Coworking with Mark Simon

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Mark Simon is VP of strategy at intelligent automation software company Celigo, which works with companies like Therabody and PayPal.

How would you describe your job to someone who doesn’t work in retail? I start by telling people that, at the simplest, I work with companies to help them automate their businesses. While we can think of integration and automation as the “invisible plumbing” of retail—and for many companies it is—I work with companies to help them think strategically and use automation as a business differentiator to drive their top-level goals. At 90% of companies, when everything works, no one thinks about its integration and automation. When it doesn’t, it’s all anyone can talk about. You can take a look at Shopify’s Cyber Monday breakdown last year, for example, which showcased how important e-commerce infrastructure is to so many businesses. My job is to help retailers see the opportunity to accelerate their growth and ensure customer experience excellence by taking a proactive approach. We can make sure orders, inventory, payments, and customer data are all talking to each other (through integrations) so teams can focus less on putting out fires and more on actually growing the business.

One thing we can’t guess about your job from your LinkedIn profile? Most people assume I’ve always been a retail consulting or strategy person at a software company, but I actually started as a software engineer in the wild west days of e-commerce on the front lines. I was writing code, breaking things, fixing them, and learning in real time how messy retail systems really are. Later, I ended up as CTO on a founding team, which forced me to zoom out from “Does this work?” to “Does this actually move the business?” That for me was the big transition from being a technologist to being a business leader. That early, very hands-on experience is still how I think today: Strategy only matters if it survives contact with real systems, operators, and customers.

What’s your favorite project you’ve worked on? It is impossible to pick a single project; what jumps out to me is any project where the customer comes in asking us to solve a narrow-focused problem, like integrating their new e-commerce platform with their ERP. It is always very fulfilling to work with experienced teams who will let us take a step or two back and understand why their existing solutions don’t meet their needs, learn their business and the goals, and then provide a solution both to the short-term need but also show them how Celigo can help the entire business run better by allowing them to not only build Order to Cash automations more quickly, but also help them manage those automations much more efficiently by leveraging less technical resources that are closer to the business problem.

Which emerging retail trend are you most excited about right now, and why? The trend I’m most excited about is AI finally moving into the “boring” parts of retail. When AI helps prevent stockouts, resolve order issues automatically, or smooth peak-season operations, that’s when it stops being hype and starts delivering real results.

What’s your go-to coffee order? I grew up in Seattle but didn’t start drinking coffee regularly until I had kids and to keep things simple, I adopted my wife’s order. Ten years later, it’s still my go-to: a split-shot Americano topped with steamed soy.

Worst piece of advice you’ve received? To “just add more people” instead of investing in automation and modern cloud systems while I was leading technology at a high-growth e-commerce startup. I quickly ignored it, and I’ve since seen how transformative the right systems can be for a company.

What was your favorite retail product when you were 15, and what’s your favorite retail product now? When I was 15, my favorite retail product was my first real piece of outdoor gear: an REI down sleeping bag I used for hiking and backpacking. Now, my favorite purchase is a great pair of skis, since skiing is the sport I love most and enjoy with my family.