A legacy of dedication
Gerry began his journey as an advisor in 1989 with a simple but powerful goal: to provide exceptional service by truly understanding each Client's needs. Over the years, the philosophy has remained unchanged. What started as a one-person practice has grown into a dedicated team that includes his son, Michael, DJ, and a skilled support staff - bringing together over 45 years of combined experience in life insurance, health protection, and wealth strategies.
While our team has grown, our commitment to personalized care, trust, and long-term relationships remains at the foundation of everything we do. Whether you're planning for retirement, building your business, or protecting your family's future, we're here to guide you with honest advice and solutions designed to fit your life. Many Clients have been with us for decades - and now trust us to support the next generation.
We're proud to be a team that puts people first, always.
O'Brien and Associates Financial Services Inc.
Your financial strategy should be as unique as you are. Whether you’re just starting out, about to enter retirement, or somewhere in between, a strong financial roadmap can help you reach your short and long-term goals. Let’s work together to protect what matters most to you and help you secure your future. Reach out to get started. Let’s get you there.

Gerry O'Brien
Gerry O’Brien is a seasoned CERTIFIED FINANCIAL PLANNER® with over 36 years of experience guiding Clients through the complex world of insurance, retirement, and wealth planning. As the founding advisor behind O’Brien & Associates Financial Services Inc., Gerry has built his reputation on trust, transparency, and results. His holistic approach blends strategic financial planning with a deep understanding of each Client’s goals - whether they’re individuals, families, or business owners.
Known for his creative problem-solving and depth of knowledge, Gerry focuses on advanced estate strategies, business succession planning, and long-term wealth preservation. Over the decades, he’s helped generations of Newfoundlanders make confident decisions about their financial futures - and now serves Clients both locally and across Canada.
More than an advisor, Gerry is a mentor and trusted voice in the industry. Client relationships often span decades, with many now entrusting him to guide the next generation.
Outside the office, you’ll likely find Gerry spending time with his family at the cabin, enjoying the peace of nature, or out on the golf course.
Job Title: Financial Planner, Sun Life, CFP®
BBA, CH.F.C., CLU®, RHU
Phone: (709) 706-0046
Email: gerry.obrien@sunlife.com
Address: 40 Commonwealth Ave

Michael O'Brien
Michael O'Brien is a dedicated Sun Life advisor with 7 years of experience helping Clients create and preserve their wealth. Having grown up in the industry alongside his father, Gerry O'Brien, Michael brings both generational insight and a modern approach to financial strategies. A proud graduate of Memorial University with a degree in business, he holds both insurance and wealth licenses and is currently finalizing his Certified Financial Planner designation.
Michael works with a wide range of Clients - from families and first-time homebuyers to professionals, business owners, and high net-worth individuals. His goal is always the same: to provide personalized strategies and trusted guidance that help Clients in Newfoundland and beyond build lasting financial security. With early exposure to advanced planning through years of mentorship and shadowing Gerry, Michael brings clarity and confidence to every Client conversation.
Outside the office, you'll find him playing soccer in the top-level Provincial League Challenge Cup, or spending time with his partner and their two huskies.
Job Title: Advisor, Sun Life, BBA
Phone: (709) 706-0046
Email: michael.obrien@sunlife.com
Address: 40 Commonwealth Ave

DJ Clarke
DJ Clark is a dedicated Associate Advisor at O’Brien & Associates Financial Services Inc., committed to helping Clients across Newfoundland and beyond navigate their financial journey with clarity and confidence. Whether it’s purchasing a first home, planning for retirement, growing investments, or managing life’s unexpected turns, DJ delivers personalized strategies and trusted guidance tailored to each Client’s goals.
Rooted in transparency, trust, and genuine care, DJ takes pride in building lasting relationships and helping Clients make informed financial decisions that support long-term stability and peace of mind.
Outside of work, DJ enjoys spending time with his wife, Kira, and their two dogs, Harper and Dobie - often found out for a walk, a game of catch, or enjoying the outdoors together.
Job Title: Associate Advisor, Sun Life, B.Comm.
Phone: (709) 706-0046
Email: dj.clarke@sunlife.com
Address: 40 Commonwealth Ave

Ryan McFarlane
Ryan began his journey with O’Brien & Associates as a Memorial University work-term student four years ago. After graduation, he joined Sun Life as an advisor, where he gained valuable experience helping young professionals begin their financial journey. He’s excited to be back with the O’Brien team in a new role and finds motivation in working within a team that is deeply committed to maintaining a high standard of Client service.
Outside of work, Ryan enjoys staying active at the gym and experimenting with new recipes to share with his family and friends.
Job Title: Associate Advisor, Sun Life, BBA
Phone: (709) 706-0046
Email: ryan.mcfarlane@sunlife.com
Address: 40 Commonwealth Ave

