When Rebecka Kilkenny (pictured) looks at the insurance industry's technology problem, she doesn't start with software. She starts with submissions. As the chief strategic technology officer at K2 Insurance Services, Kilkenny is navigating the challenge of modernizing underwriting operations across more than 30 business units - with a strong focus on prioritization, governance, and scalable execution across the portfolio - and doing it in a way that actually moves the needle.
"That's where a lot of the friction lives," she said of the submission triage and ingestion process. "That's where you tend to find the most friction, cost, and inconsistency."
K2, the parent organization of program administrator Aegis and a range of other specialty insurance entities, sits at an unusual intersection: a holding company that must deliver scalable technology solutions across a diverse portfolio of businesses, each with their own workflows, carrier relationships, and risk appetites. Kilkenny's role is to bring coherence to that complexity.
Kilkenny's immediate focus is the front end of underwriting - specifically, how submissions are ingested, cleaned, prioritized, and triaged before an underwriter ever touches them.
"The innovation for us is really about improving underwriting quality," she said. "Getting those submissions in, cleaning them, scrubbing them, prioritizing them, and making sure they're being triaged appropriately - so the team is working the accounts that are ready to be quoted and bound, versus ones where we may be wasting our time or that don't belong in our queue at all."
The goal is straightforward: less time chasing missing data, more time underwriting. Reducing cycle time at the submission stage creates downstream efficiencies that ripple through the entire workflow. For an organization operating across 30-plus business units, even incremental gains compound quickly.
That same philosophy extends more broadly across K2, with a focus on ensuring teams are consistently working on the highest-value opportunities across the portfolio.
K2's approach relies on a cross-functional model that brings together IT, underwriting, operations, and information security - coordinated through a PMO-driven model with clear governance and prioritization frameworks to ensure initiatives are aligned to business value. According to Kilkenny, executive sponsorship and cross-functional alignment are as critical as the technology itself. "We're not in the business of innovating for the sake of innovating," she said. "We want to make sure we get true value out of any effort we put in."
Change management is the real challenge
For Kilkenny, the greatest obstacle in any transformation isn't the technology - it's the human and organizational systems around it.
"Technology is never the problem," she said plainly. "It's the change management and workflow alignment that go along with implementing the technology. That's where the real challenge lives."
Her team's approach involves rolling up their sleeves and getting inside a business unit's workflows before any tool is introduced - mapping the process end to end, identifying where disruption would occur, and designing around it.
"You don't always know where the bodies are buried until you start digging," she said. "So we get in with a business unit and ask: how would this actually work, from beginning to end? Where would it disrupt you, so we can get ahead of that? The goal is to make sure the disruption isn't one that sends us backward — it should be a disruption that moves us forward. Disruption isn't always a bad word."
That philosophy has shaped how K2 selects and scales solutions. Rather than treating every implementation as a one-off, the leadership team has become more deliberate about identifying tools that allow for scalability and governance, creating a more repeatable model across the enterprise - extracting economies of scale from both a pricing and throughput standpoint.
With the Insurtech market awash in AI-powered platforms promising underwriting transformation, Kilkenny has developed a sharp filter for evaluating external providers. She and her team spend significant time assessing vendors — and she makes no apology for being selective. "We joke that we kiss a lot of frogs before we find the ones that actually work," she said. Her perspective on evaluating insurtech vendors in the US market is grounded in decades of combined experience across K2's leadership team.
Beyond technology capability, she looks hard at the team behind the product. "What's their knowledge base? Do they actually understand insurance, or are they just looking to make a quick entry into our industry and sell us a tool that won't hold up in a real insurance or underwriting environment?"
The stakes are high. K2 is heavily reliant on external solution providers, which means every vendor relationship carries meaningful risk. Kilkenny frames it in terms the industry understands instinctively: "At the end of the day, no matter what external provider you sign with, you're taking a risk. Insurance is about risk management - and so is managing your external solution providers. It comes down to how you structure that relationship and contract to ensure it's a win for both sides."
If there's one area where Kilkenny's tone shifts from measured optimism to something closer to vigilance, it's artificial intelligence.
The explosion of AI tooling across the industry has accelerated a parallel challenge: information security has moved from a supporting function to a front-line consideration in every technology decision K2 makes. At the same time, the focus isn’t just on adopting AI, it’s on capturing real value from it while thoughtfully managing the new security and operational risks that come with it.
"With the explosion of AI over the last few years, making sure we're doing the correct due diligence on any toolset from an information security standpoint is more important now than it's ever been," she said. "A lot of companies thought they were doing a good job a few years ago, and many were — but AI has introduced new risks that everyone is figuring out as they go. There's no established playbook. Every day you can read about the latest problem or breach that nobody anticipated. The questions being asked today are ones that didn't even exist a few years ago."
For insurance carriers and MGAs watching from the sidelines, Kilkenny's experience at K2 offers a grounded counterweight to the hype. Transformation at scale isn't a technology story - it's a governance, collaboration, and discipline story. The tools matter less than the frameworks built around them.
At K2, those frameworks are actively being built and rolled out across the organization, with a focus on disciplined execution and measurable business impact. But Kilkenny sounds confident about the direction. "Disruption isn't always a bad word," she said. And in a sector long overdue for modernization, that may be exactly the mindset needed.
