How Empathy Landed 9 of the Top 10 US Life Insurers by Testing 5 Verticals Simultaneously

After Ron Gura's colleague at eBay lost his wife to cancer, Ron visited his house to pay condolences. There, he encountered something unexpected: mountains of paperwork about estate settlement, taxes, and a term he'd never heard before—probate.

"I left that house that day," Ron recalls. "I was like, somebody needs to build a headspace for grief. And also a turbotax for estate settlement. I didn't know it's gonna be me, but I was like, trying to teach that to friends and tell them I'll back it and whatnot. But eventually couldn't get over it."

In a recent episode of BUILDERS, Ron Gura, Co-Founder & CEO of Empathy, shared how his company went from that insight to working with 9 of the top 10 life insurance carriers in the US and Canada, covering over 40 million people. The path there reveals specific tactics about vertical selection, category creation timing, and enterprise sales in markets defined by avoidance.

Testing Five Verticals in Parallel With Artificial Constraints

Most B2B startups test markets sequentially—one vertical, learn, pivot, next vertical. This approach protects runway but creates a devastating risk: you might quit before finding your strongest signal.

Ron's team took a different approach. They identified 10+ potential verticals but deliberately constrained themselves to testing exactly five simultaneously. This artificial limit forced prioritization while compressing discovery time.

"We identified more than 10 meaningful verticals because we came to this business from a very resourceful perspective," Ron explains. "We said we're going to tackle five of them at the same time and see which one is kind of the most interesting from a pool perspective."

The five: hospices, funeral homes, employers, and two others including life insurance at position five. Life insurance wasn't their hypothesis—it was nearly an afterthought.

The breakthrough came from New York Life. Ron's team pitched user experience and continuity of care. New York Life heard asset retention and generational loyalty. "We didn't know that at the time. We were thinking about it in a much more simplistic way," Ron admits.

This language mismatch became the key insight. Life insurers weren't buying better customer experience—they were buying multi-generational asset retention. The beneficiary relationship could extend the customer lifetime from one generation to three.

Finding Innovation Teams Within Conservative Structures

Breaking into life insurance required acknowledging an uncomfortable truth about risk aversion. "These organizations, as risk averse as they might be, and to be fair, I actually think they have a really good chance, a good reason to be risk averse," Ron notes. "Like more than any other vertical, these guys are supposed to weather the storm no matter what. You kind of want them to be big, profitable risk averse companies because your kids money is just there."

The tactical move: target innovation teams with dual mandates. New York Life Ventures handled both business development for the carrier and venture investments. This structure created natural alignment—they could invest in Empathy while simultaneously piloting the technology.

"We try to make sure that they have a competitive advantage if they work with us," Ron explains. "And that worked really well for both of us."

After New York Life: Guardian, MetLife, then 40 more carriers. The category proof from the first deal accelerated subsequent closes.

Recognizing Ecosystem Architecture, Not Building It

The expansion from life insurance to employee benefits wasn't strategy—it was pattern recognition. Ron discovered that half his life insurance carriers were group life carriers, meaning they sell exclusively to employers, not consumers.

"Employee benefit and life insurance have a really strong overlap," Ron explains. "Half of our carriers are group life carriers. So think about Prudential, Aflac, Voya, giants like MetLife, they sell primarily and most of them the brands I just mentioned, only to group to employer groups."

The implication: MetLife doesn't have a consumer website where individuals buy policies. If you work for AT&T, you're covered by MetLife through your employer's group policy.

This creates dual enterprise entry points to the same end user. When an employee at Paramount loses a family member covered by their MetLife group policy, the beneficiary calls MetLife. When that same employee loses a sister not covered by insurance, they call Paramount HR for bereavement leave.

"If Amanda is healthy, but God forbid she lost her sister, she's unable to bring her whole self back to work," Ron illustrates. "Tomorrow morning she's calling Paramount. She's not calling MetLife."

Same person, same moment of need, two different organizational touchpoints. Ron didn't build this triangle—he recognized it already existed. "This is an existing triangle. We are proud partners of Paramount and MetLife."

The lesson: before choosing your wedge vertical, map who else touches your end user in adjacent contexts. These aren't future expansion opportunities—they're architectural realities that determine whether you're building into an ecosystem or against it.

Brand Investment as Friction Reduction When Fighting Aversion

Empathy made what most seed-stage B2B companies would consider Series A investments: acquiring the premium domain empathy.com, developing comprehensive design systems, and establishing rigorous tone and voice frameworks.

