Welcome to The 6 a.m. CFO, where finance chiefs share how they jump-start their days and engage with the tasks that are in front of them.
Today, Pegasystems’ CFO and chief operating officer, Ken Stillwell, shares his morning routine and how he starts each day.
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Pegasystems
- An enterprise platform for AI decisioning and workflow automation
- Year founded: 1983
- Number of employees: Over 5,000
- Revenue: $1.50B — Up 4.5% from FY 2023
MORNING ROUTINE
Weekday wake-up time: Typically, around 4 a.m. It is rare that I sleep past 6 a.m. I can operate normally on around four to five hours of sleep a night, which I certainly use to my advantage.
Morning beverage choice: Coffee with a little milk. When we built our current house, I had the opportunity to install a built-in coffee station. It brews all different styles of coffee like lattes, cappuccinos and even different teas and it is controllable by Wi-Fi — life-changing!
Any non-work-related morning activities? Almost every day, before anyone else in the house gets up, I am in ‘learning mode.’ Whether that’s researching market information or learning about a new topic (like generative AI) or watching something educational on my iPad. It’s a sacred time that I set aside to sharpen my knowledge of whatever is relevant at that time for me.
Workday start time: I check emails as soon as I get up, but never from bed — the phone is not near me when I sleep. I jump on my laptop and get a bunch of email follow-ups from overnight before most people get online. With a large contingent of Pega people across the world, inevitably someone replies across the globe, so that begins my engagement for the day. I head for the office normally just after 7 a.m.
How I usually spend the first hour of my day: As soon as I get to the office, I’m packed with morning meetings. Sometimes its one-on-ones, external calls or team catchups on a variety of topics. It’s rare that my mornings aren’t packed back-to-back through lunch.
Time I send out my first email: Around 4-5 a.m.
Best advice for writing an effective email: I am very informal. My emails are like how many teenagers’ texts are: abbreviated, emojied, short and to the point. My general rule is, if you really have to closely proofread the email, then maybe it’s just better to pick up the phone instead.
First dashboard I review: Our sales automation tool. I like to look at the closed updates and deal movement. Naturally, being in enterprise software, this is more interesting as you get into the last month of the quarter. But nonetheless, I like starting there as client growth is the most important component of a healthy business.
How I structure my morning meetings: I am a bit less structured by nature, so my business manager/chief of staff is the one that really enforces an agenda, the clarity on the topics, and the outcome of my meetings. This is very helpful for me to ensure that our teams stay focused on the bigger themes.
Mid-morning snack of choice: I don’t snack in the mornings or at least I try not to! I am bouncing around from coffee to water to tea pretty much all day. That’s how I get my snack fix.
How do you adjust when a morning doesn’t go as planned: Often, I will get an instant message from someone at Pega across the globe with a challenge or urgent topic. My role at Pega can sometimes be a “fixer” or an advisor to lots of the groups to help shake loose something to push toward a goal. I pride myself on being accessible and available to anyone at Pega. I don’t think enough people take advantage of that (perhaps that will change after they read this admission!), but it does require agility by me and my EA to shuffle things around quite often.
INSPIRATION AND LEADERSHIP
Favorite quote or mantra: “Everyone has a plan until they get punched in the face.” – Mike Tyson. It sounds like a violent quote, but it’s really not. It hits so directly on the importance of being agile, being ready for whatever comes at you, and most importantly, be ready to get knocked down and jump right back up again to respond to the challenge of the moment.
Favorite leadership lesson: Leadership is not about the leader. Leadership is about helping your team see a path forward and supporting them as much as they need. As soon as you make it about yourself, you have failed your team. And we all have to work on this.
Something important to know about me that you wouldn’t know from my business bio: I would not have accomplished anything in my career without my faith and the support of my family.
Favorite number: 23. Michael Jordan was a massive influence on my life growing up as a basketball player. I wanted to be like Mike and, to be honest, I still think he is an amazing human being who had the drive to be the best and he will always be in my eyes.
Most noteworthy items in my workspace: Coffee mug, phone charger, and pictures of my favorite athletes — typically from the Celtics, Steelers and Red Sox.
Do you have a pet? I have two English Cream Retrievers — London McCartney and Bristol Harrison. My wife loves England and the Beatles, so hence the cool names.
Favorite app on my phone that is not related to business: Ok, make fun of me, its Clash of Clans. I used to play Clan with my youngest son’s friends. Silly, but I still really like it!
The year, make and model of your first car: 1978 Honda Civic. It only had a first and second gear and came equipped with ‘climate control,’ which I used to brag to my friends was better than air-conditioning, but it was really just a fan.
Most influential or famous person you’ve ever met: My grandfather was my best friend growing up. His idol was Frank Sinatra, and I got to go on stage and shake his hand at a concert when I was about eight years old. My grandfather was so proud.
Most inspirational person in your life: My mother. She has since passed on from cancer and she had a rough life. Nothing was easy for her, and she always put me first and tried to give me any chance at a better life than we had growing up.
Although things never were easy for us financially, I think she instilled a sense of resiliency and toughness that made me succeed in a lot of things in my life. She also made me figure things out growing up, which built my confidence from a very early age
