Ridge’s senior vice-president for technology professional liability Cindy Manek (pictured) says the real challenge in modernization is not software selection but persuading underwriters to abandon old habits. In a market racing towards automation and AI, she argues that judgment, trust and disciplined governance will determine who prospers.
Manek did not begin her career with a fixed ambition to enter insurance. After graduating with a degree in economics, she was working in hospitality and looking for a role that would allow her to combine client service with analysis and commercial decision-making. A conversation with a friend introduced her to underwriting, and from there she began pursuing entry-level roles in the sector.
It was not an immediate success. Manek said she applied repeatedly before receiving a response, eventually pushing the matter directly with the company leadership. Her bilingualism helped secure the opportunity, particularly because French was needed for part of the Montreal portfolio. Once inside the industry, she was given a choice between miscellaneous and technology underwriting and opted for technology, a decision that would shape the rest of her career.
That early decision placed her in a part of the market that would become increasingly important. Cyber, she noted, was once far less prominent than it is today, but over time became central to the technology insurance landscape, particularly after the disruption of Covid. Her career subsequently took her through Victor, Travelers and Markel before she joined Ridge to build out its technology professional liability portfolio.
Digital transformation in insurance is often sold as a matter of speed: faster processing, quicker turnaround, less re-keying, fewer manual errors. Manek offers a less fashionable but more convincing account. For her, the central aim has been consistency in underwriting and sharper visibility across the portfolio, not merely acceleration for its own sake.
Speaking about Ridge’s development over the past five years, Manek described an operation that was still heavily dependent on Excel-based processes when she joined. The business later moved to the insurance platform Insly, which is now connected with Power BI and API integrations to support underwriting workflow and documentation.
Her account will sound familiar to many insurance executives: the technology itself matters, but change is won or lost elsewhere. “Digital transformation is actually about people more than technology,” she said.
Manek did not arrive at Ridge to maintain an inherited structure. She was recruited to help build one. Before that, she had worked at Travelers on international business and later at Markel, where she was involved in establishing a technology practice with support from an existing UK foundation. At Ridge, by contrast, the task was broader: building the portfolio, sourcing capacity, developing wording and guidelines, and assembling a team.
That background matters because it explains the cast of her remarks. This was not a theoretical discussion about innovation, but a practical one from an executive used to translating specialist underwriting judgment into operating systems and workflows.
The most interesting part of Manek’s case for investment is her insistence that speed, while welcome, is secondary. Specialty lines live or die by disciplined selection. Better infrastructure, she said, improves how information is collected, analyzed and documented; more importantly, it gives underwriters and leaders a stronger view of emerging exposures, accumulations and loss trends.
This is a more serious rationale than the usual rhetoric around efficiency. In professional liability, cyber and other complex lines, the danger is not simply frictional cost. It is inconsistency: two similar risks assessed differently, weak documentation, or a portfolio whose concentrations only become visible after losses emerge. Manek’s argument is that digital investment should first serve underwriting discipline and managerial sightlines, and only then the pursuit of convenience.
Manek is also candid about implementation. Technology programmes are routinely oversold, she said, and the reality is usually messier. New systems expose compatibility problems with older ones; temporary reversions to manual work are common; and duplication of effort is often unavoidable before the gains begin to show.
Her sharper point, however, concerns behaviour. Insurance remains a relationship-driven industry with long-established habits, and any process shift can feel disruptive. At Ridge, adoption was handled in stages, with management helping to build product schemas, underwriters testing the platform, training rolled out across the team and, eventually, a firm cutover from the legacy process.
Rather than presenting transformation as a triumph of executive will, Manek spoke of patience, walkthroughs and the need to recognise that what appears simple to one person may be difficult to another. Her biggest challenge, she said, was encouraging underwriters to think more broadly about data interpretation and technology awareness while remaining sensitive to different tolerances for change.
The eventual payoff has been most visible in time saved. Tasks once handled through spreadsheets, Word templates and mail merge can now be produced much more quickly, reducing administrative burden for underwriters and support teams alike.
No discussion of insurance technology now avoids AI, and Manek does not try. Her position is neither breathless nor dismissive. AI, she said, is already useful in document processing, data extraction, analytics and pattern recognition. But in complex specialty lines, its role is “more as a support tool rather than a decision maker tool”.
That distinction is central. In technology and cyber liability, underwriters must understand context, business models, contractual structures and operational dependencies. Those are not merely data points; they are judgment calls. Manek’s broader defence of human underwriting is that brokers and clients still depend on trust, openness and emotional intelligence when discussing risk.
She also pointed to agentic AI as a significant issue for the coming years. Systems that can make autonomous decisions and act on behalf of users may create efficiencies, but they also raise difficult questions about privacy, compliance, transparency and accountability.
Outside work, Manek’s routine is notably active. She teaches three spin classes a week, something she says gives her both an outlet away from the computer and a way of staying connected with people, particularly as she is based in Ottawa while many colleagues are in Toronto or Vancouver.
She also took up skiing this year, determined to correct what she saw as a surprising omission for a Canadian approaching 40. At home, she lives with Mia, her seven-year-old miniature poodle.
Those details are not incidental. They also feed into a broader view she has of the insurance market itself. Manek suggested that the sector’s networking culture could do with some updating, with less reliance on bars and late nights and more space for healthier forms of connection such as walking, yoga or spin-based fundraising events.
For insurance professionals, the value of Manek’s argument lies in its restraint. She is not offering the fantasy that a new platform will solve everything, nor suggesting that AI will soon remove the need for judgment in specialty underwriting. Her message is more measured: invest in systems that improve consistency and portfolio insight, accept that change management is fundamentally human, and treat AI as powerful but incomplete. In a market crowded with promises, that is a serious message, and a useful one.
