The Business of Getting to Work | Matt Caywood at Transitscreen

In part one of my conversation with Matt Caywood, the founder and CEO of Transitscreen, he told us about his efforts to help organizations manage the complex transportation needs of their employees.

In this second part of our conversation, Matt goes into more detail about some of the unique strategies he employed to land his first customers, and he also shares some interesting hiring philosophies that involves ascertaining where a potential employee can go, not just where they’ve been.

More information:

Matt Caywood is CEO and co-founder of Washington, DC-based TransitScreen. Matt has a PhD in neuroscience from the University of California San Francisco, and degrees in neuroscience and computer science from Cambridge and Harvard.

Matt is a frequent speaker on transportation, data, neuroscience, and entrepreneurship, including at Harvard, MIT, Northwestern University, the World Bank, Dubai RTA, Consumer Electronics Show (CES), and Transportation Research Board (TRB). Matt has pitched world leaders like President Barack Obama and Australian Prime Minister Malcolm Turnbull.


DISCLAIMER: Below is an AI generated transcript. There could be a few typos but it should be at least 90% accurate. Watch video or listen to the podcast for the full experience!

Matt Caywood 0:00
The biggest challenge for us as a growing technology company was always, you know, being able to focus on the needs of the customer segment that was going to be the early adopter of our product. Right. And, and not just on, you know, the, you know, sort of higher profile, you know, smart cities.

Alexander Ferguson 0:30
In part one of my conversation with Matt Caywood, the founder and CEO of Transitscreen, he told us about his efforts to help organizations manage the complex transportation needs of their employees. In the second part of our conversation, Matt goes into more detail about some of the unique strategies he’s employed to land his first customers. And he also shares some interesting hiring philosophies that involves ascertaining where a potential employee can go, not just where they’ve been.

Matt, I’m excited to continue our conversation now to understand for you this seven years to grow your own startup and continue to scale it with its I’m sure your your, your own choice of hurdles to overcome. Can you share any insight? What is it like to take, okay, you have the technology and as a one who understands eminently that the technology itself as an engineer, now being able to market it and grow the company, if there was one insight that you could share with another technology leader, another entrepreneur, what would you share?

Matt Caywood 1:36
I think the biggest challenge for us as a growing technology company, was always, you know, being able to focus on the needs of the customer segment that was going to be the early adopter of our product. Right. And, and not just on, you know, the, you know, sort of higher profile, you know, smart cities, you know, very exciting area, a lot of potential long term projects that are maybe not going to deliver in any reasonable timeframe or at all right. So, when we, you know, had to kind of look at opportunities early on, we were looking at everything right as, as you do when you’re trying to go to market. And I think that the challenge for us was always, you know, saying, you know, this is what we’re going to be we’re going to be a company that helps businesses with their transportation challenges, and we’re not going to be, you know, working in the, you know, transit agency space as much as we’re not gonna be doing, you know, Smart City, Dubai projects, right, we’re going to be, you know, really focused on what we do. And and that’s, that’s a, it’s a challenge, it’s hard to let go of these things, right. You know, when when you think, Oh, that wouldn’t be so cool. If you know, and that’s, that’s, that’s always the challenge. But if you’re going to be successful, you have to have to really have a strong focus, you know, you can’t be b2b and b2c at the same time just doesn’t work.

Alexander Ferguson 3:02
Having that focus allows you to then probably put all of all your efforts in one place to make sure you can achieve the success. I imagine, as you continued on that journey, you’re you honed the messaging and the product itself. If you could share one tactic that you found has worked well, when you’ve kind of started to make that first couple initial clients who said, Oh, yeah, I’ll try this out, I’ll do it. What what did you find that had worked to say, to get them on board, and then to start to grow that customer base,

Matt Caywood 3:34
to actually go in with partners in government, because we came from a government program. And I think we’ve benefited a little bit from this kind of regulatory environment, governments were very interested in helping their you know, real estate developers with solutions that would, you know, align them with, with the transportation outcomes, they were hoping for, meaning, you know, fewer single occupancy vehicles for your cars, etc. So, we would often kind of go in and approach with some of these governments with their, their, you know, some of their regulatory requirements for new development buildings. And, and, you know, that would be our introduction to a customer would be, you know, we’re solving your, your government problem. But from there, you know, it became something that was very, you know, appealing to people because once they saw a transit screen live, they would, it would really resonate with them, and they’d say, you know, why don’t we have this in, in all of our urban you know, properties instead of just this one, you know,

Alexander Ferguson 4:34
so using the marking tactic of regulations, so they already have to follow these anyways. So, you come in, you’re like, Oh, you’re solving a problem regulation problem. Oh, actually, I like the product itself. That’s it. That’s a fascinating tactic. That makes sense.

Matt Caywood 4:49
Yeah, it’s sometimes called or it’s been called regulatory hacking. And and it’s, it’s an interesting, interesting methodology. I don’t know you know, that it applies to every single company, but for those that than it does, it can be very powerful.

Alexander Ferguson 5:02
For over the years now to grow, you as a, as a business leader, your team has grown what what does your team look like right now? And how have you developed that?

