Meet the Team at Rich Strike Estate and Investment Planning

At Rich Strike Estate and Investment Planning, our team is more than just financial experts — we’re a tight-knit group of individuals dedicated to guiding you toward your financial goals with a laid-back approach and a touch of camaraderie.


John Saikaley CHS®, CEA

Founder And CEO - Rich Strike Estate And Investment Planning
Financial Advisor*

John Saikaley is a seasoned professional with over three decades of experience in the financial services industry, known for his keen financial insights and adventurous spirit. Beyond the boardroom, he’s just as passionate about cheering on his favorite teams, from the Miami Dolphins to the thrill of horse racing. You’ll often find him trading golf swings for stories with friends on Fridays, valuing camaraderie over keeping score. Committed to making a positive impact, John actively engages in charitable endeavors, embodying a humble dedication to giving back to the community.

John is licensed for mutual funds in the Provinces of Ontario and Quebec, and Life and Health Insurance in the Province of Ontario.

*Mutual funds are distributed through Desjardins Financial Security Investments Inc. 

Ben Headrick

Financial Advisor

Ben Headrick is an Investment Specialist on John Saikaley’s team at Rich Strike Estate and Investment Planning, dedicated to crafting and safeguarding clients’ wealth. Armed with an Economics degree from Carleton University in 2020, Ben brings a blend of analytical prowess and strategic insight to financial security planning. Off-duty, he’s often found hitting the ice or the green, drawing on lessons of teamwork and perseverance from his love of hockey and golf. Ben’s genuine passion lies in helping clients realize their financial aspirations, committed to walking alongside them as a trusted guide toward a secure financial future.

Ben is licensed for mutual funds and Life and Health Insurance in the Province of Ontario.  

Rebecca Saikaley

Director of Marketing and Communications - Rich Strike Estate & Investment Planning
Administrative Assistant

Rebecca Saikaley is an integral part of John’s team, driven by a love for growth and forging meaningful connections while amplifying the brand. Whether crafting engaging marketing strategies or navigating the ever-changing market landscape, Rebecca seamlessly blends creativity with strategic vision. With a knack for seeing the bigger picture, she thrives on tackling new challenges with enthusiasm and finesse. Rebecca’s genuine commitment to fostering growth and delivering value to both the team and clients alike sets her apart as a reliable ally in the journey toward success.

Jodi Keefe

Financial Advisor

Jodi Keefe serves as a dedicated life specialist on John Saikaley’s esteemed team at Rich Strike Estate & Investment Planning, driven by a genuine desire to secure clients’ financial futures. With a focus on transparency and integrity, Jodi partners closely with clients to navigate their financial journey, providing tailored strategies and peace of mind. Drawing on nine years of industry experience, she brings a wealth of expertise to every interaction, ensuring clients feel empowered and informed every step of the way. Jodi’s unwavering dedication to her clients’ financial well-being is matched only by her down-to-earth approach and commitment to delivering personalized solutions.

Jodi is licensed for mutual funds and Life and Health Insurance in the Province of Ontario.

Tori Smith

Executive Administrative Assistant

Tori Smith serves as John’s executive assistant, specializing in efficiency and organization. With a keen eye for detail, Tori ensures seamless support for our clients and smooth operations in the office. From scheduling appointments to coordinating client meetings and processing transactions, she manages various administrative tasks with precision and care. Tori’s meticulous attention to detail and dedication to providing exceptional support enable John to focus on delivering personalized financial solutions to his clients. Committed to providing outstanding service, Tori is here to assist you every step of the way on your financial journey.