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# Interview: Richard Hughes - Insurance Technology CRO ## Metadata **Date:** December 15, 2025 **Duration:** 30 minutes **Interviewer:** Sarah Martinez, Enterprise Sales Director, Salesloft + Clari **Interviewee:** Richard Hughes, Chief Revenue Officer, InsureTech Innovations **Company:** InsureTech Innovations (Regional Carrier, $150M ARR) **Recording:** Yes **Follow-up:** Scheduled --- ## Transcript **[SARAH]** Richard, thanks so much for taking the time this morning. I know you've got a packed schedule as CRO, so I really appreciate it. Before we jump in, I'm curious—how long have you been in the insurance space, and what's been the biggest shift you've seen in how carriers approach revenue operations? **[RICHARD]** Thanks for having me, Sarah. I've been in insurance for about fifteen years, and honestly, the biggest shift has been realizing that we can't just rely on relationship selling anymore. When I started, a carrier could get away with having a handful of strong broker relationships and just renewing contracts year after year. But now? The competitive landscape has completely changed. We've got new entrants, we've got aggregators, and we've got consolidation happening at breakneck speed. The margin pressure is real. **[SARAH]** Absolutely. And that's actually why we wanted to talk today. A lot of what we're hearing from carriers is this tension between—and I want to be respectful here—between the growth expectations investors are putting on you and the actual sales cycles you're working with. Is that something you're feeling right now? **[RICHARD]** *laughs* You could say that. Our board is sitting on my shoulder saying, "We need 30% growth year-over-year." And I'm like, "Great. Commercial insurance sales cycles are 6 to 9 months. We've got regulatory approval timelines. And our customers are having budget conversations in October for January implementation." It's not like selling SaaS where you can close a deal and turn it on next week. There's a disconnect, and it's creating real tension in how we staff, how we forecast, and honestly, how we think about whether we're investing in the right capabilities. **[SARAH]** That's helpful context. And I imagine that tension gets worse when you're trying to invest in modernization—the IT stuff—and your CFO is saying, "Prove to me the ROI on this." How much of that dynamic is playing out on your side? **[RICHARD]** It's a significant problem right now. We actually deprioritized a carrier IT modernization initiative six months ago. And you know what? I'm not even sure we made the wrong call, but let me explain the context. We had this three-year plan to upgrade our policy administration system, modernize our backend, and build API integrations so we could move faster. The estimated cost was around $8 million. The CFO asked the right question: "Richard, what's the immediate revenue impact?" And I couldn't give him a number. I could say, "In year three, we'll be able to onboard faster, we'll reduce our actuarial underwriting cycle by 30%, we'll be more responsive to partners." But that's theoretical. Meanwhile, our board is asking us to find two or three new growth initiatives this year that we can close quickly. So we made the call: let's defer IT modernization and invest that money into sales, marketing, and partnerships instead. But honestly? We're going to regret that decision in about eighteen months. **[SARAH]** That's really candid. So it sounds like the deprioritization happened because of a lack of a clear business case, not necessarily because you don't believe in it. What would it take to get IT modernization back on your roadmap? What would actually move the needle for you? **[RICHARD]** Great question. Here's what I'd need to see. First, we'd need executive alignment. Right now, my CTO and I are on the same page, but our CFO and our Chief Underwriting Officer—they're skeptical. Our CUO is more worried about maintaining risk discipline and meeting our regulatory obligations in twelve different states. She doesn't have time to think about whether our backend is modern. Second, I'd need a clear, near-term business trigger. Not "in three years." Something like: "If we modernize within the next eighteen months, we can close this partnership with a national broker that's worth $15 million in ARR." That's the kind of thing that gets executives aligned. Not features. Not efficiency. A number they can point to. And third—and this is probably the biggest one—I'd need proof points. We'd need to see another carrier do this and show real ROI. Honestly, if Hanover or AmRisc came out and said, "We spent $10 million on IT modernization and it enabled us to close $50 million in new partnerships," that would change the conversation overnight. But right now, everyone's cautious. **[SARAH]** That makes sense. And partnerships are on your mind, which is interesting because I think that connects to another thing we've been hearing a lot about. You've got the investor growth pressure. You've got the sales cycle realities. But you also have internal stakeholders who are skeptical about new approaches—whether that's technology or, in some cases, new sales methods. I'm thinking specifically about your actuarial team. Have you run into that dynamic with them? **[RICHARD]** *pauses* Oh man, yes. This is probably