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Ai Insurance Organization

Meet Ai Insurance Org's 'A-Team'

Ai Insurance Organization continues to grow. Here’s where you can learn more about the wonderful people that make up our amazing team! Click on our individual images to read out bios and connect with us on LinkedIn.

Senior Management Team

Randy Carroll

Chief Executive Officer

Adrian Dacanay

Director of Operations

Andy Friyia

Director of Business Development

Paul Vaughan, Director of Sales Leadership at Ai Insurance Organization

Paul Vaughan

Director of Sales Leadership

Chris Mustakas

Chris Mustakas

Director of Marketing

Aaron Truax

Chief Marketing Officer, Miller Co.

Our Team of Insurance and Surety Experts - Main Office

Jennifer Bernier

Account Executive

Judith Carrillo

Judith Carrillo

Administrator – Surety

Timmins Insurance Broker, Roxanne Crawford

Roxanne Crawford

Commercial Lines Executive

Lisa Crocker

Lisa Crocker

Sr. Commercial Lines Executive

Doug Dombroski

Sr. Commercial Lines Executive

Sabin Gautam

Bookkeeper

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Jennifer Greenway

Commercial Lines CSR

Leesa Kelly

Personal Lines Executive

Nour Khatib

Commercial Lines CSR

Sam Kotob

Commercial Lines Executive

Edwin Little

Sr. Commercial Lines Executive

Neil Macleod

Sr. Commercial Lines Executive

Muhammad Saad

Muhammad Saad

Performance Marketing & Analytics Manager

Dustin SanVido

Sr. Commercial Lines Executive

Eros Shegani

Accounting Manager

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Ada Shkalla

Operations Lead

Samantha Smith

Administrator, Surety

Naresh Vyas

Manager, Ai Life

Our Team of Experts - London Division

For more information, please visit our London Division’s page

Bradley Beer

Director of Commercial Insurance

Royston Fernandes

Commercial Account Executive

Chris Tower

Commercial Account Executive

Our Team of Experts - Lambton Division

For more information, please visit our Lambton Division’s page

Jamie Penney

Commercial & Personal Insurance

Our Team of Experts - Golden Horseshoe Division

For more information, please visit our Golden Horseshoe’s page

Ali Benham

Managing Partner, Golden Horseshoe

Our Team of Experts - 705 Insurance Division

For more information, please visit our 705 Insurance Division page

Tom Putman BW

Tom Putnam

Managing Partner, 705 Insurance Division

Shawn Tomby BW

Shawn Tomby

Commercial Account Executive

Ready to Join Our Team?

Contact Us

Randy Carroll
Chief Operating Officer

Randy Carroll is an innovative, strategically focussed advocate and architect of value creation. He is a seasoned leader who has worked with the highest level of federal and provincial politicians, government and regulatory officials, industry leaders, corporate and volunteer boards of directors, and top talent of all stripes in the pursuit of association and industry excellence.

He is a veteran of the property and casualty insurance industry and has extensive experience in a range of insurance-related organizations, from multiple vantage points, giving him unprecedented industry insights.  Coupled with this is his ability to bring complexity down to positive, actionable steps, and the tenacity to see them through to fruition, sharing successes with his team along the way.

During his insurance career, he has been an insurance broker, insurance brokerage owner, manager, and CEO of Canada’s largest Insurance Brokers Association.

He is also a Queen Elizabeth II Diamond Jubilee Medal recipient for his volunteer work with a host of insurance-related organizations, a sought-after public speaker, and a registered lobbyist.  On a personal note, Randy is a proud husband and father, softball supporter, and enjoys fishing, boating, and travel in his limited spare time.

Adrian Dacanay
Director of Operations

Adrian Dacanay is a tech-savvy insurance operations leader. He excels through people, process and systems, improving business efficiencies while maintaining regulatory requirements.

He previously worked in a sales operations and business development capacity with global analytics firms which translated well with Adrian’s foray into the insurance industry. He cemented his operational understanding of the business by servicing brokers as an insurer rep and subsequently becoming a licensed broker and co-launching his own startup brokerage.

Born and raised in Toronto, Adrian now enjoys the suburban life of Whitby, ON. He leads a very active lifestyle and enjoys running, biking, volleyball, and boxing, among other sports. In his spare time, he hones his handyman and D-I-Y skills with small home improvement projects but also longs to become a BBQ grill master.

Andy Friyia
Director of Business Development

By all accounts, Andy Friyia is a steward of the Canadian insurance industry and a trusted voice with nearly 30 years of experience as a producer, brokerage owner and VP of one of Canada’s largest pleasure craft MGA’s. He is passionate about helping others succeed through leadership, coaching and inspiring. Andy, one of Ontario Insurance’s favourite public speakers.  His education seminars have been referred to as both, “entertaining and informative” by the hundreds if not thousands that he has taught.

