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Humans of Product: Regan Davis

By Rebecca Dorsay
Humans of product: regan davis

Meet this week’s Humans of Product, Regan Davis. Regan may be an experienced and creative Product Development Strategist now but his story actually starts when he was an undergraduate studying as a Theatre major at University.

“I got a whole degree in breathing, lying on the floor and moving around. Jokes aside, I studied Theatre at University and was directing plays, which I didn’t know at the time was just like Product Management. 

It is similar because you have to get a bunch of people who all have different opinions aligned. They’ve all got very specific specialties, such as your costume designer, lighting designer and the actors and you have to sell them on your vision. Then you only have about six weeks to get everything done, because it all has to be ready by opening night. Looking back, it is surprisingly similar to what I do now and it feels like I have been doing this for a while.

I moved to Chicago and I was actually doing Strategy Consulting for a while, where I fell in love with research. On the other hand, I did not fall in love with staying up till 2am writing decks for private equity firms.

I left consulting in 2008, was a freelance designer for a while and got picked up by a search engine to do their web design. However, I quickly automated myself out of a job because I wrote a batch script for all of their design requests and I wasn’t needed anymore. 

It was the beginning of the recession so it was not a smart move for me. But then Stephen, the CEO, asked me if I had ever used Excel. They were trying to understand the 5 billion keywords that they had coming through their search engine. This was definitely a job for the engineers so we took them from the team, and I managed them. We built an entire categorization system to categorise the internet and then we sold it to advertisers for search retargeting, and pivoted it a few times to find a customer base we could grow with. 

Humans of product regan davis

It finally occurred to me that I was a Product Manager.

Along the way, I learnt extremely valuable and necessary technical skills. I knew some of them, like front-end development because I was a designer, and I had learnt API’s from the engineers I worked with. 

I also taught myself distance algorithms for figuring out how to categorise keywords, so when I went on to my next job, one of the first things they asked was “Can you talk to engineers?”. Of course I could, they’re just people! However, if I had to code, that would have been hard because I don’t know how to code anything!

After realising he was a Product Manager and mastering some complicated technologies, Regan is now busy in the Product Leadership side of things.

Currently, I am the Senior Director of Product at SpotHero, which is a two-sided marketplace. It’s an app to help people find parking in the United States and Canada. I joined the team 30 days before COVID hit, so it was a very different company 30 days in than I expected. 

As soon as people stopped going to work, a lot of activities were stopped. Events were cancelled and people didn’t need parking anymore, because they weren’t leaving their houses. You would think that parking is a recession proof industry, but it was not a pandemic proof one!

It was definitely hard, so we redid our strategy and pivoted it a couple of times. We knew traffic would come back, so we focused on how our teammates could be more effective at their jobs and how our customer service team would respond when it returned. It was definitely a different experience but it was great. With millions of users, it meant I got to experiment a lot.  

Regan’s journey was never about getting from A to B as quickly as possible. He excelled at turning a problem into a vision and then bringing this to life! He has particularly enjoyed hopping across multiple industries and domains.

“Search was a technical challenge but advertising was not a great mission fit for me. I enjoy solving really hard problems that people struggle with, so I really liked healthcare because it was helping people in the United States.

In the US, you have to pick health insurance every year. Your company offers you many different choices and it’s a super complicated and stressful decision. Finding ways to help users make that choice and feel confident that they were making the right one felt really impactful. 

SpotHero, where I am now, is an app that helps you navigate the real world and whilst there’s so much that’s out of our control, I find that really fun.

I believe that within 6 months, a Product Manager is able to figure out the domain they’re working on and will become naturally better at identifying problems. When I talk to people wanting to get into Product Management, I tell them that there’s only about four traits necessary for Product Managers. It is CURIOSITY, EMPATHY, STORYTELLING, and JUGGLING. In your day job, you’ll do all of those four things any hour of any day.”

Regan is the definition of a Product Lover! He is someone who lives and breathes Product and significantly contributes to the wider community. When he gets the chance, he is teaching startup ounders through an incubator in Chicago called 1871.

