Claims Expert Laura Haber on ‘Umpire Assistant’, Brutally Honest Negotiations and Why In-Person Meetings Take the Contention Away
…I think that if people would meet others who were completely different from them, thought about things completely differently, sat with them for two or three days, played cards, and talked with them, we wouldn’t be so scared, angry, fearful, or feel like we have to hate. I think that would help a lot…
I had the pleasure of talking with Laura Haber, and to understand where she is going, you first have to understand where she came from. Haber’s life began on a literal dividing line, a detail that feels almost prophetic for a woman who has spent her career trying to bring opposing sides together. She grew up in Bristol, a city sliced in half, sitting partly in Tennessee and partly in Virginia.
“I think the Geico commercial jumps over the line and says, ‘Now I’m in Tennessee, and now I’m in Virginia,’” Haber says with a laugh. But growing up in the late-1960s and early-1970s those lines were more than just geography. “It was an interesting way to grow up… there were a lot of controversial things going on in the world. It mattered if you lived on this side of the tracks or that side.”
Haber’s background is a tapestry of American complexities. She was raised Catholic only to later discover she was also Jewish as well as an aristocrat. Her grandparents ran a restaurant where Al Gore’s aunt would bring the future Vice President for Sunday lunch. It was a childhood of fishing, boating, and eventually, the revelation of a “real musical family” after moving to Florida. “My mom was a singer, my dad is a drummer and percussionist, and my brother is a triple-threat,” she recalls. “Our grandmother played classical piano as did her father, and his father was an orchestra conductor. My father is a well-known jazz drummer and his brother was a jazz and blues piano virtuoso. Together they played with all jazz and R&B greats from the 1950s to the present from the streets of Miami and New York to most all of the renowned jazz clubs around the world. My kids and grandkids are keeping the tradition going, with my grandson not only being a natural percussionist and drummer, but taking it to the next level with EDM, hyperpop an these new groundbreaking genres. Our family is a true band, or even an orchestra.”
But the rhythm of her life shifted from music to the chaotic percussion of storms. After a stint in construction and bookkeeping, Haber found herself in the insurance business just as the weather turned violent. “Andrew hit, then Wilma — all of these hurricanes,” she says. She entered the world of adjusting, handling property claims in the wake of disaster. It was here, in the wreckage of people’s homes, that she saw the wreckage of human communication.
She was “immediately pushed into the disputed claim arena,” a space where insurance companies and contractors waged war while homeowners waited in the rain. Haber describes a landscape defined by miscommunication and greed on both sides. “Sometimes the insurance company is getting claims where the repairs are only $5, and the contractor wants $100. There was just this back and forth all the time.”
The cost of this friction wasn’t just financial; it was measured in time and misery. Haber watched as claims spiraled into litigation, leaving damaged houses to rot for years before a resolution was reached. “I said, ‘There’s got to be an easier way to look at these disputes and take that emotion out of it,’” she says. “The insured is sitting in a house that’s leaking.”
Haber, who admits to having “attention deficit disorder,” found her clarity in data. She loved Excel. She “had this big spreadsheet where I’d go from one section to the other,” trying to make the math make sense. In 2018, she decided to turn that logic into software. Her passion, vision and drive for solutions were and are a tour-de-force, so much so that she was determined to create something as easy as possible to turn problems into solutions for all parties. It wasn’t a smooth road — she burned through three developers before finding her partner, Daniel Chartock — but the result was Umpire Assistant.
“The industry doesn’t need more noise — it needs a clearer way to see the dispute,” said Laura Haber, “Umpire Assistant was built to help professionals bring structure to the comparison, clarity to the decisions, and defensibility to the final documentation — without changing what the job is. It simply makes the work easier to execute and easier to stand behind.”
The platform isn’t just about crunching numbers but cooling tempers. It uses programming to handle the math and AI to “polish” the discrepancies, helping opposing sides see where they actually differ. “You can see it so clearly that you don’t have someone at the desk working for the insurance company and someone representing the insured looking through 75 different pieces of paper,” Haber explains.
For Haber, this is less about technology and more about psychology. She tells a story of a dispute in California involving a fire loss. The two sides were $150,000 apart, and the anger was palpable. One appraiser was convinced the other was trying to take advantage of the customer. Haber flew out, sat them down with her laptop, and walked them through the reality of the situation — that the demolition had already removed the items they were fighting over.
“We sat with my laptop at lunch, and his eyes lit up,” she remembers. “He said, ‘You know what? I think you’re right.’” By the end of lunch, they signed the award. “I get a lot of concessions in person,” she notes. “Being in person takes a lot of the contention away because you can understand easily what the dispute is about so that people can start being people again.”
