Speeding up 250,000 daily payments.
How I made 5.2 million policyholders forget they were paying their insurance bill
“I Couldn’t access real users due to compliance restrictions. Listened in on support calls tied to paying a bill and interviewed front-line staff. Patterns emerged fast once we connected real stories to usage data.”
When Each Payment Only Buys Another Bill Arriving in 30 Days
The call came on a Tuesday morning that would change everything.
"Bryan, we're drowning. Call volume is up 40%, and 60% are people who can't figure out how to pay their bills online. They're abandoning the payment flow and calling us instead."
I stared at the current payment flow. 14 million active policies. Hundreds of thousands of daily transactions. And somehow, paying a bill had become a shitty experience times two.
Something fundamental was broken here.
The insurance industry is viciously boring. There's no return on investment—folks hope not to file claims, so their cash disappears into investment portfolios. But if you can't make a crookedly regulated industry better, you have no business leading user experience.
Every abandoned payment was a policy at risk of lapsing.
I had three sprints to solve a problem that had been festering for years.
Research Proved What No One Wanted to Say Out Loud
Day three of user interviews, and the pattern was clear.
"I always feel like I'm making a mistake or missing something," said Danielle from Wisconsin. "Sometimes I just give up and call customer service. I don't want to think about it anymore."
That phrase kept echoing: "I always feel like I'm making a mistake."
I spent a week in call center recordings. Hour after hour of frustrated voices describing the same disconnect: they wanted to pay what was due without getting canceled. Our system made it hard for folks to give us money.
Analytics showed 66 seconds on the review form before converting or abandoning. But sessions revealed what those seconds contained: Looking, clicking, relearning, guessing, then quitting.
Users weren't slow. Our interface was making them slow.
The Breakthrough: During stand-up, I asked our 11-person team: "Raise your hand if you like paying your insurance bill." One hand went up, then slowly sank.
We forgot how much insurance sucks.
The revelation came from my e-commerce experience. Six years of optimizing online shopping taught me: to improve our painful payment flow, make it feel more like the shopping experience we actually enjoy.
Stop trying to make paying insurance easier. Make it feel like it's not insurance.
Making People Forget They're Paying Insurance
The solution felt obvious once I started thinking like someone sneaking in a quick online shop before a 7 AM virtual stand-up.
What if we used a mental model people actually enjoyed? Add to cart, edit cart, "I'll pay this now and save the other for next week."
The New Logic:
One form instead of multiple
Two to three steps instead of potentially five.
One "Edit Payment" button
Mobile-first across all platforms
Getting buy-in meant navigating corporate politics. Product leadership wanted me to use inherited components that were recently redesigned (before I joined) so I was stuck with subpar form elements. I spent one week designing and building a prototype and two weeks testing it, proving users could pay 40% faster … even with less-than-optimal building blocks.
Sometimes you have to make magic with what you inherit. Imagine the stats if I could've started from scratch.
The real test was in production.
Week One: Call volume dropped 23%. Payment abandons dropped 41%.
Week Four: Task completion jumped from 34% to 78%. Time in flow dropped from 3.7 minutes to 1.4 minutes.
Week Eight: 12% increase in on-time payments. 8% reduction in policy lapses. 22% faster premium collection.
The real victory: more policy-related support calls, less billing-related.
What I Learned About Designing for Insurance
Insurance flows will never trend on Dribbble. But there's something satisfying about taking someone's most despised financial moment and making them forget they dislike it.
The best insurance UX is invisible UX.
Fourteen million policyholders could now pay without calling, without guessing. They could see what they were paying and move on with their day.
That's not just good design. That's conversion.
Design Philosophy: People don't pay insurance bills because they want to. They pay them because they have to. If I can design clarity in insurance, I can design clarity anywhere.
“I Couldn’t access real users due to compliance restrictions. Listened in on support calls tied to paying a bill and interviewed front-line staff. Patterns emerged fast once we connected real stories to usage data.”
When Each Payment Only Buys Another Bill Arriving in 30 Days
The call came on a Tuesday morning that would change everything.
"Bryan, we're drowning. Call volume is up 40%, and 60% are people who can't figure out how to pay their bills online. They're abandoning the payment flow and calling us instead."
I stared at the current payment flow. 14 million active policies. Hundreds of thousands of daily transactions. And somehow, paying a bill had become a shitty experience times two.
Something fundamental was broken here.
The insurance industry is viciously boring. There's no return on investment—folks hope not to file claims, so their cash disappears into investment portfolios. But if you can't make a crookedly regulated industry better, you have no business leading user experience.
Every abandoned payment was a policy at risk of lapsing.
I had three sprints to solve a problem that had been festering for years.
Research Proved What No One Wanted to Say Out Loud
Day three of user interviews, and the pattern was clear.
"I always feel like I'm making a mistake or missing something," said Danielle from Wisconsin. "Sometimes I just give up and call customer service. I don't want to think about it anymore."
That phrase kept echoing: "I always feel like I'm making a mistake."
I spent a week in call center recordings. Hour after hour of frustrated voices describing the same disconnect: they wanted to pay what was due without getting canceled. Our system made it hard for folks to give us money.
Analytics showed 66 seconds on the review form before converting or abandoning. But sessions revealed what those seconds contained: Looking, clicking, relearning, guessing, then quitting.
Users weren't slow. Our interface was making them slow.
The Breakthrough: During stand-up, I asked our 11-person team: "Raise your hand if you like paying your insurance bill." One hand went up, then slowly sank.