the biggest blocker we have internally. Our actuarial team—and they're brilliant, by the way—they are deeply skeptical of AI and machine learning. And I get it from their perspective. Insurance is a risk business. The actuarial function is the soul of a carrier. They're responsible for pricing, for reserve adequacy, for capital efficiency. If an AI model recommends pricing that doesn't reflect actual risk, that's not a small problem. That could be a regulatory issue. That could be a solvency issue. So when I came to them two years ago and said, "Hey, we should use machine learning to optimize our quote pricing and improve our conversion rates," they basically said no. Their concern was: "We don't understand how the black box works. We can't explain it to regulators. We can't validate that it's actually capturing risk properly." **[SARAH]** That's a really legitimate concern, though. It's not just skepticism for skepticism's sake. **[RICHARD]** Exactly. And that's what makes it hard. They're not wrong. So we've actually had to change our approach. Instead of going to them and saying, "We want to deploy AI," we're saying, "Here's the data science proof we have. Here's how we validated the model. Here's how we tested it against historical outcomes. Here's how we're going to monitor it for bias. And here's how our actuarial team maintains visibility." When we frame it that way—focusing on technical validation, proof points, and risk communication—they're more open. But it takes time. And it takes executive sponsorship. We've brought in a third-party data science firm to validate one of our models just to get our actuaries comfortable. That's expensive. But it's necessary if we're going to move forward with any kind of intelligence-based selling or pricing optimization. **[SARAH]** So the skepticism isn't a "no," it's a "show us the work" kind of no. That's actually really healthy. But it does slow things down. And I imagine that's another pressure point—you've got this growth timeline, and internal validation takes time. **[RICHARD]** It does. But here's the thing: we're not going to move forward with something our actuarial team doesn't support. That's a hill we'll die on. If we deploy pricing logic that our actuaries can't defend, and we get hit with a regulatory action or we underprice risk, that's the company. So yeah, it's slow, but it's the right call. **[SARAH]** I appreciate that perspective. Now, let me shift gears a bit because I think this relates to a lot of what we do. You mentioned regulatory oversight. You're operating in twelve different states, right? **[RICHARD]** Fourteen now. We've been expanding into more regional markets. And state-by-state regulation is actually one of my biggest headaches as CRO. Every single state has different rate filing requirements. Different approval timelines. Different consumer protection rules. Different data privacy rules. Some states still require manual rate reviews. It's not like a federal system where you can standardize once and scale. **[SARAH]** And that creates a ton of complexity for your sales team, I imagine. Because you can't just say yes to every deal opportunity. **[RICHARD]** Right. So if a national broker comes to us and says, "Hey, we've got a large commercial customer that needs coverage in all 50 states," we can't serve that. We can serve the fourteen states where we've got filed rates and regulatory approval. But even within those fourteen states, different products have different approvals. So one of my sales managers might spend three weeks working a deal, get the customer excited, only to realize we can't close it because the coverage requirements span two states where we don't have a presence, or we don't have a specific product filed in one of those states. **[SARAH]** That's a major pipeline killer. How do you coach your team through that? Because it's got to be demoralizing. **[RICHARD]** It is. We've actually built a pre-qualification process. Before a deal even gets real traction, we have our compliance officer do a quick assessment: "Can we service this across our approved states and products?" It saves a lot of wasted effort. But it also means we're leaving money on the table constantly. And when your board is asking for 30% growth, turning away opportunities is painful. **[SARAH]** But I imagine it's better than the alternative—getting tangled up with a regulator. **[RICHARD]** Absolutely. The regulatory risk isn't worth it. We've got peers who tried to be aggressive with regulatory interpretation, and it cost them millions in remediation and legal fees. Plus, it damages your reputation with state insurance commissioners. Once they lose trust in you, everything becomes harder. **[SARAH]** So state-by-state fragmentation is basically a competitive moat for companies that have already invested in navigating it, but it's a barrier to growth and scaling your sales operation. That's rough. **[RICHARD]** Exactly. And it ties back to the IT modernization question we talked about earlier. If we had a modern system, we could probably manage state-specific compliance requirements more efficiently. We could build workflows that automatically flag when a deal crosses into states where we need additional product approvals. We could have better data to show regulators that we're compliant. But without that investment, it's a lot