John Kessler (pictured) started his career at a Columbus, Ohio, insurance carrier in 1984 as a programmer trainee. He never left. Forty-two years later, as executive vice president and chief strategy officer at Encova Insurance, he has helped spearhead one of the most ambitious transformation programs the super-regional carrier sector has seen.
Encova, which holds approximately $1.4 billion in written premium, a surplus in excess of $2.3 billion, and more than $5.5 billion in assets, was not always the unified organization it is today. For much of Kessler's career, the company grew through an affiliation model, writing financial notes to prop up smaller mutual carriers, assuming key leadership positions, but allowing each entity to maintain its own identity, brand, and infrastructure.
"Through that model, we accumulated 16 companies across 26 states," Kessler said. "Because we allowed each to maintain their identity, we layered infrastructure on top of infrastructure as we grew. Long story short, we became an organization that was bloated and deep in technical debt."
By 2011 and 2012, the company's expense ratio and combined ratio both deteriorated significantly. The president and CEO at the time recognized the organization was on an unsustainable path. His response was to write a 31-page vision document outlining what the company needed to look like in 10 years, a plan to go from 16 companies to one.
The IT strategy Kessler devised rested on three pillars: standardize, modernize, and rationalize. Across more than 30 core systems covering policy, billing, claims, finance, and agency management, the team went to market and selected Guidewire Insurance Suite as its target-state architecture for property-casualty lines.
"We took a true greenfield approach," Kessler said. "We called it the Commercial Lines Transformation Program. We pulled leaders from every discipline across the organization into an integrated project team, and we burned the boats; everything was net new going forward."
The Guidewire implementation launched in 2015, with commercial lines going live in initial states in 2017 with all-new products and pricing. Personal lines followed in 2019 under a program called Reinvent Personal Lines, where the team introduced a new company into the market rather than retrofitting the old one. All legacy businesses have since been converted, and the old systems decommissioned.
Around 2017, a merger with BrickStreet Insurance of Charleston, West Virginia, a monoline workers' compensation carrier dominant in that state's privatized market, added workers' comp capabilities to Encova's commercial lines package. That merger, combined with a 2019 rebrand away from the near century-old Motorists Insurance name as well as BrickStreet Insurance, completed the journey to one company, one brand, one solution. Encova Insurance was born.
Kessler is direct about what he believes separates successful transformation programs from failed ones: organizational alignment, not technology selection.
Before any execution began, the company's CEO spent roughly two years conducting a regional engagement tour, bringing employees from different affiliated companies together at integrated locations, not siloed by brand, and reading all 31 pages of his vision document aloud. The exercise was repeated across the full footprint until every employee was exposed to the plan.
"He needed to get buy-in from associates across 16 different companies, that's not a small undertaking," Kessler said. "What he did was remarkable. That's how he built an initial buy-in."
From there, integrated teams representing every company and discipline conducted SWOT and gap analyses, eventually defining a body of work that consisted of 10 strategic directions spanning 5-10 years each, 26 to 28 supporting strategies covering 2-5 years each, and 350 to 400 individual objectives, each scoped to 12 months or less. For system integrators, Kessler's team chose PwC for the Guidewire implementation, a relationship that has continued since 2015 through commercial lines, personal lines, state rollouts, and legacy conversions.
Kessler describes the same integrated teaming principle as the engine behind ongoing vendor feedback loops. "Being siloed off from the business is a perpetual challenge in this industry," he said. "We solved that by adopting a guiding principle: everything we do goes through integrated teaming. Whether it's a project, a program, or a business discussion, we always have representation from commercial lines, personal lines, IT, and finance."
As insurance carriers across the US wrestle with how to operationalize artificial intelligence, Kessler argues that the condition of an organization's core architecture determines whether AI is an opportunity or an obstacle.
For Encova, he says, the hard infrastructure work is behind them. The company now runs workers' compensation on Sapiens CoreSuite, preserved from the BrickStreet merger, where it had been heavily customized and proven effective, and all other property-casualty lines on Guidewire Cloud Platform, with Duck Creek handling agency distribution management. That rationalized stack, from more than 30 systems down to two core platforms, is what Kessler calls Encova's "innovation ecosystem."
"Because we've built on modern platforms, we're now well positioned to take on the challenges and opportunities that come with AI," he said. "We don't have to solve the operational challenges of the past first. We feel well positioned to truly pursue our AI strategy from a position of strength."
Encova closed out its transformation journey last year. Under the current president and CEO, TJ Obrokta Jr., who took the reigns in 2020, the company successfully completed conversions and sunsetting of all legacy systems; received an AM Best rating upgrade of an A from an A- in 2022, which included a score at the "significant" level for innovation for several consecutive years; and is now stronger financially than ever before. Kessler says Encova is well positioned for growth and further expansion, fueled by the foundation of modern strategic architecture.
Kessler, who is set to retire at the end of 2027, has seen the company through its most consequential chapter. After 42 years, the programmer trainee who started in 1984 is leaving an organization that looks the way the 31-page vision said it should.
