The BreakLine Arena · 14 min
Key moments - from our scoring
Substance score
16 / 100
Five dimensions, 20 points each
Jackson Fairburn, Mission Success Lead at Swarm Aero, shares his journey from nine years as an Army aviation operations officer and AH-64 Apache pilot to civilian tech leadership. After transitioning through Brakeline's workshops and effects-based hiring methodology, he joined Evolve Technology as a solutions engineer, progressing through promotions to staff and strategic solutions engineer roles overseeing multibillion-dollar projects. He then moved to Swarm Aero to return to his passion for aviation. Fairburn emphasizes that transitioning service members often underestimate the difficulty of civilian job search skills - elevator pitches, storytelling, and interview preparation require deliberate practice. His key insight: being open to yes, even when opportunities don't match initial checklists, can lead to unexpected career success. He completed 35 Brakeline workshops during a challenging 2022 tech market correction, leveraging community support and coaching to secure roles aligned with his core mission-orientation. For military veterans entering tech and defense roles, Fairburn advocates resilience, trust in the transition process, and leveraging peer networks within communities like Brakeline.
He served nine years as an aviation operations officer and AH-64 Apache pilot in the Army, progressing from flight school through roles as platoon leader, battalion staff officer, and company commander for Alpha Company, 1st of the 14th - the training company for the AH-64 - where he became an instructor pilot.
Jackson completed approximately 35 workshops as part of his commitment to learning civilian job search skills, including elevator pitch development and interview preparation, during the challenging 2022 tech market downturn.
Initially, Jackson was heavily restricted by what he thought he needed (no travel, DC-area only), but after being told to 'be open to yes,' he attended interviews for the Evolve opportunity despite it being 75% travel - a decision that led to one of his most fulfilling roles.
Jackson is a Mission Success Lead at Swarm Aero, where he returned to his passion for aviation after gaining civilian tech experience at Evolve Technology.
Resilience, being open to yes rather than rigid checklists, trusting the transition process and coaches, practicing communication skills (like elevator pitches), and recognizing that first roles are stepping stones rather than permanent positions.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode is almost entirely a promotional testimonial for BreakLine with no novel, actionable insights for B2B operators. The only candidate 'insights' are generic motivational platitudes repeated multiple times.
resilience is key, especially like when you're making a transition
you have to trust that it's like going to be okay
The episode recycles standard career-transition motivational advice with zero contrarian or first-principles thinking. 'Be open to yes' is the closest thing to a distinct phrase but it is not a genuinely original or counterintuitive idea.
be open to. Yes. And be open to the process of Breakline because it served me well twice
trust the process. Trust the coaches that are giving you the advice
Jackson is a legitimate AH-64 pilot and army officer with real operational experience, but in the civilian B2B world he is a junior-to-mid-level practitioner and primarily functions here as a BreakLine customer testimonial rather than a seasoned operator with scalable lessons.
I became a uh, solutions engineer. Every six months I got promoted to two new levels
now I'm here as a mission success lead and loving every man of
A handful of specific details exist - 35 workshops, AH-64 pilot, 9 years service, 75% travel role, 'multibillion dollar projects' - but these details serve a promotional narrative and provide no actionable, transferable data for B2B operators.
I did like 35 workshops
the evolve opportunity to me which was like 75% travel
The host asks entirely leading, promotional questions designed to elicit praise for BreakLine, with zero pushback, no follow-through on substantive claims, and no productive tension at any point in the conversation.
What were some of the things that you took away from the workshops and the prep that you felt you've been able to carry throughout your interviews in your career?
to kind of close this out, I'd love for you to share some insights or tips that you have for fellow brake liners
Computed from the transcript - who did the talking, and the words that came up most.
