Fall family walk

About Our Team

Olivera (Hollie) Winkelaar

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.

Job Title: Financial Planner, Sun Life, QAFP®

Languages spoken: English, Romanian, Serbian

Phone: (825) 551-0444

Email: hollie.winkelaar@sunlife.com

Address: 6700 Macleod Trail SE, 7th Floor, Calgary, AB, T2H 0L3 Canada

Olivera (Hollie) Winkelaar

Navigating the complexities of the financial world can often induce fear and uncertainty. Having faced the realities of entrepreneurship and the financial pressures that come with it, I understand these challenges personally. As a Financial Planner at Sun Life, I aim to alleviate these pressures and fears and provide a pathway to financial security and growth.


Moving to Canada when I was 14, I experienced the challenges of adapting and rebuilding life in a new country. This journey instilled in me strong resilience and an understanding of diverse perspectives. This greatly informed my approach to financial planning.


My diverse professional experiences, spanning various roles within the banking sector and managing my own business, have equipped me with a unique perspective on financial matters. This allows me to genuinely understand each Client's financial concerns and devise strategies tailored to their needs and objectives.


The value of continuous learning has been a guiding principle in my career. With a Financial Diploma, a bachelor’s degree, a QAFP™ certification, and currently pursuing a Financial MBA, I bring a robust and holistic approach to financial advice. This academic expertise and practical experience enable me to provide Clients with well-rounded financial advice.


In my role at Sun Life, my aim is to help Clients shed their financial fears. By working together, we can develop a financial plan that respects your present circumstances and future ambitions. I look forward to being part of your journey toward financial stability and success.

Job Title: Financial Planner, Sun Life, QAFP®

Languages spoken: English, Romanian, Serbian

Email: hollie.winkelaar@sunlife.com

Address: Calgary, Alberta

Cassandra Winkelaar

Cassandra Winkelaar is the office coordinator for Olivera (Hollie) Winkelaar.


She is currently enrolled in the Haskayne School of Business at the University of Calgary, Cassandra Winkelaar fosters a rich skill set, including accounting, law, Client relations and administrative management. Cassandra’s talent for understanding and anticipating Client needs amplifies her professional acumen, making her an integral team player.


Outside her professional life, Cassandra was an international artistic swimmer and is currently a national level technical controller and judge in the sport. This competitive background has fostered resilience, teamwork, and problem-solving abilities which she has seamlessly transitioned into her professional persona.


Embracing continual growth, Cassandra is diligently working towards her Life License Qualification Program (LLQP) certification and embarking on an exciting journey to learn American Sign Language (ASL). These pursuits showcase her unwavering commitment to personal and professional development.


With her multifaceted skill set, commitment to excellence, and leadership abilities, Cassandra makes an important contribution to our team. 

Job Title: Advisor Assistant, Sun Life

Languages spoken: English

Phone: (825) 551-0400

Email: cassandra.winkelaar@sunlife.com

Address: Calgary, AB

Braelyn Bogdanov

Braelyn Bogdanov is the Marketing Coordinator for Olivera (Hollie) Winkelaar.


Braelyn is a Bachelor of Technology graduate and is a dynamic individual with a unique blend of technical expertise with a background in Interior Design Technology. Born with an innate curiosity, Braelyn has successfully merged her passion for design with a keen interest in the ever-evolving world of digital marketing.


With a background in Interior Design Technology, Braelyn brings

a discerning eye for aesthetics to her marketing adventures. Her ability to seamlessly integrate creativity and technology sets her apart, making her a versatile professional ready to tackle the challenges of the digital era.


Beyond the academic realm, Braelyn's multifaceted personality is

evident in her diverse range of interests. In her spare time, she immerses herself in the world of literature, drawing inspiration from various genres. An avid reader, Braelyn finds solace in the pages of a good book and uses it as a means of broadening her perspectives. Braelyn finds joy in spending quality time with her fiancé, Megan, and their two dogs, Toretto, and Douglas.

Job Title: Advisor Assistant, Sun Life, B.Tech

Languages spoken: English

Email: braelyn.bogdanov@sunlife.com

Address: Edmonton, AB

Estate & Financial Planning Services (EFPS)

EFPS team collaborates with the Financial Planner to facilitate aid with Estate Planning, Taxation Strategy, Business Continuation Planning, Estate Planning, Succession Planning, and Retirement Planning.

Have questions?

Here to help answer your questions, provide clarity about products and get you started on the road to achieving your goals.