Since graduating from Radio College of Canada and working in the technology industry for 5 years, he found his passion for the insurance industry, producing, managing, and partnering with some of Ontario’s largest and well-known insurance brokerages. Recognized for his talent, Andy was recruited by the provincial association to sit on various committees to contribute to the success of the broker and the viability of the broker distribution channel. Andy has been credited for authoring and contributing to a number of information and education documents for the provincial association and the Insurance Institute.

Originally from Sault Ste. Marie, Ontario, and currently residing in London, Ontario, Andy married his high school sweetheart and is the proud father to Cole and Jillian. When Andy isn’t watching his children compete provincially and nationally on the golf course, you might actually find him playing a round or two of golf himself. Andy’s current passion is his Mt. Brydges Bulldogs hockey team of the Provincial Junior Hockey League, where he has served as the Coach, General Manager, Director of Hockey Operations, and currently in his third term as President and Director of Opperations.

Chris Mustakas
Director of Marketing

Chris Mustakas is a dynamic and highly energetic marketing and communications professional with over fifteen years of experience, and a track record of success in the professional sports, entertainment, public sector, and insurance industries. He is passionate about adding value to clients’ experiences and developing brand awareness through lead generation programs and designing websites.

Chris graduated from the University of Waterloo with a Honours degree, majoring in Speech Communication and minoring in Human Resources Management in 2004. While at the University of Waterloo, Chris served as Speech Communication President and President of Delta Epsilon Chi Ontario (a business and leadership organization that competed in business simulations across North America). He also wrote for the Imprint, UW’s student newspaper.  After graduating, Chris worked as the Communications Specialist for the Centre for International Governance Innovation and a Community Support Specialist for IGLOO (International Governance Leaders and Organizations Online). He went back to school in 2007 and graduated from the University of New Brunswick with a Masters of Business Administration and a Masters of Sports and Recreation Administration in 2009.  Since then, he has worked for a number of organizations including the Ottawa Senators Hockey Club, a self-storage facility, two marketing agencies, and as the Director of Marketing for two insurance companies.

Chris is originally from Waterloo but currently lives in Ottawa, Ontario. When he is not working at AI Insurance Organization, he is a freelance Marketing specialist and enjoys playing Mario Kart with his two kids, collecting vinyl records, camping, and writing a novel he intends to publish in 2021.  Pre-COVID 19, Chris could often be found at numerous concerts, following the Dave Matthews Band on tour, and playing golf, hockey and softball. He has an affinity for vintage port, sour beer, unpasteurized orange juice, and enjoys bold shirt and tie combinations.

Neil Macleod
Sr. Commercial Lines Specialist

Neil MacLeod is a dynamic and highly energetic insurance and bonding professional with over fifteen years of experience. Neil has an undergraduate in Law from Carleton University, and holds multiple insurance designations including Canadian Risk Management CRM, Associateship of Canadian Surety Bonding ACSB and the Fellow Chartered Insurance Professionals FCIP. Neil is working on the Canadian Managing General Agent (CMGA) designation

Prior to becoming a broker, Neil worked for a major Canadian insurer for over 15 years specializing in personal lines, commercial lines and Surety & Warranty business.

Neil is originally from the U.K. and emigrated to Canada as a child, growing up in the GTA. He is a huge fan of Toronto FC and is one of the original season ticket holders from 2007 and can often be found in section 119.

Jennifer Bernier
Account Executive

Jenn Bernier grew up in a family where both her parents were in the insurance industry. It therefore seemed inevitable that her career path was pre-ordained.   Jenn started her insurance career in 2002 as a receptionist at a brokerage in Durham Region and quickly learned that she genuinely enjoyed the interaction with customers.   Before too long she obtained her RIBO license so that she could assist customers with their insurance needs.

Developing relationships with her clients was extremely easy for Jen and she loved the interaction with them and the fulfilment she got from helping them migrate through the insurance process.

During her time as a broker, Jenn and her husband were fortunate enough to bring 3 beautiful children into the world – 2 boys and a girl.   After living in Durham Region for most of her life, she and her husband decided to start a new adventure and moved to Belle River in the Windsor-Essex area.   This has now become their home and they all love it.

When Jenn is not watching her kids play sports she enjoys knitting and crocheting, reading, or taking her 4th child (their French Bull Dog) out for walks.

Judith Carrillo
Administrator – Surety

Judith Carrillo brings a broad background in customer service and administration to the Approved Casualty & Surety team. New to the Surety Bonding field, Judith is excited to learn and grow with the dynamic and informative bonding team.

Continuing education has always been important to Judith and after graduating from Centennial College from the Hospitality & Tourism Administration program, she took accreditation programs in Small Business Accounting, and Administrative Studies.

