Founder and CEO of the learning software Workramp takes us from his early days as a student athlete to his time working on product at Box and eventually starting Workramp. He also shares the insights he’s learned from business leaders — from Aaron Levie to Bob Iger and Mark Benioff — and how he models those lessons in his own company. Our transcript has been edited, but you can listen to the full podcast episode here.
You were a student athlete at Santa Clara University. Can you tell us about being a student athlete in college and what your mindset was like back then?
Yeah, I played tennis at Santa Clara. I’d played competitively most of my life and then walked on to the team and played for two years. I did that while doing electrical engineering. It was definitely a challenge. I remember my grades were slipping because you’re putting in 20–25 hours a week, you’re traveling, and you’re missing labs while all of your friends are studying and going to all the extra learning sessions. But what is taught me is how to time manage while in college. Especially as a CEO now, I have to learn to juggle multiple things. I wouldn’t want to trade that experience for the world.
I want to talk about Box where you were a product manager. Was that your first job out of college? And did you know that you wanted to go straight into product, or is that something you had to discover?
That was not my first job out of college. I actually had two stints before that. One was at Cisco right after school. I got recruited into essentially a mini MBA program out in Raleigh, North Carolina, and I was there for about three and a half years. Then I had a stint of a failed startup that I founded called StuffBox. When that startup failed, I realized I had to go learn how to actually build a startup and learn from the best. That was when I started at Box.
I knew I was going to go back into product. When I was interviewing around right before I joined Box, I had a plethora of different opportunities I was chasing. l decided to do sales and get paid a boatload of money at the time compared to what I was making, which was nothing. I knew that if I could get that background in selling a SaaS product, that’d be a good entry way. So it was always with a short-term mindset, but I knew I wanted to go crush it for a couple of years and then move back into product.
Can you paint the picture for me of what that team looked like at Box? They have a great product, so I imagine that their product team is reflective of that. What did it actually look like?
At Box, product was definitely one of the top teams in the company. It was definitely a team that people aspired to to join. When you go into a lot of these different companies, the DNA of the company typically comes from the CEO or one of the co-founders, and Aaron Levie (Box co-founder and CEO) was definitely a product guy at heart, even though he is pretty funny and vocal. That’s where he spends most of his time.
What I liked about that team was that they actually owned some core parts of the product that they consider a “platform”. So you got some actual experience on the product itself, but you also got some experience into the ecosystem, like the APIs and the technical nitty-gritty. I was really excited to kind of straddle both sides of the fence there, both with the core product and also the technical ecosystem side of the house as well.
What were some of your key takeaways from being part of that product team? And was there anything unexpected you learned from Aaron?
Probably one of the coolest things I got to do was spend time watching Aaron do his magic. There are so many cool startup CEOs now, but at that time there weren’t many cool startup CEOs like Aaron. He was really trailblazing.
I think the biggest learning from him was that he knew what the market wanted and where you should position yourselves. For example, everyone now during COVID is talking about digital transformation, like Benioff and ServiceNow CEO McDermott. Aaron was talking about digital transformation back in 2013. He had this foresight where he knew exactly what messaging would resonate, even if he had built nothing around that specific area.
If you think about Box, it’s really just file sharing, right? There’s not anything extremely special about that, but then he would reframe that to say, “Hey, as a business, your company runs on your files. In the next 5 to 10 years, the whole world’s going to digitally transform, so that’s why you need a service like Box to be the foundation of that digital transformation.” So he took something as boring as dropping a file in an uploader to saying, “This is the crux of your entire revenue stream of your business.” He would reframe the products he was selling to match what the industry and customers wanted. Benioff does that extremely well too. I would say the two of them are some of the best I’ve seen in terms of that reframing.
Interesting. And they weren’t wrong. The value of Box is huge. Now I’d like to transition to talking about delivering value to users. This is something that comes up all the time today, especially in product circles. Amazon focuses on customer delight for example. What does delivering value mean to you and how have you done it in practice?
I had this founder tell me something really insightful a couple months ago. He runs a pretty big business, and he said that companies will spend $10 million with Accenture, for example, and say, “I want you to go deliver a faster time to market for our product team.” That’s the outcome they want to buy, and they’re going to write a $10 million check and guarantee that they’re going to reduce that time by let’s say 20%. And the ROI for them on that $10 million is $100 million, so it’s $90 million ROI that they’re getting.
He said that is what needs to happen in the software space, especially in enterprise. You need to guarantee your clients the business outcomes they want to see.
For us, a great example is that you might buy us to reduce ramp time of your sales team. If you could reduce ramp time from five months to four months, you’re seeing a 20% reduction in ramp time, which for one individual rep might mean a hundred thousand dollars for you. So that ROI for one rep can be easily quantifiable by the software you bring in.
