April 2, 2021

The Women of DevOps: Leigh Kastenson

Table of Contents

Key takeaway

Welcome to Women of DevOps, part three! New month, new guest - and today is Leigh Kastenson, a wonderful DevOps engineer at LeafLink. My partner actually hired Leigh, and I was SO PUMPED for her to join since she was the first woman on the team. 

Leigh’s not only awesome at DevOps - she has really cool hobbies like surfing and hiking, and it turns out that we have a bunch in common when it comes to travel. We like the coooooold places: we’ve both been to Iceland and Nordic countries. You’ll soon understand why they love these places so much.

‘Til next time,


The Women of DevOps, Ep. 3

Can’t listen to the audio? Read on below for a transcript of our conversation. 

Rox: Hey, everybody, thank you for joining us for Women of DevOps, Episode 3! Today we have Leigh from LeafLink. Leigh, could you tell us a little bit more about yourself, please? 

Leigh: Hi, I'm Leigh Kastenson. I live in Oregon. I'm in the middle of moving from Portland to Lincoln city, which is on the coast, and I'm very excited about it. I have a ton of hobbies like surfing, which is why I'm moving to the coast. I like hiking, which Oregon is great for. I like eating. [laughs] And I also like the Wim Hof Method, which is cold exposure and breathing and all kinds of crazy things. [Note from Rox: Leigh and her partner are huge fans of ice baths, polar plunges, etc. They’ve traveled to Iceland and Finland!]

Leigh Kastenson
Leigh Kastenson, Women of DevOps 3!

Rox: Very interesting. And right now you work at LeafLink, correct? Can you tell us a little bit about what LeafLink does, because I feel like they're kind of pioneering an entire industry. I'd like for our guests to hear a little bit about that. 

Leigh: Totally. So LeafLink is a wholesale cannabis marketplace. Basically, what we have is a platform that allows dispensaries to buy from producers, and it kind of helps coordinate the whole thing. Besides doing that, we're also working on financing some of the purchases, we're working on delivering some of the purchases, logistics, things like that. It's really booming, and I'm really excited to work for LeafLink. 

Rox: Right, with the four states that just legalized in one form or another, this past election, it's going to explode. 

Leigh: Absolutely. 

Rox: Very cool company to be part of right now. So how long have you been in tech? And what was your career progression like? 

Leigh: Professionally, I've been in tech for about six years. So I actually majored in an entirely different field: biosystems and bioproducts engineering. Actually, when I graduated, there were no jobs open. It was after the recession and no one was investing in that area. So while I was trying to find a job, I was like, “Hey, I'll just try to learn coding.” So I started studying Ruby on Rails, and I went to meetups and things. I actually got a job from a meetup, which is pretty awesome. After doing Ruby on Rails Dev, I just had a handful of DevOps jobs, both contracting and full-time. And now I'm settling in at LeafLink. 

Rox: Was there anything in particular that drew you to DevOps? I'm curious about that progression, specifically.

Leigh: DevOps, I feel is a ‘jack of all trades’ kind of thing. You need a really broad base to do DevOps, whereas dev work is a little more specialized. I really liked all the DevOps Engineers I knew, and everyone that worked at my first company as a DevOps Engineer, I just liked seeing how they were working on totally different things all the time, and they always got to learn new things. That was exciting to me, and that's how I like to learn.

Rox: I'm kind of biased, obviously, but it's all the different aspects to it. You can really get into monitoring, you can really get into databases - there's just so much to learn. It's one of those careers where you're never going to be an expert in everything, and that's so cool. 

Leigh: Totally.

Rox: So what's your take on education there, if you had sort of that non-traditional path? Do you believe a four-year degree is the way to go? Do you encourage bootcamps, self-learning? What's your take on education?

Leigh: I think it depends on what you want to do in your tech career. If you want to really stick to a specific thing - pretty much the opposite of what I'm doing [laughs] - if you want to deepdive into one topic, or maybe you want to go into academia or something like that, then yeah, a four-year degree or even higher education is right for you. But if you just want to get your foot into tech and test the waters, see if you like it, then I think you can get pretty far with a bootcamp, free online courses, things like that.

Rox: Nice. If you could go back and do it all over again, what would you change, if anything? Is there any advice you'd give your younger self in regards to your career?

