Playing With No Reserves

Working at a startup or a small company is a bit like drafting your fantasy football team with no reserves — to win, you had better make sure the players on your roster aren’t prone to injury, have complementary skills and weaknesses, and ultimately are dependable in delivering results. Every decision, even seemingly insignificant ones, counts more at small businesses, as there is nowhere to hide, no bench to sit on, and every employee’s actions have a direct impact on the company’s results. As such, I thought I’d share some of the insights I’ve gained from experience at both large and small companies, and how that shapes my approach to leading YCharts since taking the role of CEO.

When I worked at larger, similarly high-performing corporations, it was akin to having a fantasy football team complete with a stable of reliable running backs and wide receivers — imagine if your first five picks panned out every week of the season. If and when we lost a key player to an “injury” or “bye week,” we had reserves ready to step up. We had the coffers necessary to spread or hedge our bets, and also to mitigate our single points of failure and other risks.   Bigger organizations often have the flexibility to try scores of different strategies and lineups with the idea that, if just five of them come through, the C-suite is happy, and the results are delivered.

You simply can’t work that way at a smaller organization. All counted, our team is just under 40 people strong (for the moment). Here we work to be laser-focused on the things we want to do really, really well, and use that same focus to allocate resources toward aligning our team, innovating our product to meet our market’s key needs, serving our customers, building a roadmap for marketing and sales, and properly adjusting our operational approach to achieve our targeted business objectives. As a leader, it is my job to ensure that I am pulling the right strings to put my team in a position to win. When someone takes a vacation, goes on maternity/paternity leave, or has a personal challenge, there are no reserves to bring in. We adapt — and adapt quickly.

My experiences at both big and small firms have helped me understand how important it is to build an ever-evolving, adaptive company culture, and to be rigid in only hiring and retaining the best. We don’t have room for reserves. At YCharts, ours is a culture of collaboration and transparency — that’s why I’m not hard to find at our office. In fact, you can often find me at my desk, right in the middle of the action. I don’t like the concept of corner offices. Being in the flow of things is really important to me. It makes me feel like I’m back in my early startup days again,  back in the mix as a “flex” player and seeing how the team operates on an hour-by-hour and day-to-day basis.

What energizes me is having my finger on the pulse of the company I work for and being close to the action. When I’ve been in the “corner office” in the past, my ability to understand and contribute was stymied by doors, walls, and information and metrics dashboard latencies. I never could get comfortable feeling like I sat on some lofty throne, with counterproductive protocols, inhibitions, and people to shield me from the flow.  

Here at YCharts, I aim to be a connected leader. I insist on being part of the flow — listening to our sales team deal with the triumphs and frustrations of cold-calling and closing deals. I know of our wins and losses before they ever end up in our CRM system or dashboards. I know when we submit our Peapod order. I know when the shared Nutella spread and pretzels I rely on are depleted. I’m just one hand wave, ball throw, or Slack message away from the leading indicators of our business success. There are no barriers.

This is how I want our company to continue to operate. When I worked as a junior employee at other companies, I always felt more emotionally invested in the business and my work when I knew the leaders of the company and the intensity that they brought to bear each day. I loved understanding how they operated, and got to see firsthand, in raw form, how they dealt with their small victories and defeats. I loved being able to “connect” with them on a personal level.  At YCharts, I make an effort to know my team as people — to remember their birthdays and their significant others. Heck, I even know some of their pets’ names and favorite hobbies (the employees’ hobbies, not the pets’). I want everyone at the company to come to me directly anytime I can provide a helping hand or a vote of confidence. Helping on the small stuff makes me happy and keeps me grounded.

We spend a lot of time at work at YCharts. We’re a business that is transitioning from a startup to a growth company, so we’re definitely not your typical 9-5 environment. With that said, it would break my heart if it weren’t fun for my team to come in every day and work toward our business goals; if you’re working long hours, it should be enjoyable and memorable. You should laugh a lot at work. At the very least, I want my team to think after their workday ends, “That wasn’t a bad way to spend 10-12 hours of my day. It didn’t really feel like working.”

So what does this all mean? It’s important to me to share my perspective on leadership, as I believe leaders should be open to sharing more about their companies and their unique cultures. I also wanted to say on-the-record how grateful I am to be able to lean on my smart, capable team and our vibrant environment at YCharts. I feel invigorated and energized to be back at a growing business, especially in the dynamic Chicago fintech space. Even though we have room for improvement (there always is), I love competing alongside my team, and I think we match up really well with our competitors. That’s important, because this isn’t fantasy football — it’s the real thing.

Interested in what we’re up to or want to learn more about YCharts? Get in touch with us at info@ycharts.com, and make sure to follow us on Twitter and LinkedIn.