Interview with Anthony Chen, Employee #1 at Flexport

This article is part of a series revealing the stories of early employees from the most successful tech companies of the past few years. You’ll walk away having learned about what these individuals experienced, what they wish they knew, and the advice they’d give to others joining high-growth startups. Key takeaways are at the top and you can find the full interview below. 

This interview is with Anthony Chen. Anthony was the first employee at Flexport in 2014 and working for 6 years across product, special products and strategic development. Flexport was most recently valued at $8.0b and has nearly 2,700 employees. Below is an edited version of a conversation he had with us here at Compound. 

Key Highlights

• On the first Flexport interview – “I walked up to this office – I think it was on 4th and Townsend – and there’s just an open garage door with a single car and no lights on. I remember I even took a photo and sent it to my girlfriend at the time and told her the name and address of the place in case I didn’t text her in an hour. I was about to walk into this dimly lit office and didn’t know what to expect.”
• On how they prioritized what to build early on – “We kept asking ourselves those questions in the early months and it led us to a lot of really insightful product discoveries and prioritizations. If customers aren’t using certain features, there’s no point in building them. I think being able to feel your customer’s pain is actually really good for companies and because at Flexport we were dogfooding our product, we felt the pain. It was very helpful.”
• The pitch to join Flexport in 2014 – “The entire physical world is here because of logistics and supply chain. It’s one of the most underutilized and under optimized industries in the world – and we’re going to make it 10x better. If you join us know, you’re in a position to create a foundation that could impact hundreds of thousands of people or more. Yes, you will work a lot. But for the right person it will be worth it.”
• An early ritual that was key to Flexport’s success – “The first was a bi-weekly process improvement workshop. We’d had folks from our ops team, our sales team and sometimes even our product and engineering teams (7-10 people) all come together to understand what was happening in a particularly flow. What was broken? What was the bottleneck? How can we improve it? We trained ourselves to be adaptable and to solve problems. Everybody builds and everybody sells.”
• On the product Anthony was most proud to build – “But personally, one of the early products I built that I’m very proud of is what we call the action item system. It’s basically a digitized atomic action list of all these processes and the action steps that need to happen for an international shipment to be done. We turned it into an action item system that allows our team some semblance of automation to have consistent, accurate and efficient ways to get their job done. It would take us half as long to do something our competitors did.”
• On advice for other early employees – “...ask yourself how you can create as much leverage as possible for those that you work with. It’s very easy to just get your job done – you’re here to do ABC, so just do ABC. And that’s fine, but for folks that are actually going a step beyond that and thinking about how they can create leverage for them or their team, it makes all the difference. It’s super important for early folks and helps them think like a business owner.”

How did you first find Flexport and what made you want to work there?

I started my career on Wall Street then shifted over to venture capital in the Bay Area. I always wanted to get my hands dirty and be a real operator. One day there was a post on HackerNews for a jack-of-all-trades for this logistics and customers brokerage company (who knows what that means, anyway?). I thought it was pretty interesting – I saw them present on demo day and I applied just for fun. 

My background at the time was on the business and finance side, in undergrad I had studied computer science and I also picked up design by myself too. The combination of those three skills met their “jack-of-all-trades” requirements and I vividly remember getting an email back that said, “Hey meet me in my office”.

I walked up to this office – I think it was on 4th and Townsend – and there’s just an open garage door with a single car and no lights on. I remember I even took a photo and sent it to my girlfriend at the time and told her the name and address of the place in case I didn’t text her in an hour. I was about to walk into this dimly lit office and didn’t know what to expect.

When I got up there, I met Ryan [Petersen, Flexport CEO] for the first time and realized that that’s just what startup interviews were like. Him and I had a great conversation and they made me an offer shortly after. I left VC to join Flexport right as they were going through Y Combinator. 

What was the first thing you worked on at Flexport?

The biggest mandate that came before anything else was making sure that we could actually service customers. In the first two or three years my primary responsibility was building the operating model of the business and translating that into software product. How do we actually do the work? How do we serve clients? How do we execute digital paperwork? Then how do we productize it. 

It was fantastic because I was building the manual in real life – process flows and logic for how we actually service the customers.

From 8:30am until 6:00pm, I’d be on the phone with customers, executing, getting stuff done. Then, during nighttime, I’d be working with Ryan and our developers to build our software. Writing specs, figuring out how to make it better – I would be dogfooding the stuff that we were building day in, day out. I’d work from 9:00pm until midnight then take the CalTrain back down to Palo Alto where I lived at the time and finish the China side shift around 2:00-4:00am. 

How did you prioritize which products to build? 

There’s a lot you can do. Some of it is founder instincts and part of it was what customers react to. The biggest clue was identifying the biggest pain point for us. If it was really painful for us, it must’ve been really painful for our customers too. As long as we were honest with our own problems, then we could build a better process flow or a better software tool to solve the problem. 

We kept asking ourselves those questions in the early months and it led us to a lot of really insightful product discoveries and prioritizations. If customers aren’t using certain features, there’s no point in building them. I think being able to feel your customer’s pain is actually really good for companies and because at Flexport we were dogfooding our product, we felt the pain. It was very helpful. 

If you were trying to convince a candidate to join Flexport back in 2014, how would you pitch them?

Everything you see around you, in this physical world, is here due to the power of logistics and supply chain. From the chair you’re sitting on to the computer you're using. This is one of the largest, oldest and most stagnant industries in the world untouched by technology – and we’re going to make it ten times better. Come join us to improve the user experience for global trade.