of manual work, a lot of tribal knowledge, and a lot of deals that don't close. **[SARAH]** That's actually a really compelling argument for revisiting IT modernization—not just as a backend efficiency play, but as a sales enablement and risk management tool. Have you made that case internally? **[RICHARD]** We're starting to. My CTO and I have actually been having more conversations with our Chief Risk Officer and our Chief Regulatory Officer. The thesis is: "If we modernize our systems, we actually reduce regulatory risk and increase our ability to scale responsibly." That's a different conversation than "This will make us faster." It's "This will make us safer and more compliant." **[SARAH]** I like that frame a lot. Okay, so let me ask you something that's a bit more strategic. You've deprioritized IT modernization as a capital investment. But I'm curious: how are you thinking about the build-versus-buy question? Are you looking at acquiring capabilities? Are you looking at partnering with platforms? Or are you pretty committed to building everything in-house? **[RICHARD]** *leans back* That's the million-dollar question right now, and honestly, we're torn. Our historical instinct as a carrier—especially a regional carrier—is to build. We have deep domain expertise. We have proprietary underwriting logic. And frankly, we've had bad experiences with buying. We did a major acquisition eight years ago that integrated a smaller carrier, and the integration took three years and cost us a lot more than we expected. So the build instinct comes from: "We understand insurance. We understand our customers. We should own our own technology and our own capabilities." And there's truth to that. Our underwriting rules, our pricing logic, our customer segmentation—that's IP. That's our competitive advantage. But here's the tension: building takes time. And we don't have unlimited capital. So we're looking at a middle path. We're not going to buy a whole platform. But we're exploring partnerships and integrations. For example, we're talking to data providers about leveraging external data to improve our underwriting without having to build that capability internally. We're looking at partnership opportunities for some of our back-office operations. **[SARAH]** So it's more of a "build the core, partner for everything else" strategy. **[RICHARD]** Exactly. And the speed question is critical. If we could buy something and integrate it in six months and it was superior to what we could build in twenty-four months, we'd buy. But I'm skeptical that vendors understand insurance well enough to sell us something off-the-shelf that we could just plug in. Most of the platforms we've looked at are built for a much larger carrier or for a different type of insurance altogether. **[SARAH]** That's fair. What would it take for you to seriously consider a buy decision for something like sales enablement, pipeline management, or rev ops capabilities specifically? **[RICHARD]** Price, first. If we're going to buy, the total cost of ownership needs to be significantly lower than building. Not just license cost, but implementation, training, integration, ongoing support. We've been burned by that before. Second, it has to work in our regulatory environment. A lot of SaaS solutions are built for B2B SaaS companies, not for regulated industries. So we'd need proof that it works for insurance. That means either case studies from other carriers or a willingness from the vendor to customize for our specific needs. Third, and this might sound obvious, it has to make us faster, not slower. We've had bad integrations where the software itself became a bottleneck. Our team was spending more time working around the system than working for our customers. **[SARAH]** Those are really fair criteria. Let me ask you this: if there was a platform that combined sales pipeline intelligence—like real pipeline visibility, predictive close probability, that kind of thing—with revenue operations workflows that were specifically built for insurance sales cycles and regulatory constraints, would that be interesting to you? **[RICHARD]** *pauses and nods* It would be worth a conversation. Honestly, we're flying blind on a lot of our pipeline health metrics right now. I have a gut feeling about what's going to close and what's not, but that's based on experience and gut, not data. And as we scale, that's a weakness. The challenge is: insurance sales cycles are weird. You've got the sales cycle. You've got the underwriting cycle. You've got the regulatory approval cycle. Most sales intelligence platforms think of a deal as "opportunity created" to "won." But for us, a deal is "opportunity created" to "underwriting review" to "rate filing" to "regulatory approval" to "customer execution." That's 6 to 9 months, and the deal can die at any of those stages for reasons that have nothing to do with sales. **[SARAH]** So you'd need something that understands the full customer journey, not just the selling phase. **[RICHARD]** Exactly. And that's rare. Most platforms we've looked at have a very linear view of the sales process. They don't account for regulatory gates or underwriting risks that could kill a deal. So if you could build something that maps to our full revenue process—sales, underwriting, regulatory, execution—that would be genuinely