Her philosophy is simple but radical in an industry built on adversarial conflict: “People can understand that when we cut ourselves, we all bleed red. There’s no reason why we have to be mad and yell at each other over a claim.”
Haber’s work is a form of high-stakes mediation without the separate rooms. She forces people to look at the facts rather than their egos. “I think talking out loud about what they’re presenting… helps,” she says. “If you can’t get them to talk and interact, you’re getting a one-party signature every time.”
When she isn’t navigating the entrenched trenches of insurance law or teaching certification courses, Haber is trying to find her own center. She meditates, does yoga, and drinks beet juice. She believes the qualities needed to survive in her field are “discipline… empathy… and you have to be able to hear people — not just listen to them, but hear what they’re saying.”
Ultimately, Haber’s vision extends beyond insurance claims. If she could inspire a movement, it would be to dissolve the fear of the “other,” much like she dissolves disputes over drywall and roofing. “If people would meet others who were completely different from them… sat with them for two or three days, played cards, and talked with them, we wouldn’t be so scared, angry, fearful, or feel like we have to hate.”
In a world that loves to draw lines — between states, between religions, and between bank accounts — Laura Haber is busy trying to erase them.
Yitzi: Laura Haber, such a delight to meet you. Before we dive in deep, our readers would love to learn about your personal origin story. Can you share the story of your childhood, how you grew up, and the seeds for all the amazing work that has come since then?
Laura Haber: I was born in Tennessee. My mom and dad — I share a father with my brother and my mother with my sister — were together at that time and separated shortly after. I grew up in Tennessee in a city called Bristol, which is half in Virginia. A brilliant Geico commercial from 2016 jumps over the line and says, “Now I’m in Tennessee, and now I’m in Virginia.”
It was an interesting way to grow up and gave me a well-rounded view of the world. I was born in the mid to late 1960’s, and in that period, there was so much adversity and division, as well as controversy not only in America but all around the world. It definitely mattered which side of the tracks you lived on then.
We moved to Florida in the early 1980s to follow my grandparents when they retired. That’s when I got to meet up with my brother and my father and learn about the other side of my heritage. We all played music and we were all multi-faced in our talents, education and interests.
From there, I started to get into the insurance business. It started with health and life, and then we started having major hurricane after hurricane. Andrew hit, then Wilma — those were the catalysts. I had done a little bit of construction; my mother worked with the developer that built Bonaventure. I said, “Maybe I’ll try this adjusting thing and learn how to handle property claims.” That was way back in the early 2000s.
This is how I learned about insurance claims, how they worked with different insurance companies, and some of the contention that would rise into disputes. Sometimes it came from the top and worked its way down from the insurance company, and sometimes it came from the contractor. Either they miscommunicated, or there was greed; there were problems on both sides. I was immediately pushed into the disputed claim arena.
During that time, I learned about appraisal, which is similar to arbitration. It is not appraising the value of a house, but appraising the damages because there is a dispute. The carrier might send an estimate based on what somebody they hired saw, saying, “Hey, here’s the amount of your loss and here’s what we saw that was damaged.” Then the other side looks at it like, “You missed all these things.” They hire a contractor, a public adjuster, or an attorney, and it becomes a disputed claim.
It became more and more contentious the longer I was in the industry, to the point of being unbelievable. Sometimes claims would be in a dispute, end up in litigation, and somebody’s poor house would sit there for four years before they got it resolved. I said, “There’s got to be an easier way to look at these disputes and take that emotion out of it.” We’re all professionals; we’re all here to try to fix this. The insured is sitting in a house that’s leaking. Sometimes the insurance company is getting claims where the repairs are only $5, and the contractor wants $100. There was just this back and forth all the time.
I had this big spreadsheet where I’d go from one section to the other. I loved spreadsheets and loved Excel. I thought, why can’t we have an app that does this? I started working on this thing in 2018. I’ve gone through four developers. I’m on my fourth developer, and thank God for this one. You’ll be talking to him soon. I think you know him. His name is Daniel Chartock. He is amazing.
Along the lines of making this all happen, my brother, Lon Haber, an actor and musician at heart, from the start, is also a public relations, marketing and branding expert and jumped right in with his amazing team to help us get the word out
Now we’ve released it, and we have a lot of interest. It has several platforms. One is for the Umpire; when the two appraisers can’t settle the claim, they go to the Umpire. Appraisers, Arbitrators and mediators can also use it. That’s called the UA platform. We have another one called the ADR, Alternative Dispute Resolution platform. It can be used by public adjusters, insurance companies, and third-party administrators — big companies that have insurance people working for them to settle the insurance contract. Attorneys can use it too.
