Moving Up and Trying New Things
TL;DR: I’m starting a new role at Workbrew in October! I’m excited, but I wanted to share my feelings and reasons.
I’ve been doing client platform engineering (CPE) or CPE-like work for almost 20 years now. I got into this by accident. When I was in college, I was asked to manage our digital media lab and all of its various devices and servers. Back then, I was using NetRestore and DeployStudio and upgrading Xserves from 10.4 to 10.5. It was definitely a simpler time for me; I only had to worry about 20 devices and a handful of servers. It was all also locally managed and my customers were my fellow students (and later just my students).
Flash forward to today and I’m managing over a thousand devices remotely with an increasingly complex security stack at a highly compartmentalized US defense contractor. Additionally, as with any CPE role, I’m working around ever-competing priorities every single day. New OS betas, break/fix of infrastructure, testing and updating security software, all while still handling tickets.
As a CPE, I should only be getting tickets for the most complex tasks, my tier 1-2 folks should handle things like printers and questions about tokens, right? Unfortunately, at my current org, Macs are still not a full first-class citizen. Leadership doesn’t see the value in hiring people who can focus on Mac issues, so I resort to trying to train up our existing staff to support Macs better. This works a little, but when you’re also fighting against RIFs (reduction in force; a fancy term for layoffs) and high turnover from those other groups, it becomes very hard to keep up. This all bubbles up and now I’m spending countless hours trying to do my engineering work alongside helping John Q. Uselessman install a piece of software they’re not approved for and explaining to them that they’re not following the processes that are in place for this, or sending Riley J. Developerson the same KB article that I’ve sent 50 times that week.
It’s quite exhausting putting out fires, writing documentation for the staff that never reads it, training people over and over again, and more RIFs, all on top of doing my normal work…
Yeah, I’m approaching burnout. Moreover, I’ve lost any trust with leadership.
The Build-up
For the last year and a half I’ve been looking for a new job. It started out as an “if a nice role drops in the #jobs-board on Slack, I’ll apply. But I’m not going out of my way to search” until maybe January of this year. Then, in February, we had our first round of serious layoffs in my org. I lost one of my two direct reports, which completely halted any work and support for an entire platform I owned (one that took the company 4 years to get off the ground). What hurt the most was the way leadership did it. A lot of secrecy and “will they won’t they” before anything happened, leaving most of the direct managers (including me) in the dark until the day it happened. Seriously, I wasn’t told my direct report was officially going until the day it happened.
That was when I started really ramping up my search to actively seek an out. I started applying to a lot more roles, doing a good deal of interviews, and talking to friends about openings.
Complicated Feelings
A quick aside about feelings
I know I’m lucky. I still have a job while doing this search. I have many friends and colleagues that are doing this while unemployed, and that does sit with me a bit.
I asked myself, “Should I take a job from them if they need it more?” more than once. I chatted with some folks about it and they all basically said the same, “Do what you need to do for yourself,” which made me feel a bit better (not entirely, but a bit). I just share this to say that I had complicated feelings about it, and this is why therapy is important! :)
I was a finalist for a few positions, but never crossed the line. I also knew some of the folks that got the roles over me, and I was happy for them! I really was, but I then started having my own internal crisis. This felt like what I went through before at other jobs. I have years of experience, but it’s all dated. I’m not keeping up with the trends, I got comfy for the last 6 years, and now I’m paying for it.
It’s not that I did this on purpose; I legitimately made efforts to learn new skills and even tried to get certs. I did courses for AWS and Azure, I have a homelab with lots of tools that I should know and learn. But, since my company is highly compartmentalized, I never had professional experience managing these at scale. I wasn’t allowed to unless I changed teams/roles. I was even beginning that process a few months ago, going to start working on IaaS stuff and learning how to manage that. Then I got pulled into another job that took priority, doing a lot of the same work I was already doing. I was able to learn a lot about AI tools, which has been extremely useful, but it was short-lived. Leadership pulled dozens of people out of the project, and of course the backlog of other work got larger. So I just went back to what I was doing again, nothing new.
So, yes. I tried to branch out. I did learn new tools (Fleet, Intune), but I never was able to use them at scale. Additionally, the tools that companies want CPEs to know (Okta, CrowdStrike) are things I have very limited experience with. Again, because of the compartmentalization.
And then a new set of RIFs started. Something like a 20% reduction.
My group specifically had a 30% reduction in February, now we’re getting reduced more. And the work is still increasing. All because of “analysts” and shareholders.
Happy Hour
I attended and spoke at the MacAdmins Conference at PSU again this year. During a happy hour, I was chatting with my friend and colleague Scott about all of the above. The happy hour was hosted by a sponsor and a company that was actively hiring. After maybe 30 minutes of chatting, Scott told me, “Just go over there and tell them you’re looking for a new job.” I chuckled, and continued drinking my free bourbon.
“No, I’m serious. Introduce yourself to the CEO and Brandon,” he said. “It’ll at least get a conversation going.”
At that moment, I was actually called over by them before I got a chance to even get out of my seat. They were chatting about something I was working on and wanted some input. I chatted them up and casually dropped the “Well, I am looking for a new role and I know you guys are hiring.”
Their CEO, John, (who I’ve conversed with before) handed me his card and said, “Come by the table tomorrow and let’s chat.”
The Interviews
The next day, John came to find me and asked if we could chat. The next thing I knew, I was in a job interview. I chatted with John and Brandon for over an hour. The interviews ended with a handshake and a “We’ll set up interviews next week with our COO and another person on the team.” And just like that, I was a finalist for a job I didn’t even officially apply for. Because I spoke up.
The next interviews went very well. The COO and I met for brunch at a local spot in Philly, and the other team member and I hit it off. Also, I randomly had drinks with Brandon in NY while at a Mac Admins event and we chatted a good long time.
It felt great.
The process took just 2 weeks. I was given an offer a week later, and I signed a week after that. And with that, I had my next path set!
The Future
On October 26th, I start my time as a Solutions Engineer for a small startup company called Workbrew. Anyone in the Mac Admins world most likely knows Workbrew; they have a product to manage Homebrew.
I used to avoid startups because I didn’t like the uncertainty and lack of job security. But it seems that even with a company of 30,000 employees, job security is not a thing anymore. I know layoffs happen at large companies all the time, but when you have colleagues with 30+ years invested at the company just get shoved out because some analyst says, “the company didn’t do as well as we predicted,” that’s really eye-opening.
I am extremely excited to start this new role with Workbrew, but I will admit that I am also nervous. This will be my first time at a startup, my first time at a software company, and, scariest of all, my first time not doing CPE work as my primary job since 2007. I’m no stranger to working with customers/clients, writing documentation, presenting, working with sales folks, etc. But it hasn’t really been my primary job before. When I worked at Edu-Tech, I did a lot of that, but I still also did CPE work.
I’m thrilled at the opportunity to do more public facing work, and I’m hoping the flexibility of a startup will be a breath of fresh air from my current tightly controlled environment.
Time will tell, but right now I’m just ready to go! I want to have fun again!
Speaking of fun, one last thing you may be wondering, what are you doing for the next month while off? Well, Alessa and I are going on a cruise around Korea and Japan! We’ve been planning this trip for about 2 years and the timing just worked out well. I got bored and made a silly site where you can follow along with us (not actually live/GPS of course). 나중에 봐!