Chantelle Lynch
Chantelle Lynch, our supportive Office Manager, has been a proud member of the Sun Life family for over a decade. She’s committed to creating a fair, healthy, and efficient workplace where every team member feels appreciated and empowered – helping us deliver the best possible Client experience.
Outside of work, Chantelle is family-focused, sharing life with her husband, two teens, and their beloved rescue dog, Ozzie. A passionate supporter of animal rescue, she enjoys volunteering, staying active outdoors, and finding joy in the simple things and the beauty of nature.
Job Title: Advisor Assistant, Sun Life | Office Manager, O'Brien and Associates Financial Services Inc.
Phone: (709) 706-0046
Address: 40 Commonwealth Ave

Sarah O'Toole
Sarah has been a valued part of the O’Brien & Associates team since June 2022. In her role as a Client Service Assistant, she strives to deliver exceptional customer service and takes pride in helping Clients make informed financial decisions with confidence.
With many years of office experience across different fields, Sarah brings both knowledge and versatility to support Clients’ needs. She also enjoys assisting her co-workers and is always ready to lend a helping hand—believing that a collaborative work environment is essential to any business’s success.
Outside of work, Sarah enjoys going for walks with her dogs and spending quality time with her spouse and daughter. She’s also an avid golfer and enjoys connecting with friends and family.
Job Title: Advisor Assistant, Sun Life | Client Service Assistant, O'Brien and Associates Financial Services Inc.
Phone: (709) 706-0046
Address: 40 Commonwealth Ave

Morgan Knee
Morgan has been a part of the O’Brien and Associates team since 2022 as a licensed Service Associate. She is dedicated to helping people navigate their needs and achieve their goals. Her background in business equips her with the skills to provide effective support and solutions.
Outside of work, she enjoys spending time in nature and camping with her fiancé, along with their two dogs and cat - something that keeps her grounded and inspired. She believes that fostering positive relationships is key to success, both personally and professionally.

Jodi Dodge
Jodi has been with O’Brien and Associates since June 2024. She brings over 30 years of experience in both administration and Client care. She is proud to work alongside like-minded professionals who are committed to supporting Clients' success and working collaboratively to help them achieve their financial goals.
She thrives in a fast-paced, positive work environment. In her spare time, she enjoys refinishing wooden furniture and crafting, allowing her to hone in on her creative side.

Rebecca Sheppard
Rebecca started working in the financial industry in 2018 where she deepened her understanding of the financial sector and achieved her Mutual Funds registration. In November 2024, she transitioned to O'Brien and Associates, and is excited to continue her professional growth and provide exceptional service to Clients.
In her spare time, she enjoys running during the summer months and skating in the winter, which allows her to maintain an active lifestyle and enjoy the outdoors. Balancing professional and personal interests is important to her, and she strives to bring that same balance to her work, helping Clients with care and dedication.

Nick Skinner
Beginning as a work term student at O’Brien and Associates, Nick quickly moved into a part-time role focused on business development and assisting the advisors. While continuing to work on his business degree at Memorial University, he supports the advisors by helping grow the business and improve the overall Client experience.
With plans to become an advisor after graduation, Nick have gained early and valuable experience in financial planning and Client service. Being part of a team that supports each other’s growth and is dedicated to helping Clients has had a big impact on his career path.
Outside of work, he enjoys staying active through working out and martial arts. He also loves spending time with family and friends, exploring new business ventures, and travelling.

Alissa Brothers
As a Client Service Assistant, Alissa is dedicated to helping Clients while ensuring a seamless and personalized experience. She brings a strong foundation in customer service and a unique perspective from her previous career as a teacher. These skills enhance her ability to listen, understand, and empathize with Clients’ needs.
Alissa is passionate about building lasting relationships and is committed to delivering service that reflects both care and professionalism. Her transition into the financial industry is driven by a desire to make a meaningful impact on people's lives through clarity, support, and trust.
Outside the office, Alissa enjoys getting lost in a good fantasy novel, spending quality time with friends and family, and planning her next travel adventure.
Job Title: Advisor Assistant, Sun Life | Client Service Assistant, O'Brien and Associates Financial Services Inc.
Phone: (709) 706-0046
Address: 40 Commonwealth Ave

Shivani Thakur
Shivani recently joined O'Brien & Associates and brings a background in physics along with a growing passion for finance, marketing, and Client service. She enjoys being a part of the team's marketing efforts and especially value the opportunity to engage with Clients and support their financial journey.
She is someone who appreciates actionable goals and enjoys connecting big-picture thinking with practical, people-focused solutions. Outside of work, you'll often find her stargazing or exploring the beautiful trails around St. John's.
Job Title: Advisor Assistant, Sun Life | Client Service Assistant, O'Brien and Associates Financial Services Inc., B.Sc.
Phone: (709) 706-0046
Address: 40 Commonwealth Ave

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