Scout InsurTech Interview with Kevin Ostrander

Kevin Ostrander is the Chief Revenue Officer at One Inc, the leading digital payments network for the insurance industry, unifying premium collection and claims disbursement onto a single platform. Kevin was interviewed by Chris Luiz, Co-Founder and CEO at Scout InsurTech.

Kevin, insurance has traditionally been built around a single core system, and now it's shifting toward point solutions that share data with each other. What's driving that, and where does it go from here?

“A lot of it comes from the core system modernization carriers have gone through over the last 20-plus years. As systems like Guidewire came into the market, many carriers invested in upgrading their backend infrastructure around policy, billing, and claims. The market has changed dramatically since then, especially as we've gone through the pandemic and customer expectations have risen. It's no longer okay to simply be insurance and not have digital experiences. 

The backend upgrades carriers have made from an operational standpoint have enabled API-based and cloud infrastructure that lets them move faster and shift away from back-office core systems toward solutions that modernize the customer experience. That drive from customers to have an optimized experience is really what's pushing carriers to change the infrastructure they're investing in, so they can deliver on those expectations for policyholders.”

"Ecosystem" gets used constantly in this industry. What does the word actually mean to you, distinct from just having a vendor list?

“It's certainly an overused term. A true ecosystem has real connectivity, shared workflows, and compounding value for every participant. In P&C, that value grows as more carriers, vendors, policyholders, providers, lenders, and partners take part. It's not just an integration on a slide. It becomes the operating infrastructure that makes each transaction faster, easier, and more reliable for everyone involved.”

Most technology purchasing in insurance still runs through RFPs, and few people think that process produces the best outcomes. Why does the industry keep doing it anyway?

“RFPs persist because insurance is high stakes. It's a regulated industry, there's significant operational impact, multiple stakeholders, and long-term commitments to vendors and partners. Procurement teams need a process that creates measurable comparability across vendors that often claim to deliver similar outcomes. The problem isn't the RFP itself, it's when the RFP becomes a checklist instead of a conversation about business outcomes. RFPs often miss the real complexity behind the outcome a carrier is trying to achieve. 

You have to ask: What are the requirements around adoption? How is change managed? What does the integration depth mean, not just for the vendor, but for the workload the carrier is taking on? How will the solution perform three to five years down the line, not just at the demo stage? 

I understand why the structure exists. Procurement needs it, legal and compliance need documentation, IT needs a checklist. But the process can unintentionally flatten the important differences between vendors when everyone gets put on the same level playing field. It can be improved by starting with the business case rather than a feature list. What's the outcome you're after? Work with vendors on how they'd solve your specific workflows and challenges, and evaluate adoption, servicing, and measurable ROI rather than a checklist of features.”

How can carriers and vendors better engage to start relationships on stronger footing?

“There's a mindset shift that would benefit both sides. The way organizations buy software and build partnerships has changed. It's moving away from vendor selection as a rigid process and toward the beginning of a partnership, where both groups are evaluating their ability to deliver mutual value. Vendor selection is really just the starting point. The key issue is moving from features to outcomes. ‘Can you support this function?’ isn't enough for an RFP. A better question is how a vendor reduces manual work, improves adoption, and delivers the customer experience outcome you're expecting. We often see a rigid procurement process run by a narrow buying team that doesn't reflect who's actually affected by the decision. Procurement and IT may lead the process, but claims, billing, finance, CX, and compliance are the groups that feel the impact. 

A better approach is to down-select to a few vendors and really get to know them, since a carrier can miss better approaches by narrowly defining the problem instead of learning from what vendors have seen work elsewhere in the ecosystem. Strategic vendors should help shape the solution, not just respond to requirements. The best relationships start when both sides are honest about the complexity of what they're taking on together and how they'll work through it. Starting on the wrong foot usually means treating implementation as a purely technical exercise instead of the beginning of solving the business outcome that drove the RFP in the first place.”

Two vendor relationships can look identical on paper and turn out completely differently five years later. What's the early signal that tells you which one you're in?

“The early signals show up in how a vendor talks about the outcomes they've delivered for similar carriers. It's not enough for a vendor to say they can deliver a feature or that they have the technology. How will they partner on integration? How will they partner on change management? How will they partner to deliver the business outcome you're after? A lot comes down to how the first hard conversations go. Strategic partners lean into complexity, while transactional providers avoid it or overpromise. Watch for whether the vendor asks better questions- not just what feature you need, but what outcomes you're trying to drive, and what success looks like in year one versus year five. 

Another signal is shared accountability. Strong partnerships define success metrics early, clarify ownership across both teams, and build around business outcomes rather than just the launch date. Strong partners challenge assumptions early, bring industry expertise, map implementation and adoption risks, align to measurable outcomes, and stay engaged after go-live. That's how One Inc operates. We're built for the operational, regulatory, and business needs of insurance before go-live, during implementation, and long after, so we can build a mutually beneficial relationship for the long term.”

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