valuable. **[SARAH]** That's really helpful. I want to come back to growth expectations for a second, because I think that's the through-line here. Your board wants 30% growth. You've got a 6 to 9-month sales cycle. You're operating in a fragmented regulatory environment. You've deprioritized IT modernization. You've got internal skepticism about new technologies from your actuarial team. How are you actually planning to hit growth targets in that context? **[RICHARD]** *laughs* That's the question I ask myself every morning. Honestly, we're betting on partnerships and market expansion. We can't rely on organic sales growth to hit 30% because the math doesn't work—you'd need impossibly large pipeline growth and conversion rates. So we're looking at strategic partnerships with brokers and aggregators. We're looking at expanding into new geographies where we can grow without the regulatory approval complexity we face in some of our existing states. We're also betting that attrition stays low. A lot of our growth projection is based on holding onto the business we have. Any customer churn above our internal projection puts us underwater on the growth target. **[SARAH]** So it's not really an organic sales growth story. It's more of a M&A, partnership, and retention story. **[RICHARD]** That's fair. And honestly, I'm more comfortable with that. I don't think we can build a sales organization that can do 30% organic growth in insurance. But if we can find 2 or 3 solid partnerships, acquire a niche carrier in an adjacent segment, and keep churn below 5%, we can hit the number. **[SARAH]** That's a more realistic framework. Which brings me to—and I'm curious about your thinking here—how much of your energy is going into retention and account growth, versus new customer acquisition? **[RICHARD]** We're probably 60-40, new to retention. Which is probably still not enough weight on retention. Our best customers are generating good margins, they've got sticky products, there's high switching costs. So expanding within those accounts and keeping them happy is actually higher ROI than chasing new logos. But our board thinks about revenue, and revenue is revenue, whether it's new customer or expansion. **[SARAH]** And if you actually invested more in retention and expansion—hired retention specialists, built account management capabilities—that could actually be higher ROI than just blasting growth with new sales hires. **[RICHARD]** It could be. And it's something we're thinking about. But there's a cultural piece here too. Insurance carriers are historically very sales-driven. We measure success by "new customers acquired" and "new revenue booked." The idea of having a team whose primary job is to keep customers happy and grow existing relationships is still a bit foreign to some of our leadership. It's changing, but slowly. **[SARAH]** That makes sense. Okay, let me ask you about your sales team structure specifically. How are you organized right now? **[RICHARD]** We're mostly organized by geography and product line. We've got a Northeast team, a Southeast team, a Midwest team, and a West team. Each team focuses on different products—commercial auto, commercial property, liability. The challenge is that some of our biggest customers are operating across multiple regions and multiple product lines, so we often end up with internal handoffs and coordination issues. **[SARAH]** Classic challenge. And I imagine with the regulatory fragmentation we talked about, your reps in the Northeast are probably selling a different set of products or facing different constraints than your West team. **[RICHARD]** Exactly. Which is why pre-qualification is so critical. A deal that works in the Northeast might not work in the Southwest because of different state regulations. **[SARAH]** Have you considered reorganizing by customer segment or by partnership type instead of just by geography? **[RICHARD]** We're exploring it. Our biggest opportunity right now is actually with national brokers and aggregators who can send us volume. So we're thinking about creating a dedicated team that focuses on those relationships and on the partnerships we want to build. That team would handle the full customer journey—sales, but also making sure underwriting reviews are streamlined, making sure regulatory approvals happen on time, making sure implementation is smooth. **[SARAH]** That's a really smart structure for where you're actually trying to grow. And it would allow that team to really own the customer relationship and the ROI. **[RICHARD]** Exactly. The challenge is we'd have to move some really good people, and there's always organizational resistance to that. But I think it's the right call. **[SARAH]** Yeah, people are always the hardest part. Okay, so let me just try to summarize what I'm hearing, and you can tell me if I've got it right. You're facing a gap between investor growth expectations—30% YoY—and the realistic growth you can achieve through organic sales, given the market, the regulatory environment, and your sales cycle. To hit growth, you're focusing on partnerships and market expansion rather than scaling direct sales. You've deprioritized IT modernization in the short term, even though you know it would enable better scaling in the future. Your actuarial team is skeptical about new technologies like AI, but they're open if you