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How Drizly Is Using Technology to Keep Their Employees Connected
Taylor Willerup: Network Administrator at Drizly
November 14, 2019
Interview by Sophia Bernazzani

Taylor Willerup is the Network Administrator at Drizly, the world's largest online marketplace for alcohol.

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Taylor Willerup is the Network Administrator at Drizly, the world's largest online marketplace for alcohol. In this interview, Taylor shares how she uses tools like the Meeting Owl Pro to keep Drizly's distributed employees connected.

Owl Labs (OL): You're a Network Administrator at Drizly. What brought you there?

Taylor Willerup (TW): I started working at Drizly in July 2017 as a Customer Experience Representative, and I switched to my current role last December. Drizly was growing and there was a need for some sort of IT department. I knew coming out of school that I wanted to be in Boston, and Drizly seemed like it was comprised of incredibly smart people and on an interesting mission. They're hardworking and I like the startup culture; Drizly has allowed me to take this new role and shape it to what it needs to be for the company.

OL: What made you take the leap from working in customer service to IT?

TW: I worked at the IT help desk in college, so I came to Drizly with that customer service experience. We didn't have a solid process in terms of how to handle IT needs internally at Drizly so I began doing tasks for one of the engineers who had taken it on. In my off-hours, I cleaned up the existing processes and made new ones. In December they decided they needed someone full-time, so I made the switch.

OL: Tell me a little bit about the team at Drizly that you're supporting in your role. How many employees are there across how many offices? How many conference rooms are you solving for?

TW: We have about 120 employees at the company, with 100 at our headquarters in Boston's Back Bay. There are 11 people in Denver and then a few folks in Los Angeles and New York. They come to the headquarters every month or so for important meetings but we do have a remote presence. I manage all the conference room equipment here in Boston. We have 13 conference rooms between the two floors and an auditorium style set-up in the kitchen for our company meetings.

Drizly was growing and there was a need for some sort of IT department. I knew coming out of school that I wanted to be in Boston, and Drizly seemed like it was comprised of incredibly smart people and on an interesting mission.

OL: What's the company culture like at Drizly?

TW: It's pretty fast-paced; we work hard but make sure we're having fun doing it. We’re provided with a bunch of opportunities to stay balanced with events like yoga, spin class, knit night, the list goes on.

There are plenty of times where we’re heads-down, trying to get stuff done, but it’s a high energy environment, especially as we take on Q4 (our busiest quarter). It's an open office and I've found that to be motivating in terms of feeling like everyone's working towards the same goal. Our sales and customer service teams are naturally a power source as they're constantly interacting with customers, but it's not uncommon for you to see some of our technical teammates bringing the energy up as well which is pretty special.

OL: I love that. I was reading about you guys in 'Built In Boston' and I saw you have an all-hands week every year so everyone can spend time together in one place. What does that entail?

TW: We held all-hands week this past August and brought everyone into Boston. We had all moved up to the fourth floor of our current building in July while we renovated the third floor, and began working between both floors on the first day of All Hands.

The week incorporated a field day, a brewery tour, and a company-wide solve-it challenge where we brainstormed some of the bigger issues that we're up against and ways to solve them. That was a cool experience because we collaborated with people we might not typically work with during our day-to-day. We presented our ideas at the end of the week and it culminated in a celebration in the new space with our friends and family!

OL: That sounds awesome. I like the inclusion of friends and family! I don't usually hear about that happening at company parties.

TW: Everyone's supportive of work-life balance, so it's nice that we can bring external people into the space and make them feel welcome too.

We held all-hands week this past August and brought everyone into Boston ... The week incorporated a field day, a brewery tour, and a company-wide solve-it challenge where we brainstormed some of the bigger issues that we're up against and ways to solve them. That was a cool experience because we collaborated with people we might not typically work with during our day-to-day.

OL: What are the biggest challenges that get in the way of keeping Drizly employees connected over those different locations and people working remotely?

TW: We have recurring daily meetings and stand-ups that are usually held in the same room for the week. My job is to make sure each room is set up with the best video conferencing that we can support. We have five Google Chromeboxes throughout the two floors which have been helpful since they're tied to our conference room calendars. You can just click into those but you need a strong network connection and a video link.

We have Apple TVs in the conference rooms that don't have the Chromeboxes, which are great for presenting your screen wirelessly; we leverage these conference rooms for a majority of internal meetings that do not need remote access. In that case, usually someone will have to present from their laptop and that can be distracting.

OL: You use the Meeting Owl at Drizly. How do you use it and what problems does it solve?

TW: We currently have the Meeting Owl in our Fishbowl room which is one of our larger meeting rooms and it’s where we hold many of our meetings with teammates or vendors who are working remotely.

It's great that you can see the 360° view versus a stationary camera that might otherwise be focused on someone who might not be talking. The autofocus functionality that follows the person speaking has been helpful.

We currently have the Meeting Owl in our Fishbowl room which is one of our larger meeting rooms and it’s where we hold many of our meetings with teammates or vendors who are working remotely. It's great that you can see the 360° view versus a stationary camera that might otherwise be focused on someone who might not be talking.

OL: Do you get good feedback from remote people and from the in-person people?

TW: I've heard the remote people have enjoyed that they can see everyone in the room. It makes them feel more connected to the meeting in general. For those in the room, some find the moving picture somewhat distracting but I can use the Meeting Owl app to focus the camera on a specific speaker if need be.

OL: That's awesome! I'd love to know what you guys were most excited about when you started beta testing the next generation Meeting Owl.

TW: It's been great! The app works well and it's nice that you can just plug the Meeting Owl into any conferencing equipment and it can be used as the speaker and camera. It seems like a pretty seamless transition and it's nice to have all of those elements in one unit.

OL: That's great to hear. Do you or other Drizly employees ever work remotely?

TW: Yeah, we have a pretty flexible work-from-home policy as long as you’re able to get your work done. I've been able to work remotely, but it's a lot easier as our only IT person to troubleshoot any issues that come up in-person instead of via Slack. It's also motivating to hear other people working around me rather than just sitting by myself.

OL: What do you love most about working at Drizly?

TW: The people. It's a smart group that genuinely cares about each other’s personal and professional growth. I feel like I could go to anyone and get help or advice, it's a great environment to be in.

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