What does resilience look like when the market turns against you? In Episode 78 of the BreakLine Arena, Team BreakLine’s own, Natalia Peddycoart, sits down with Jackson Fairburn, a former U.S. Army AH-64 Apache pilot, company commander, and now Mission Success Lead at Swarm Aero, to unpack his journey from nine years of military service into a volatile 2022 tech hiring market. Jackson shares how he translated high-stakes aviation leadership into civilian impact, landed a solutions engineering role at Evolv Technology during a downturn, earned rapid promotions, and ultimately returned to aviation-focused innovation by staying open to unexpected opportunity. This conversation is about more than transition. It’s about reinvention. Reassessing priorities as life evolves. Trusting the process when outcomes feel uncertain. And adopting a mindset Jackson calls: “Be Open to Yes.” Whether you’re navigating a pivot, leading through ambiguity, or searching for true mission fit, this episode offers a grounded, tactical look at resilience in action.
Transcribed and scored by The B2B Podcast Index.
Jackson Fairburn: You know, resilience is key, especially like when you're making a transition. I remember mulling over whether I was going to make the jump out of the military or not. I loved the military. I was leaving for more personal reasons, you know, and family matters. And it was, it was hard to walk away, especially walking into the unknown.
Narrator: Welcome to the arena. At Brakeline, we believe the arsenal of democracy is our people.
Narrator: We use our field tested effects based hiring methodology to connect top performers from all backgrounds with mission driven companies shaping the future of tech, defense, AI and beyond.
Narrator: In this space, you're going to hear real stories from the builders, operators and leaders redefining what's possible. Whether you're a founder, future founder, or not quite sure what comes next, you belong here.
Narrator: Get ready to step into the arena.
Natalia: Hi everybody. I am Natalia and I play for team Brakeline. With me today is Jackson Fairburn. He is one of our favorite brake liners who has recently transitioned into a role with the swimming form Aero team as a mission success lead. Now, Jackson came to Brakeline as he was transitioning out of the army as a company commander in aviation operations. He leveraged our workshops one on one prep, has been very active in our community and originally got hired by one of our partners, Evolve technology. Even as an alumni, he stayed connected, came back for support with promotions and as I mentioned, he has recently stepped into a new role with Swarm Eero. So Jackson would love to hear a bit more about your origin story. So tell me about your time in the military and what you were thinking about as you were transitioning to something new.
Jackson Fairburn: Yeah, well, thanks Natalia. I know we have a long history together at Breakline. It's been great. So I'm really, really happy that we're doing this. So, yeah, nine years overall as an aviation operations officer and age 64 pilot in the army. Started off, you know, flight school like every, every candidate that does a year and a half doing that, you know, the groundwork of, uh, learning the Apache and getting to a point of being a competent aviator. After that, spending a year and a half immediately as a platoon leader in charge of, you know, about 15 personnel pilots and crew chiefs and warrant officers in the deployed environment and also back home, spent two years on battalion staff doing uh, supporting operations for multiple companies, uh, at that level and then spending another two years in the brigade operations cell where my career culminated as the company commander for Alpha first, the 14th, which is the training company for the A64. So kind of came back home and was able to become an instructor pilot and teach new students how to fly the Apache. At the end of my career, which was, which was incredibly rewarding from that time I, you know, as I made that, that kind of transition, reached out to you guys for, for transition assistance through Brakeline and the program was absolutely fantastic. Got, got me into Evolve Technology, a very mission driven company around protecting the public through AI security hardware and software. And I became a uh, solutions engineer. Every six months I got promoted to two new levels from, from a senior uh, solution engineer to staff where I managed the southeast region to then strategic solutions engineer where I was in charge of overseeing multibillion dollar, you know, projects and proposals and sales. So decided I really wanted to get back in aviation. That was my heart, my love. And so you know, went back to you guys and Swarm Aero, a company I'd been looking at for a long time, popped up on your radar and I was like, I remember texting you saying like swarm Arrow, Swarm Aero. And and so we went down that path fully committed together and we made it happen. And so now I'm here as a mission success lead and loving every man of.
Natalia: That's awesome. Yes. I feel like we've had such a long journey together. But let's go back to the beginning. So you joined Brakeline, you're fresh out of the army. I remember us being in one on one workshops where I was like, Jackson, can't say it that way. You gotta say it a different way. You gotta think in you know, a commercial like civilian perspective. What were some of the things that you took away from the workshops and the prep that you felt you've been able to carry throughout your interviews in your career?
