Why would anyone in their right mind voluntarily leave a rising star of a company that’s redefining commerce to a century-old business wildly grasping at relevance?
Ian Clarkson admits it’s a fair question.
It was a “seemingly stupid decision,” he said, to quit Amazon six years ago to take a job at Sears. But he’d been at the online juggernaut nearly 15 years, right out of completing his MBA, and was ready for something different. His new role was to lead the digital transformation of Sears Home Services, a massive organization providing in-home repairs of appliances across the U.S.
“The interesting professional opportunity was, could you take something that was at scale, and could you extricate it from a dying entity and turn it into a modern business?” Clarkson said.
It didn’t go well. Clarkson had taken for granted Amazon’s laser-focused leadership and largely smooth operations, thinking that’s just how companies are run. At Sears, the company’s top leaders encouraged internal competition, which led to conflicting goals and priorities, he said. “It was like the worst manifestation of corporate culture.”
Clarkson’s 18 months at Sears did provide an essential, positive lesson. He gained valuable insight into the challenges of managing the “human aspect” of delivering a service. At Amazon, Clarkson’s roles included creating and leading the Amazon Fresh home grocery initiative. But it’s a relatively straightforward task to manage delivery drivers compared to overseeing thousands of trained people coming into homes to repair complicated appliances.
That part of the Sears gig was a great preparation for Clarkson’s current job as president and chief operating officer for edtech company Varsity Tutors. In 2016, the St. Louis-based tutoring company launched its Seattle-based operations with Clarkson at the helm.
Varsity Tutors was initially a marketplace for in-person and then online tutoring. Over the years it expanded to include large, online test prep courses classes, DIY self-study solutions and other instruction.
Then COVID-19 hit the U.S. and schools began sending students home in March, forcing millions of kids into remote learning.
“It felt like there was need in the market,” Clarkson said. “Your choices were sort of nothing, video games or YouTube.”
To meet this new demand, Varsity Tutors quickly ramped up a wider range of instruction. Its offerings now include smaller classes to supplement regular school, complete home schooling for grades K-8, less intensive “edutainment” and so-called “star courses” that feature noted experts and luminaries. One-on-one and smaller classes require payment, but a wide variety of large courses are free.
“The goal is to get kids — or anyone — excited about learning again,” Clarkson said.
We caught up with Clarkson for this Working Geek, a regular GeekWire feature. Continue reading for his answers to our questionnaire.
Current location: Mercer Island, just east of Seattle. But since COVID, I have worked from Colorado, Utah, Michigan, Idaho, San Juan Island, my car a fair amount and even from a motor home going down Interstate-80. Prior to that, we had an office on the waterfront in Seattle on Pier 56.
Computer types: MacBook Pro. I’ve been an avid Apple user since I was a kid. I have two 27-inch monitors that flank the MacBook. I am deep into the Apple ecosystem, so consider that as full disclosure.
Mobile devices: iPhone 10 Pro Max, Apple Watch Series 6
Favorite apps, cloud services and software tools: I am pretty traditional on this front. We use Google Docs, Slides and Sheets for collaboration. Excel is still my go-to heavy analytics tool, Slack for messaging, Hangouts primarily for meetings. We are a document company so the majority of our time is spent in Google Docs. Obviously our engineering, product and design organizations use different tools like Jira, Miro, Trello, etc.
Describe your workspace. Why does it work for you? I am very lucky that I have a dedicated home office. I am doubly lucky that we have done a couple of major home remodels and my office was built with a fair amount of noise isolation. Even prior to COVID I had been working from home two days a week for the past six years, so I’ve had a fair amount of practice. I have a full office set-up, standing desk, two 27-inch monitors (on monitor arms), external keyboard mouse, etc. As importantly, I have external speakers so I can listen to some “tunage.” And lastly, the space has windows that open, so being able to get some fresh air is awesome.
Having watched some of my colleagues struggle with this, I would say you need to commit to working from home and not view it as temporary.
Your best advice for managing everyday work and life? I have been practicing this for years and Varsity Tutors has grown up as a remote company, so we have a lot of experience. And my last role at Amazon was managing about 1,000 people in eight countries, so managing from a distance is something that I have been doing for over a decade.
On the specific question, I’m dogmatic about making time for the things that are important. For me that means making sure I have time to exercise during the day, so I block my calendar and it’s not negotiable (unless a board member wants to meet). Being with my family is important, so when the kids have free time (weekends and evenings) I make a point to leave my office and put the phone down. We also have two dogs that need to go out, so that also creates another forced break.
On a more professional point, I also am very thoughtful about using my calendar to drive my day. We have built a bunch of push notifications so I never spend time looking for information. When I wake up, in about 15 minutes I can catch up on how the business performed the day before. If something went “bump” I am aware of it and it doesn’t fester. As importantly, if everything is fine I can move on with my day.
