The CMO Files: Leigh Segall, Smart Communications

What keeps CMOs awake at night?

Get inside the minds of the world's top marketing professionals. In 20 questions we find out what they love most about their job... and what keeps them awake at night.

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 Leigh Segall

Organization: Smart Communications

Job title: Chief Marketing Officer

Location: New York, USA


1.         Where were you born and raised?
I was born and raised in Louisville, Kentucky.

2.         What was your first job?
I started out building candy bouquets in a local candy shop.

3.         What was the first product you got really excited about?
Technology was always what got me really excited – my dad had us playing on the Apple IIc at a young age, and that was the start. But my family will tell you the product that first captured my heart was a kitchen appliance that I set my sights on when I was still too young to really navigate alone in the kitchen, but old enough to want to cook. It was a popover maker that allowed me to go into the pantry, navigate, explore, and create something for others to “enjoy” – I loved it!  

4.         Who has been the biggest influence on your career? 
My first boss Ellen Miller – Ellen led a series of national not-for-profit organisations and did so with passion, conviction, humor, intelligence, and grace. More importantly, she built teams of people who loved working with her and for her. 

5.         What has been your greatest achievement?
My greatest achievement will come when I’ve helped to raise great kids who recognise and execute on their ability to contribute meaningfully to the world around them. 

6.         What has been your biggest mistake?
I’m grateful for every opportunity I’ve had to be in environments that place a premium on innovation and entrepreneurship, which means moving fast even if that involves making mistakes, learning, and adapting as you go. The biggest mistake I’ve made is failing to fully understand the subtleties between digital and in-person conversations. Sometimes we move too fast to get things done, and we fail to recognise how things might come across in a different medium. As we continue to operate in environments with more texting, emailing, and virtual conversations, ensuring that messages are delivered with clarity of tone becomes that much more important. I’m constantly reminding myself to think about the channel as I consider the message.

7.         What is your greatest strength? 
Cutting through the clutter to get to the real meaning of something.

8.         What is your biggest weakness?

9.         What do you think is the aspect of your role most neglected by peers?
Marketing has become so consumed with data that we’re starting to neglect where it all began – conversations. Data is critical, but people talking to one another and engaging in conversations that actually hit on a topic the other person cares deeply about, and then moves the dialog forward – that’s when we win as marketers. The data follows. 

10.       Which word or phrase is your mantra and which word or phrase makes you squirm?
‘Scale the conversation’ has definitely become my mantra of the moment, as we relaunch the Smart Communications brand. Buzzwords make me squirm. 

11.       What makes you stressed? 
Plenty of things make me stressed, but I believe a healthy level of stress – deadlines, tight turnarounds based on unanticipated opportunities, etc. – creates a more dynamic work environment. The key is managing through this to avoid pretend fire drills – or ones that could have been anticipated.

12.       What do you do to relax?
Spend time with my family and outdoors.

13.       What is your favourite song?
I love you more today than yesterday by Spiral Starecase

14.       Which book taught you most?
I wish I could take a chapter from a handful of different books and assemble them into one notebook. Similarly, I’d write a book from each manager I’ve worked for and each team I’ve worked with, because I’ve learned as much on the job as through the pages I read. A handful of good books include Delivering Happiness, Made to Stick, and Messy: The Power of Disorder to Transform our Lives.

15.       Do you have a team or sport that you follow?
UL Cardinals, Basketball

16.       Which country would you like to work in?
I wish I could work part-time in the US and part-time in the UK, working side-by-side with our phenomenal team in London. 

17.       Which company do you think has the best marketing? 
I love to watch what other B2B organisations are doing to raise the marketing game. I’m currently watching Terminus in Atlanta, and I always think Hubspot does a great job building thought leadership in its category. 

18.       What do you love most about your job?
We’re changing the way the world’s largest companies are talking to their customers. We’re all on the receiving end of these changes – I know how important it is to be reached by my bank, insurance company, healthcare provider etc. in a format that works for me. I’m proud that we’re the technology solution behind many of these companies, scaling the conversations in ways that make life easier for all of us. 

19.       What is your favourite book?
The last one I read is generally my favorite! Most recently that was All the Light We Cannot See by Anthony Doerr. 

20.       What keeps you awake at night?
I’m a big proponent of the expression: “sleep on it.” I’m often kept awake mulling over what I’m most excited about. When I eventually drift off, I find that I often awaken with a new idea, or clarity around an approach we’ve been discussing. The seeds of some of my favorite programs or initiatives have been planted through a mid-night awakening.