On Point - Insurance Journal

What could an insurance company finance guy bring to the On Point Podcast table? Turns out a lot of insight about the business… And some fun as well. We chat with Rob Looney, Westfield’s CFO. Rob grew up destined to be a numbers whiz—his mom was an insurance exec herself and his dad a banker. He is rooting for his peers around the insurance business to be more strategic, analytical and long-term focused—versus just crunching numbers. Finance professionals “are no longer in silos,” Rob says. “We used to just audit what happened in the past. Now we really require a focus on next year and the year after that.” He says an ideal state is for insurance leaders to be “calling finance before they make a decision… instead of just asking about last year.” Rob sees his leadership role as helping people do their jobs better and faster. “It’s very important to make decisions with sometimes imperfect information and stay calm under pressure,” he says, adding: “I tell people I want to hear about bad news right away. I’m not going to kill the messenger. I learned early on that clarity matters. I cannot possibly micromanage people who work for me, so I need to know what matters and teach them to make decisions and take risks—as long as they can back it with reasoning.”

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After working at carriers for 20 years, strategic consultant Brando Guerrero offers up some strong opinions on the future of insurance distribution. Listen as he dishes out some tough love. Driven by tech and competitive forces, the model is splitting into two very different paths, he says. Path 1 is high-touch, relationship-driven distribution, with independent agents providing consultative advice, deep expertise in complex risks, and higher premiums justified by service and risk selection. Path 2 is low-touch, tech-enabled distribution, with direct-to-consumer platforms, straight-through processing, and volume play with razor-thin margins. “Trying to be both won’t work, Brando argues. “Carriers that try to compete on price and service end up being mediocre at both.” He outlines ways carriers can get out of the middle. Who are the real winners in all of this? Probably MGAs and program administrators, Brando says. “They can bridge both sides with narrow risk classes. Their entire model is built around specialization. They don’t have the legacy problems carriers have. They can gin up capacity and go to the market very fast.” Agents and brokers too must face the music: Specialization is key. “If you’re a generalist agency trying to be everything to everyone, you’re in the same trap as a generalist carrier.” Brando is bullish on the future of the IA channel, especially for more complex risks. “Relationships have become more important. You need a human who understands the risk. AI can’t do that.”

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Here’s an engaging chat with Heather Wilson, who challenged herself early to grow in her career—starting with Girl Scout cookie sales in grade school. Then, professional work beginning as a teenager in health care and financial services consulting in Japan and Russia launched a tech career. “I was just mesmerized” by data, she says. “I had a knack for language and…data was a language to me. I had an epiphany, and it was: This is the future. Not just for financial services, but for every industry.” Today, Heather is CEO of CLARA Analytics. The firm provides AI-driven models for carriers and self-insured firms to improve back-to-work and litigation reduction in BI claims. The claims process will improve, she says. Today, the adjuster’s load is very task oriented and administrative. “We will see AI take those over. Then the adjuster can really spend time with the patient and gain trust…” Heather says the insurance business doesn’t get enough credit for adopting change. “I find insurance executives are right there with other industries. They’re in their labs trying new things. All of them are just trying to figure it out, given the environments they’ve inherited…” In the same way she was mentored by teachers and bosses, Heather outlines some advice for young professionals: “You are going to have to do some grunt work and be scrappy at times. Learn the details. Have a work ethic. Be the eager beaver, be a listener and learner. Sign up for more, go the extra mile. Attitude is so worth it.”

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We check in with Joe Zuk, an insuretech guru with private equity firm Altamont Capital Partners. It’s an “exciting” time to evaluate new and established firms, he says. After a bit of a lull in insuretech chatter over the last few years, “Now we’re seeing a resurgence.” Joe outlines several categories of action: Augmented underwriting vendors using third-party data to bring risk fidelity and granularity in underwriting and claims. Data organizers using large language models to organize foundational data in the insurance value chain. Predictive AI in climate, weather tech and liability. Category disruptors working to upset the value chain in going direct to consumer or truncating the value chain with AI or other technology. And the MGA and program sectors remain hot. At the same time, AI is not a panacea, Joe cautions. “We still work in a heavily regulated industry…  A lot of folks are saying lets slap AI onto everything and surely that’ll be the fix. I’m really worried about a loss of institutional knowledge and foundational and fundamental skills in underwriting, risk selection, aggregation management and claims. And let’s not forget the relationship aspect of it.” In his PE work, Joe likes to “underwrite people first and foremost” when choosing where to invest in firms. He loves insurance. “I get to never be bored. I get to challenge my mind to solve problems daily. I see it as a big puzzle. It’s a very addicting and fun industry.”

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Imagine a world where we all loved our work. And work loved us back! Okay, that’s just not gonna happen, says professional development and executive coach Jenn Urso. And this is okay, because employees and employers still can reach a peaceful coexistence and understanding amidst a stressed-out world. On this engaging conversation Jenn unpacks lots of insight for improving work focus, productivity and personal happiness, which are tightly connected. Jenn built her company, The Leadership Project, after a six-month sabbatical traveling the world. During her time abroad she learned that people in all cultures and countries share a deep connection with their work; and, simultaneously, they feel “frustrated and burned out and swallowed up by work.” Jenn believes that “work is not meant to love you.” A profit-making organization doesn’t always align with many employees’ yearn for warm-and-fuzzy emotional connections. Over the last 100 years, and evolving more recently, “work originally was about survival, and then stability, status, self-actualization, and now a state of stress,” Jenn says. Listen as this leader whisperer outlines what we can do about the stress, with On Point host Peter van Aartrijk!

