to bring the best in service and solutions to our clients.

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Our
Founders

Frank
Ciccolini Sr.

Founding Partner (1966 – 2020)

The late Frank Ciccolini Sr. co-founded Masters Insurance with his brother Sam in 1966. His foresight and compassion laid the foundation for the company’s acclaimed customer service.

Our Tribute

In Loving Memory 

In the 1950s, Frank Ciccolini Sr., a recent arrival in Canada himself, recognized a pressing concern among fellow newcomers in the booming construction industry – many were equipped with ambition and skill but lacked a financial safety net to withstand life-altering accidents, injuries, or liabilities. Frank Sr. felt a deep connection to these hardworking individuals and made it his mission to safeguard their dreams and livelihoods.

He bridged the language barrier between insurers and the Italian community, advocating fiercely on their behalf. He juggled demanding hours at a cardboard factory with his ambition to build an insurance business that truly cared.

Each evening, after his cherished 5 p.m. mealtime with family, Frank Sr. would visit potential clients in their homes. His wife Jennie arranged these appointments, each one a step towards securing a better future for his community. Not surprisingly, Frank Sr. became one of the top producers for Mutual of Omaha, Canada.

Sam
Ciccolini

Founding Partner

A Founding Partner of Masters Insurance, Sam Ciccolini is an entrepreneur, active volunteer, philanthropist and, most importantly, a friend to all.

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Sam Ciccolini Founding Partner 

A Founding Partner of Masters Insurance, Sam Ciccolini is a highly regarded figure in the insurance industry. Sam’s approach to business has always been personal and collaborative; he believes in working alongside staff rather than above them, constantly staying attuned to their daily concerns, as well as the needs of clients.

Beyond his entrepreneurial success, Sam has always been deeply committed to charitable causes. Over the years, he has given his active support to more than 80 organizations in Canada, underlining his longstanding commitment to building resilient communities and elevating the quality of life for those less fortunate.

Sam’s commitment to his community has been recognized through many distinguished awards, including the Canada 150 Community Leader Award in 2017, the Vaughan Chamber of Commerce Philanthropic Business Person of the Year Award in 2011, and the National Congress of Italian Canadians-Toronto District Order of Merit Award in 2010. He was also a recipient of Her Majesty the Queen’s 50th Jubilee Medal for his contribution to the community and is a member of the Order of Canada, Order of Ontario, Order of Vaughan, and a Commander of the Order of the Star of Solidarity, an honour conferred upon him by the Italian Republic. In 2013, he was vested with a doctor of law honoris causa from Assumption University of Windsor, and he was honoured as a Master Philanthropist by Community Living Mississauga in 2018.

 A sports enthusiast, particularly when it comes to hockey, Sam has founded or chaired several prominent hockey leagues in the GTA. He fervently believes that nurturing a love for the sport among today’s youth not only upholds Canada’s cherished hockey tradition but also shapes players into responsible citizens.

Sam cherishes the love and support of his wife, Donna, his pillar for over 57 years. Together, they have two children: Michael, now a second-generation partner at Masters Insurance, and Cristina (1975-1985), whom they lost tragically young to Fanconi’s Anemia. Cristina’s memory remains vivid in the hearts of the Ciccolini family. Sam’s joy in life is further amplified by the presence of his three cherished grandchildren.

Max
Ciccolini

Partner

Shifting from education to insurance, Max Ciccolini joined his brothers at Masters Insurance in 1972 and currently guides our accounting operations.

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Max Ciccolini Partner 

In 1972, Max left a teaching career with the Toronto Board of Education to join his brothers at Masters Insurance. He oversaw administration and finances, strengthening the foundation of their growing insurance agency. An alumnus of the Ontario Institute of Secondary Education at the University of Toronto, Max taught history and economics at Danforth Collegiate. Today, Max is the backbone of Masters’ finance operations. His meticulous oversight spans accounting, compliance and policies, delivering efficiency and excellence to both clients and staff. His strength of character, financial acumen and organizational skills place him at the heart of Masters’ operations.

Gary
Corby

Partner

Since 1981, Gary’s expertise and recognition in the surety industry have been vital in shaping Masters into a respected brokerage with strong community ties.

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Gary Corby Partner 

Gary Corby, a Founding Partner of Masters Insurance, brings with him a wealth of experience and recognition in the surety bond industry. Hailing from the east end of Toronto, he has been instrumental in shaping Masters Insurance into a respected insurance brokerage deeply rooted in the community. 

Beginning his career in the early 1960s, Gary joined the Aetna Casualty and Surety Company, a global leader in the surety industry. His dedication and expertise took him to various locations across the US before returning to Toronto. He then joined The Guarantee Company of North America, where he served as the bond manager for Ontario and Western Canada.

