Christopher Ewing and the trouble with ordinary things

Christopher Ewing’s next business problem could fit in a car, provided somebody first did something about the spaghetti. He had already spent years helping insurance companies deal with payments, software and the administrative clutter that follows money around. Now he was considering a different kind of inconvenience: Italian food was enjoyable at a table and rather less cooperative on the road.

The answer became Notty’s Italian Burrito. Getting there involved dough experiments and an air fryer, a considerable change of equipment for the co-founder and former chief executive of One Inc. There is a pleasing lack of ceremony about the food venture. A person who once discussed core insurance systems could also spend a long time trying to make lunch behave itself.

The connection between those ventures is an interpretation of his career, rather than a claim that restaurants and financial technology obey the same rules. In each case, though, Ewing’s account begins with a familiar activity made needlessly awkward. His particular contribution was to take the awkwardness seriously enough to work on it.

The customer before the company

Ewing grew up in Sacramento and studied business administration at the University of California, Riverside. He went on to earn a law degree at the University of the Pacific’s McGeorge School of Law. His law school years, from 1990 to 1993, included law journal editing and membership in the Order of the Coif. Before the insurance businesses came work as a securities attorney.

It is an education in the less decorative parts of business: how an organization is financed, how its obligations are written down, and what happens when a promising idea has to become an operating company. Those subjects would recur in his working life, alongside a more direct interest in technology.

In 2003, he began his insurance-industry career as president and CEO of Keenan Holdings. At Cost-U-Less Insurance Center, he served as chief technology officer and general counsel as the retailer expanded from 32 locations to more than 100. Written premium grew past $500 million before he helped lead its sale. Those are insurance premiums, a measure of business written, rather than a claim about software revenue.

He also co-founded and led Stonewood Insurance Services, where written premium reached $2 million per employee before the company’s sale. Other roles combined technology and law at ClearSide General Insurance Services and GreenPath Insurance Company. By the time he started selling software to insurers, he had occupied several of the chairs around their conference tables.

One company for the awkward parts

One Inc began in 2012, co-founded with Tim Tyannikov. Its early proposition was expansive. The InsureOne suite offered core applications for property and casualty insurers, helping them replace older systems and support distribution. Policy administration, billing, customer management and payments belonged to the same broad ambition. An insurer would have fewer disconnected pieces to nurse along.

That breadth matters to Ewing’s story. He came to the market with the experience of running insurance organizations, where a payment is attached to a policy, an account and a relationship. A processor that could transfer funds still left the insurer with work to do if the surrounding records did not agree.

Ewing later described seeing too many vendors working separately inside the payments process. Information became divided among systems, while reliability suffered. His question was whether one company could bring those tasks together. The attraction of specialization was practical: understanding insurance’s particular requirements could make the entire transaction easier for the people administering it.

The complications were concrete. Premium collection brings money into an insurer. Claims disbursement sends it back out, sometimes to several interested parties. In the Invenger technology One Inc later acquired, those recipients could include policyholders, vendors, mortgagees and lienholders. Moving money and keeping everyone’s place in the transaction straight were parts of the same job.

In his writing about insurance technology, Ewing also emphasized the customer. He described insurers considering different routes to distribution, from direct sales to new partnerships. The shared challenge was to make core systems support those changing relationships. His attention kept returning to how an insurer actually interacts with the people buying its policies.

The business gets a bigger table

In September 2014, One Inc announced a $16.7 million Series A round led by H&Q Asia Pacific, with Camp One Ventures and AGI Partners participating. The stated uses included sales, marketing, implementation and customer service. It is a revealing list. Selling enterprise software requires people who can help customers introduce it and keep it working long after the contract is signed.

By April 2017, the company reported more than 225 employees globally and said revenue had tripled in each of the previous three years. Ewing was named a semifinalist for the EY Entrepreneur Of The Year Northern California award. His response put the emphasis on colleagues: “Our continued growth is powered by the commitment of our incredible team members.”

