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About Helewa Financial

Helewa Financial Group Inc. is a GTA–based holistic financial planning firm that has been in business for over 50 years. Our experienced team provides honest advice, helping individuals achieve their financial goals through personalized planning and strategic investment strategies.

With a strong track record of success and commitment to excellence, we pride ourselves on building long-term relationships based on trust, integrity, and results. We will provide honest advice, every time.

The Motivation Behind the Vision

My father immigrated to Canada in 1970 with two young children to support. He began selling insurance door-to-door with Prudential, likely unaware of the legacy he was creating as he knocked on doors throughout the 1970s and 1980s. My brother and sister both pursued careers as actuaries, and I believe my father hoped I would follow a similar path.

While I loved math and problem-solving, my true passion lay in connecting with people. I knew I wanted to follow in my father’s footsteps but convincing him would be my greatest challenge. I joined him in 2003, where he dedicated his days to coaching and pushing me—perhaps in hopes I would reconsider and become an actuary instead. The financial services industry was evolving, with estate planning and independent business models still emerging concepts. Yet, I could already see the solid foundation my father had laid.

As I immersed myself in the business, I fell in love with it. I witnessed my clients starting families, small accounts blossoming into larger investments, and the business my father had built beginning to thrive. I celebrated significant milestones with my clients and learned to provide steadfast support during challenging times. Simultaneously, my own family was growing, and as the company expanded, I realized I was building it all for them.

In my drawer, I keep a sheet of paper listing the goals I set for myself. Once a year, I revisit it, amazed at how many our team have accomplished. I dreamed of owning my own corporate office, focusing on helping families build generational wealth, establishing an employee benefits sector, and creating a workplace where employees would feel proud to belong. Through hard work and dedication, we’ve turned those dreams into reality.

Today, my goal is to keep building a company that my kids might want to work for one day—but who knows, they might decide to become actuaries instead!

Our Team

Paul Helewa

Senior Partner

Paul Helewa

After completing his studies at York University, Paul joined the family business, working closely with his father and gaining invaluable experience in the financial sector. His passion for the industry and his commitment to the family legacy led him to acquire the business in 2010. Under his leadership, the business was incorporated and established as Helewa Financial Group Inc.

Paul’s entrepreneurial spirit and dedication to excellence drove the continued growth of Helewa Financial Group Inc. In 2020, he partnered with Courtney West to create Northway Financial Consultants Ltd., a venture focused on employee benefits.

Courtney West

Senior Partner

Courtney West

Courtney attended Western University, focusing on Political Science and Women’s Studies. Courtney’s professional career began in the insurance industry, where she held various roles at major insurance companies. Her expertise and dedication led her to her final position as an Account Executive for Group Benefits at one of Canada’s top three insurance carriers.

In 2020, Courtney founded Northway Financial Consultants Ltd., driven by her vision to offer superior client service and support. Under her leadership, Northway quickly gained recognition for its commitment to integrity and client care. Courtney has now taken a more active role in running the day-to-day operations of both Northway Financial Consultants Ltd and Helewa Financial Group Inc, bringing the companies together with a combined vision and direction.

Crystal Armstrong

Director of Operations

Crystal Armstrong

With over 15 years of experience in the insurance industry, Crystal has built a rewarding career in sales and operations. Since 2007, she has specialized in providing exceptional customer service and optimizing efficiencies. Currently, her primary focus is on operations, where she supports the team in ensuring seamless service and performance. Crystal’s deep industry knowledge enables her to equip the team with the necessary tools and support for success. Outside of work, Crystal enjoys camping with her husband and their energetic boys, creating lifelong memories.

Donna Macklem

Executive Assistant

Donna Macklem

With over a decade of experience working with clients, Donna’s goal is to always ensure a friendly voice on the other side of the phone. She prides herself on being detail-oriented and efficient in everything she does. In her spare time, Donna enjoys spending time with her husband, daughters, and grand dogs.

Alana Capesky

Executive Assistant

Alana Capesky

Making sure clients feel heard and valued is Alana’s top priority. She takes pride in being attentive to clients’ needs and working diligently to address them with care and fairness. Alana strives to see things through to completion, ensuring every detail is taken care of, allowing clients to focus on what matters most to them. In her spare time, Alana enjoys spending time outdoors and enjoying quality moments with her loyal companion, Hudson the dog.

Elizabeth Calderone

Director of Employee Benefits and Pension

Elizabeth Calderone

With over 12 years of experience in the insurance industry, including a decade as an Account Executive with a major insurance carrier, Elizabeth has managed small to medium-sized clients nationally. Before pursuing a career in insurance, she earned a Bachelor of Science in the U.S. and a Master’s in Human Biology and Nutritional Science from the University of Guelph. An accomplished soccer player with experience in both Canada and the U.S., Elizabeth is passionate about sports, health, and nutrition. Outside of work, she enjoys spending time with her husband and three young children.

Katrina Stocco

Director of Client Service – Employee Benefits

Katrina Stocco

An experienced professional with a customer-first focus in the Employee Benefits industry, Katrina has a proven track record of delivering positive and relatable employee benefits education sessions, as well as plan administration training. With 8 years of experience working with a top insurance carrier, Katrina has gained a deep understanding of the diverse needs of businesses when it comes to managing their benefits plans. On a personal level, Katrina enjoys spending time with friends, hiking, being outdoors, and playing board games in her free time.

Alex Nehme

Paraplanner

Alex Nehme

Alex graduated with a bachelor’s degree in accounting from the University of Guelph in May 2024, where he developed an interest in financial planning and asset management. In July 2024, he joined Helewa Financial as a Paraplanner, assisting with portfolio construction, updating financial plans, and participating in client meetings. Alex is also a CFA Level 1 Candidate, working towards certification. Outside of work, Alex enjoys sports, fitness, and spending quality time with family.