Alexie Harper & Ori Ratner - Smartly

As flexible work arrangements become more common place and more people begin to telecommute, many companies with traditional offices will need to figure out how to communicate with team members in multiple locations. Companies have long dealt with the issues of multiple office locations, but having numerous employees and contractors working from home, in different timezones, and with different schedules presents a new set of challenges.

Smartly (part of Pedago) has had to figure out both -- connecting two nearby office locations along with several remote employees and contractors spread out across the country. Below is an interview with two of Smartly's cofounders -- Alexie Harper and Ori Ratner -- on how they're managing to make it all work.

What does Smartly do and what's your role there?

Harper: Smartly is a new educational technology company that's out to change how we all learn. We help companies and individuals succeed by making learning dramatically faster and more effective, with highly interactive lessons conceived for the smartphone era.

We offer a highly selective MBA degree with courses in Finance, Marketing, Management, and Entrepreneurship that is completely free for admitted students. We partner with great companies that recruit Smartly students looking for new career opportunities. These companies pay us for the privilege, which helps keep the MBA free to every accepted student.

Ratner: As CTO, my team and I are responsible for constructing and maintaining the Smartly web and mobile apps, including our internal content authoring platform.

Harper: As the CPO of Pedago, I collaborate with Ori on designing the product experience and lead the content creation team in developing Smartly content.

How many people are at the company now and how spread out are you?

Harper: We have 21 employees spread across seven states. Our main office is in Washington, D.C., but we have a small office in Harrisonburg, VA as well. Six of our employees work remotely from Los Angeles, San Francisco, Boulder, College Station, New York City, and Indiana. We also have employed contractors spread out around the world for various projects.

Why did you decide to start hiring outside of the company's home area?

Harper: As soon as we expanded beyond the founding stage, we set up our two offices in DC and Harrisonburg, VA. We had previously worked at a company with offices in both locations (Rosetta Stone). Even though we were based in the DC area, we knew a great group of people in the Harrisonburg area that we were eager to work with. Because we set up our company structure to work with multiple locations, it wasn’t a stretch to hire contractors around the country to work with us in the early days, and many of those contractors went on to become full-time employees.

You have both an office and a group of people working around the country. There are some remote work advocates who believe that it's an either/or proposition -- you can't have both an office and a remote team or you end up with divergent rules and cultures. How have you kept everyone in sync?

Ratner: A few things have worked out in our favor. First, we actually started out not with one office, but two. So instead of a “home base” and “remote worker” dynamic, it was more like two satellite offices. Second, the founding team knew each other, so there was trust and shared culture despite the distance. Finally, from the very beginning we were very deliberate about setting up tools to support remote work and encouraged their use. In practice, this means favoring chat rooms and video hangouts for meetings, pair programming, etc.

What are the biggest challenges you face with remote work and how do you overcome them?

Ratner: At the basic human level, we want to keep the team feeling connected to one another. We have a lively chat room culture, like many tech companies, but we also have found that other modalities, including video chat and screensharing, are equally important.

There’s still no replacement for getting together and brainstorming in the same physical space.

From a management perspective, it’s important to be able to track time and deliverables from employees in disparate time zones and with differing work schedules. Tools like Toggl can be very helpful in this regard.

On the flip side, what are some of the benefits that you've noticed from having part of your team work remotely?

Harper: Retention is much easier when you support remote work. Since founding the company, several employees have had kids, moved across the country, and even lived abroad for a period of time. In all of these cases, having the mechanisms in place to support productive work outside of the office has allowed us to retain good people. And of course, hiring is easier when you don’t need to restrict your search to local or open-to-relocation applicants.

Do you think anything is lost when working remotely? Is there ever a time you wish everyone was just in the office with you?

Ratner: Despite all of the technology available today, there’s still no replacement for getting together and brainstorming in the same physical space.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Harper: In our case, we found it was making time for face-to-face conversations over video chat. There’s an empathy gap that can develop if you don’t take the time to have a conversation and look each other in the eye.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

Harper: Operationally, tools like Toggl and Trello help us track time on task and project progress. Our daily standup meeting over video chat is helpful to collect thoughts and concerns from the team. The most effective strategy is also the most obvious: communicate with one another regularly, building in enough schedule flexibility for ad-hoc conversations.

What sort of culture does your company have? Is it harder to build cohesive culture with some team members living on opposite coasts?

Ratner: The most important ingredient in a company’s culture is who you hire. We’ve had good luck hiring people that are self-starters who appreciate both the increased freedom and responsibility that remote work entails. Unsurprisingly, people like this enjoy working with other driven, self-motivated people, remote or otherwise. The rest is details.

Have you done anything fun in the past to bring remote and office team members together? Like what?

Harper: We’ve had a few all-company events to bridge the gap between remote employees. Holiday and launch parties have been opportunities to bring everyone together, including family. Before we expanded to additional locations, we would often have sprint planning at a 4H summer camp (!) that was located roughly halfway between our two initial offices.

You also work with a number of contract writers who are spread out around the country. How do you fit them into the mix? Is it easier to deal with contractors because you already have the remote framework in place or does it make it more difficult to separate full-time and contract employees since you don't have the natural barrier of physical location?

Harper: We work with a variety of contractors in different capacities, but typically they are looking for more schedule flexibility than our full time employees.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

Harper: We look for people who are self-motivated and passionate about what they do.

How do you keep distractions to a minimum? How do you measure efficiency?

Harper: On the content team, we set ambitious but fair goals for ourselves. We create target dates for each lesson based on past performance and use tools like Trello, Toggl, and Microsoft Project to keep on track.

Ratner: On the dev side, agile processes like Scrum give us a set of metrics to track progress within the Sprint and the mid-range plan. The daily standup meeting allows us to observe and readjust if things get a little off-track.

What are some of the tools you couldn't live without as a remote company?

Ratner: HipChat, Trello, Toggl, Google Hangouts, Screenhero, Drive, Dropbox, Git, and Google Docs.

What do you like to read?

Harper: A few of our favorite authors, books, blog, and articles:

What advice would you give to a company heading down the remote working path?

Ratner: Minimize email. It’s the lazy way out, and in our experience leads to fatigue in a way that chatrooms, video chat, task boards, and wikis don’t. Think hard about what type of information belongs in each tool, and establish expectations up front. Make a conscious effort to model the behavior your want to see in your employees, from documenting decisions on a wiki to simply announcing when you’re stepping away from your keyboard in chat.

Harper: When you’re remote, even the small gestures can make you feel more connected to your coworkers.

Josh Catone
Josh has been the Content & Community Manager at feedly, the Executive Director of Editorial Projects at Mashable, the Lead Writer at ReadWrite, and the Lead Blogger at SitePoint.