Ron's logic: "The barrier to entry in the end of life space isn't a regulatory barrier and isn't necessarily a technology barrier. It's us humans trying really hard not to think about and not to contemplate our own self mortality. So it's aversion that I'm fighting against. So I need to add positivity into the mix."

When your core barrier is psychological avoidance, brand isn't marketing—it's distribution infrastructure. Every element that reduces friction to engagement becomes ROI-positive earlier than in traditional B2B markets.

"From the beginning we raised a meaningful seed round and we invested heavily in our tone, our voice, our brand, our ligatures," Ron says. "Our domain, as you said, was not $10."

The website navigation reveals the dual-audience challenge. Grieving end users need emotional support and practical logistics. Enterprise buyers evaluating the platform are in their normal workday, thinking about comp strategy and leave policies.

"When you're dealing with bereavement, you don't want to show people because it's not your loss," Ron explains. "But at the same time, when you're trying to convey a message to a decision maker who works in Citibank or TIA or MetLife or Google or Microsoft, they're not sad right now, they're not bummed, they're not in a crisis. They're just in the middle of their workday."

Empathy's solution: the website now includes stock photography and faces—elements absent from their early brand identity—to signal professionalism for enterprise buyers while maintaining the emotional intelligence required for end users.

Activating Buyer's Lived Experience as Core Sales Motion

Enterprise buyers evaluate vendors through budget authority and ROI models. But Empathy discovered their strongest conversion asset wasn't features or pricing—it was activating personal memory.

"Everyone we're talking to, even if they're, you know, head of comp or head of benefits, you know, at Carmax or head of claims in Sun Life, they're humans," Ron observes. "They have parents, they had loss, they went through probate, they know what grief is. They attended a funeral and many of them just experienced it just in the last few months if it's their mother in law."

The most common response after demos: "Damn, I wish you called me a few months ago. That's like I needed this a year ago with my mom."

This isn't empathy selling—it's recognition selling. The product demo triggers the buyer's memory of their own experience navigating probate, deactivating accounts, managing estate settlement while grieving. The evaluation shifts from "does my organization need this?" to "I needed this."

For B2B founders in universal human experience categories—caregiving, bereavement, financial stress, parental leave—structure discovery to surface the buyer's personal experience before presenting product. Their lived reality becomes your strongest proof point.

Category Creation as Resource Strategy With Known Tradeoffs

Ron explicitly acknowledges category creation's double edge: "There's a lot of pros and cons of trying to define a category. It's helpful in many ways when you attract resources, talent, capital. It also creates a very fertile ground for a number two future sympathy.com to come along and learn from this podcast and many other bits of information out there, like how to compete and what to go after."

Every positioning document, every podcast appearance, every vertical discussion publishes your playbook. Future competitors learn which markets converted and which didn't, which messaging worked and which failed, which verticals to target first and which to avoid.

The decision to pursue category leadership is a conscious bet: trade competitive opacity for talent and capital velocity. If you can't defend your position once it's public, stay in stealth longer.

When entering new verticals, Ron reduces category education costs by mapping to existing budget lines. With employers, he positions bereavement care alongside caregiving, fertility, and parental leave programs.

"You need to kind of paint the line between, well, this is a life transition happening in my own intimate house. Just like, just like say a new baby," he explains. "They already have caregiving solutions. They have generous leave of absence. They have fertility programs, maternity programs."

This frames bereavement care not as net-new category requiring new budget, but as logical extension of existing family benefits spending. The ROI conversation becomes reallocation, not creation.

From Bereavement to Life Transitions

Ron's long-term vision extends beyond loss into multiple challenging life moments. "At some point, everyone is going to face a moment they didn't plan for and didn't choose everyone," he says. "Loss is universal. Disability is universal. Natural disasters are universal. Divorce is universal."

The strategic question: which other infrequent, high-stress life transitions could leverage the same infrastructure—emotional support plus practical logistics delivered through existing organizational touchpoints?

"You're going to see empathy in more moments and more markets," Ron concludes.

For B2B founders building in markets defined by psychological barriers: test multiple verticals in parallel with artificial constraints, recognize ecosystem architecture before building strategy, invest in brand as barrier reduction, and structure sales to activate buyer's lived experience. The strongest GTM motion isn't always teaching buyers something new—sometimes it's helping them remember what they already know.