We forgot how much insurance sucks.
The revelation came from my e-commerce experience. Six years of optimizing online shopping taught me: to improve our painful payment flow, make it feel more like the shopping experience we actually enjoy.
Stop trying to make paying insurance easier. Make it feel like it's not insurance.
Making People Forget They're Paying Insurance
The solution felt obvious once I started thinking like someone sneaking in a quick online shop before a 7 AM virtual stand-up.
What if we used a mental model people actually enjoyed? Add to cart, edit cart, "I'll pay this now and save the other for next week."
The New Logic:
One form instead of multiple
Two to three steps instead of potentially five.
One "Edit Payment" button
Mobile-first across all platforms
Getting buy-in meant navigating corporate politics. Product leadership wanted me to use inherited components that were recently redesigned (before I joined) so I was stuck with subpar form elements. I spent one week designing and building a prototype and two weeks testing it, proving users could pay 40% faster … even with less-than-optimal building blocks.
Sometimes you have to make magic with what you inherit. Imagine the stats if I could've started from scratch.
The real test was in production.
Week One: Call volume dropped 23%. Payment abandons dropped 41%.
Week Four: Task completion jumped from 34% to 78%. Time in flow dropped from 3.7 minutes to 1.4 minutes.
Week Eight: 12% increase in on-time payments. 8% reduction in policy lapses. 22% faster premium collection.
The real victory: more policy-related support calls, less billing-related.
What I Learned About Designing for Insurance
Insurance flows will never trend on Dribbble. But there's something satisfying about taking someone's most despised financial moment and making them forget they dislike it.
The best insurance UX is invisible UX.
Fourteen million policyholders could now pay without calling, without guessing. They could see what they were paying and move on with their day.
That's not just good design. That's conversion.
Design Philosophy: People don't pay insurance bills because they want to. They pay them because they have to. If I can design clarity in insurance, I can design clarity anywhere.
“I Couldn’t access real users due to compliance restrictions. Listened in on support calls tied to paying a bill and interviewed front-line staff. Patterns emerged fast once we connected real stories to usage data.”
When Each Payment Only Buys Another Bill Arriving in 30 Days
The call came on a Tuesday morning that would change everything.
"Bryan, we're drowning. Call volume is up 40%, and 60% are people who can't figure out how to pay their bills online. They're abandoning the payment flow and calling us instead."
I stared at the current payment flow. 14 million active policies. Hundreds of thousands of daily transactions. And somehow, paying a bill had become a shitty experience times two.
Something fundamental was broken here.
The insurance industry is viciously boring. There's no return on investment—folks hope not to file claims, so their cash disappears into investment portfolios. But if you can't make a crookedly regulated industry better, you have no business leading user experience.
Every abandoned payment was a policy at risk of lapsing.
I had three sprints to solve a problem that had been festering for years.
Research Proved What No One Wanted to Say Out Loud
Day three of user interviews, and the pattern was clear.
"I always feel like I'm making a mistake or missing something," said Danielle from Wisconsin. "Sometimes I just give up and call customer service. I don't want to think about it anymore."
That phrase kept echoing: "I always feel like I'm making a mistake."
I spent a week in call center recordings. Hour after hour of frustrated voices describing the same disconnect: they wanted to pay what was due without getting canceled. Our system made it hard for folks to give us money.
Analytics showed 66 seconds on the review form before converting or abandoning. But sessions revealed what those seconds contained: Looking, clicking, relearning, guessing, then quitting.
Users weren't slow. Our interface was making them slow.
The Breakthrough: During stand-up, I asked our 11-person team: "Raise your hand if you like paying your insurance bill." One hand went up, then slowly sank.
We forgot how much insurance sucks.
The revelation came from my e-commerce experience. Six years of optimizing online shopping taught me: to improve our painful payment flow, make it feel more like the shopping experience we actually enjoy.
Stop trying to make paying insurance easier. Make it feel like it's not insurance.
Making People Forget They're Paying Insurance
The solution felt obvious once I started thinking like someone sneaking in a quick online shop before a 7 AM virtual stand-up.
What if we used a mental model people actually enjoyed? Add to cart, edit cart, "I'll pay this now and save the other for next week."
The New Logic:
One form instead of multiple
Two to three steps instead of potentially five.
One "Edit Payment" button
Mobile-first across all platforms
Getting buy-in meant navigating corporate politics. Product leadership wanted me to use inherited components that were recently redesigned (before I joined) so I was stuck with subpar form elements. I spent one week designing and building a prototype and two weeks testing it, proving users could pay 40% faster … even with less-than-optimal building blocks.
Sometimes you have to make magic with what you inherit. Imagine the stats if I could've started from scratch.
The real test was in production.
Week One: Call volume dropped 23%. Payment abandons dropped 41%.
Week Four: Task completion jumped from 34% to 78%. Time in flow dropped from 3.7 minutes to 1.4 minutes.
Week Eight: 12% increase in on-time payments. 8% reduction in policy lapses. 22% faster premium collection.
The real victory: more policy-related support calls, less billing-related.
What I Learned About Designing for Insurance
Insurance flows will never trend on Dribbble. But there's something satisfying about taking someone's most despised financial moment and making them forget they dislike it.
The best insurance UX is invisible UX.
Fourteen million policyholders could now pay without calling, without guessing. They could see what they were paying and move on with their day.
That's not just good design. That's conversion.
Design Philosophy: People don't pay insurance bills because they want to. They pay them because they have to. If I can design clarity in insurance, I can design clarity anywhere.
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