Leigh: I can't say I’d change that much. I actually like having a four-year degree in a totally different field. It's kind of like a little party fact or fun thing. [laughs] But, I would actually tell my younger self not to worry so much about  trying to find the right job or trying to worry about forward career progression and things like that. I worried a lot when I first started about, “Oh, is this the right thing for me?” I think it's better to just flow with it and see where your career takes you. 

Rox: Yeah, that's actually interesting with the whole separate degree. The second episode that I recorded a little bit ago, she [Patricia Anong] actually came from psychology. So it seems like there are a lot of people that just completely leave what they were meant to do, and just go to tech because that's just where everything is.

Leigh: Yeah!

Rox: The future is tech! So another question here, which is kind of my favorite of all this. What has your experience been like, as a woman in tech? 

Leigh: Sure. I would say it's been mixed. In general, it's fine and good. But I can't pretend that I haven't had some negative experiences. I think a lot of my negative experiences stem from companies that just want to bring women and diversity on, but they don't necessarily have a platform or system in place to support women and diversity in tech. They want you there, but then once you actually have to represent yourself - and unfortunately, if you are the only woman, you kind of have to represent all women, which is like a huge task - there's not really support in place. So yeah, I’d say it's mixed. I've met tons of supportive people. I've met lots of great women. But you also run into some people here and there that aren't, fully supportive of you. 

Rox: Yeah, Tampa is odd for tech, generally speaking, and then even odder for women in tech, because it's just so rare. I had interviewed a woman a long time ago who heads

Suncoast Developers Guild, which is a school here (bootcamp). She told me that she used to be the only woman in the room. She'd go to conferences, she'd speak, and someone would come to her after like, “Thank you, I was starting to feel like I didn't belong in tech. But because you're here now, I feel like I have a place.” [laughs] It's hard, but at least it's progressing now. 

Leigh: Yeah. I do have to say there's one positive - just trying to be an eternal optimist and always looking for at least one positive - when you go to conferences, the lines for the bathroom - there's no line. [laughs] The lines for the men’s bathroom are like around the corner. So that's one positive.

Rox: We'll take what we can get! [laughs] On that note, do you have any advice for a woman looking to start a career in tech, but who might be afraid or don't feel like they belong? What's one thing you could say to encourage our readers/listeners to just do it?

Leigh: Totally. I would advise to find mentors, other women in tech, even peers that are at your same level - and just talk to them. It's so great to have camaraderie with other women, and also to get advice from other women. I've gotten a lot of good advice from women in tech to, you know, avoid potential pitfalls, or certain things that you should do to get to a different place in your career. And yeah, made a lot of great lifelong friendships with women in tech. So that's one thing to look for, is that bond with other women.

Rox: Nice. Completely separate note, but just generally career-speaking, what's your favorite project you've ever gotten to work on and why? 

Leigh: I don't have a specific one because I feel like I would just go into nerdy little technical details. But I would say in general, startups. I love working at startups because you have such a potential to make a huge impact and you're not really limited by systems or politics or things like that. If something is broken or not ideal, usually you have the opportunity to go in and fix it, and sometimes, even just completely start something from scratch again, which is really exciting.

Rox: That is awesome. Startups, for that reason. You're just making such a big impact.

Leigh: All the time. Yeah. 

Rox: I kind of feel that at Harness too. We're three years in, I think, and you still feel like you're at the ground level just making things happen. It's really cool. Is there anything exciting coming down the pipeline for you? Certifications, mentorship, speaking engagements, anything that will further your career? 

Leigh: Nothing really right now. I'm just trying to stay alive during the global pandemic. [laughs]

Rox: Any final thoughts you'd like to share with everybody? Maybe a note of encouragement? 

Leigh: Yeah, totally. If you're a woman in tech, or you want to be in tech, you can do it. Don't get discouraged by bad environments. Don't get discouraged by certain individuals. Just keep moving forward, and eventually you'll find the right spot for you. 

Rox: Awesome. Thank you so much for your time today. This was great. 

Leigh: Thank you, Rox!


Catch Women of DevOps in May for Carmen Saenz, Senior DevOps Engineer at PEAK6 and PhD student.

Did you miss Episode 2? You can find it here: meet Patricia Anong!

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