-- Name: Dylan Smith, co-founder and CFO
-- Age: 26
-- Time with company: 6 years
-- Education: B.S. economics, Duke University
-- Headquarters: Palo Alto, California
-- Number of countries: Sell globally, with one office in Palo Alto.
-- Number of employees total: 300+
-- Number of employees the CFO oversees: Four direct, with about 30 who report to them.
-- About the company: Box offers an open, secure content sharing and management platform.
1. Where did you start in finance and what experiences led you to the job you have today?
I got my start in finance on the job at Box. But in terms of entrepreneurship in high school, I started a little tutoring company with a couple of my friends and ramped that up, and I found that finance was what I liked doing. I went to school thinking I'd be a pediatrician, but I realized that entrepreneurship is what I like to do. I think my relationship with [co-founder and CEO] Aaron Levie has really been influential in solidifying that career path as well. [Smith and Levie met in middle school.] Math has always been my strong suit, so I really always liked numbers. I was the type of kid where in 7th grade I took a bus to the high school every day because they ran out of math classes for me.
2. Who was an influential boss for you and what lessons did they teach you about management and leadership?
Never having had an actual boss, I've never reported to anyone -- I have my board of directors who have been very, very valuable in shaping me as a leader. But I think in terms of shaping me, our COO Dan Levine has been influential. He's helped me in thinking about performance management and building an organization. I think the single most important person in helping shape my management and management style would be Dan.
3. What are the biggest challenges facing CFOs today?
I think some of the bigger challenges are really in trying to play the balance between hitting this quarter's numbers -- you really need to be thinking about the now in meeting the numbers -- but also investing in long-term growth. One challenge I don't see a lot of, but that I hear about just in talking with my peers, seems to be positioning the CFO as a real strategic leader and a partner, and not just managing the budget and being the bean counter, but really managing the company structure and helping the others in the management team develop a strategic mission. Another one for me is navigating all the new rules and regulations especially as we gear up to become a public company. There are a lot of things that aren't actually related to growing the business or being successful or allocating resources on that front. I don't have a deep background in that area, so just being mindful that we're not putting the company in a difficult position.
4. What is a good day at work like for you?
My typical day, I try to keep the mornings pretty clear to really work on the projects such as budgeting, or building models or the stuff that I really like to do. So a good day is when I can carve out a couple of hours to work on those projects of mine. But also anytime I can be really helpful to our sales leaders and our marketing leaders, where I really dive into our data so they can say, 'Dylan, that's really helpful to us.' Whenever I can dig into and get useful information for the team is a great day.
5. How would you characterize your management style?
I'd say I'm a very hands-off manager. I tend to hire people I can trust who can do the job I'm asking them to do. I put a lot of trust in my team. I'm not one of those managers who likes to spend a lot of time micro-managing and holding peoples' hands along the way. [I tell them] 'here's what we're trying to do -- x,y and z' and then let them get there.
6. What strengths and qualities do you look for in job candidates?
The biggest thing is really the passion and it doesn't necessarily need to be about the job they're currently at but just in the course of conversation, talking about what projects they've done or even what hobbies they have. Because people can get really fired up. If I can do my job and get them fired up about Box, then they can be incredibly productive and successful. The other thing is the experience of working at a company with rapid growth. I look at someone's resume and see they've been through this sort of rapid growth [like Box has gone through] at companies I respect -- that is something we definitely look for.
7. What are some of your favorite interview questions or techniques to elicit information to determine whether a candidate will be successful at your company? What sort of answers send up red flags for you and make you think a job candidate wouldn't be a good fit?
There are two things that I really try to get through in an interview. One is how passionate they are and have they done their homework about Box and know what we're all about. And then related to qualities and strengths of the candidate, I ask them to anticipate the problems and the challenges in our growth, so in the next two or three years, where would they dive in, and then I have them walk me through a specific example of how they solved a real business problem that we're facing, giving them specific examples of what we're facing at Box to see have they really done that [kind of work] before and what would be their thought process.
On the second point, a red flag would be if they aren't familiar with our product and our space. And another red flag would be people speaking really generally about something. When I ask for specific examples and people don't have those, that would be a red flag too, when they speak in more general terms.
8. What is it about your current job, at this particular company, that sets it apart from other chief finance positions?
It is a pretty unique situation, for both my role and relationship with our CEO and just my history with the company. I think I have a lot more say in the strategic vision of the company and just setting the culture, which comes down from Aaron and me. I really focus on the growth and delivering the right information to our executives. Box is growing at an unprecedented rate for a SaaS company, other companies haven't seen the growth we are seeing. Just because we've changed the types of customers we are selling to and we're ramping up our products, that makes it a challenge. We have to set up the forecasting and budgeting process so that we can quickly adjust month-to-month. ... So, I think it's a much more dynamic role than most CFO positions would be.
9. What do you do to unwind from a hectic day?
The two big activities would be either cooking, which is very therapeutic, so I do that, as well as just getting out of the office and going for a run.
10. If you weren't doing this job, what would you be doing?
I guess if I hadn't had the opportunity with Box and I was still on that pre-med path, I would probably be training to be a pediatrician right now. But now that I have had this experience and how much I enjoy it, I think I would be doing something similar, with a high-growth company. I would maybe want to create that at a different company. But there's no [other] job I'm really envious of at this stage.
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