1. What have you found most challenging as a leader of a small or medium enterprise?

The biggest challenge is saying “no.” Everything is “urgent,” so it’s critical to identify what’s “important” and to prioritize your and your team’s time accordingly. Resources will always be finite, so you need to ask yourself if that shiny new opportunity will help you to achieve your company’s strategic and financial goals faster than what it displaces?

2. How did you become a leader of an SME? Can you please briefly tell the story?

My two partners and I sold our South Boston tech startup. The CEO of the acquiring company asked me if I’d like to do a little marketing work for him, as he didn’t have anyone in the role. Seven years later, that “little” marketing work has evolved into my current CMO role focused on enabling customers’ success across dozens of countries by helping them to fully leverage the capabilities of UIB’s conversational AIoT platform’s omnichannel MSP API.

3. How do you structure your work days from waking up to going to sleep?

While no two days are the same, due to all of the different time zones, the first half of the day is often spent collaborating live with customers, partners, and team members, while the second half of the day is spent on the work that can be done asynchronously.

4. What's the most recent significant leadership lesson you've learned?

When you’re rolling out new technologies, you must help your customer to engage their functional experts across all departments. The people with their hands-on-the-keys need to understand the “why.” Success doesn’t come from the technology, it comes from people using the technology.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

I’m a marketer, so I’m of course going to tell you that it was the first book I co-authored. The book taught me that leadership, especially when you’re managing creatives, is not about pushing your ideas, but creating an environment in which everyone’s ideas can be heard. The process of pulling together a book taught me how to help people to unleash their creativity and value their unique voices.

6. How do you build leadership capacity in an SME?

As flat organizations, SMEs have an outsized advantage in developing leaders. With so much to be done, there are fewer barriers to people taking on duties, including leadership roles, outside the confines of their formal job descriptions. There are no “passengers” in an SME. Everyone needs to drive.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

I had asked the executive of a well-known company in Singapore what he saw as the value of our collaboration and his answer was our innate agility. Speed, creativity, and the ability to pivot are so critical to our survival, that it’s part of our team’s collective unconscious competence. He reminded me that the invention we did without even thinking is one of a SMEs’ core assets.