Shift Is Tackling the Ultimate UX Challenge: The $750B Used Car Market

User feedback drives a technical team with real-world impact

Job Portraits
Job Portraits
12 min readJan 13, 2016

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This portrait was commissioned by Shift and produced by Job Portraits, which highlights fast-growing startup teams. For the interview below, Job Portraits spoke with Head of Engineering Jon Vincent, CTO Christian Ohler, engineer Mikey Lintz, and designers Erica Burnett and Paul Shen at their office near Castro and Market in San Francisco.

Left to right: Jon, Erica, Christian, Paul, and Mikey.

What is Shift and how are you making people’s lives better?

Jon: We’re disrupting the used car marketplace by making the process of buying and selling a car easy, transparent, and data-driven. But that’s just the beginning. The long view is to improve the entire experience of car ownership, all the way down to things like maintenance.

Sometimes when I tell people about Shift, their reaction is, “Used cars? Really?” It’s kind of the opposite of sexy, and people don’t know much about the market. It turns out there are 45 million used cars sold in the U.S. every year, a roughly $750 billion market. It’s the largest retail market in the country and the second-largest market overall, after housing.

People are rarely excited about buying or selling a used car, but Shift can change that. There are so many opportunities for technology to fix problems that have been around for decades, and it’s exciting to see the impact Shift is already having. We’re on track to be the biggest car seller in the Bay Area. I think that’s pretty darn cool for a company of our size.

For anyone who’s never bought or sold a used car, tell us more about the current experience and why it needs to be improved.

Erica: As an example, my husband and I recently decided to get rid of one of our cars. The first step was going to the dealership, where it’s very hard to know if you’re getting a fair deal. It wasn’t a great experience, but my only other option was Craigslist, and I didn’t feel like I knew enough about cars to sell one on my own. Also, going on test drives with strangers didn’t feel safe, so the dealership was the better of two less-than-ideal options. Shift is a great solution for people like me who want to make more money from the sale of their car but don’t have the time, knowledge, or desire to sell it themselves.

Above: The Shift offices sit near the intersection of Castro and Market streets. Below: The office’s top floor, with engineering in the far corner.
The engineering team at work. Above: Yufei, Mikey, Andrew, and Jonathan (left to right). Below: Paul (left) and Lindsey.
Left to right: Erica (design), Yufei (engineering), and Rob (design) talk through new financing UX, while Andrew (engineering) ponders a user flowchart.

What is it like to sell a car with Shift?

Mikey: First, we send a Car Enthusiast to the car owner’s house. They do a half-hour inspection and log everything in our app, and provide the owner with a quote for their car. Then the Car Enthusiast drives the car back to the Shift hub, where we make repairs, photograph it, publish it on our website, and take it to potential buyers so they can test drive it at their convenience. Once we find a buyer who’s interested in the car, we take care of all the paperwork and send a check to the seller.

“We do a lot of work on the back-end to make it an almost magical experience for the seller.” –Jon

Jon: We do a lot of work on the back end to make it an almost magical experience for the seller. Basically, it’s like, “Push a button and get a check.” Likewise for the car buyer: if you like a car on our website, we can have it in your driveway for a test drive in as fast as an hour.

Tell us more about the Car Enthusiasts. They’re not paid on commission, right?

Jon: Definitely not. No one wants to invite a pushy car salesperson to their house. We are really careful to incentivize team members around customer satisfaction and not just raw volume of sales.

Mikey: The Car Enthusiast is the point person for customer service. These team members are passionate about cars, they understand the mechanics, and they like to work with people. It’s a hybrid position; they’re mechanics and salespeople.

Above: Peck (operations) greets Jon (head of engineering), Matt (technical recruiting), and Taylor (technical recruiting). Despite the company’s focus on cars, many employees prefer to commute by bike. Below, left to right: Minnie (COO), Yuval (acquisitions), and Justin (CFO) discuss ways to improve remote inspections at a seller’s house.
With a fast-growing team, Shift is quickly outgrowing its space, so team members work where they can (the stairs are popular). Above: Tobi (left) and Matthew (both operations).
Above left: Andrew (engineering) and Zhuoxun (operations). Above right: Taylor (technical recruiting) and Laily (executive assistant).

This sounds like an interesting logistical challenge. Is it also interesting from a technical standpoint? What are you currently working on?

Mikey: I have two big projects. The first is our internal iPad app that our Car Enthusiasts use to evaluate cars, and which helps them provide the customer with a concrete value for their car. The second project is a public-facing iPhone app that gives potential sellers a rough estimate of how much their car is worth.

Jon: You should say something about the notification project.