Recognition supplied a personal milestone, but the team would keep changing. Growth meant bringing in capital, additional technology and executives with experience beyond the founding group. For an insurance operator turned software founder, the task now included building an organization capable of serving many other operators.

Great Hill Partners led a recapitalization in February 2020. One Inc reported average annual payment-volume growth of 77 percent and planned to expand engineering, sales and marketing. Ewing’s explanation was characteristically close to the transaction: “Payments is the most important touchpoint for insureds.” That sentence gives the business its human scale. Customers encounter insurance through paying for it and, when a covered loss occurs, receiving payment.

“Payments is the most important touchpoint for insureds.”

Christopher Ewing · February 2020

In August that year, One Inc acquired Invenger Technologies, including Invenger-InsurPay. The combination added claims payment capabilities and brought a combined portfolio of more than 160 customers. It also brought together technologies intended to give recipients choices about how they were paid. Ewing’s original complaint about disconnected services was becoming a problem his company addressed through acquisition as well as product development.

The transaction also sharpened the meaning of the company’s insurance focus. Invenger’s product accommodated single and multiple payees, and adjusters could use it across devices. These were features intended for the people handling claims all day. The difficulty of replacing a familiar process lay in preserving its useful functions while removing the delays and manual work around it.

December brought an expanded executive team, with appointments covering operations, finance, marketing and sales. These are the jobs that make a growing company less dependent on one founder’s reach. The sequence is instructive: new investment, additional technology, then more management capacity to support the customers already using it.

A founder changes seats

On August 10, 2021, One Inc announced Ian Drysdale as its new CEO, effective August 5. Ewing became chief strategy officer. Drysdale had joined the board as executive chairman that January and brought a career in payments. Ewing’s public statement welcomed his operational expertise and described working together on the company’s strategic direction.

At the transition, One Inc reported 475 employees, nearly 200 clients and more than $18 billion in annual payments. Those figures describe the business at a particular handover, rather than its present size. They also show how far the assignment had traveled from the founder’s original irritation with payment vendors.

The change in title preserved a place for Ewing’s industry experience while putting a payments specialist in the chief executive’s office. It is a useful detail in a founder’s biography. Building a company includes decisions about who should run it at different stages, and how the founder’s work should change as the organization grows.

Then came the air fryer

Alongside that corporate chronology sits a smaller experiment. In 2021, Ewing and Katie took an RV to an airsoft event to test Notty’s with strangers. The company recounts selling 50 on the first day and 75 on the second. After years of insurance measures and payment volumes, the unit of progress had become something a customer could hold.

The eventual product uses thin, pizza-style dough around Italian fillings. Ewing spent roughly two years developing the dough, seeking a balance between structure and softness. Each batch takes three days to make. Convenience for the eater evidently required a fair amount of patience from the person making lunch.

By 2025, the concept had reached Rocklin, and a June report described plans for a Lincoln location. The menu allowed for familiar pizza combinations as well as more elaborate fillings. Ewing described wanting affordable choices while keeping the more expensive options within reach. The practical questions had changed from systems integration to what a customer would order and pay.

By the time he appeared on The Business Line in June 2025, Ewing could discuss both the technology business and the restaurant venture in the same conversation. The changes of industry make an entertaining résumé. The less glamorous continuity is the development work: a software implementation must fit an insurer’s operations, and a recipe has to produce the intended result repeatedly.

A handheld meal provides immediate feedback of a kind enterprise software rarely gets. The product has to carry well, taste right and justify another visit. The separate businesses should keep their separate measures of success. Yet together they give Ewing’s career a recognizable texture: time spent close to a process, followed by a willingness to try a different arrangement.

His path has taken him through legal documents, insurance offices, software teams and a compact kitchen. The kitchen photograph is particularly apt. There is cooking equipment, a container on the counter and Ewing in a knit hat. The next idea has reached the stage where somebody has to stand there and make it work.