JumpCloud – 1 Year Later

Written by Pam Lefkowitz on August 25, 2022

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Many years ago I did a presentation at PSU MacAdmins about Ageism in Tech. What struck me was that the session was way more crowded than I ever thought it would be (Imposter Syndrome run amok). I think there were ~100 people, which surprised the heck out of me. Obviously, I was well aware of sexism in tech – I experienced it daily over my entire career. But I had been so heads-down growing and running my own company that I hadn’t noticed the ageism.

Then I started paying attention to conversations occurring in the general IT Admin population. And while the sexism still existed, it was being replaced by descriptions of bosses who were old and clients who were “past their prime” and other such statements. And in prepping for that preso I found out some things I knew but wasn’t consciously aware of: 

  • I read articles that said that 35 is now considered old in the tech industry. 
  • I learned that resumes should never have your college graduation year (remember, I was prepping this session around 2012 or so – we were really just uncovering some bad behaviors). 
  • I learned that vernacular mattered when communicating with others. 
  • And I learned that knowledge is power and there are a lot of people who are threatened by that power.

So when it came time for me to take down the shingle and find a job, I should not have been surprised at how difficult it was to get noticed. Time after time I was ghosted. I could not figure out how to take 25 years of business and tech experience and shape it into something that was “hiring manager” acceptable. 

There was entirely too much feedback containing the word “over experienced”. Too many times I was told that my experience didn’t fit the job description (how do you put “I did it all” into a task-oriented job without writing a novel?). And how do you put a value on “I did everything from recommend equipment to set up the network to install and support it all to I ran every part of the business” without scaring away an employer? The answer is: on a resume you don’t. You can’t really.

Job hunting is painful (to put it mildly). One has to take rejection seriously, yet not let it become all-consuming. And it takes a very special strategy to break through the barriers when you’re dealing with bias in hiring. Everyone in my circle of influence would talk about enlarging and nurturing that circle. 

That requires a lot of patience and self-control and, often, behavior changes. Sigh. For me, well, I was simply done with reigning it in and covering up my true self. I am loud. I am passionate. I care deeply. And I’m (mostly) not afraid to share my opinions. I did what I could but, honestly, I’m just not very good at hiding my exuberance. And that turned off a lot of people I’m sure. 

But there were plenty of people in my network who believed in me and loved me in spite of – or maybe because of – those character traits. And because of my honesty and openness about what I wanted (and didn’t want) out of a career at this stage of my life, I was offered an opportunity to interview with this PLG company called JumpCloud for a job that was NOT technical.

How I Handled Interviewing

Holy cow. The last time I had interviewed for a job, consumers were being told to not feed Mogwai after midnight. It had been a minute. How was I going to handle this interview? Oh, and it turned out that it was a bunch of interviews – that was new to me. I was used to being the interviewer, not the interviewee.

I decided that I would just be me. The company, the hiring manager, may have wanted some particular traits or personality, but if I was going to “act as if” instead of just being me, then I knew things would not work in the long term. The only right way to interview was to be myself. I had the qualifications, the important part was the fit with the team and the company.

And Here We Are

We talk a lot here in the Marketing Department about Tuckman’s stages of group development. As a cynic (I know, you’re shocked to hear that!) I doubted its veracity. My previous working-for-someone-else experience was that you go through a honeymoon phase and then you either still like what you’re doing, can tolerate what you’re doing, or you hate it and find another job. Here I was, having closed any other doors, in a new space, with new people, and having new experiences… so I kept an open mind. 

And y’know what? Over the course of this past year I saw those stages in action! Forming was hard – I felt really lost for what seemed like a long time. I still feel lost a lot of times, but that’s more because the company has grown so much and, being remote, I don’t get a chance to meet people from outside my team. And every time we bring on someone new, we form again.

Storming was rough, but with the support of a terrific leader and a team that respects and cares deeply about each other, that phase was really very short-lived. 

Then we went through some operational changes within the team (who knew I could adjust to the sprint life?!) but now it is very much the norm. In fact, our sprint boards were funky over the past few days and we really felt lost. As much as I came to the Agile method kicking and screaming, this “lost without my sprint board” feeling was really ironic.

The team is operating efficiently, we all seem to be pretty happy with each other, and we are creating some incredible content. I am honored to work with these amazing people – both in my direct team, the broader department, and the company as a whole –  and frequently find myself wondering how I got so lucky.

And No Isms

Company culture comes from the top. After a year of working with people every day, you typically have seen the warts. I can honestly say that the “ism” warts have been so few and far between as to be able to be counted on less than one of Mickey Mouse’s hands. And, because of the radically candid culture here, I was comfortable talking through those blips with the other party with no lasting discomfort. In fact, I believe that being radically candid with each other has enhanced the relationships. 

My wish for you is that you get to have a great work experience too. 

The Honeymoon

It’s a year later and I’m not over my honeymoon.

It’s a year later and I still enjoy my work.

It’s a year later and I still like my teammates (that feeling may have actually grown over the year).

It’s a year later and I still feel valued and respected.

It’s a year later and I still like my manager and up the line.

It’s a year later and I still like the vision of the company.

It’s a year later and I still like the mission of the company.

It’s a year later and I still wake up thinking “I get to write cool stuff today”.

It’s a year later and I am still grateful to Tom for introducing me to JumpCloud.

It’s a year later and I’m not over my honeymoon.

Pam Lefkowitz

Pam is an IT Columnist at JumpCloud where she uses her experience as a consultant and MSP to write about IT admin life and tech. Outside of (remote) work hours, she spends her time with her dog, visiting her kids across the country, and being creative with fiber.

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