It was funny – there were a lot of people back in the early days who listened to my pitch and just kind of shrugged it off. Then, a few years later they would see us in the news and message me asking if Flexport was hiring. I would just tell them: “we’re always hiring! We have a ton to build. But the terms will be real different than before.” 

What did you look for in early Flexport hires?

We looked for three things. 

Number one was we pulled a lot of folks in who came from the industry and wanted to change it. They were champions in the space and they loved that we wanted to fix these real problems. We were bringing this magic called “technology”  to try and alleviate the pain points that existed every day. 

Second, we found software engineers that were deeply passionate about the space. It’s not just a consumer app that you intuitively understand. We needed to find engineers that actually wanted to understand what logistic was – which isn’t something most people think about day in, day out. But a lot of our early engineers were really curious. They wanted to impact this unsexy behemoth of an industry and solve real problems. 

And third, we wanted young enterprising hustlers and entrepreneurs who wanted to create a foundational product. For a lot of people, the ability to feel like you’re creating tangible value that they can see is really impactful. A lot of the things that we did in the early days is still embedded within Flexport today. 

What’s a tradition or ritual that Flexport followed that you think had an outsized impact on Flexport’s success?

In the first year there were two types of meetings that I really loved.

The first was a bi-weekly process improvement workshop. We’d had folks from our ops team, our sales team and sometimes even our product and engineering teams (7-10 people) all come together to understand what was happening in a particular flow. What was broken? What was the bottleneck? How can we improve it?

We trained ourselves to be adaptable and to solve problems. Everybody builds and everybody sells. If you’re an engineer, you’re representing Flexport and thinking of angles to grow our business. If you’re on the ops or sales side, you’re building processes, you’re building software and product. This first type of meeting kind of created a unique culture where everyone chipped in. 

As for the second type of meeting – I’m a big foodie, I love finding and eating food. In the early days a lot of our team would be grinding pretty late and at around seven o’clock at night, I’d look around at the usual suspects in the office and we would order a ton of Chinese food (or any type of food) from a restaurant in downtown SF. And people just loved it – you’re grinding, you’re in the foxhole with everyone else, and you’re eating great food. 

Who are a few people at Flexport that you learned a lot from and still inspire you in your work today? 

There are way too many great people I worked with, but I’ll pick a few. 

First is Ben Braverman, Flexport’s original CRO and first sales guy. He taught me so much about sales, building funnels and applying the right sales approach and strategy. Him and I were the first squad at Flexport and jointly built out our initial book of business. He has a unique ability for his charisma to leak through systematically to the customer that allowed him to articulate the value props very clearly. I tried to absorb as much as humanly possible from him. 

He was able to break down a lot of barriers with customers that you might usually have and simplified bureaucratic red tape into simple go or no-go. A lot of old-school customers are opportunistic and would always ask how it would impact their bottom line. In the early days we were building a lot of things but we weren’t always the cheapest. So we would use strategic sales or consultative sales to go beyond the transactional. 

Again, the list is so extensive but another person I learned a lot from is Sean Linehan. He took over product once I started going to Asia and he did a phenomenal job. I’m very happy to have laid a lot of the foundational groundwork but he definitely took everything to the next level. He’s very thoughtful, creative and can see a lot of angles a few steps before anyone else. We ended up building a product with a lot of thoughtfulness to the extensibility and scalability of what we were building. 

One final person I’ll mention is one of our early engineers named Tuan Bui. He was a front-end engineer but he was basically full-stack. I used to call him “speed demon T” because things that would normally take a full sprint he could complete overnight. And it would be even better than the specifications. He’s just a really impressive guy and one of the fastest coders I know. 

Was there ever a time you thought Flexport wouldn’t work?

I always thought we were doing the right things and I never worried that we wouldn’t have customers to serve. As with any business, I would sometimes wonder if we were growing fast enough, but those are things everyone worries about. But I think what we were doing was sorely needed by our customers and our growth over the past few years is demonstrative of that. 

What are you most proud to have worked on at Flexport? 

It’s hard – the cop out answer (but that’s true) is the organization and the team that we built. We recruited a phenomenal team and built the culture that helped lay the foundation for Flexport for years to come – hopefully for the better. 

But personally, one of the early products I built that I’m very proud of is what we call the action items system. It’s basically a digitized atomic action list of all these processes and the action steps that need to happen for an international shipment to be done. We turned it into an action item system that allows our team some semblance of automation to have consistent, accurate and efficient ways to get their job done. It could take us half as long to do something our competitors did. 

I built the system in 2015 / 2016 and some of the foundational work is still being used today (which is heartwarming). I hope it continues to get better. 

What advice would you give to early employees that’s different from advice you’d give to founders?

The dynamics are always interesting between the founders and early employees in general. From what I’ve seen at Flexport and also other companies that I know, it comes down to two things. 

Number one, ask yourself how you can create as much leverage as possible for those that you work with. It’s very easy to just get your job done – you’re here to do ABC, so just do ABC. And that’s fine, but for folks that are actually going a step beyond that and thinking about how they can create leverage for them or their team, it makes all the difference. It’s super important for early folks and helps them think like a business owner. 

The second thing I usually recommend is to always ask how you can add value to the customer. If they have a problem, how can you add value? Always ask be asking yourself this question. Regardless of what industry you’re in, you’ll play the long game by asking how to add value as much as you can. 

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