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Summerhill Family Office Teams

Passionate professionals at your service

Committed professionals for your success.

All our advisors at Summerhill Family Office have the experience, knowledge and dedication to help their clients build, grow and preserve their wealth. To learn more about each Advisor,

please visit their websites as linked below. 

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John Pendrith

Senior Wealth Advisor

John Pendrith is a highly accomplished Senior Wealth Advisor with over 30 years of experience in the financial services industry. Throughout his career, he has demonstrated exceptional leadership and competence, having held senior roles at three of Canada’s leading financial institutions including National Head of Sales for a prominent independent firm.

A trusted advisor to individuals, families, and businesses, John is known for his deep understanding of all facets of wealth management. His approach is characterized by meticulous attention to detail, a commitment to excellence, and a focus on building lasting client relationships. For more than three decades, John delivered comprehensive, client-focused advisory services. He has built a reputation for reliability, innovation, and delivering results in complex financial landscapes.

John’s extensive experience, strategic acumen, and passion for helping clients achieve their financial goals have established him as a leader in the industry. With an expertise in developing bespoke financial strategies, John is committed to providing best-in-class solutions that meet the unique needs of every client.

Collaborating Partners

At Summerhill Family Office, we are proud to partner with financial planners and insurance providers from iA Financial Group to offer a comprehensive suite of services tailored to meet the unique needs of each client. By bringing together a network of like-minded professionals, Summerhill Family Office serves as a collaborative hub where independent professionals can work seamlessly to deliver top-tier financial planning, investment strategies and insurance solutions. 

Our goal is to combine the experience and knowledge of our partners with a client-centered approach, ensuring personalized, strategic guidance that empowers clients to achieve their financial goals with confidence and peace of mind. 

Together, we are committed to providing exceptional service while fostering long-term relationships built on trust and mutual success.  

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Jake Sheehan

Estate Planning and Insurance Specialist
Life Design Systems
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Brett Okorofsky

Estate Planning and Insurance Specialist
OKO Financial
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*Products and services provided by third parties, including by way of referral, are fully independent of those provided by iA Private Wealth Inc. Products offered directly through iA Private Wealth Inc. are covered by the Canadian Investor Protection Fund, subject to exception. iA Private Wealth Inc. does not warrant the quality, reliability or accuracy of the products or services of third parties. Please speak to your advisor if you have any questions.

Get in touch

Our team of professionals is available by phone or email.

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Jake Sheehan

Estate Planning and Insurance Specialist, Life Design Systems

Jake Sheehan and his team specialize in guiding business owners and professionals through the intricacies of insurance, tax, estate, and retirement planning. With a focus on simplifying complex financial landscapes, Jake developed a unique modeling system, providing clients with fresh perspectives on their current situations and potential life scenarios. His mission is to streamline decision-making, enabling clients to redirect their focus towards what brings them joy.

Bringing a wealth of expertise, Jake holds designations such as Chartered Life Underwriter (CLU), Trust and Estate Practitioner (TEP), and Family Enterprise Advisor (FEA). Committed to client comprehension, he employs visual narratives to convey intricate structures, fostering a deeper understanding for both clients and professionals. Active within the industry, Jake sits on the Board of Directors for CALU and currently contributes to the STEP Membership Committee. He is grateful for the support of ChatGPT in crafting his bio.

Brett Okorofsky

Estate Planning and Insurance Specialist, OKO Financial

With nearly two decades of experience, Brett specializes in strategic planning for professionals, business owners, high-net-worth individuals, ultra-high-net-worth families, and their estates. His expertise spans wealth accumulation, tax optimization, and risk management, using advanced insurance strategies to protect and grow financial legacies.

Along with his team, Brett helps clients navigate complex financial challenges to achieve their long-term goals, crafting personalized strategies tailored to each client’s unique needs and values. By prioritizing transparency and trust, he provides clear guidance, allowing clients to focus on what matters most to them.

Brett holds a Bachelor of Commerce degree and is an active member of the Conference for Advanced Life Underwriting (CALU) and Advocis. He is also a proud supporter of Crohn’s and Colitis Canada. Outside of work, Brett enjoys spending time with his two sons, skiing, and playing hockey.