Practical Matters is a series of conversations with founders and senior executives at companies we know and love. Every month, we'll interview fellow entrepreneurs and their teams and ask them about their experience starting and running their respective companies. The idea is to ask them things we want to know and could learn from. We recently spoke with Stella Garber, the head of marketing at Trello.
This week, we’re talking to Gillian Morris, CEO of the mobile app Hitlist, which has received favorable mentions on tech sites like The Next Web, and garnered the attention of the New York Times. Ms. Morris sat down recently to talk about running Hitlist, her dispersed work force, and life as a female CEO.How did Hitlist come about?
I didn't know what I wanted to do other than travel, so I got the first job I could that would take me abroad: teaching English at a summer camp in China. The government promptly shut down the camp because of fears over swine flu. Fortunately, they still paid my full salary, so I took what I'd made and traveled overland through China, Mongolia, Siberia, the Ukraine, and Turkey. I arrived in Istanbul right around the time I was concurrently running low on funds and getting sick of living out of a backpack. I ended up working for CNN.
That covers the travel. How did the tech side of things come about?
After a few months I got an offer to join a business intelligence company as the assistant to the Middle East editor. I ended up being promoted to analyst within a few months and began doing fieldwork in countries like Kuwait and Syria. I built up a network quickly and left the company to be a freelance business analyst in the region. My favorite clients were the airlines and transport companies, and I developed a bit of expertise in the technological systems that drive the industry.
And from there came Hitlist?
I started keeping a spreadsheet of startups in the travel industry two years before I started Hitlist. I recorded the ideas, the funding, who was running them, what was working and what didn't. I wouldn't say I knew exactly what Hitlist was going to be when we started building, but I knew I needed to stop looking at spreadsheets and figure out whether I could do everything else. So I started to learn how to code and recruited a good friend to help me build a prototype, and the rest goes from there.Was there an early indicator that Hitlist was going to be a success?
In November 2013, just three months after we first had the idea. The reception was actually fantastic. The Next Web wrote this article about us, and it ended up getting picked up by Lifehacker, and some blog in Greece that resulted in nearly 10k downloads, proving that at least some Greeks are budget conscious. Then we got this awesome coverage in the New York Times, which looks great in a slide deck and made my parents very happy but wasn’t nearly as useful as The Next Web/Lifehacker coverage. We saw about 500 new users when that article came out and close to 10,000 between The Next Web and Lifehacker.
You’re based in New York, but Hitlist is a true global startup. Tell us about this.
We're a partially distributed team - there are five people working out of New York; two in Zagreb, Croatia; one in Brussels; one in San Francisco; one in Amsterdam; one in Belgrade, Serbia; and two in Madrid.
Hitlist’s global workforce does seem appropriate: people running a travel app should travel, right?
That’s a huge part of it—maybe the defining reason we started Hitlist. I love to travel and I think it's something most people don't do enough. A lot of our drive comes from a desire to get everyone to travel more. A world where people travel will be a more stable, understanding, richer, happier place.
As CEO of Hitlist, what do you think are the benefits of spreading everyone out?
When you're distributed, you have to write things down, whether in chat (we use Slack), or in task managers (we use Asana for marketing/business and Phabricator for engineering), or simply in shared Google Docs. This makes it easier to track progress and know who is responsible for what. All this being said, we do try and get together as a team around once a quarter. When you're doing more high level strategic planning or creative thinking, being in the same place really does help.
Critics of the dispersed workforce model say that management is too hard when people are spread out. Your response?
I don't think it's necessary to be in the same office every day. It's true that it's hard to build a company culture when you don't live in the same place, but there are also downsides to continually being side-by-side. You can be distracting to each other, and it's easier to lose the forest for the trees. Everything about a startup is hard. I don't think there's a right or wrong way to do anything. You'll find successful companies (and plenty of unsuccessful companies) with all types of makeup.
How is it being a female CEO in a male-dominated industry?
I worked for three years in the Middle East and never felt like my gender was an issue. There was definitely some reverse culture shock coming to the US. For the first time, I felt like my gender was being taken into consideration when people were deciding how competent I was. I've only experienced outright discrimination a few times, but whenever something (an investment, negotiation) doesn't work out I always wonder: would that situation have played out differently if I were a male? But there are a lot of opportunities for female founders these days. Because we're still so rare, there's a higher probability that we'll be asked to speak on a panel or attend a conference, since there's a lot of attention being paid to addressing imbalances at those types of events.
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