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In this series, Leader Board, we speak with CEOs, managers, founders and others who lead organizations to learn what makes them tick, what they look for in new hires and even where they eat lunch.
Imagine walking into an office for a professional meeting, and upon opening the door you’re welcomed by a crowd of busy, shoeless workers. And before you go any further, you too have to take off your shoes. Welcome to Gusto.
Gusto is an online payroll, benefits and HR service that seeks to reimagine and simplify human resource practices for businesses across America. And one of the brains behind Gusto and this shoe-less office is its CEO and co-founder Joshua Reeves.
So, why the “no shoes” policy? Reeves was raised in a “no shoes” household, and when he and his co-founders began working on Gusto in an upstairs bedroom of a Palo Alto house, they continued the tradition. And while the company began to grow, the tradition remained.
Even before Gusto, Reeves was no stranger to Silicon Valley. Prior to the HR company, Reeves was the CEO and co-founder of software-as-a-service startup Unwrap. Facing one of his toughest business decisions ever, Reeves and the team decided to sell Unwrap to Context Optional in 2010. It didn’t take long before Reeves was wrapped up in his newest and greatest venture — in 2011, Reeves and his co-founders Edward Kim and Tomer London launched Gusto.
Six years and 450 employees later, Gusto has become a leading all-in-one HR platform supporting modern companies across the U.S. Valued at $1.1 billion, the company serves more than 40,000 customers, with offices in San Francisco and Denver.
With experience running two successful companies in the competitive Bay Area area, it’s no doubt that Reeves knows a thing or two about being an effective leader. And through the years, he’s developed his own take on leadership: “My role is to be of service, to be a steward, to go enable others, to empower them to go do great work,” Reeves shared with Entrepreneur.
From having a “shoes off” office to running welcome workshops with new hires, here is Reeves’s take on leading, including important traits, habits, team-building exercises and more.
On the most important leadership traits:
“I think the first one is introspection — understanding yourself, understanding your motivations, your values, having a sense of what you stand for, what drives you.
“Second, I think it’s really important to realize that my role is to be of service, to be a steward, to go enable others to do great work. In our org charts, I’m at the bottom — I’m here to enable and empower others.
“And then the third is being OK not knowing something and being OK being wrong at times. I would call this ‘growth mindset’ — constantly wanting feedback, realizing that everything we do can get better. There’s no top of the mountain. It’s just a continual climb to improve.”
On leadership style:
“My leadership style is to make sure that everyone at Gusto understands what our ‘due north’ is — our purpose, our mission — and have that be baked into our hiring. But then from there, I’m a steward, I’m a guide to help us navigate that journey.”
On habits that help him lead:
“Introspection. Every day I either try to garden or go on a run. It’s very therapeutic and invaluable to realize, especially in nature, all of the things that are much bigger and broader than us. Exercise is great because it’s a repetitive action, you can have the mind wander — daydreaming is really valuable, it’s not a time of being in control to look at an email or to respond to a message or to speak about a specific topic. I try not to have anything smartphone related, 30 minutes after waking up and 30 minutes before bed.
“More professionally, at least monthly, I go through how I spend my time and was it aligned with how I intended to spend my time.”
“In some ways Gusto every six to 12 months is almost a whole new company because there are a bunch of new people. So a lot of the puzzles that I think about are around scaling: What’s right for a 450-person company vs. a 50-person company? At 50, I was the one that could talk to everyone, I made every offer, I onboarded each person. That doesn’t scale.
“It forces you to revisit: What is right for this next phase of Gusto? Not just what’s worked really well in the past. And that matters in hiring: What is the right person for this role, for this next phase of Gusto?”
On the most important traits in a new hire:
“We have three pillars to hiring and it’s all about alignment — values alignment, motivations alignment and skill set alignment. For values and motivation, every company is different and you have to find out what you stand for.
“Motivation is hugely important because motivation is if someone really cares about the problem we’re fixing and if they’re really going to be proud and excited.”
On recognizing employees:
“I think even prior to [recognizing achievement] is making sure that there’s an alignment around what is the goal and what is success. So the heart of that conversation is the one on one that happens between the individual and their manager. At Gusto, you talk to your manager, you share with them what goals you have, they share with you the goals the company has, you find alignment and you get feedback. And when something is successful, there should be really strong validation of that. Over time that can lead to things like promotion.”
“Early on we would do something called ‘work-cation,’ which was the whole company spending a week in an Airbnb and basically doing a hackathon. We would choose projects on the first day, organize into teams and then on the Friday do presentations of what we worked on. We would also go hiking and do outdoor activities.
“With the larger company, we do something we call ‘Gustoway.’ It’s something we do annually and it evolves every year. Last year we did it at a Boy Scout camp and it was mostly a set of workshops, and also just relaxing, having a campfire and enjoying being in nature.
“I think these things should feel really organic. It should feel like a community — these are people that care about each other and we want that to feel natural, and then we want to create these different programs to augment that.”
On managing meetings:
“For me joining meetings, I go in very deliberately making sure people understand if I’m the decision-maker or if I’m there to give input. It’s important to clarify that because people tend to be biased not wanting to disagree with a leader.
“And I think it’s really important if the leader is not the decider or just is giving an opinion, it could definitely be wrong. We’re all just people. I’m not going to have all the ideas — I want people to agree or disagree, and push back often.”
“I work closely with my CEO team on scheduling and time management and we use Google Calendar as our tool. The goal is to be deliberate and make sure that how I’m spending [my] time aligns with the priorities I have for that week.”
On office setup:
“Our office is set up as an open floor plan. We like to have folks be able to chat, connect and talk to each other across different teams. People do have different groupings but the open floor plan gives us the chance to have more of the natural interaction.”
“I eat lunch with the team. We have dining in the office and a space that’s set up where we bring in food every day. Usually I join a random table or if I’m doing a planned team visit then grab an area together to sit in.”
On a strong company culture:
“To me, culture is simply your values and your traditions. Traditions are things that develop organically and values are something that are very core. It’s spending the time to understand what that core value system is and in the way it’s maintained, and that should really drive hiring.
“There’s no right or wrong culture — there are many ways to build a company and many ways to have a culture. I think what’s most important is leaders in a company being opinionated and being authentic. It should be a byproduct of what feels natural.”
On his biggest culture win:
“I do ‘welcome workshops’ every two weeks with every person joining Gusto. They’re mostly a discussion around our values, our mission and our market. I tell everyone this is how I connect to these values and this is why I care about the problem we’re trying to fix for small businesses. And you’re here because I know you also care about it because that’s why you joined. This is my company, this is your company, we’re all equity holders — this is our business.”
On his role model:
“Every ‘welcome workshop’ I do I play a video clip from Steve Jobs. It’s a 1995 video clip where he talks about how the world around us was created by people that are no smarter than us and how we can change this world, we can improve it, we can make our mark upon it. If you poke life, it will poke back.”
On his favorite leadership book:
“It’s called The Monk and the Riddle, written by Randy Komisar. It’s about life and approaching the topic of purpose, but I think it’s just as relevant to a leader as well.”
On where most leaders go wrong:
“I think a very clear pitfall is thinking that the way [leaders] do something is the way others should do it. It’s an interesting dynamic — as an individual what makes someone most successful is doing it their own way. In school, if you’re going to study for an exam, it’s all on you. Once you understand your best way to study, you can be successful. But there are many ways to study, and when you’re a leader it’s kind of analogous.”