In 1981, Gary Corby joined close friend Sam Ciccolini, alongside Frank Sr. and Max, to solidify the Masters partnership. With Gary’s invaluable contributions, the agency emerged as a construction-oriented commercial insurance leader, known for its unwavering commitment to the industry and community. 

Gary’s passion for sports, exemplified by his hockey career at St. Lawrence University, reflects his enduring enthusiasm for excellence.

With 35+ years in the insurance industry, Rita is dedicated to improving the lives of others. After graduating from York University in 1984, she joined her late father, Frank Sr., at Masters Insurance, leading the Personal Lines unit. In 1997, Rita took the helm of the Groups Benefits Unit at Masters Life Insurance Agency Limited, continuing her commitment to enhancing client experiences.

Rita
Ciccolini

Partner | Group Benefits

Frank Jr. joined Masters in 1986 at the inception of Masters Life Insurance Agency Limited, specializing in life, estate and investments and as a general partner in Group Benefits and Pension Consulting. He achieved his Bachelor of Commerce degree at the University of Toronto.

Frank
Ciccolini Jr.

Partner | Financial

Following her studies in the Mathematics for Commerce program at York University, Cathy joined Masters Insurance in 1987. She leads the Commercial/Construction team, fostering industry partnerships and overseeing relationships for our largest clients.

Cathy
Ciccolini

Partner | Commercial

A highly respected Wealth Advisor, Patrick specializes in life insurance and investment needs for individual and corporate accounts at Masters Life Insurance Agency Limited. He joined Masters in 1994 after receiving his Bachelor of Commerce degree at the University of Toronto.

Patrick
Ciccolini

Partner | Financial

After achieving a Bachelor of Arts and Political Science degree at the University of Western Ontario, Michael began his career at a major Canadian insurance firm. With his experience and industry insight, he joined Masters in 1996, leading the Commercial Lines department and driving the company’s growth initiatives.

Michael
Ciccolini

partner | Commercial

Robert achieved his Bachelor of Business Administration (BBA) degree from York University’s Schulich School of Business, specializing in marketing and finance. He leads the Commercial and Construction Insurance departments, and oversees production and marketing initiatives for the company.

Robert
Ciccolini

Partner | Commercial

Anthony drives Master’s operational initiatives, liaising with industry partners to ensure product innovation. He also oversees IT operations and provides support to the Accounting department. Anthony completed his Bachelor of Commerce degree at York University’s Schulich School of Business and joined Masters in 2004.

Anthony
Ciccolini

Partner | Commercial

After graduating from Virginia Tech on a full golf scholarship, Doug joined Masters in 1987 and led the opening of the Hamilton office in 1989, specializing in Contract and Developer Surety. His wife, Heather, and their three children, Doug Jr, Rebecca and Will, also work at Masters.

Doug
Corby

partner | Surety

After graduating from Michigan State University, Wade joined Masters’ Surety department in 1989, upholding our legacy as Canada’s top surety provider. His daughters Annie and Kailey also work at Masters.

Wade
Corby

partner | Surety

After graduating from Virginia Tech University, Mark joined Masters in 1993, overseeing the Commercial Lines department in Hamilton with his brother, Doug. A hockey and baseball coach for over 20 years, he’s also deeply committed to family, including his kids, Jacob and Mary, who are members of the Masters team, and his youngest child Beau.

Mark
Corby

partner | COMMERCIAL

Our
Business Development Team

Adam
Beck

Surety

Adil
Darr

Surety

Angela
Slokar

Commercial

Angie
Procopio

Commercial

Annie
Corby

Commercial

Christina
Rocchetta

Human resources

Domenic
Tucci

claims

Doug
Corby Jr.

SURETY

Elena
Piacentini

Financial

Eric
Ciccolini

commercial

Erik
van der Schyff

OPerations | IT

Erwin
Luzar

commercial

Felicia
Molella

Group Benefits

Frank
Scarano

Personal | Programs

Glen
McCurdie

Commercial

Jake
Corby

Commercial

Jason
Osborne

training | operations

Joe
Tucci

Personal

Justin
Burke

Surety

Kailey
Corby

Surety

Karen
Ramsey

Surety

Karen
Yiin

Marketing

Kim
Gilmour

personal

Lee
Okrainec

claims

Linda
Brown

human resources

Linda
Valente

Group benefits

Lucy
Marra

Commercial

Mary
Apreda

Accounting

Mary
Corby

Commercial

Mike
Naples

SURETY

Rebecca
Corby

Accounting

Sean
Caley

Commercial

Tom
Kersch -baumer

Commercial

Victoria
De Toma

Human Resources

Will
Corby

Financial

Zachary
Patterson

Group benefits

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