By: Guillermo Salazar • 08 April 2025

Lessons from Mason Mello

The Accidental InsurTech Evangelist

Mason Mello never imagined joining the insurance industry. He admits he didn’t even know what "insurtech" meant before landing at Sure. But like any great story, the best journeys often start by accident.Mason launched his career in entrepreneurship. At the University of Florida, he co-founded Greek House, a custom apparel startup that became an Inc. 5000 company. Building something from the ground up and creating real impact fueled his passion. When he discovered Sure, he saw an opportunity to transform an industry desperate for change.“Something about the company just drew me in,” he says. “It was the people, the leadership, and the chance to make a big impact.”Today, Mason leads the Connect division at Sure, helping brands and carriers embed digital insurance products directly into customer journeys. Think of Sure as the rails and infrastructure—like what Visa and Mastercard built for commerce—but for insurance.

Insurance is Broken (and Everyone Knows It)

Insurance is essential, but it’s broken. For renters, property managers, and even major carriers, the process stays clunky, manual, and outdated.Mason lays it out: “Only about 1% of insurance gets transacted digitally. That means 99% of the market stays stuck in the past.”Renters insurance highlights the problem. Many property managers require it as part of lease agreements, but compliance remains chaotic. Nearly 40% of renters cancel their insurance mid-lease. That leaves property managers exposed to serious risk without realizing it until something goes wrong.Even worse, leasing offices still rely on snail mail and spreadsheets to track coverage. “It’s wild,” Mason says. “Staff manually scan documents and emails just to figure out who’s covered.”The cost of inaction is steep. When tenants cancel coverage and accidents happen, landlords pay. If they file claims on their landlord policy, premiums spike. Across 20,000 units, the risk multiplies.Still, many property managers don’t realize they can fix this. Mason emphasizes that education comes first. “Our biggest competitor isn't another software platform,” he adds. “It's the status quo.”

Creating “Hell Yes” Moments

So, how do you go from “meh” to “Hell Yes” in sales?Mason answers: get real about the cost of inaction.“Everyone talks about ROI,” he says. “But you can’t skip COI—the cost of inaction. That’s what creates urgency.”This shift defines the "Getting to Hell Yes!" sales mindset. Mason helps buyers realize what they risk if they don’t act. Instead of starting with product features, he leads by quantifying their pain:

How many renters cancel mid-lease?
What does one uncovered loss cost?
How much time does the staff spend tracking coverage manually?

When buyers see the numbers, the light bulb goes off. “If this happens once, it can happen across your entire portfolio. That’s when they realize: we can’t let this continue.”But Mason doesn’t rush. His secret? Patience.“We all want to move fast,” he says. “But good things take time. You have to guide buyers, not push them.”He also speaks their language. “If you don’t understand their business better than they expect, you can’t sell to them. Period.” That means knowing how property management works, where bottlenecks exist, and what keeps leasing teams up at night.“I spend a lot of time studying the operations side,” he says. “Because that’s where the real pain shows up. If you can solve a pain that’s buried under paperwork, you earn trust fast.”It also means delivering solutions that fit. That’s where SureVerify comes in: an AI-powered insurance verification tool that automates tracking and eliminates paperwork and manual follow-ups.“The goal is zero coverage gaps,” Mason explains. “If you automate compliance, you free your teams to focus on what really matters—growing the business.”And yes, it works.

Embedded Insurance as the Win-Win-Win

Mason believes embedded insurance is the future, and Sure leads the way. Here's how everyone wins:Property Managers

Automate insurance tracking.
Reduce exposure.
Free up leasing teams.

Renters

Buy insurance digitally, in context.
Maintain ongoing coverage.
Gain peace of mind.

Brands and Carriers

Open new distribution channels.
Boost conversion and retention.
Offer better customer experiences.

Mason compares it to booking travel or ordering food: quick, seamless, and built into your journey. “Insurance shouldn’t be different,” he says. “You should buy it when you need it, without jumping through hoops.”That’s especially true in property management. Lease signings involve a high-friction moment, and requiring tenants to leave the process to find insurance adds stress. With Sure, it all happens in the flow. With SureVerify, property managers can track policy status throughout the lease, avoiding last-minute surprises.And this is just the beginning. “We started with renters insurance, but this applies to auto, travel, and more. Anywhere insurance fits, we want to power the experience,” Mason says.

3 Key Takeaways About “Getting to Hell Yes!”

1. Start with Education, Not the PitchMost buyers don’t know what’s possible. Show them the better way. As Mason puts it: "We’re not competing against another tool. We’re competing against the old way of thinking."2. Quantify the Cost of Inaction (COI)Before you pitch ROI, highlight what they risk by doing nothing. Use actual numbers: dollars lost, hours wasted, risk exposure.3. Speak Their LanguageUnderstand the buyer’s world. What matters to them? What pain keeps them from scaling? Don’t sell—solve.

Final Thoughts

Mason Mello didn’t plan on becoming an insurtech leader. But today, he’s helping reshape the industry by showing people what’s possible. Through empathy, insight, and patience, he guides buyers from confusion to clarity—and from "maybe" to “Hell Yes.”“You’re not just selling a product,” Mason says. “You’re helping someone protect their assets, save time, and sleep better at night. That’s a powerful reason to show up every day.”Next time you’re in a sales conversation, don’t just talk about what your buyer gains. Ask what they lose if they do nothing.That’s how you unlock momentum.

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