can show them proof points and technical validation. State-by-state regulatory fragmentation is a major constraint—it kills deals, creates tribal knowledge, and makes it hard for your team to be efficient. And on the build-versus-buy question, you're inclined to build your core capabilities but partner for everything else—IF the partnerships actually deliver value and reduce costs compared to building. **[RICHARD]** That's a fair summary. And I'd add one more thing: the real bottleneck right now is that we're not optimizing our sales process for the reality of our business. We're still using sales structures and processes that assume a traditional 3-month software sales cycle. We need a sales and revenue operation that's actually designed for a 6 to 9-month regulated sales cycle. That's where I think a tool like what you're talking about—something built for insurance—could really help. **[SARAH]** That's a really important clarification. So it's not that you need a generic sales intelligence tool. You need something that understands your unique sales process. **[RICHARD]** Right. And if you could build that—something that helps us navigate the full customer journey, gives us visibility into pipeline at each regulatory and underwriting gate, helps us qualify early whether a customer is even viable for us—that would be genuinely transformational. **[SARAH]** I really appreciate you laying all this out. I know you're a busy guy, and I've taken up most of our thirty minutes. Is there anything else that's top of mind for you that we haven't covered? **[RICHARD]** One thing: help us understand how other carriers are thinking about growth and modernization. Are we an outlier in deprioritizing IT investment? Are other carriers also struggling with the partnership model? What are the best-in-class carriers doing differently? That context would actually help us have better conversations internally about whether we're making the right calls. **[SARAH]** That's a great ask. We've worked with a number of regional carriers, and I can definitely share some best practices and case studies. I'll follow up with some examples of how other carriers are structuring teams and thinking about partnerships. **[RICHARD]** Perfect. And look, I think there's potential here. If you can build something that's actually designed for insurance—that understands our sales cycles, our regulatory constraints, and our customer journey—we'd definitely want to pilot it. Send over a deck on what you're thinking. If it resonates, we'll set up a deeper technical conversation with my team. **[SARAH]** Absolutely. I'll put something together this week and get it over to you. And Richard, I really appreciate the candor here. This has been super valuable context for us. **[RICHARD]** Thanks for asking good questions. It's nice to talk to someone who actually understands the insurance business and isn't just trying to sell us generic SaaS. --- ## Key Takeaways ### Growth Pressure vs. Sales Cycle Reality - **Challenge:** Board expects 30% YoY growth; insurance sales cycles are 6-9 months with multiple regulatory gates - **Current approach:** Focusing on partnerships, market expansion, and retention rather than organic sales scaling - **Implication:** Direct sales hiring alone won't close the growth gap ### IT Modernization Deprioritization - **Reason:** Lack of immediate ROI proof and competing capital priorities - **Cost:** Will likely require refocusing on modernization within 18 months as scaling constraints emerge - **Opportunity:** Framing modernization as regulatory risk reduction (not just efficiency) could change executive alignment ### Actuarial Skepticism on AI/ML - **Root cause:** Legitimate concern about regulatory risk, pricing validation, and explainability - **Solution:** Third-party technical validation, proof points, and transparent risk communication frameworks - **Timeline:** Adds 3-6 months to any AI-powered initiatives ### State-by-state Regulatory Fragmentation - **Impact:** Pipeline killer; forces manual pre-qualification; limits partnerships with national brokers - **Current mitigation:** Pre-qualification process, but it leaves money on the table - **Systemic need:** Requires either IT modernization to manage state-specific rules automatically or more compliance expertise ### Build vs. Buy Decision Factors - **Bias:** Prefer to build core IP (underwriting, pricing, risk models) - **Willingness to buy:** Only if TCO is significantly lower, solution works in regulated environment, and integration is proven with other carriers - **Partnership path:** More open to partnerships and integrations than platform buys - **Key requirement:** Solutions must be designed for insurance, not generic SaaS ### Revenue Operations Redesign Opportunity - **Gap:** Current sales structure assumes traditional software sales cycles; doesn't account for underwriting, rate filing, and regulatory approval phases - **Opportunity:** Revenue ops platform built specifically for insurance sales cycles, with visibility across all customer journey gates - **Potential impact:** Could improve pipeline visibility, reduce wasted effort on non-viable deals, and enable better partnership execution --- **Interview conducted by:** Sarah Martinez, Enterprise Sales Director **Recorded:** December 15, 2025 **Status:** Follow-up scheduled with deck and case studies