CEO Perspective: Jeff Dickerson, DaySmart Software

A conversation with Jeff Dickerson, DaySmart Software

Jeff Dickerson is CEO of DaySmart Software, a provider of business management software for appointment booking, staff management, payment processing, marketing, and customer communications for small businesses worldwide. Jeff has 25+ years of experience building software companies and developing technology that empowers and drives real business results for customers.

Q: Tell us a bit about your career path. What brought you to DaySmart Software?

Dickerson: There wasn’t much doubt, even as a kid, that I would go into sales. I’ve always been passionate about people and problem solving, which led me to high tech sales. I held several managerial and executive sales positions at various software and telecommunications firms through the 80s and 90s before taking on my first CEO gig in 2003 for eCredit, which we sold to Fidelity Capital in 2006. I’ve served as CEO for a number of tech companies since then, including Sonian (acquired by Barracuda Networks in 2017), The Neat Company, Nutonian (acquired by DataRobot in 2017) and now DaySmart Software.

The enormous market potential and unmet need are what first attracted me to DaySmart. I took the reins from two founders who had built a robust software firm serving multiple small business verticals. It had reached an inflection point and it was clear the business was ready for its next growth stage. That challenge, and the prospect of providing hundreds of thousands of small businesses with a tool that would generate real value every day, were the driving forces behind my decision to join the company. I love the energy of small business owners, entrepreneurs, and their employees.

Q: DaySmart recently experienced a significant recapitalization. What was that process like? What other growth milestones has the organization achieved since you’ve been CEO?

Dickerson: It was a process, that’s for sure. Months of preparations, and lots and lots of meetings. We are thrilled that it ended with us partnering with LLR Partners and Parthenon Capital. We three share a real vision for what this company can become, and we’re zeroing in on exactly how to do that. You ask about milestones, and that was certainly the big one that we established when our Chief Product Officer, Patrick Curley, and our Chief Marketing Officer, Steve Martin, joined me here in early 2017. Our entire team is now laser-focused on turning our new operational leverage into real market advantage. More investment means faster product innovation and delivering more value to our customers, both of which translate into continued growth. Now, we can continue to focus on our acquisition strategy – which started with PupKeep early last year to broaden our pet services functionality – to expand our current solutions and enable us to embrace entirely new market opportunities.

For the last decade, DaySmart has been consistently growing 25+ percent year-over-year. We’ve also been named to Inc. Magazine’s list of the 5000 fastest-growing U.S. companies for nine consecutive years – which is something less than 1 percent of companies named to that list ever achieve. It’s also something that started long before I got here, and for which hundreds of people who have worked here over the last 20 years are responsible. Some big things lie ahead for us too, with ambitious growth goals in the coming 12-24 months that will vastly exceed anything we’ve done to date.

Q: You commute from Boston to Ann Arbor every week. How does that work?

Dickerson: I make it work. I made a deal with myself, and my two daughters, that I’d be home every Thursday night. Friday nights are “date night” with my youngest daughter, which is my chance to catch up with her. In a way, it’s given us the opportunity to spend more quality time together every week. Of course, nobody is ever disconnected from work anymore, especially CEOs, but I’ve always thought the concept of ‘work/life balance’ implied these were two opposing forces that needed to cancel each other out for anybody to find balance. That feels too simplistic to me; instead, I think it’s about enjoying the time you’re spending, however you’re spending it. That includes my commute time. When used properly, that critical time can be leveraged to focus on bigger issues, talk longer with job candidates, burn down my inbox, etc. I find ways to make sure time out of the office is not time out of the loop. Frankly, the flight is short and pleasant (shoutout to the good people at Delta!) and, like anything, you acclimatize and adapt.

Q: What about running a software company keeps you up at night?

Dickerson: What doesn’t keep me up? DaySmart, like any meaningful player in an active market, faces challenges on all sides. Every day we compete for customers, for employees, for partnerships, for media attention. Outside of competition for these kinds of growth resources, every business faces threats (e.g., litigation, data breaches, market forces). If you focus on everything that could go wrong, you’ll drive yourself crazy, though I do try to plan for as many contingencies as possible.

For example, the dangers in SaaS center around disruptive models, for which you are not prepared, can upend your markets with expectations or price points you can’t match. The second, maybe larger, potential threat is service disruption. If your services are not reliable, available, durable, etc. you’ll not only lose subscribers, but you’re also taking out someone’s business and costing them customers. I take that responsibility seriously and it is a constant concern.

And while I have seen disaster planning makes all the difference, I do try to spend the majority of my energy engaged in finding ways to deliver more value to my team, our customers and our partners.

Q: How would you describe your leadership style?

Dickerson: I think a better question might be “how would your team describe your leadership style?”, and I hope they’d say I am transparent with them. I think I owe that to my colleagues, and it is something I ask of those around me. That desire to be open led me to start a regular “all-hands meetings” where the entire organization comes together in one room – which is still possible - to talk about what’s going on with the company. Obviously, I can’t always share everything, but I do strive to ensure everyone is on the same page by delivering them all the same message at once. I think it reduces confusion, and I hope it allays fear.

After transparency, my second obligation as a leader is to engage with the team. I ask open-ended questions of everyone I work with – from my employees to our customers and partners – and let them teach me something so I can better inform my opinions and guide my decision making. I came up in sales, so I really enjoy getting to know people and discovering what motivates them. These relationships, this personal touch, is often overlooked by executives hyper-focused on “running the business.” Some consciously avoid it because they don’t think they’re good at it but taking the time to get to know people is what separates leaders from managers, in my opinion. Knowing somebody well is the only way to foster trust, and that’s the main ingredient in building and running high-performance teams.

Q: What’s the best advice you’ve ever received?

Dickerson: “Don’t forget where you came from.” I learned this lesson (and so many others) from my dad when I was in the earliest stages of my sales career. Right after I had been promoted for the first time, he encouraged me to always remember what it was like to be in that entry-level position and the importance of having a sales manager swing by my desk to ask how I was doing or to see if they could coach me on a problem. I know dad was making a larger point, too. He knew me well enough to know that I could probably use a little more modesty, and I got his point. But his literal meaning also stuck with me throughout my career, and I always try to check in with team members to ensure they feel valued and supported. I find opportunities for improvement most often in these interactions; people will tell you what needs to change. Proving I’m committed to making those improvements starts with hearing them out.

Q: What would you be doing if you weren’t leading a software company?

Dickerson: Well, it would have to be as interesting as software, so I don’t know. I have lived on the water most of my life, so I think a big part of me would like to spend more time in a boat. Pulling lobster traps at my age probably wouldn’t last a week, but maybe running a fishing charter out of some exotic locale, getting to know different clients each week, that could be a lot of fun. Ultimately, I do believe I would miss the whole “expansion stage SaaS game.” It’s exciting and continually evolving. The fact that doing it right (in my experience) means dozens, if not hundreds, of people pulling together with that sole purpose in mind is a real rush. You’ll encounter one hundred problems, and some of them will be very, very large. Your ability to overcome and make progress is measured every day and the stakes can be huge. Plus, software experts are special people and they can do amazing things to transform business and society. How could I leave that?