Matt Caywood 5:13
Yeah, so we have a team about 30 to 35, based in Washington DC, you know, under under normal circumstances, we’d be all in the same office with only a couple remote people. And, you know, everyone would be either taking metro or biking or walking, or, you know, scootering to work, no one drove, and, you know, so it talks about, you know, using your own product, talking about both both in terms of transportation in terms of the information, we really, really do that. So, you know, it’s, that’s been a kind of key value for ours of ours for many years. You know, we also have a very, we’ve got a diverse team, Washington DC is a great market for that, as well as, you know, one that, you know, is well divided up between, you know, engineering and sales and marketing and, and customer support, you know, it’s not really dominated by, by one group or another, it’s really more more kind of even distribution of skill sets across the organization,

Alexander Ferguson 6:15
any insights you can share of what you’ve learned in growing a team, that you’re like, Wow, I’m, I’m glad I know, this, now. You can share,

Matt Caywood 6:28
I think, you know, when you’re growing a team, you know, to that size, you know, you really have to focus on and, you know, I think and maybe this will be obvious in retrospect, but you have to focus on, on bringing in people who have the skills already, to get you to the next level, right. And so, it’s always helpful to, you know, look at people with backgrounds, companies, you know, one step above, or maybe two steps above, but not like 15 steps above, you know, like, like, you know, basically, you’re trying to hire for this, you know, the skill set that’s going to serve you well over the next, you know, 24 to 36 months. And, you know, if those people can, can can grow with you, then that’s even better. Right. And, and, you know, many of the people that we’ve we’ve hired have been, you know, coming from previously successful startups or other other enterprises in the DC area, and, you know, but but they’ve also been people who are, you know, capable of a lot of personal growth and professional growth. And, and I think that’s, that’s the pattern, you know, when when we make good hiring decisions,

Alexander Ferguson 7:35
what kind of difficulties do you see, you’ll need to overcome to be able to grow in this new environment, but also you as a leader in the way your organization is, and taking to the next level?

Matt Caywood 7:47
Yeah, so, you know, being remote, you know, at least temporarily has been, you know, challenged for I think, everyone and certain parts of organization, like our, you know, engineering staff were already very much set up for being remote. So that that’s an easier for, for that part of the team. But, you know, in sales, you know, harder to do remote, right, as we all know that. And so, you know, the biggest challenge really, you know, for the next next couple months, is just just making sure that, that our organization is continuing to, to operate at at a high level, you know, in a time when, you know, everyone’s, including our customers are dealing with a lot of challenges, right, so, so we’re, we’re very much, you know, in this in this mode, where we’re trying to get through it, and then we’ve got, you know, as I mentioned, a couple of very exciting new products that are, you know, larger kind of enterprise products that we’re working on. And that are going to be, you know, very impactful for us, as a company, really take us more into the relevant price type company, over the next, you know, six months to a year. And, you know, we want to be as, as successful with that transition, as we have with, you know, the growth of our, you know, software as a service product. You know, I I continue to think that, that the people who are best placed to solve, you know, transportation challenges are often, you know, not necessarily the, you know, the people you think of, you know, not necessarily the UPS or Uber or, you know, transit agencies, the operators, it’s often the people who are actually, you know, changing the incentives that affect people’s behavior, right. You know, it’s just like with the transformation of the workplace with, you know, you know, hot desking and offices and flex work, like it’s the same thing, but for transportation, and this is something that that I think is a is a pervasive trend that’s going to be affecting us, you know, remote work, distributed work as part of it. But even within an office environment, it’s also everything is getting more flexible, and that’s, that’s really the power of, you know, automation and information technology right, applied to this area and the sector of the economy. That was previously not highly Automated?

Alexander Ferguson 10:01
What do you see as overall technology innovations? As you pay attention to different trends and things? What do you see as tech innovations that you predict we’ll see in the near term next year to end long term? 10 years?

Matt Caywood 10:14
Yeah, so in the, in the, in the short term, or the next couple of years, I’m, I’m very bullish on on E bikes, I think, you know, has the potential to really transform a lot of cities, you’re starting to see us in Europe, right, like a lot of cities are a lot of people in countries like Germany, you know, not just the Netherlands, not just Amsterdam, but like, you know, Germany, Paris, like, you know, other places, people are actually buying more bikes than they are buying regular pedal bikes, right. And so, you know, suddenly, that really expands the footprint of places that you can, you can commute, you know, and using using a bike, primarily, I’m mainly a bike commuter, I do that probably 75% of the time. And so, you know, if we can kind of, you know, catalyze that, you know, reshape our cities a little bit, you know, we talked to a lot of employers are actually giving bikes to their employees, because they’re not sure you know, what’s going to happen in a few months, you know, with transit. So, so everyone gets an E bike right? Now, you got to figure out how to park those. So there’s a lot of potential to, to change, you know, pretty significant fraction, obviously, not going to work for every city, and, you know, every every, you know, suburb or ex urban office site, but but a lot of urban sites, I think could be really impacted by this, you know, in the in the slightly longer term, you know, I think, you look at some of the changes that you’re going to see from autonomous low speed shuttles. So, you know, maybe not that, you know, high speed personal, you know, vehicle that that’s been on the horizon for a very long time now, but like, you know, just a shuttle that moves people around an office park or a large, you know, facility that’s autonomous like that, that that kind of technologies is, is getting very close. And it’s, it’s something that needs to be integrated into the rest of the transportation framework, right. So so as as as providers of information, we can help with that integration process. And so that’s another thing I’m pretty excited about.

Alexander Ferguson 12:09
That concludes the audio version of this episode. To see the original and more visit our UpTech Report, YouTube channel. If you know a tech company, we should interview, you can nominate them at Or if you just prefer to listen, make sure you’re subscribed to this series on Apple podcasts, Spotify or your favorite podcasting app.



YouTube | LinkedIn | Twitter| Podcast

Decrypting the Commute | Matt Caywood at Transitscreen

Collaborating in VR | Gabe Paez at The Wild