From the South to Silicon Valley: Gusto Chief Security Officer Flee’s Career Journey
“The Blind Ambition with Jack Kelly” provides a candid look into the top tech companies. Go behind the scenes with tech and workplace leaders and explore engineering and work culture, what it takes to land a role at these companies, and how to build, scale and succeed as an engineer or technologist.
Fredrick “Flee” Lee is the chief security officer at Gusto. Gusto is a people platform that serves more than 200,000 small and medium-sized businesses nationwide. It automates payroll, employee benefits and HR.
Below are some highlights of the podcast featuring Flee. Listen to “The Blind Ambition with Jack Kelly” above or on your favorite podcast app.
How to become a chief security officer
There’s no one specific way to actually become a chief security officer. When it comes to me in particular, [it] isn’t what I… sought out to do… CISOs actually aren’t cookie-cutter, and I, in particular, especially being here in Silicon Valley, I am definitely not cookie-cutter.
Navigating your career as a technologist
I don’t look like what… a lot of people think of immediately when they think of a Silicon Valley executive… dressing up is me wearing Dickies.
How I began my career… was actually focusing on the things that I was both passionate about and also good at and in trying to find places that would amplify both of those things.
One of my very first jobs was at the Center for Analysis and Prediction of Storms, so scientific computing. I kind of had this dream that I always wanted to be a builder, and I wanted to actually focus on things that could allow me to actually reach new things, empower more people, use technology to actually make life better. By helping predict tornadoes and storms… I was trying to actually help make lives better and learning at the same time.
Intentionally and unintentionally, I’ve [been] building this toolset… like preparing to be a carpenter or something along those lines. I was… going through all these various apprenticeships. And as I was getting older and more mature, I started to become a little bit more focused about how do I continue adding more tools… how to actually go out and actually find that perfect hammer, how to actually go out and actually find and differentiate between using a driver versus just a normal drill, and those kinds of things.
Why working at a big bank was indispensable
… After doing some of the dot-com stuff, I recognized that I didn’t have any big enterprise experience. So I ended up taking a chance and joining Bank of America, which sounds almost antithetical to actually being like a Silicon Valley-type person.
It was so empowering [to]… actually go and see what things actually look like at scale, deal with technology at scale, [and] also the implications of technology at scale, which I later learned was actually a super important skill.
Bank of America… actually made me more attractive when I went back to startups… Now I have this additional skill that a lot of startups are actually missing.
As I got older… going into Silicon Valley, I started to actually refine how I wanted to use those tools. So my journey started shifting from tool collecting to… seeing… where are my tools actually useful, right, what are the things I can actually do with these tools.
… But by taking and placing those bets on great companies [that] plac[ed] those bets on me… and then placing those bets on great people, that’s fundamentally how I really realized this path of actually becoming a CISO.
Professional development involves taking bets
… When I look at my career in hindsight… my LinkedIn profile actually looks almost like a sine wave, right? But the sine wave is actually gradually going up and to the right, meaning that I was actually taking some chances. And also taking some sure bets and kind of measuring those out of what this fundamental just crisp vision of what I really wanted to be like, that vision always gets refined.
My career has just been me iterating and iterating on my MVP [minimum viable product]. I got this degree, I did all this other kind of stuff, I was like a little baby hacker back in the day, and I was just iterating on that.
Like if it weren’t for those mistakes, mak[ing] improvements upon that, and also… hav[ing] that grit and determination to keep pushing through, even through adversity and also even through prosperity. That’s one of those things… you have to stay motivated, even when things are going great.
When to move to another job
… One of the things I try to do before I even take an offer or switch jobs or think about other companies is I try to actually do some calculus:
- What is it?
- How am I going to grow from this?
- What about this company is going to make me better?
Obviously, everybody wants to care about financial prosperity and things like that. I think more about personal prosperity, which is much broader than finances. And that means, hey, how can I continue growing?
At some point, you’re gonna have all the material things you want or whatever. But you still need to actually continue that human journey of improvement, and that’s really, at least in my opinion, what being human is about; it’s about being better than you were last week, and learning from mistakes, embracing mistakes, and embracing risk-taking to some extent, so you can constantly improv[e] for yourself and also for your community and others.
The power of just saying “yes.”
Be greedy about opportunities; be greedy about learning; be greedy about growth.
… I think one of the best things that people can do for themselves, especially if you’re trying to get more tools, is learn to say yes more and learn to embrace embarrassing themselves…
The importance of company values
… One of [the] things I love about Gusto is that I’m never ashamed of what we do here at Gusto. That’s not something that all companies can offer, and that’s not something that all people can actually say.
What I mean by that is I know for a fact that if I do my job well, when I go to sleep at night, somebody’s life is actually better. I know that when I wake up in the morning, and I go to work, and I do the best that I can, that somebody’s life is going to be better. And at no point is an action that I perform is going to harm someone and that, for me, is deeply important.
Facing fears at work
Bravery can only be shown in moments of conflict and moments of fear, so I’m [a] very fearful person, but I feel like I’ve risen to the occasion when it’s called for.
We think that being brave is something that you’re born with, or some people have a certain inclination towards that. Bravery is a muscle, and it’s something you can practice. It is something you can actually do small steps at a time.
For the people that might be a little bit shy about approaching their manager or… someone who’s really there to try to help you grow your career is to recognize that your leaders want you to grow, and they want to take chances on you.
… Don’t say no to yourself first. Let somebody else say no to you… Oftentimes we limit our own careers because we’re actually saying no to ourselves… And more often than not, you’re actually wrong.
… A lot of leaders… want to hear [from] people that want to place bets on themselves. They actually want to encourage that. And so that’s one of the things I always recommend: just ask for it. The worst thing you’re gonna get is the no that you’ve already told yourself, right? Because if you’re not asking them all, you’ve already told yourself no.
Why Flee will help you leave his team if you ask
… I always try to remember that you lead with empathy. And that’s actually one of the best things you can do is to be empathetic to people and letting them actually see that. Let them see you fail. Let them see you be vulnerable. One of the things I do at Gusto is I share my performance review with everybody.
I think the other thing is actually talk honestly with people about their career and their career aspirations, and ask them how you can help them… If there’s another company out there you might be a better fit for, let me know, and I will go to bat for you. I will try to help you.
If you’re trying to actually launch your own little startup [and] that’s your actual dream. Let me know. Maybe there’s a VC [venture capitalist] in my network I can help you pitch to, and you can get funding from [them].
Maybe the best way to actually boil it down… is… being sincere about investing in your people. And that’s either with time, that’s with opportunities, that could be with words of encouragement, that could also be like challenges.
Gusto’s no-title company culture
One of the great benefits is it levels the playing field. Good ideas come from everywhere. We have great features launched by interns… It’s because… everybody at Gusto is an owner, and you operate like an owner.
Now, if you have hierarchy amongst all that, if you say oh, well, I have to wait until this certain person with the title says X, Y and Z or oh, I can’t do this because I don’t have that title. Fundamentally, we’re not doing what’s best for customers.