Topher Wheeler: IT Manager, Classpass

Topher Wheeler: IT Manager, Classpass

A deep dive with Topher, IT Manager at Classpass,

What do you ACTUALLY do?
Running a pretty lean team, I definitely wear a lot of hats but the end goal is simplifying tech so it’s a best, a positive modifier for end users work experience and a worst, something that invisibly just works without any thought.

What types of devices do you support?
We have about 500 Apple devices and 5 Windows machines for end users. We just completed a roll out of Google Meet hardware in the majority of our conference rooms and Crestron automation for our large team areas, so we have standardized as much as we can for now.

What’s your favorite piece of tech?
My Pixel 2XL. It can handle about 80% of my day to day, while macOS is a burden to bear – I don’t miss my iOS days at all.

What tools or apps are most important to your job?

  • JAMF – This was deployed in January and has been game changing in the ability to scale in terms of end users as well as geographic regions. No more monthly patching of new images to spread far and wide!
  • BetterCloud – GSuite is so great at being platform agnostic, which is very important, but it’s management tools are far from ideal. BetterCloud’s workflows in particular save a ton of time by automating the mundane tasks of on/off boarding new users.
  • JumpCloud – While not the most robust turnkey SSO solution out there, this cloud directory has been very handy in consolidating RADIUS, SSO and SSH Key stores all in one in place and providing a simplified process for access to the bulk of our mass deployed SaaS.

Do you prefer hands-on, or troubleshooting from afar?
Hands on for sure – it’s more efficient and connecting with people is what keeps my tech centric brain balanced. However, as a rapidly expanding global company, remote support is critical. JAMF’s remote support and screen sharing on Slack Calls has made it really easy to get end users comfortable with always on support.

Favorite thing about your IT environment?
Not being entrenched with any one service. We have the ability to evaluate any number of solutions and deploy based on merits and not the barriers of legacy systems.

Thing you’d most like to change about it?
Simplification/Consolidation of SaaS tools – there are so many niche and edge case tools and we use most of them!

What’s on your desk?
It’s pretty minimalist but mostly because I’m rarely at my desk. My main driver is a 13” Macbook Pro for portability, and an Elgato dock for easy accessories. I use Jabra Move headphones for drowning out the sounds of an open office when needed and as I’m not at my desk for long periods of time, the standing desk is essential for fast getaways! Obligatory cold brew a must.

How did you start your career in IT?
I started working as a help desk technician for a local ISP in upstate New York. computers had always been a hobby but it was actually working in the field that I realized it could be a career.

What are the biggest misconceptions of your role, internally or externally?
There was a great photo that went around LinkedIn awhile ago about IT misconceptions. There was a picture of NORAD, titled “What I think I do”, a picture of a guy crawling under a table hooking up a desktop titled “What my mom thinks I do” and a hand holding a lot of money being lit on fire titled “What CFOs think I do”. I got a kick out of it because IT/Technology is so nebulous for different organizations as well as different end users.

What was your proudest professional moment?
Becoming Director of Technology at the Brooklyn Navy Yard was definitely a big joy for me. I had joined a completely depleted department, was handed a bunch of systems across 330 acres that had been ravaged by time and Hurricane Sandy and was given the tools to completely rebuild from scratch a scalable system of network links, access control, virtualization and disaster recovery. It was an immense project that allowed me to stretch in 100 different directions (usually at the same time) and I enjoyed every minute.

What are the biggest challenges in your work?
Staying on top of all the new things! There’s a new product or service to fix every imaginable inconvenience and end users are on top of these things as well as integrating new hires who come from companies using different platforms than we choose. It’s a balancing act to control costs of cloud services as well as deliver the most functional tools to the largest group of people.

Most cringeworthy request?
“I can’t print” It’s hard to get jazzed about diving into that one.

Do you stay hydrated at work?
I try to balance my coffee intake with equivalent amounts of water, but I’m not sure even that is 100%.

CLI or GUI?
CLI was my bread and butter in networking but it’s becoming less viable for the tools in use day to day. (And I will admit that Meraki’s Cloud Dashboard for remote deployment and management of network infrastructure is very pretty)

DIY or turnkey?
DIY if I have the time and interest, it’s much more fun and rewarding to be connected as much as possible to all the parts. Again, if it’s about printers though, I just don’t care!

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