Kerry Buckley: Managing cloud and on-prem infrastructure

An interview with Kerry Buckley, Lead IT Infrastructure at Greylock Partners.

What do you ACTUALLY do?

Like most members of a small IT staff, I wear many hats. My main role is managing our cloud and on-prem infrastructure across our 3 office locations. I also really enjoy managing and driving projects. Some days you’ll find me knee deep in Powershell or firewall configs, others days I’m partnering with members of our Ops team on a Salesforce CRM implementation.

What types of devices do you support?

We support whatever people need to get their work done. It’s how we roll.

What’s your favorite piece of tech?

Macbook Pro and my iPhone X. I’m glued to both of them (too much!)

What tools or apps are most important to your job?

I live on the East coast (Greylock is primarily a west coast firm), so I’m remote 95% of the time. Thankfully, technology makes this a non-issue.

Without these tools, I’d be lost:

Do you prefer hands-on, or troubleshooting from afar?

Nothing can replace being in a room with someone, but given my physical proximity to our users and infrastructure, troubleshooting from afar is my jam.

Favorite thing about your IT environment?

I love that it’s totally ours. There’s really no red tape or management hoops to jump through in order to make changes or get stuff done. I feel like this makes us SUPER productive and allows us to provide top notch IT experience to our users. It also means the business inherently trusts us, which is super empowering.

Thing you’d most like to change about it?

I always joke that I’d love to start with a clean slate, it would just be so much easier to start all over again. Migrating off legacy apps and hardware is always a challenge and never goes as quickly as I’d like it to, but we are getting there!

What’s on your desk?

Ahh, my home office setup (where I mainly work). Let’s see: really old Thunderbolt display, Macbook Pro with 5 different adapters (thanks, Apple), keyboard, trackpad, several drawings from my 2 kids. Family photos, a Sumologic Sumo wrestler. Falmouth Road race mug (always sporting running swag).

How did you start your career in IT?

I’ve been passionate about technology since before I can remember. I was fortunate to have tech related work studies and summer internships throughout college. I got my hands dirty and learned a bunch, which helped build my resume enough to land a decent consulting gig shortly after graduating. My first real job was working for an IT consulting firm, mostly with VC’s in the Boston area. I worked a LOT of hours and gained a ton of experience in a short period of time.

What are the biggest misconceptions of your role, internally or externally?

People think because I work in tech I simply “fix computers”. It used to bother me but now I can laugh about it. Yes, I do roll up my sleeves at times, but working in technology is about more than providing support. IT has the opportunity to partner with and add value to the business: we seek to understand workflows, and build technology solutions to solve problems. The break/fix IT mentality is fading away. Sure, being super technical is great, but it’s no longer everything.

What was your proudest professional moment?

I used to be one of the youngest (least experienced) employees at an IT consulting firm. Our company sent us all to Cisco training for the CCNA certification (back when it was one exam and insanely hard!). Out of the 15 or so of us, I was the only one to take and pass the exam, becoming a CCNA. I was super proud of that.

What are the biggest challenges in your work?

Anything not related to technology. AKA changing end user habits or behaviors – change is hard…technology is easy!!

Most cringeworthy request?

Oh man. I remember back in the day, being asked to touch some pretty dirty keyboards. (yuck) When I was in college, I had to support student computers and let’s just say that the content (desktop wallpaper) on some of the machines made things…awkward at times. Glad those days are long gone!

Do you stay hydrated at work?

Coffee in the morning, always. Outside of that, I drink an obscene amount of water.


Both. I prefer GUI for the routine stuff, but I’m definitely not afraid to jump into CLI – sometimes that’s the only way to really get it done.

DIY or turnkey?

Given we are a small shop, it’s tough to devote a resource to DIY an entire solution, so I mostly lean towards turnkey.

Where can people follow you online?


Are you an existing atSpoke user?