Coworking with Andrew Helms

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The customer’s always journeying: Retail, like life, is about the journey—the customer journey, that is. In our State of Stores report, we dive into how retailers need to use every tool in their kit (including the POS) to meet the ever-expanding expectations of today’s shoppers. Read it here.

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Andrew Helms is CEO, USA at fintech company SumUp.

How would you describe your job to someone who doesn’t work in retail? Every single one of us goes shopping at least on a weekly basis. Whether you are buying groceries, clothes, coffee, or the latest video game, you are interacting with local merchants, stores, and the community around them. Ultimately, my job is to provide the tools to help merchants build their business—products like payments systems, POS, kiosk, loyalty, invoicing, bookings, and handhelds. We focus on the complicated tools, thus freeing merchants up to focus on running their business successfully and connecting with their customers.

One thing we can’t guess about your job from your LinkedIn profile? Being successful in such an incredibly fast moving field like fintech requires bringing together people with an incredibly diverse set of perspectives, backgrounds, and life experiences. Oftentimes, the best ideas come from those who don’t have a more classical “business” background. Like many of my colleagues, I took a long roundabout way to fintech, spending time in the Middle East as an aspiring journalist, helping grow a meal kit company out of Chicago, and eventually jumping into fintech with a wide variety of experiences and perspectives that brings our business forward. I could spend all day telling you stories about the backgrounds of our people who come from around the world and bring a passion and fresh set of eyes to helping merchants build a thriving business.

What’s your favorite project you’ve worked on? It’s more of an ongoing practice at this point, but every week, I’ll send a Slack message to our entire US team titled “Here are the seven things you need to know this week.” I distill down and prioritize a huge amount of information across the business and tailor it in a way that seeks to keep hundreds of people on the same page about our priorities and strategic direction. The goal is to give as much context as possible, so that I can give up more control and let people run with their great ideas, passion, and intrinsic motivation to accomplish things.

Which emerging retail trend are you most excited about right now, and why? Community! I think we are finally seeing the tipping point where consumers are frustrated with their big box retailers, the generic cookie-cutter chains and franchises, and the businesses providing little to no value to their communities. Consumers are once again looking to frequent local businesses, where they know the people, they know where the products are sourced, and where they know they can connect with others in their community that are just as passionate as they are about building the world around them.

What’s your go-to coffee order? Large black coffee, no sugar.

Worst piece of advice you’ve received? I don’t remember who told me this, but the worst advice I ever received early in my career was, “Don’t ask too many questions.” Maybe the advice was well intended, but it was a very strange thing to enter the professional world terrified to ask any questions, yet—let’s be honest—knowing absolutely nothing about how business really works. Fortunately, after a performance review or two, I quickly realized that my boss wanted a competent employee, not a silent drone, and I turned that one around. Now, I aggressively give the opposite advice to anyone entering the work world.

What was your favorite retail product when you were 15, and what’s your favorite retail product now? In all honesty, I would have just had my driver’s permit [at 15], so I was in love with the hand-me-down black Honda Accord with 200,000 miles and a large dent in the side that my brother and I shared to get around town. We didn’t get there in style, but we got from point A to point B faster than walking or biking! Now, a few years later, I would probably say that my favorite retail product is Spotify or my AirPods. I’m constantly listening to music and podcasts and I love the different perspective that the right song or thought-provoking podcast adds to the experiences of daily life.