This section is by PBY Capital.

How three family offices use ‘shadow AI’ to manage complexity

Commonly available AI tools are not a replacement for human expertise. But they can be ‘a speedy complement’

AI is slowly infiltrating the family office space, helping advisors manage meetings, analyze swaths of data and engage employees.

Story continues below

But while few firms are undertaking major, enterprise-size AI projects—a recent MIT study found that only 5 per cent of AI pilot programs achieve revenue acceleration—the use of so-called “shadow AI” is thriving.

Employees using personal tools like ChatGPT or Microsoft Copilot are often getting more tangible results than any sanctioned, top-down initiatives.

Jaz Gill

Jaz Gill, senior vice-president for technology and operations at Northwood Family Office, says AI is a catalyst that can drive operational excellence and improve both client and employee experience. “Unlocking the potential of AI, while ensuring robust data governance and maintaining the security of our client information, is paramount,” he says.

How are Canadian family offices using AI? Most, it turns out, are using it to simplify and speed up administrative tasks, prepare reports on investment outcomes, crunch numbers and help inform decision-making. They are using Perplexity, ChatGPT and Grok 3, which are general-purpose, conversational AI tools.

Some are employing more sophisticated software, however, that uses industry datasets to help investment managers and asset managers enhance their research, automate tasks and improve decision-making. 

“I firmly believe that AI is not a replacement for human expertise—it is a speedy complement,” says Vancouver-based Thane Stenner, senior portfolio manager and senior wealth advisor, Stenner Wealth Partners+ CG Wealth Management Canada and USA.

“The technology reduces administrative burdens and accelerates workflows. But the judgment, editing, context and strategic advice that clients rely on remains firmly human-led.”

Here are some ways AI is being put to work in family offices across Canada.

Data analysis

Gill says Northwood uses Microsoft’s Copilot to transcribe and summarize internal and external meetings in real-time. “This allows all attendees to be focused on the conversation while ensuring that critical decisions and action items are documented and shared,” he says.

Story continues below

They also use the software to process data from inside and outside Northwood, which improves decision-making, he says.

Stenner Wealth Partners+ uses ChatGPT, Microsoft Copilot, Perplexity and Grok 3 to “accelerate the work that once consumed hours of manual effort,” Stenner says. “Whether it’s distilling complex market data, automating reports or preparing investment scenarios, AI allows us to turn information into insights more quickly, supporting sharper and more timely advice.”

Tracking investments

Since 2023, First Avenue Investment Counsel in Toronto has been licensing a machine-learning tool from Boosted.ai, a company that develops AI-powered software aimed primarily at the financial industry.

Photo of Thane Stenner
Thane Stenner

First Avenue’s equities team integrates the tool’s AI models into its daily workflows, says Brian Madden, chief investment officer. Specifically, they use Boosted.ai’s proprietary Battle Royale Noise Reduction algorithms to train proprietary models that help manage two of its equity funds.

“The machine learning/model training process identifies clusters of factors and patterns comprised of accounting data or financial ratios, stock market data and macroeconomic variables. These have proven empirical efficacy in identifying stocks likely to outperform a benchmark,” he says.

“The challenge—but also the beauty—in making inferences using these models is that the patterns are not always intuitive to humans.”

The best ideas, he adds, lie at the intersection of all four disciplines: “opportunities that our team likes fundamentally; that are consistent with our macro-thematic outlook; that technical analysis indicates the market is recognizing and rewarding; and that the cold, clinical logic of machine learning also corroborates.”

Knowledge sharing

On the communications side, AI has transformed how Stenner Wealth Partners+ captures and shares knowledge. Stenner says his firm uses Zoom AI transcription for client meetings and internal strategy calls to record and summarize them, creating searchable transcripts so no detail is overlooked.

Story continues below

“We then need to refine and edit those client notes,” he adds, which “are likely only 70 to 80 per cent accurate today.”

ChatGPT also enables them to draft concise client updates, internal memos and thought-leadership content for LinkedIn and other social channels, he says. “This combination of precision and speed ensures that our communications remain clear, relevant and client-centered.”

Photo of Brian Madden
Brian Madden

Employee engagement

Northwood leverages AI to help improve the employee onboarding experience by building out personalized learning and development programs based on their new roles, Gill says.

“We are also leveraging Microsoft Copilot to enhance collaboration internally within Microsoft Teams and Outlook,” he says.

Research

Larger, diversified multi-family offices are experimenting with AI-powered research tools, says Amanda Bassin, president of Persuit Group, a Canadian executive search firm that specializes in executive recruitment for North American family offices.

Among them is AlphaSense, which scans filings and transcripts, compressing weeks of work into minutes.

“Families looking to buy or expand businesses are starting to use AI in modelling and due diligence, stress-testing assumptions and identifying risks faster,” she says.

She points out, however, that AI is still in its infancy. “Most information is exchanged through trusted networks, not dashboards, and insights are shared on a phone call or over dinner.” 

Artificial intelligence is everywhere in finance now, she adds, but family offices are different. “Adoption isn’t sweeping or standardized; it depends on each office’s size, investments, culture and risk appetite.”

The human element is still key.

“AI in family offices will never be cookie-cutter. … The real decisions—about capital, governance and legacy—remain firmly human.”

AI won’t run a family office, she adds, “but it can remove noise so people can.”

Anna Sharratt is a business and health reporter and editor with more than 20 years of experience. Based in Toronto, she has written for Canadian Family Offices since 2021. A regular contributor to the Globe and Mail, she has written for Inc.com, Forbes, Business Insider, Canadian Business, MoneySense, the National Post, The Toronto Star and other publications. She is the former managing editor of smallbiz.ca, health editor of Chatelaine and senior health writer for the CBC.

Story continues below

The Canadian Family Offices newsletter comes out on Sundays and Wednesdays. If you are interested in stories about Canadian enterprising families, family offices and the professionals who work with them, but like your content aggregated, you can sign up for our free newsletter here.

Please visit here to see information about our standards of journalistic excellence.