Friends in tech: Jon Penland

Chief Operating Officer

Jon Penland





Time in this Industry

5-7 Years

Origin Story

Early in my career, I went to work for a company that manufactured custom-engineered mechanical equipment. While I enjoyed the role and learned quite a bit, the industry was well-established and slow-moving, and I worried that opportunities for advancement would be few and far between as a result. At the same time, I also knew that I wanted to work remotely, and while this has probably changed over the last 10 years, I didn’t see many (or any) opportunities for remote work within that industry. 

So with the goal of equipping myself to work remotely for a modern technology company, round about 2008 I began learning HTML, CSS, JavaScript, PHP, WordPress, and the basics of website design and development. It took several years and quite a few false starts, but my studies eventually lead me to my very first foray into internet space when I began doing some freelance writing on a part-time basis. Eventually, freelancing on the side grew into full-time freelance writing; something I did for about three years. As a freelance writer I specialized in web hosting and WordPress and over time really developed a high degree of expertise in both areas. 

This is where Kinsta entered the picture. While I enjoyed freelancing, I knew from the start that it was a means to an end. It had always been my goal to join an up-and-coming company where I could be part of the company’s growth story. Kinsta first approached me to work as a freelance writer in early 2016. As a hosting and WordPress writer, I already knew about Kinsta and was excited about the opportunity to move one step closer to the company. Finally, in late 2016 the stars aligned and I was able to hang up my freelancer hat and join Kinsta as a Support Engineer.

I’ve now been with Kinsta for about four and a half years and during my time at Kinsta I’ve been involved with Sales, Support (and every other customer-facing team), Finance and Accounting, Legal, HR, and Operations. Working for Kinsta has been the culmination of many years of hard work that started over a decade ago when I first learned my first few lines of HTML.

A Typical Day

In terms of scheduling, my typical workday begins at 6 AM when I get up and walk my dogs and then either go running or spend some time on my stationary exercise bike. By 7:30, I’m showered, sipping coffee, diving into Slack and email, and setting up my priorities for the day. I try to take a full hour for lunch sometime between 11:30 and 2 PM. During my lunch hour, I spend 20-30 minutes doing a quick light bodyweight workout and then spend the rest of the hour eating lunch and letting my brain rest up. I usually finish up my formal workday at around 4:15 when my “Dad duties” begin and I start shuttling kids to activities they’re participating in COVID-permitting (swim, baseball, softball, etc). Finally, I usually have one last informal check-in sometime in the evening where I spend a half-hour to an hour checking in on Slack, clearing my inbox, and planning my priorities for the next day.

In terms of what I actually do each day, most days I’ll have anywhere from two to five meetings and in general, I spend at least half of my time getting ready for, participating in, and following up on action steps based on these meetings. I have a few other routine things I do every week or month: a weekly short video shared internally highlighting the most important company-wide info from the past week, monthly update blog posts and OKR (goal) updates, a monthly all-hands video call we call the “Kinsta AMA”. Aside from that, I make time to focus on any projects I’m involved in and do my best to stay a step or two ahead of the needs of the company and my departments (Operations, Legal, & HR).

Current Workspace

Back in early 2020 we bought a house and for the first time ever I gained a dedicated office. I love it! I work nearly exclusively from a standing desk in my office, though I do have a couch which I use for an hour or two a couple of times a week. When the weather is nice and I don’t have any meeting on the agenda I also like to start my day from the back porch.

My work computer is a 2020 13″ Macbook Pro with an M1 processor and 16 GB of RAM. It’s a fantastic machine and if you’re on the fence about the M1, get off the fence and go buy it. When I work from my standing desk I connect to a 27″ monitor, Sony a6000 camera (set up as a webcam), Yeti Blue mic, Apple magic keyboard (with the number pad), and Apple magic trackpad. When I work from the couch or back porch I just prop the laptop on my knees and that’s that.

Daily Software

These days my role is not technical so my software needs are really minimal. I’m focused on HR and Operations and my primary task is communication in all its various forms. So these days the primary apps I use are Google Chrome, Slack, Sublime (for note-taking), and various browser-based software (Google Workspace, Confluence, Jira, Blissfully, etc.). When I create short simple videos I use QuickTime and iMovie. 

However, I can’t pass up this opportunity to harp on the importance of using a password manager. I’ve been using a password manager for many years now and as a company, we insist that all of our team members use 1Password for all work-related accounts. We’ve gone so far as to put in writing in our handbook that the only password you should know is the password for your password manager. Let your password manager do its job by generating and storing strong passwords. I really do believe that is a best practice everyone should adopt.