Judith was born and raised in Toronto and enjoys spending quality time with her husband, two kids, and extended family. In her spare time, she likes to read, watch the latest movies, and dance salsa.

Jessica Cheshire
Digital Project Coordinator

Jessica is an enthusiastic, dynamic and organized professional with over five years of experience executing projects. Her ability to cultivate business relationships and work collaboratively along with her expertise in strategic planning, customer service, and marketing helped Jessica stand out from the rest of our applicants. She specializes in planning communication campaigns and analyzing KPIs/metrics.

After graduating from Brock with a Bachelor of Arts in Psychology, Jessica returned to school to complete her Advanced Diploma in Sports Management at Niagara College. Recently, Jessica was the Tournament Coordinator, Professional Championships for Golf Canada. There she developed two accessibility programs targeting diversity, equity, and inclusion for Professional Championships, assisted in the collaboration between the PGA TOUR, LPGA Tour, and Golf Canada for player and volunteer support, communicated with the PGA TOUR regarding event logistics and maintained relationships with vendors including hotels, AV, venues, and hospitality to support 156-player field. She coordinated volunteer training, orientation, and appreciation events attended by over 3000 participants, oversaw 20+ managing committees for each event including scoring and player hospitality, supported marketing department with email marketing deployment and CRM management, spearheaded projects including: PGA TOUR Volunteer Management Project, Professional Championships Volunteer Strategic Plan and conserved budgetary funds in 2022 by implementing virtual components to events at the Professional Championships

Sam Kotob
Commercial Lines Specialist

Sam Kotob is your everyday friendly insurance professional with over 10 years of experience in the field both inside and outside of Canada. His area of expertise lies mainly in property and casualty as well as personal lines.

Armed with experience in both commercial and personal lines, Sam helped many individuals with their entire insurance portfolio, thus bringing savings, broader coverage, and streamlined policies to his clients.

Sam graduated from Beirut, Lebanon, and worked in Lebanon, Saudi Arabia, and Dubai before immigrating to Canada in early 2018. He mixes very well with everyone and has a very friendly and professional manner.

When not working, Sam can be found reading a book, playing sports, or planning his next scuba diving trip. Sam just got married and is looking forward to building a new family in Canada.

Edwin Little
Commercial Lines Specialist

Edwin Little is a Commercial Manager with Approved Casualty and Surety. He has been with the company for the past 5 years as a broker and enjoys the different daily challenges that being a broker provides.

His family has a proud history of being in the insurance industry and his mother worked in the insurance industry for over 25 years. During his career, he has worked in a host of different industries including production, transportation and construction.

Edwin’s clients are a mix of mid-to-large contracting firms, independent business owners, and specialized occupations. Having the ability to support his clients and watching them grow is Edwin’s favourite aspect of being a broker. In fact, several of his clients were small startups when they began working with him, but have now grown their business and are on a great path for future success.

Edwin is a happy husband and stepfather to two great kids. During his downtime, Edwin enjoys being outside, renovating, reading and relaxing.

Dustin SanVido
Sr. Commercial Lines Specialist

Dustin SanVido is the in-house bonding expert and as Sr. Commercial Lines Specialist in the Bonding division for Ai Surety Bonding, he works with companies and individuals across Canada and internationally to facilitate their regular and niche bonding needs. Whether commercial or private sector, Dustin’s specialties include Fiduciary, Contract, Transportation/Customs, and Finance.

It doesn’t matter if you need to learn a basic understanding of bonding or receive assistance in either simple or complex bonding needs – he can answer and facilitate them quickly with precision.

Dustin comes from a telecommunications and construction background, bringing an unmatched enthusiasm and workman-like attitude to every interaction. He resides in Toronto, Ontario with his girlfriend and pair of Boston Terrier siblings. He has a passion for fitness, football, film, and his family. Dustin is also currently studying at McMaster University for his professional industry designation via The Surety Association of Canada.

Bradley Beer
Director of Commercial Insurance

As the Director of Commercial Insurance for Ai Insurance Organization’s new London, Ontario office, Brad Beer builds professional relationships and specialize in commercial insurance products for automotive dealerships, residential and commercial real estate, residential and commercial builders and the manufacturing sector.

Royston Fernandes
Commercial Account Executive

As a Commercial Account Executive, Royston Fernandes brings over 13 years of experience working in commercial lines builds relationships with property managers, non-profit housing, condominium owners, manufacturers, and automotive garages in London, St. Thomas, Strathroy, and surrounding areas.

Chris Tower
Commercial Account Executive

As a Commercial Account Executive for Ai Insurance Organization’s new London, Ontario office, Chris Tower builds relationships and specializes in commercial insurance products for contractors, tradespeople, home builders, and craft breweries.