Jackson Fregeau and the cost of a thousand clicks

The complaint Jackson Fregeau remembers was wonderfully precise. An insurance agency owner described the job as “death by a thousand clicks.” No catastrophe, no spectacular failure of imagination. Just the same small movements, repeated until the working day had disappeared. For a founder looking for something useful to build, this was a promising kind of misery. It had a customer, a routine and a cost.

Fregeau had already met a version of that problem. Before becoming the co-founder and CEO of Quandri, he ran operations at a technology startup. People on his team were doing repetitive data entry. He taught himself to build bots, saw what they could do, and began discussing the opportunity with his brother Jamieson. A company grew out of work he had actually needed done.

The operator before the founder

His route into entrepreneurship ran through the unglamorous departments. After business school, he joined a young company close to its founder, taking on invoicing, hiring, financial models and the processes that keep a business upright. He eventually became its chief operating officer. The position offered an education in what happens between a promising idea and a customer who expects something to work.

He has a neat description of his early proximity to the founder: “I wasn’t getting him coffee, but I went with him to get coffee.” There is a whole apprenticeship in that distinction. He was near enough to watch decisions being made, while taking responsibility for the operational details that followed.

His formal training was finance at the University of Calgary’s Haskayne School of Business, where he studied from 2013 to 2017. Automation became a practical interest afterward. The combination helps explain his attention to the time consumed by a process. A task can be essential to a business and still be an expensive use of the person performing it.

“The renewal is really the cornerstone of the brokerage.”

Jackson Fregeau, on the yearly client relationship

A brother, a map and a narrower market

The brothers began with complementary jobs. Jackson talked to customers, examined their processes and drew flowcharts. Jamieson developed, tested and maintained the digital workers. Their first customers included Jackson’s former employer and the company where he was still working. After the first bot, customers asked for more. Repeat orders supplied a fairly persuasive answer to whether the work was useful.

The early setup was a Vancouver apartment, a website made in Squarespace and meals from Tacofino. In his account of the launch, Jackson recalled getting a business plan, website and first customer together in three weeks. The burrito deserves its place in the story. New companies do occasionally begin somewhere other than a conference stage.

They tried several industries before concentrating on insurance after working with their first brokerage customers in May 2021. The decision gave the business a narrower field of study. Each new customer could teach them something relevant to the next one. Custom projects began to point toward a repeatable product.

By October 2022, Quandri had received the Insurance Brokers Association of Ontario’s Innovation of the Year award. Recognition from the industry mattered for a company whose founders had arrived from outside it. The next test was whether they could keep turning that early welcome into software agencies wanted to use.

Copenhagen on the calendar

For part of the company’s early life, Jackson added a complication of his own: he was in Copenhagen while the people he needed to work with were in Canada. “I tried to be a long-distance founder,” he later said. The available overlap in the working day was limited. A conversation that drifted had a larger price when another convenient conversation was hard to arrange.

He describes learning to give meetings a clear purpose and make communication move work forward. The seed round was raised while he was still based there. Geography had imposed an operating discipline. Calendars, usually among the least romantic objects in a startup, had become part of his management training.

Working with Jamieson supplied a different advantage: trust built before the company existed. Jackson says they listen to each other’s perspectives and often defer to the brother who feels more strongly about a decision. It is a practical account of a family partnership. Disagreement still happens; their method gives it somewhere to go.

The annual appointment nobody has time for

Insurance renewal became a central focus of the business because it sits where service, revenue and repetitive work meet. Fregeau argues that many clients have little contact with their broker outside that annual exchange. It is the moment to explain a changed premium, examine the coverage and demonstrate why a professional is involved at all.

The job expands quickly. An agent must compare the previous policy with the new one, account for changes and decide whether alternatives should be quoted. A useful message to the client comes after that work. Fregeau has estimated that a personal-lines renewal can occupy between 45 minutes and an hour and a half. Multiply the task across a book of customers and good intentions encounter arithmetic.

His argument is that attention gets rationed. The most urgent cases receive it; quieter accounts can receive less than an agency would prefer. That makes automation a service question as well as an efficiency question. The time recovered has to turn into something a customer can notice.

Quandri’s platform organizes this work into analysis, quoting and communication. In an August 2026 interview, Jackson described approximately 150 agency customers, split roughly between Canada and the United States. The US business, he said, was growing faster. The same operational complaint had travelled across the border with little need for translation.

A robot needs to know the fine print

Fregeau’s public writing becomes most specific when he explains how much an automation system must understand. Consider a recommendation about sewer-backup coverage. The software has to know whether the carrier offers it, whether it is available in that region, whether it is already included in the package or an endorsement, and whether the customer is eligible.

That is a considerable amount of knowledge hiding behind an apparently simple suggestion. An experienced agent supplies it so naturally that an outsider can miss the effort involved. Fregeau’s point is that the system needs access to those distinctions before a brokerage can trust it to represent the business to a client.

His August 2026 essay makes the standard clearer: people need to understand why a recommendation was made, trace it to the underlying information and override it when necessary. Exceptions need to be identified. The attractive demonstration is only the beginning of the work.

There is some restraint in the sales argument, too. A Quandri article carrying his byline discusses circumstances where automation may be premature: manageable workloads, limited repetitive work, costs that exceed the expected benefit, or an organization unprepared for the change. For an operations person, a purchase still has to make sense against the actual task list.

The money arrived after the work

Quandri initially grew without an intention to pursue venture funding, according to Fregeau’s account of its seed round. The company was profitable and adding customers. When sales and marketing activity increased demand, the constraint became how much work the team could deliver. Financing offered a way to expand that capacity.

The 2022 fundraising environment complicated the plan. Investors withdrew, and the company had to reconfigure the round. It ultimately raised about C$2 million, or US$1.5 million. The episode puts a useful wrinkle in the progression: customer demand and available capital do not always move in step.

A US$8.5 million Series A followed in June 2023, led by FUSE. The announced plan was to develop the digital workers, expand the team and reach more customers. By then the business had a defined industry and a product problem investors could examine.

In 2025, a further US$12 million financing brought Framework Venture Partners and Intact Ventures into the investor group, alongside returning backers. The round supported expansion across Canada and the United States and more engineering investment. Separately, The Peak included Jackson on its 2025 Emerging Leaders list in technology. His name was becoming more visible alongside the company’s.

From a renewal desk to the whole agency

On September 23, 2026, Quandri announced AI Workflows, extending beyond renewals into client servicing and revenue growth. The release also introduced its first commercial workflow, a policy check-in. The product’s scope was widening inside the industry the brothers had chosen to study.

That direction follows a consistent concern in Jackson’s work: how much of a professional’s day is consumed before they reach the person they are supposed to help? The company now applies the question across more agency operations. The answer will depend on the details of each job, the accuracy of the software and the confidence of the people using it.

His career gives the question some weight. He has been the person responsible for the processes, the customer conversations and the team doing the repetitive work. Before there was an insurance platform, there was an operations manager who had become sufficiently irritated to learn how to build a bot. A thousand clicks turned out to be worth counting.