Lightspeed: A coming of age story

When I joined Lightspeed, there were 6 of us crammed into a tiny apartment hoping to change retail. Although I was hired to write the user manual, it quickly became apparent that our job descriptions, if we’d had them (we didn’t), would have been comprised of a couple bullets about our general area of focus, as well as a cryptic “and whatever else is required.” Event planner, culture officer, trainer, and, of course, sales and support were all part of our day to day responsibilities. We had 3 developers, including our founder, Dax, and over the course of the next 7 years, we slowly built up our engineering team to include more devs and QA, and introduced Product Management. I joined the PM team a little more than a year ago, and since then have seen firsthand the importance of how product management collaborates with other departments: sales, marketing, support, and, of course, engineering.

Customers have always driven our strategy. Independent business owners tend to be very passionate about what they do, and very vocal about what they need (thank god). In the early days, we built what our customers asked us to build, as long as it was within reason. It wasn’t uncommon for a particularly difficult support call to result in some sort of new functionality. We didn’t have processes in place for anything; we had conversations. And if we didn’t all agree on the next move, it usually didn’t happen. The more Lightspeed did, the more it fired up the imaginations of our customers, and the longer the list grew of features to include. At one point, the growth rate of our customer base and the growth rate of our feature requests outpaced our ability to keep up. We started having to make decisions about where to focus our attention. Some of these decisions were (and, spoiler alert, continue to be) very difficult. We needed to prioritize. It is out of this need that Product Management became an official department at Lightspeed.

In the beginning, there were two support agents doing double-duty as Product Managers for our Mac-based, on-premise product. As we realized that cloud-based solutions were the future of the industry, we expanded into that space for retail, then hospitality and eCommerce, and grew our engineering and product management teams as well. Within an agile framework, prioritization has become the absolute center of everything that we do, factoring in customer feedback, input from support and sales, market strategy, resource allocation, performance and stability, product usage data, and opportunity costs. Without prioritization, our product strategy would be directionless, our teams would be misaligned, and our efforts would be duplicated. The reality is that business health is a balancing act, with continual calibration, product and process improvement, and even the occasional crisis management all requiring a place at the table. Our customers know this balancing act intimately, and the ability to accurately, fearlessly, and decisively prioritize is the only way to survive and grow.

Growth is hard and not without its share of pain and uncertainty. You are in perpetual pursuit of predictability, and yet you never fully find it. In the 12 years I have spent at Lightspeed, however, adaptability is directly linked to relationships, to each other and to our customers. Products as deep and far-reaching as Lightspeed’s cannot properly improve without strong relationships between Sales and Support, Support and Product, and Product and our customers. Communication, diversity, and empathy keep those relationships strong and defined. Flexible processes make good communication and even a significant degree of predictability possible. And so, prioritization becomes both an act and a test of collaboration, as a healthy organization recognizes, values, and nurtures the contribution of each smaller piece toward the common goals.

Looking back, there are things that I would do differently. Better tools earlier, roles and responsibilities clearer, maybe a little less whiskey at the year-end parties. Overall, though, I am honored to be a part of this company, and to be serving the customers that we do. Lightspeed today is a very different company than when we were a handful of optimistic noobs. We are quickly approaching a count of 600 people in 6 countries, and, while our culture and mission remain the same, we need to continually reinvent ourselves to meet the challenges before us, as we are bound together.

Part of our promise to the customers who have entrusted their businesses to us is that we will be here tomorrow, and ten years from now. I myself have managed retail stores for many years and I know firsthand how much blood, sweat, and tears go into making a business grow. Knowing that we have this in common with our customers assures me that this is a partnership built for the long haul.