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When the insurance market gets tough—and it has been in recent years—the entrepreneurs get going. New products, new coverage alternatives and new service bolt-ons are created. Dylan DiMarchi is in the middle of it. He emerged from the real estate world, frustrated with the unpredictable cost of insurance, and developed Premium Lock, which guarantees insurance cost on a property for up to three years. “If a fixed-rate 30-year mortgage is a thing, why not at least a three-year guarantee for an insurance policy?” he says. Premium Lock is not insurance per se. Customers pay an average of $20 per month and are reimbursed if premiums rise over the agreed amount. His firm reviews a number of sources to predict how every carrier will price every piece of property in the U.S. That includes macro-economic factors like construction cost inflation, carrier profitability, regulatory behavior, and weather dynamics. Dylan believes Premium Lock is educating consumers on the impact of climate change. He also credits his fellow insuretech founders who are working to prevent property losses, such as fortifying homes. “Right now it’s expensive to do, but I have hope that carriers will show real financial ROI” on investments in mitigating property risks,” he says. Listen to this new On Point episode with host Peter van Aartrijk today!

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Happy New Year, On Point Nation! Let’s start with a fresh look on improving your sales techniques. Let’s face it: We are all in sales in some way, right? And our guest Amy Reczek is a terrific sales coach. On this recording Amy unveils some techniques she discovered herself along the way as a trainer and speaker. Your posture, what you’re doing with your hands and eye contact are three critical nonverbal tools to master, she outlines. People buy from people, and not from companies, she adds. They are looking for people they can emotionally connect with. “Don’t pack in a lot of words,” Amy advises. “Ask more questions like, ‘Tell me about X?’ They answer. Then you say, ‘Can you tell me more about X? And about this?’ Stay with the client. Ask ‘why’ multiple times. You are gaining knowledge. Don’t flip right to the solution. Sit with the client more to really discover what’s happening. All value is what really matters to the client; it has nothing to do with you. We need to listen more on that.” Bonus: Amy outlines a number of sales-killing words we typically say and write. “Just checking in…” and “Just following up…” are, well, “just” two of them!

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Jennifer Palmieri is chief people officer at Westfield, which certainly isn’t a regional p/c carrier anymore. She has witnessed growth in specialty lines and international risks. It’s nearing $5 billion in revenues and 4,000 employees. We checked in with Jen on how human resource strategies are playing out. “My leadership philosophy centers on authenticity, shared accountability and purpose,” she says. “That means being able to lead with transparency and deeply listening. And to really understand what motivates people. When that happens, you see people flourish and develop and transform companies, businesses, cultures in an exceptional way.” Listening is something Jen prioritizes daily. “We live in a highly distracted world. One thing I learned early in my career — and it’s an old leadership philosophy — is, ‘Be here now.’” The employer brand is on her mind as well, especially with talent needs and expectations differing by region. “Employer branding in a competitive talent market obviously is essential. We like to reflect on our purpose. Being authentic — that travels well.” With five generations working side-by-side, she notes that “each brings something valuable. Boomers have deep experience and history and perspective. Younger people are highly digital and focused on flexibility. How do we create a culture that honors the differences and… creates something that we can all harness together?” So Westfield fosters mentorship across generations. Finally, Jen advises younger professionals: “Be more curious, ask more questions, ask more about ‘the why.’ Be more thoughtful and intentional about your work.”

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On this installment we tee up three segments from our onsite discussions at Applied Net 2025, a leading insurance tech conference held recently in Vegas. First: Why was the Geico Gecko basking in the crowd at an independent agent channel exhibit hall? This is intriguing! Take a listen as another direct-response carrier takes an interest in appointing agents. Next, insuretech expert, advisor and pundit Mark Breading joins On Point to reflect on AI’s impact on the industry. Are we heading toward a future where the traditional carrier model becomes obsolete? Or will it adapt and thrive? Mark weighs in. Finally, Brenna Johnson, an executive with agency management system EZ Lynx, walks us through how AI can free up producers and agency service staff for “hero work” — instead of busy work.

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Yours truly has met many interesting people in my 43 years of hanging around the insurance business. Few are as fascinating, complex and rule-breaking as Peter Anderson. He leads a dominating musical instrument insurance program with 18,000 customers in the U.S. and around the world—90% of them arriving via the website. Listen to his origin story (starting at age 4) of falling in love with playing instruments, singing in church and eventually earning a spot with the Boston Symphony Orchestra Chorus (aka Boston Pops). And then how he got into retail insurance to protect his musician friends. “I was a music major who needed a day job,” he says. Like a lot of high-value and collectible things, musical instruments and related equipment aren’t properly covered by standard policies. That’s where the Anderson program comes in. Some of the stated values of the instruments are astonishing. At age 73, Peter is going strong and offers listeners some interesting rants. As for instruments, the tuba is his favorite. “A ton of personality.”

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