That’s really how I think about the value you can deliver with software. What are the outcomes you drive for your client? And then everything else comes after that — the features, the usability, the prettiness of the design. But if you could deliver the business outcome, the client will keep coming back to you.
I want to go back a bit and ask about starting your company in 2015. Box had just gone public, and you were working there. Why did you decide to start a company at that point? And what was the core issue you were trying to solve?
In 2015, we actually just had our first daughter. For me, I think that was a kick in the butt. I told myself that if I wanted to do this, I should do it now. I think I had just turned 30 at the time, and I thought that there was probably no better time to do this than now. I didn’t want to wait until my forties or fifties to start my own company for the first time. Then once I got into that mindset, it was just about what market that I want to go into. What was I passionate about?
My criteria was pretty simple. What is a big pain point? What has a huge TAM (total addressable market), and what is a market that I’m pretty equipped to service with my background? When we looked at learning software, it basically checked all those points. The TAM is gigantic. There’s $270 billion per year spent on corporate training, and then there are many people that have a sales and product background in enterprise SaaS that want to go start a company in Silicon Valley in the learning space. I recruited one of my good friends and now co-founder who worked early at Box as well, and then we just started building the product from there.
Can you tell me what your most exciting moment has been so far as a CEO? I’m sure you’ve had plenty, but is there one that stands out?
There’s so many. I would say there are a lot in every different phase of the business, but there is a good one when we were just starting out. We’d just got our first significant paying client, $5k a year. I remember we were basically living off savings, trying to make this work, and I remember opening up the mailbox and seeing this $5,000 check, and we didn’t have a bank account at that time. I don’t even think we had incorporated officially yet.
I remember that right away, we filed all the paperwork to incorporate, and we opened up the bank account. I was just so proud walking to the teller and saying I wanted to deposit this $5,000 check into the business. When you’re working at other companies, you think that stuff is all automatic, but when you see it tangibly, you’re in awe of it. You realize you’re actually providing an outcome to clients through online software, and they’re going to pay you money for it. That was pretty exciting. Obviously in all the other phases, there are fun stories like that, but from the early days that was one of the most exciting.
That’s an exciting moment. So you took me to the top of the mountain. Now let’s go to the bottom of the valley. What was your biggest moment of despair as a founder and CEO?
I remember very early on, we were experimenting with the market and looking for product market fit. There was a very large tech company testing out our platform. At that time, I would sell to someone’s mom or brother or cousin- anybody who wanted to buy our software. I was driving up to San Francisco every day from San Carlos and meeting with this buyer.
I was bragging about them to potential future investors, and then after a good two months, this buyer emailed me and said that they weren’t going to move forward with us. And I remember getting that email, walking into our master bedroom and just shutting off the light in the middle of the day and laying on the bed in silence and just thinking, “Man, is this ever going to work?” I was pitying myself for about an hour, and then I got out of the bed, opened the blinds and was like, “You know what, that’s ok. That was not the best use case.”
I kind of knew in my heart of hearts that it wasn’t a good fit, but I’m so glad that happened because it showed me that you shouldn’t force a square peg in a round hole, even though it’s a great name brand. In the micro evaluation of it, you think the world has ended, but when you look back on it, it’s probably the best thing that could’ve happened to the company, even though it was really harmful in the beginning.
You have done so much at your age, and you seem like a guy that gets a lot done and has it all together. So I want to know what inspires you. Do you have a person or another company that you sort of model yourself after?
It’s funny, I only read non-fiction business books. Before COVID, I was listening to business books on tape pretty much every single commute. I would crush through a book a week or listen to a really good business podcast. I’m kind of a junkie on business literature, so I would say I do admire a lot of different executives, the most recent one being Bob Iger from Disney. I read The Ride of a Lifetime about a year ago.
What I loved about him was that he took such a humble approach to being a CEO, and he had such a clear strategy of what he wanted to get done at Disney. During our all-hands kickoff for 2020, before COVID, we modeled our themes of the business around how he did that at Disney. There were basically three things that he wanted to get accomplished. It was to become more international and integrate with countries like China. The second one was to move digital, and he basically created Disney Plus from thin air. The last was to essentially focus on the content, so he acquired a ton of companies during his tenure, like Marvel and Lucas.
It made Disney the powerhouse that it is. So for me, I strive to be humble, but also have a very, very clear direction with the team and get everyone flowing in the same direction. Just like Bob, I started this year with three key messages to the team and said that we’re going to go conquer those three things, and every quarter we’ve come back to those three things — even with COVID they were still really relevant — and we got everybody rowing in the same direction. So that’s probably who I’ve admired the most, especially with his approach and also his strategy.
Listen to the full podcast episode here.