Humans of product regan davis

“I am a big learner and teaching is one of the ways that I learn and process information. 

I mostly teach founders about the importance of engaging in customer discovery and talking to customers before they start building anything. I am an advisor to a couple of startups, and I speak at events around Product Culture. 

I look at the impact that I can have through my influence at different companies. If I can help a company make more successful product decisions and carry those practices to their next role, I’ve done something right. The ultimate goal is to teach product people how to make decisions that will help users and solve problems as they scale.

I enjoy working with mid-phase startups that have been around for 5-10 years. My sweet spot is usually when a company’s team expands to about 90 people and they start to realise they have scaling problems, and they can’t just get everybody in a meeting room together anymore. Now there has to be a process to make decisions, because the team leader can’t just make them all. 

You need to come up with either principles that are well known, or values that help people make those decisions. The strategy is not focused on all the things you are building, the strategy is around the goal. If you can get to the root question, then people can start making decisions on their own and they’ll go faster.

I think the biggest thing is that there’s a need at every company for somebody who’s a Product Manager. You’re probably doing some of that role without realising it. If you can identify problems or opportunities, then you are basically a Product Manager. Rather than getting frustrated at problems in your team, find ways to solve it. It’s not gonna be the perfect solution right off the bat.

For me, I try to encourage all my teams to change their process and try one thing different to improve their current product. This is what Product Management is to me. I believe it is a valuable way that people can practice Product no matter what job they have.”

Many people have a significant moment in their career that they never forget. Whether it be a major triumph or breakthrough, or a really small thing that made a huge impact. For Regan, it was when he was at Jellyvision, a video game development company that made Jackbox Games before they split.

“We were making this product called Alex and it was a goofy cartoon voiceover that walked you through all your health insurance options and told some jokes along the way. I learnt the importance of delight, an actual product value that you can’t compromise on. 

There was one complicated section of the product where we had to explain to users prescriptions in a very complex table. We had a writer at the time, Lacy, who went into the voiceover booth in our office, recorded audio tracks so that if you wanted to hear some soothing chicken noises, you only had to click a button. Only about 3% of people even clicked on it, but when we looked at our surveys and user feedback, 10% of all the feedback was all about chicken noises.

All it took was for Lacy to record herself doing chicken noises, and it became a huge multiplier. Everyone loved it! Users said that it was the best insurance explainer ever, just because of this one moment that took us maybe 30 minutes!

That’s when it really clicked for me. You have to make space in your product releases for delight. Just try stuff and have fun. You have to find ways to just throw stuff in that you think might be cool and be willing to find out if your users like it as well.

 It is pretty clear that Regan exudes creativity and imagination. Not only does he bring this to life in his job, but Regan loves spending time with his wonderful 9 year old son making stop motion animation.

“I’m a big fan of the Olympics and so every time the Olympics is on, my son and I do a photo shoot of us recreating Olympic events and put them together to create a stop motion animation. For the 2020 Olympics, we did long jumps and made hurdles in our house.

We usually build them out of cardboard. We’ll figure out how to build it together.  Sometimes I’ll hand draw the stop motion graphics. For example, I hand drew about 500 frames for the hurdle jumping video. It is super tedious, but it really forces you to slow down and we both love creating them. That’s our special bonding time.

For our first stop motion, I got my son to do a headstand and took about 80 pictures. Then I hand cut each one of them and built a zoetrope – a classic animation spinning machine invented in the 1800s. It is a lot of fun! It has been a great creative outlet, especially the past 2 years when I haven’t been able to direct improv and theatre.

 As a beautiful parting word, Regan shared what it is he loves about Product Management the most.

“I love Product Management because it means I am genuinely solving important problems. I love the aspect of tactical research, talking to people and figuring out what’s valuable. Then, I can’t wait to fix it for them!”

To learn more about Regan, visit his website:

Humans of product regan davis

Want more humans of Product? Read last week’s feature on Connie Kwan OR follow us on Instagram!

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