It brings the two estimates that are in dispute into a clear picture. It has extensive programming, and then we polish it with some AI. The programming makes the math work; the AI polishes it and helps you fix other things. For example, if there are two different types of estimating software that word things differently and wouldn’t normally match up, you can train the AI to see the differences. That’s what we’ve done.
We lead that into lots of different avenues for folks to settle with an initial dispute summary. You can say, “Hey look, there’s this dispute. You missed this whole building,” or, “You missed the side of the house,” or, “Your number is really low on the roof. Why? Was the roof really damaged?” You can see it so clearly that you don’t have someone at the desk working for the insurance company and someone representing the insured looking through 75 different pieces of paper or asking ChatGPT to figure it out, which becomes a mess. It’s real programming. You can adjust the numbers properly with overhead and profit, depreciation, and price increases or decreases. You can look at the dispute and make selections when you agree on items to come to a final dispute summary — which is like an estimate but much cleaner and easier to understand — and then an award form or a release form. Contractors have their own platform called SettleFast. I know I talk really fast, without using any unnecessary words, but that’s the way it goes.
Yitzi: Laura, you are a great storyteller. You probably have some amazing stories from all of your great work, all the different cases you’ve worked on, and the people you’ve helped. Maybe this is hard to single out, but can you share a story that most stands out in your mind from your professional work? Or, if you were writing a memoir about your life, can you share a story that has to be in the memoir about your career?
Laura Haber: Hmm. That’s a tough one. I think it would be when I looked at some of the actual stats from a state — we’ll pick on Florida because they had the biggest state-run insurance companies, although the carriers stopped insuring because of all the hurricanes. We found that the average disputed claim that went to litigation cost over $100,000 to settle. When it went to appraisal, it cost on average $4,000. Those are the costs, not the estimates or the amount of loss.
I handled a big claim right here in Colorado where the two sides were very much at odds. We have a lot of people that don’t understand the industry. Part of the app includes a list of subscribers that have access to all the different states and their rules because people get confused by case law versus statute.
I had two people who were really mad at each other. One said, “Those other two sides of the house weren’t damaged by hail.” I said, “I know they weren’t, but we have case law for matching. So, we’re going to put that under a coverage that says matching.” He asked, “Why do we have to do that?” I said, “Unless it’s excluded in the policy, that’s how case law works. If it was a statute, we wouldn’t have to put it under matching; it’d be automatically covered under the regular coverage.”
It took a long time and a lot of sitting down. I had the dispute summary that I had printed, and it was really nice to see the temperature come down. Those cases have happened a lot, where two people are so far apart, but when they both sit down and we can see things, we can logically guide them: “Look, you’re only $54 higher than him. Can one of you concede?” “Yes.” I get a lot of concessions in person. Being in person takes a lot of the contention away because you can understand easily what the dispute is about so that people can start being people again. People can understand that when we cut ourselves, we all bleed red. There’s no reason why we have to be mad and yell at each other over a claim.
What we should be doing is understanding the claim, understanding the state we’re working in, and being able to settle it. I had another case in California with a fire loss. When there’s a fire loss, there’s a thing called abatement, where you tear out all the fire damage and get the soot out. If you tore out all of that stuff, when you write your build back, you’re only writing to put it back. This was a newer appraiser on the policyholder side, and he was so mad at the other guy. He said, “You’re $150,000 apart from me. You’re trying to take advantage of my customer.” I flew out to California, sat them both down, and said, “Look, the abatement tore all of the drywall, insulation, and electrical out. So your estimate should just be to replace those items, not to remove and replace them again. Look at the differences here.”
We sat with my laptop at lunch, and his eyes lit up. He said, “You know what? I think you’re right.” I said, “You’re really only $20,000 apart. If I give you that $20,000, will you sign an award?” They both signed the award. We had lunch, and they weren’t mad anymore.
It’s just trying to bring down the tone. It’s naturally contentious. I could tell you story after story like that in different states, but that’s what brought me to trying to find a platform that I can give to an insurance company to put on their claims management system. When they get a demand or a supplement request, they can click on the app, drop both estimates in, and go, “Oh, they’re asking for paint. And there’s the picture; the paint was damaged. Let’s just go ahead and add that.”
