Summary List Placement
I’ve experienced the good and the bad of large companies and transformations, and found my happy place working in SaaS and modern technology.
My first C-suite role was as CIO with L Brands.
I then moved to the Gap, where I learned to lead, put the right senior people in the right place, and clear the way for them to do their job.
After the Gap, I took what I thought was my greatest career risk but turned out to be the biggest transformation when I joined the C-suite at Zendesk. I learned that at a smaller company, I could have a more meaningful impact, and within my tenure helped drive 30% to 40% revenue growth every quarter and grew the organization from about 1,000 employees in 10 offices to close to 4,000 employees in 18 offices.
I joined Hootsuite in July 2020. Complexity has been amplified by COVID-19 — I’ve never actually met the people who recruited me or that I work with.
I’ve always been more of an observer on social media rather than a participant.
Hootsuite is a social-first company, so I’ve had to step out of my comfort zone to get comfortable with actively posting and participating in conversations that are important to our company and to me.
I’m primarily focused on business-related topics on LinkedIn and Twitter and more personal topics on Facebook and Instagram. As my kids point out, I have a long way to go to becoming a social influencer.
Our dog Ringo likes breakfast at 5:15 a.m., so that starts my day.
I read a lot first thing in the morning. I live in San Francisco, so there’s a lot of East Coast content out when I get up.
I usually consume newsletters like Stratechery, DealBook, The Auburn Observer, Platformer, Money Stuff, and The Information and podcasts like “Pivot,” “Sway,” “The Daily,” “SmartLess,” “Pomp,” and “The Prof G Show.” I scan Twitter and LinkedIn, as well as the San Francisco Chronicle, New York Times, and Wall Street Journal. I then watch the opening of the markets.
My brain works best in the morning. I draw and write things in my notebook — business models, org models, partner models. It’s all just scribble, but it helps me think. There’s something about the tactile nature of putting pen to paper that can’t be duplicated electronically. I’ve become much better at iteration — starting things, roughing them out, and then revisiting over several days and weeks until they come together.
At 6:30 a.m., I start my workout.
I absolutely love my Peloton. I was riding my bike before, but now I’m doing two to three workouts a day.
I’ve gotten into weight lifting and yoga as well. I ride a lot with Jess King, who’s a senior Peloton cycling instructor and a certified life coach. Andy Speer is a Peloton instructor I prefer to lift weights with. I really like his commitment to teaching good form and technique.
I’ve also expanded from only early-morning workouts to sliding them in whenever I have 30- to 45-minute gaps in my calendar. No one can really see you sweating on video anyway.
My workday usually starts at 8 a.m.
I spend most of my time on video calls, attending one-on-one meetings with direct reports, updates with teams, Q&As with our different global offices, customer meetings, and meetings with investors.
I believe strongly in a weekly cadence and rhythm to business, so consistently touching base with every part of the business is important.
I try to take 30 minutes for lunch, although it never seems to be at the same time every day.
I have a standing desk that I spend about half the day at — the other half is at our dining room table, depending on the happiness of my knees that day.
Every once in a while I notice I haven’t been outside for a day or two and drop everything to go for a walk or run.
I rely on notes and lists.
I’ve been using the same engineering notebook for 25 years (Laboratory Notebook Company WE-100-152 made in Holyoke, MA) and I won’t diverge from it.
In fact, my executive assistant has to call to order them for me. They’re not even available online, but it’s really the only notebook I’ll use.
I’m an active listener and note taker, which I then use each evening to sum up the actions that I need to take. It’s reassuring to have a system of review and follow-up, even if it seems very old school working in tech. People have always made fun of me for it, but it works for me.
I typically end my workday at around 5 p.m.
Where my wife and I used to go out to eat quite often, we now cook dinner together, and it’s become a unique time that we’re thankful for.
I’m a huge sports fan and a season ticket holder of the Golden State Warriors, so that was often what I would be doing in the evening. Since the onset of the pandemic, I’ve had to get that fix in other ways, so I usually keep up with them via social media.
We’re fortunate that our kids are mostly grown, independent adults. Two are off at university attending classes via video and living in off-campus apartments (we all tried to live in the same house at the beginning of the pandemic, which proved to have its challenges). One is finishing up high school via video schooling, which, to be honest, is really hard on teens.
Our WiFi bandwidth quickly proved to be an issue. I’ve had to install a mesh router in our home to make sure it doesn’t drop in the middle of important calls.
I’ve met only a handful of people from Hootsuite in person and forged most of the relationships I have with our team over video.
I’ve always traveled a lot for business — movement, change, and social and human interaction give me energy.
Initially, I felt completely disoriented and anxious by only being on video (by initially, I mean about four months), but I’ve found a way to both accept and embrace this new reality.
One thing I recommend to my teams is that we embrace the fact that we’re in each others’ homes and not be afraid to have more personal conversations about how we’re feeling about this new working situation, the interruptions that might take place because of it, and our levels of comfortability.
I’ve also always dreamed of working in shorts. It’s now been almost a year since it’s become reality!