Mikey: Oh, right. I’m also helping think through what notifications to push to customers while they’re selling their car. People love that selling a car through Shift is so hand-off, but we’re realizing it shouldn’t be too hands-off. We’re finding that customers are happiest when they are kept in the loop throughout the sales process. This is really the human side of what we do.

“This is really the human side of what we do.” –Mikey

We’re figuring out which notifications we absolutely need to send — like, your car is sold, here’s how to deal with insurance — and which notifications just make people feel better about the experience — like, we took your car on a test drive and people said it was awesome. That’s something we can build out on mobile with push notifications, but it’s also something we can start iterating on immediately through email.

And how much of those two apps do you personally own?

Mikey: Me and Paul are the two iOS engineers, but then Paul switched to design so, by default, I’ve been working on both of them. But I’m splitting the customer-facing one 50–50 with Alex.

Jon: I think it’s pretty fair to say Mikey is the overlord of those projects.

Above: Over lunch, Andrew explains Loggly, which he’s been trying out, to the rest of the engineering team. Eventually a comparison with BigQuery surfaces, and Lindsey jumps in to share his experiences. Below: Lech (operations) looks on. Engineering likes to do their learning lunches in the open so other teams feel free to join in.
Above left: Bradley, Mikey, and Christian (left to right). Above right: George (Shift’s CEO) joins the conversation for a bit.
Above: Although it’s growing fast, Shift’s engineering team (plus Lech) still fits around one table. Below: One-on-one conversations continue after lunch breaks up.

Tell us why you decided to join the Shift team. Are you all into cars?

Paul: Not at all. I love my car, but that’s not why I joined Shift. For me it was the caliber of the people here. I was at Facebook before, and a lot of people also left high-profile companies to come tackle this problem. The other thing that brought me to Shift was going on Yelp and reading the customer reviews. People were raving about this service! This is the type of business where you’re interacting with customers every day—it’s less abstract than, say, a social network.

“This is the type of business where you’re interacting with customers every day.” –Paul

Christian: I’ve been through the experience of buying and selling a used car, and it was pretty painful. I like the idea of making that better. But just in general, I like working on real-world problems. Before Shift I was building software at Google and Dropbox; if you’re only constrained by software, you’re not very constrained at all. You can go in any direction. But if you’re trying to solve a problem in the real world, with real cars, it’s different. Each of those cars is a couple tons of steel and they take up real physical space. That constrains what you can do, and I think that forces you to build products that are actually going to be useful.

“If you’re only constrained by software, you’re not very constrained at all.” –Christian

Jon: I really enjoy picking apart a super complex process, like financing a used car, and making it simple. We’re a diverse bunch of people here, but I think we all like using technology to improve real-life experiences.

Mikey: At Google, I worked on Hangouts and YouTube. I was definitely not the overlord of YouTube. At startups, if you’re creative and interested in working hard, you often get the opportunity to punch above your pay grade. I mean, no company in their reasonable mind should give me this level of responsibility, but Shift did.

And how’s that going?

Jon: So far, so good. We’re very happy with what Mikey is doing.

Cross-team collaboration is key to the way Shift operates. Above, left to right: Irene (product) and Michal (product manager). Below, left to right: Christian (CTO), Peck (operations), Rob (design), Mikey (engineering), and Jon (head of engineering).
Cross-team collaboration is key to Shift’s philosophy. Above, left to right: Christian (CTO), Peck (operations), Rob (design), Mikey (engineering), and Jon (head of engineering). Below left: Mark (head of design) and Yufei (engineering). Below right: Irene (product) and Michal (product manager).
Above: Leads from ops, design, product, and engineering come together for sprint planning.

Was there anything that surprised you once you started working here?

Erica: I’ve been pleasantly surprised by the culture. A lot of startups are geared toward young, single workaholics—but Shift is different. Work-life balance is a core value here. I’m very pregnant right now, so I’m glad I never had to worry about getting fired for taking maternity leave, or being forced to choose between my family and my career.

“Work-life balance is a core value here.” –Erica

I think it helps that our founders have families. They’ve been there, done that, and they understand that you can spend time with your family and also get work done. When I was in my early twenties, I would get excited about something and work, like, twenty hours a day. But that’s not sustainable. That’s how people burn out. Over time, I think you just figure out how to do your best work and how to recharge.

Mikey: I agree. We may be a startup, but we have a mature culture.

Erica: I’d also add that there a lot of different personalities here. It’s not at all a homogeneous atmosphere, but there’s a common thread that everyone cares about doing good work.

Interested in working with us? Check out our open positions.

It sounds like you all enjoy working here. Are there types of people who might not enjoy it?