Your preferred social network? How do you use it for business/work? I am pretty anti social networks (so take that for what it is worth) and I have been prior to it being cool to be anti. The social network I use the most is LinkedIn, which I use to connect with professionals and to post updates about the company.
Current number of unanswered emails in your inbox? Not that many (at least for work). Once a month I go through and audit any subscriptions I have to make sure I remove them.
Number of appointments/meetings on your calendar this week? A lot — probably 30 hours.
How do you run meetings? Depends on the meeting, but generally there is a clear leader and it’s their job to come to the meeting prepared to have a conversation. Given my Amazon background, it shouldn’t be surprising that there is an expectation that for the vast majority of the meetings there is a document to review.
Meetings fall into general categories: 1) recurring reviews — things like sprint planning, weekly business reviews, daily stand-ups, etc. These meetings are normally relatively tactical and there is some “normal content” that we review, but these are not documents; 2) program reviews — also recurring, but the program leader leads and has clear expectation of a document facilitated conversation; 3) ad hoc — if these are led by me, normally there will either be a preceding email about what we are trying to accomplish and why I’m calling the meeting, what my expectations are, and what we hope to accomplish.
Everyday work uniform? This might be a little TMI, but if we are in the circle of trust, my mornings normally start with a t-shirt and something comfortable, but this is because I exercise at lunch time. I don’t get my work uniform on until after lunch — which is jeans and a different t-shirt.
How do you make time for family? Per above: just do it. One of the things that surviving at Amazon for 15 years teaches you (assuming you want to have work / life balance) is that you have to manage your time.
Best stress reliever? How do you unplug? EXERCISE: run, CrossFit, mountain biking, road biking, hiking, more exercise. Family time, movie night, listening to music, working in the yard.
What are you listening to? If you are asking about music, I am all over the map. My “always on” is classic rock (Fleetwood Mac, The Eagles, etc.); more modern is almost any mellow rock (Norah Jones, Tristan Prettyman, Jason Mraz; Marc Cohen, etc.); then I have a tendency to go deep into genres (trip hop, funk, classical).
If you are talking about podcasts, I am pretty narrow here: “HBR IdeaCast,” “Freakonomics,” “How I Built This,” “TED Radio Hour,” occasionally “Masters of Scale” and, more recently, “Should This Exist?”
Daily reads? Favorite sites and newsletters? Subscriptions to New York Times’ email updates, I use Pocket (which is really good at curated content), The Atlantic generally has great articles, and most evenings my wife and I will watch “Nightly News” while making dinner. As a leadership team there is a pretty good group of people who share interesting things so we have our group of content curators.
Book on your nightstand (or e-reader)? I am always reading a couple of different books, normally a recreational book and a more business book. Today I am re-reading the “Foundation Series” by Isaac Asimov, on the recreational side. As for the business book, it’s “Algorithms to Live By” by Brian Christian and Tom Griffiths. Another recent and favorite is “The Inevitable” by Kevin Kelly.
Night owl or early riser? This is a funny question. In the summer, I definitely turned into more of a morning person and started getting up around 5 a.m. As fall has moved in, unfortunately I am now having a hard time getting up at 7 a.m. I do happen to believe that sleep is incredibly important.
Where do you get your best ideas? This is a great question. My super general comment, which isn’t helpful, is from all over. I would say that the one thing that is for certain is that it isn’t in your Slack or in your email. I also think it broadly doesn’t happen when you “need it to” — when you are working on something that’s consuming most of the brain function, it isn’t going to happen then. So for me it happens when I am not thinking about work — running or riding a bike are great for this.
You have to create “dedicated think time.” Prior to COVID, I used to bike commute to work and normally on the commute I would listen to a podcast and more often than not that would generate an idea. Per comments above, having a group of people who share interesting ideas and information is helpful. Also just let yourself “wander around;” give yourself permission for an hour or two a week to explore three links into something.
Have a group of people who you trust (doesn’t have to be at work) where you can talk about and work through thoughts, even if they are super immature. I have friends and colleagues (and friends who are colleagues) who I can do this with and we’ve gotten good at building ideas.
My last comment on this — and it isn’t really about the question — is that for me, the important thing is the problem you want to solve. Ideas are relatively easy, but identifying the right problems is actually the hard part.
Whose work style would you want to learn more about or emulate? I am very lucky in that I got to work around most of the senior leaders at Amazon for years — both those who made it and those who didn’t — and have been able to learn from some of the best operators and innovators on the planet. People who I would like to have exposure to is someone like Tesla founder Elon Musk (that isn’t a work-style comment, but a thinking-process comment).
