Solving Killer Problems from Customer Support to Product: Tyler’s Career Story

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Tyler’s career trajectory has been anything but ordinary. His first job in tech was at a startup called Glad to Have You in 2012, which was acquired by HomeAway a couple years later. He started in a customer support role helping property managers use and understand our software, but his real passion was in engineering. Solving customer issues and hearing product feedback gave him a taste of problem-solving, but he was ready to think bigger and take his skills to the next level.


Q: What was your day-to-day like in customer support at Glad to Have You?

“I was on the phone taking customer calls and sharing the feedback with management. I’ve always had a passion for software development so I’d ask our engineers about how we could implement new tech or solve some of the customer problems I was hearing about. I transformed my role into a more technical customer support position.”


Q: Once Glad to Have You was acquired by HomeAway, how did your job change?

“Even though I was a Customer Experience agent my first six months at HomeAway, I spent most of my time testing products and monitoring the service health under the HomeAway Mobile team, basically giving a product a thumbs up or thumbs down depending on if it worked the way it was supposed to. I always thought there was more to the scope of my role though. I think that’s what differentiated me from the other Quality Engineers, I started thinking about the design and becoming aware of the customer’s experience using our product.”

Tyler and his team at a Product offsite event. 

Tyler and his team at a Product offsite event. 

Q: As a self-taught engineer, what tools did you use to learn the tech skills needed for a product role?

“Brute force ha! It was tough at first to learn on my own since I didn’t go to school for engineering or design, but I had a lot of training from experienced engineers on my team. They would tell me why something did or didn’t work and then they would show me how we could make it better. I did networking architecture, web design, and an online coding academy. I also took advantage of the training courses that HomeAway offers through I found the real value was in learning about existing products and how HomeAway customers are using them. My philosophy is it doesn’t matter if you take hundreds of coding classes or read books about engineering, your knowledge isn’t valuable until you use it to solve a problem you care about.”

Q: Now you’re solving problems all the time as a Product Manager. How did land your current role on the Product team?

“It was really the willingness of my team to break down what my job was on paper and compare it to the work I was actually doing every day. I became a resource to my teammates and they started coming to me with technical and product questions, even though I was primarily resolving issues as a Quality Engineer. The culture at HomeAway is so forward-thinking, my team recognized that I wanted to think more about the customer’s experience and why the business made certain decisions. So I interviewed for the opening as a Product Manager and got the job, I’ve been on the Product team for six months now! It wouldn’t have been possible without the support from my team. They recognized my strengths and passion for the product to help me get where I am now.”

Q: What’s one project you’re working on?

“I’m focused on the traveler’s stay experience, so from the second a user hits ‘confirm booking’ on the HomeAway website or app, I’m handling things from that point forward. That includes pre-arrival and post-stay information. One problem I’m solving is collecting essential stay information (door codes, parking, directions, etc.) to create a more structured check-in process for travelers. I’d like to figure out a way to make it automated so it’s easier for our owners and travelers. I listen to customer support calls once a month to stay plugged into the problems both travelers and partners are encountering and this was a problem that stood out to me. Travelers have to be able to actually get into the house to enjoy their vacation!”

Q: Has your customer support experience helped you as a product manager?

"My role in customer support allowed me to think about the users in addition to the business needs and what is technically possible. Now, I’m thinking about what value our product brings to the customer. Product managers can sometimes become hyper-focused on business needs to the detriment of the customer. I view things through the lens of what the customer wants in addition to the business needs and I think it results in a better product. There’s a happy medium between being customer-centric and understanding what the business can actually do. I’m proud that I can almost immediately identify how something will impact a customer and our engineering team at the same time."

Q: What’s your advice to people in customer support or a non-technical position who want to transition into a technical position?

“Find a problem that you’re passionate about and find a mentor who’s willing to help you. I wouldn’t be nearly as close to the position I’m in now if I didn’t have those two things.”


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