Jon: Someone who only wants to solve an interesting academic problem probably wouldn’t be a good fit here. We figure out what’s going to matter most to the user, then we build it — fast. Perfectionists probably wouldn’t be happy here, either. We make mistakes and then we fix them. It’s part of the process that I think we all embrace. Some people just aren’t comfortable with the level of change at a startup; they want something more established and more structured.

Mikey: Tacking on to what Jon said, I think you have to be somewhat flexible on what you work on because the challenges change a lot day-to-day. What we’re focusing on this month might be very different than what we focus on in three months.

Above: Isabel (finance) and Bradley (engineering) head out for an afternoon coffee, passing two antique trolleys pulling into the Castro station (below left).
Isabel and Bradley met when they were both working for the Obama campaign. Above: They watch as ladies blow bubbles that drift over the coffee shop’s patrons. Below: Heading back to the office past the historic Castro Theater.

We find that probably 90% of how engineering teams work is similar across companies. What’s the 10% that makes Shift different?

Jon: Oh, interesting. One of the reasons I joined Shift is that we believe in validating what we’re going to build before we build it. That’s led us to some really interesting processes for testing things with users. And it also puts us in a great position, because we now have a product that people love.

“Our Car Enthusiasts spend a ton of time with people, so we get a lot of feedback, which really shapes our product.” –Jon

That immediate connection to customers is crucial because we’re having in-depth conversations all the time, which can be hard for companies with a big operational component. Like, Munchery is just dropping your food off, and most people barely talk to their Uber drivers. But our Car Enthusiasts spend a ton of time with people, so we get a lot of feedback, which really shapes our product.

Do you have an example of how customer feedback has resulted in an important change in the product?

Jon: Actually, the way the company started was influenced by user feedback. George initially thought Shift would be a financial product, to make it easier to get a loan to buy a car through an individual seller, not just a dealership. But when we started talking to people, they said, “What would be really awesome is if you just took my car and found a buyer.” So that’s been our first step.

Mikey: In terms of iterations, I can tell you about testing our internal iPad app, which is used every time a car is picked up. I stood next to one of our mechanics—this was an actual UX test—and I asked how he’d evaluate a car using the app. He said, “At this point it says to check the tire gauge, so I would check the tire gauge.” And then he looked at me a little funny because I said, “Okay, now I need you to actually check the tire gauge.” A key lesson came from that: it turns out checking tires in sequential order—instead of front first, then back—saves a ton of time in the aggregate.

Design wraps up the day with a team review and a beer (above) to help kick off the company’s happy hour (below).
Team members, like Minnie (above), often bring family and friends to office events.

What’s next for you guys? What things might someone be working on if they join the team?

Mikey: Car recommendations is a big one. We want to provide a really delightful experience for buying cars. That means creating an easy way for customers to browse our inventory and find something they want, even if they don’t know exactly what they’re looking for.

Christian: As an example, when I was trying to find the right car for my family, my initial questions were, “What’s a compact SUV that has smart key access, a power liftgate, and enough room for a baby seat?” There are actually only a few cars that have this. It’s a RAV4 Limited and a Ford Escape, where the power liftgate is an aftermarket add-on. But finding that out took me hours on the internet, even though my requirements were simple. There’s clearly a lot of opportunity for a computer to answer those questions. We want to make searching for the right car easy — that is a complicated challenge.

Mikey: Another important project is creating a system for generating accurate prices. Every car is different, every model is different, and people drive their cars differently, all of which affects value. There’s a lot of data that has to be considered for a price to be accurate.

“We’re working on algorithms that will give a more accurate price by looking at things like your specific geographic market.” –Erica

Erica: Right now, most people know Kelley Blue Book. There’s also Edmunds, NADA, and Black Book, but they all operate on a depreciation model. We’re working on algorithms that will give a more accurate price by looking at things like your specific geographic market. For instance, the demand for a car can change based on the time of year. We’ll hone in to get you the best price, right now, where you live.

Christian: Our prices are also better than those options because we will actually sell your car for that price.

Erica: On the customer side, I’m working on a pilot program for financing. We want to be able to own the entire experience. That way, we can make it a seamless process for the buyer to get prequalified for a loan with a good rate. This will alleviate a lot of pain points for people who want to get a loan to buy a used car.

After that, we’ll probably branch out into the car ownership experience. It would be interesting to work on a few things that extend beyond buying and selling — things like how you care for your car over its lifetime. There’s no shortage of possibilities in this market.

Join the team!

Interested in joining the Shift engineering team? Check out their job openings here, or contact Shift technical recruiting, builders@driveshift.com.

Laily (executive assistant) attempts to coax Minnie’s son out from under the table.

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Job Portraits

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