John Ryles Senior Application Engineer II Lexington, KY

John is a lifelong Lexington, Kentucky resident and a self-described “indoorsy” person, despite the city’s fame for horses and basketball. He holds a Computer Science degree from the University of Kentucky, where he spent nearly ten years before joining Great American as a Senior Mobile Application Engineer in the Crop IT Department five years ago. John has been married to his wife for 17 years—an Underwriter in the AgriBusiness Division at Great American—and they have three kids: Cameran (19), Jackson (8) and Jameson (6). They also have a Maine Coon kitten, Riker, who runs the house (and his keyboard). In John’s free time, he enjoys coffee, creating mobile appsespecially for his kids, and is passionate about advocating for the neurodivergent community. Supporting inclusiveness and accessibility-both in tech and in life-is a big part of who John is.

Describe your career in crop insurance.

Like a lot of people in crop insurance, I didn’t set out to be here - it wasn’t part of some grand plan. My background is in software and data analytics, and I spent over five years working at the University of Kentucky, primarily supporting UK HealthCare. I worked on a range of projects, from grant-funded efforts related to the opioid crisis to building internal tools for MICU workflows and pharmacy systems. Eventually, I was ready for something different- a new challenge in a space where I could still make a real impact. That’s what led me to Great American and the world of crop insurance. I joined the Crop IT Department at Great American as a Senior Mobile Application Engineer, and it turned out to be the perfect fit. Even though I was new to crop insurance, I quickly found that my skills translated well, especially in helping the team stay productive during such an uncertain time like COVID. Since day one, I’ve been focused on building and improving the mobile tools our field teams rely on every day- making sure they’re stable, easy to use and genuinely helpful out in the real world. One thing I’ve come to appreciate about crop insurance is how strangely complex and underrated it is. There’s definitely a learning curve- lots of policy rules, acronyms and edge cases- but once it clicks, you start to see the bigger picture. This isn’t just paperwork or backend logic- it’s helping protect farmers when the weather doesn’t cooperate or when prices drop overnight. I’m not out in the field, but the tools I work on are used by people who are, and that connection makes the job feel real. It’s easy in software development to lose sight of who you’re building for, but in this role, that part’s always front and center. Over the past few years, I’ve learned more about agriculture, weather patterns, and insurance regulations than I ever expected- and probably more than most software developers ever will. What’s kept me engaged isn’t just the technical challenge, but the people. The Crop team at Great American is full of individuals who genuinely care about doing the right thing, and that mindset carries through in the work. Whether it’s a busy sales season or a year with heavy storm activity, everyone steps up to make sure our tools are running, accurate, and helping the people who depend on them. It’s a team I’m proud to be part of. 

Describe a memorable moment in your career in crop insurance.

One of the more memorable moments in my time here wasn’t exactly a highlight at the time- but looking back, it definitely shaped me. When our other Senior Mobile Developer left for a new opportunity, I suddenly found myself as the last one standing. It was a mix of “okay, we’ve got this” and “…wait, do we?” With critical mobile tools still in use and plenty of ongoing projects, there wasn’t really time to panicjust time to dig in, figure things out and keep things moving. That period taught me a lot about ownership, prioritization and working across teams to keep everything afloat. It wasn’t easy, but I look back on that stretch with a weird sense of pride. It forced me to level up quickly and helped solidify the trust I now have with my team and leadership. Not exactly the storybook “win,” but definitely one of those career-defining stretches where you learn what you’re really capable of. 

What advice would you give someone wanting to get into a career in crop insurance? 

Be ready to learn a lot- and not all of it will make sense right away. Crop insurance is one of those industries where the deeper you go, the more acronyms, exceptions and “well it depends” scenarios you’ll uncover. That can feel overwhelming at first, especially if you’re coming from outside agriculture or insurance, but stick with it. You don’t have to know everything out of the gate- you just have to be curious and willing to ask questions. Also, don’t underestimate the value of good teammates. The people around you- whether they’ve been here for 20 years or two months- are your best resource. Everyone’s still learning, no matter how long they’ve been in it. And if you can find a role where your skills line up with something real- like supporting growers, agents or claims teams- it makes the work feel worth it. 

Do you have a favorite fall/autumn activity you look forward to?

Fall in Kentucky is always a nice change- cooler weather, fewer mosquitoes and finally a reason to open a window without instantly regretting it. We usually make at least one trip to a pumpkin patch. It’s a fun tradition, even if it usually turns into chasing kids through a corn maze or carrying someone halfway through because their legs “stopped working.” I think what I enjoy most about fall is the shift in pace. Things feel a little calmer, the days get a little quieter and there’s more time to just relax with family.