To fundamentally transform an industry, you have to learn to love the pain. This philosophy, rooted in Cytora’s co-founder and CEO, Richard Hartley’s, background as a ballet dancer and rugby player, posits that progress is inseparable from discomfort. Just as a dancer pushes through physical strain to achieve grace, an entrepreneur must turn the “pain” of constant rejection and industry friction into the energy required to innovate. For Richard, building a company to change how risk flows through the commercial insurance value chain has been a decade-long exercise in this specific type of resilience.

On a recent episode of the InsTech Podcast, Richard shared invaluable insights on leading fundamental shifts in the commercial insurance value chain. Drawing on his experience scaling Cytora from a niche data provider to a global platform and its recent acquisition by Applied Systems, Richard highlighted practical strategies for turning heterogeneous, unstructured data into “decision-ready risk” while navigating the “painful” realities of technological evolution.

Listen to the full podcast episode here: InsTech Podcast by Datos Insights

Richard’s approach to transformation begins with identifying the true source of friction. When Cytora launched around 2015, the initial focus was on providing better data for political violence risk. However, he soon realized that the real problem wasn’t just a lack of data, but the manual, fragmented workflows—dominated by email and spreadsheets—that made the day-to-day experience for insurance professionals terrible. To solve this, Richard focused on how risk is inherently unstructured at its source, born from a dialogue between a broker and a client.

To understand the complexity Cytora manages, think of a doctor-patient relationship: the patient describes their symptoms in unstructured, everyday language, while the doctor must assimilate that into a structured medical view. Cytora acts as that expert translator, turning the “symptoms” of raw risk data into a clear, actionable diagnosis for the insurer. Predicated on this idea, Richard adopted a leadership philosophy of being “radically agnostic” toward how information is received while remaining “extremely opinionated” about the target data structure insurers need to make decisions.

This commitment to the right solution required Cytora to cannibalize its own success to stay ahead. In 2022, Richad and his team made the hardest decision a leader can face: they threw away their existing machine learning platform to rebuild as an LLM-first company. This was a big bet that could have destroyed the company, but Richard and his team recognized that Large Language Models provided the performance and scalability necessary to handle diverse transaction types across different countries.

Furthermore, Richard believes successful transformation requires a team that balances deep insurance domain expertise with strong “product DNA”. This credibility helped fuel their US expansion, where the Cytora team insisted on being “concretely there” from day one, splitting their time between London and New York to build authentic partnerships with global reinsurers. Cytora has now moved beyond simple prototypes to a scalable platform, building a product that clients can use on a self-service basis.

In 2025, Cytora reached a milestone by being acquired by Applied Systems. Richard views this not as an exit, but as a stepping stone to reach the 70% of agents and brokers who already use Applied’s systems. He will continue to lead Cytora as CEO, with plans to more than double headcount over the next year as they scale globally.

Ultimately, the lesson of “loving the pain” remains Richard’s guiding star for the future. He notes that in a world of increased volatility, the industry has unfinished business in solving how risk moves. By embracing the discomfort of constant evolution, Richard aims to move the industry toward a reality that feels more like asset management, where risk is executed with efficiency and glides through the value chain without friction.