I think it takes the temperature down, and that was my inspiration for the app. I don’t think that either side should be paying $100,000 to settle a claim when there’s only a $20,000 disputed amount. People shouldn’t be angry, fighting, and dragging it out. Use the app. You can see it right away. Take the temperature down. It’s all about the facts. It’s not about who’s right or who’s wrong, or your personal attachment to your side. It’s, “Here’s what it is, we’re independent. Let’s take a look at these differences and see if it’s true or not. When we figure out what’s true, let’s agree to it and close it out.” I think it brings a resolution much quicker. It saves money for the insurance company and saves the insured the heartache of waiting forever with damaged stuff they can’t afford to pay for.
Yitzi: It sounds like your job is also navigating entrenched disputes when trust between two parties is broken down. It is a form of conflict resolution. Could you share some of the principles or stories you’ve learned about how to create a resolution between two conflicting parties who just can’t see the other side’s perspective?
Laura Haber: Mediators have a different story than I do because a mediator gets to take someone into a separate room, so they get to diffuse the situation that way. We don’t get to do that in appraisal as an umpire or an arbitrator because we all sit in the same place.
I like to start the conversation by lowering the temperature however I can. Sometimes you can’t. Most of the time, I think most umpires never get three-party signatures because someone is splitting the difference or they’re not really looking at it; they’re just trying to figure out who they can get to sign the award. I try to come at it by asking, “What’s really the truth here?” I’m not rewriting anyone’s estimate because I have both of yours. You’re not writing to paint this insured’s living room and dining room, but you’re painting the kitchen, and you can see all that paint. Don’t you think it’s not going to look the same? Would you do that at your mom’s house?
Then they start to think. “Would you agree that we could go ahead and do that?” “Yeah, I’ll agree to that.” “And do you agree that we don’t have to tear the drywall out in the whole house because a hail storm had a leak from the bathroom down to the living room? Would you agree we could fix those areas and then match everything with painting and make it look clean?” I think talking out loud about what they’re presenting — their positions — and getting them to talk and interact helps. If you can’t get them to talk and interact, you’re getting a one-party signature every time, and you’re not going to be able to lower the temperature. Sometimes you just can’t, but that’s how I try to bring resolution: by bringing down that temperature and getting them involved in the conversation of why they wrote for certain things. Sometimes they don’t even know.
Yitzi: Perfect. This is our signature question that we ask in many of our interviews. You’ve achieved a lot of success in the insurance industry. Looking back to when you first started, can you share five things you need to create a highly successful career in the insurance space?
Laura Haber: As far as adjusters handling property claims — and probably in all types of the insurance world — I think the first thing you have to have is discipline. Then empathy. Being super organized. Energy. And you have to be able to hear people — not just listen to them, but hear what they’re saying. You have to be a really good listener.
Yitzi: On a personal note, and we ask this in all our interviews: Can you share some of the self-care routines that you do to help your body, mind, and heart to thrive?
Laura Haber: I like to meditate. I like to venture outside in nature. I really like to do yoga. Reading and listening to audiobooks also helps. Sometimes you just have to take yourself out of a stressful environment for a few minutes to breathe and reset. Staying connected with family and friends that we love, being able to breathe, take a minute, be outside, stretch, and take care of our bodies — maybe drink some beet juice or create a healthy yet delicious smoothie. You can feel the self-care at work with each sip.
Yitzi: This is our final aspirational question. I think you may have caught this from our previous interview. Because of your great work, you’re a person of great influence. If you could spread an idea or inspire a movement that would bring the most amount of good to the most amount of people, what would that be? Because you never know what your idea can spread.
Laura Haber: I think that if people would meet others who were completely different from them, thought about things completely differently, sat with them for two or three days, played cards, and talked with them, we wouldn’t be so scared, angry, fearful, or feel like we have to hate. I think that would help a lot.
Yitzi: That’s amazing. How can our readers continue to follow your work, get the app, engage your services, or support your work?
Laura Haber: Readers can visit https://umpireassist.com/. You can catch me there, learn all about the app as well as ‘grab’ or download the app and email me and my team. You can also come to the Windstorm Insurance Conference next month in Orlando. I’ll be teaching the Umpire Certification course there with a couple of colleagues, and I will have a booth. That’s at the Gaylord Hotel, February 23rd through the 25th of this year (2026). That’s going to be my first (of many) big conventions since the launch of the Umpire Assistant app, and I was blessed to be asked to teach there as well. Everyone is welcome! You can also click here to view our launch press release with all of the details on Umpire Assistant.
Yitzi: Laura. It’s been a joy to meet you. I wish you continued success and good health. I hope we can do this again next year.
Laura Haber: Thank you, likewise. The feeling is mutual. I look forward to catching up again soon and truly appreciate you. I’m so grateful for the connection and excited about what’s to come!
Claims Expert Laura Haber on ‘Umpire Assistant’, Brutally Honest Negotiations and Why In-Person… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.