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Making a 700-Mile Commute Work

His home is in Chicago, his office in New York. Offerpop’s marketing head, Kevin Bobowski, talks about how he makes the most of his time in -- and out -- of the office.
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When Kevin Bobowski was recruited a year ago, Bobowski wasn’t in the market for a new job. Still, he was intrigued with the opportunity to head up the marketing and sales development efforts for fast-growing firm Offerpop, a leading software-as-a-service platform for companies looking to create and manage mobile and social digital marketing campaigns.

His only hesitation: “I had no plans of leaving Chicago immediately and moving to New York,” says Bobowski, 44, who at the time was overseeing product and solution marketing for ExactTarget, which was acquired by last year. (Offerpop is based in New York and has offices in San Francisco and London.)

Offerpop chief executive officer and founder Wendell Lansford offered a compromise. If Bobowski was willing to make the more than 700-mile commute, he could split his time between Chicago and New York until a permanent move made sense.

A year later, Bobowski has logged tens of thousands of frequent flier miles and learned how to structure his week so he can get the most out of his time, both in and out of the office.

Entrepreneur spoke with Bobowski about how he stays connected, and sane.

Entrepreneur: What’s your typical schedule?
I usually work from my home office on Monday, travel to New York Tuesday morning and work there for three days. Then I fly back to Chicago on Thursday night and work from home Friday. Consistency is really key. If your schedule is erratic it makes it so much more difficult for everyone else in the office to schedule meetings and plan their weeks.

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Entrepreneur: Traveling every week is, no doubt, a grind. Have your tried going less frequently and staying longer?
With most companies, particularly tech startups, the pace and momentum changes quickly. If I do four days every other week I find myself behind and disconnected. But if I’m in the office two or three days every week I can stay on top of what’s happening with a product launch or new initiative. Equally important, I can keep a good pulse on the culture and stay connected with my team.

Entrepreneur: How do plan your workweek around the dual locations?
When I’m in New York it’s all about collaboration and teamwork. Monday and Friday I typically carve out for strategic projects. When you start and end the week in a home office you have time to get out of the day-to-day minutia of the business and think more about the big picture. The counter is you don’t want to be away too long because there is incredible value in water cooler discussions. When I’m in the office, I allocate time to walk the halls and just talk to people.

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Entrepreneur: Did you figure this out on your own or by taking note of other managers?
A little bit of both. When I was at ExactTarget I reported to the CMO and the COO, both were very busy, and at one point they didn’t live in Indianapolis [where the company was headquartered]. Meanwhile, I lived in Chicago and commuted to the office for all but one of the five years I was with the company. The COO did something I found really compelling. I didn’t talk to him much in the week at all, but we had a standing one-on-one meeting for 30 minutes every Friday, and he was consistent. Having those 30 minutes with him was great because I could prepare all the things I wanted to talk about for the week and know I had his undivided attention. That was invaluable.

Entrepreneur: Has that become part of your routine?
: It has. I try to have weekly, one-on-one meetings with everyone who reports directly to me. When we meet, I avoid “dele-dumping” meetings where I walk in and say ‘Here are the 32 things I need you to do this week.’ Instead, I try to step back and see where they are with their projects, and do what I can on my end to identify any obstacles and make sure they can move forward.

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Entrepreneur: Does this dynamic affect your hiring decisions?
I’ve always looked to hire people who will thrive regardless of whether the boss is in the office, who know their goals and objectives, and feel empowered to make good decisions based on that. I’ve found that these kinds of employees actually like this environment because there’s less micromanagement.

Entrepreneur: What are your favorite tools for staying in touch when you’re out of the office?
It’s all the basics. Chat is extremely effective because it’s quick and immediate. Some of the free online screen-sharing tools, like, are pretty invaluable. Whenever you’re talking on the phone and looking at a spreadsheet, it’s so much easier to share the same screen than try to explain where you’re at. For one-on-one meetings, or when there are two or three of us in a remote meeting, I like to use video. It’s easier to read non-verbal cues, and a great way to stay aligned and coordinated. But it's still a small enough of a group where video is effective. Video is very difficult when one person is remote and there are more than four people in the room. Those conversations tend to move quickly, and the value of video is diminished.

Entrepreneur: Will you continue making this commute indefinitely?
It’s worked really well, but the travel does take a toll. We’ve put our house on the market and, once it sells, my family and I will move. I think I’ll still plan to work from home every week or two. Like I said, there’s a lot of value in regularly stepping back from the business and working on it instead of in it.