Jackson Fairburn: Yeah, I think the first, the first thing I'll say is especially as like for transitioning service members is you don't know how to do this. And maybe some are better than others but it is not a skill that that comes easily and it takes practice. I, I remember uh, the first time I ever gave like my 60 second elevator pitch and it atrocious and but everybody else was atrocious too. And so you know, you have this fear that like you're the only person who doesn't know how to do this. And that's so not true. And, but the beautiful part of like brilliant break line is like they're there to help you through that. And I went through so many workshops because I, I made it my, my commitment to like this, this is how I'm going to transition. This is the uh, the best way to do it. And these are the people to teach me how to do it. And so with that in mind, I think I did like 35 workshops. Not to say that everyone needs to do that, but, you know, I leverage, you know, Lauren all the time. She was great during the office hours and, you know, you were great with one on one sessions when, well, our interview time started to come through. And so there was a lot of resources that Brickline had and I used every single one of them that I could because I only got one interview and I, um, was able to nail it and get the job that I wanted. And that was during a time in 2022 when the tech market really was starting to very, very like, correct hard. So the opportunities were not as available as they probably are now.
Natalia: Yeah, absolutely. I remember that time where, yeah, we had to really be as open as possible with opportunities. Kind of see any flexibility around some of your kind of limiting factor, but essentially really being able to make sure that you are prepared going into those interviews because that might be the one interview you have over the next couple of weeks. Yeah, I remember you were going to workshops even, even after you got hired. You know, it had become part of your community. And you were also super helpful to other candidates who were, you know, in the same seat that you were in not too long ago.
Jackson Fairburn: Yeah, uh, I'll say that that's been one of the crazy, unexpected benefits of Brake line is like the community that comes with it. I can, I can reach out to any brake liner and on LinkedIn, you know, and, and get a response, you know, same day type of thing and open to be, be helpful and things of that nature. So. And I still have brake liners reaching out to me even in my current position. And I'm, I'm always been able backwards for them because I know that like transitions are hard, especially like veteran transitions are hard. And so it's a great community to, to have, have that support around and, and for leveraging others like, you know, or leveraging others. They could be successful in that.
Natalia: Absolutely. Now Brakeline, we utilize an effects based hiring methodology. So we often ask, you know, what are you optimizing for or for our partner companies, what effect are you hoping to achieve with this hire? Right. So really being able to pull together, being really outcomes oriented when we're thinking about connecting the right people to the right opportunities. So in the reflection that you've had in your experience, like what has changed or been achieved for you in thinking about what you've been optimizing for this whole time?
Jackson Fairburn: Yeah, I'll say that that, that definitely changes right as my career progressed and you know, things in my life that have ah, that have taken priority like you know, family and that sort of thing. You know, I always go back to our like original interactions and it was, you know, I'm coming out of the military which is high stress, high tempo, right. Not a lot of time with family. And I was like, absolutely no travel. You know, I want to stay in the D.C. area. I put all these restrictions on you. And then I remember I don't know if it was you, if it was Zane or during some workshop. Somebody said this to me and it like stuck in my head like forever, which is like be open to. Yes. And so kind of reflecting on that, you brought the evolve opportunity to me which was like 75% travel. And I was like, what are we talking about? But at that time you were just like, hey, go to the interview and see. Right. So it wasn't what I was like necessarily optimizing for but also like didn't really know what I was optimizing for. You were kind of like guiding me through this process, especially as someone who's like inexperienced in the civilian, you know, market and like, you know, you're like, hey, just, just feel it out. We can always say no after you've, we've gone through this and started falling in love with the company as soon as I did the phone screen and things like that and ended up loving the travel. And so, uh, ended up working with an amazing team, you know, and with a great sense of purpose, which is exactly what I wanted coming out of the military. And so the, everything aligned very, very well. I think it was because I was open to yes when I was initially, you know, not. And then, you know, the second part of that is like when, you know, my wife and I were serious about, you know, starting a family and the travel was going to be kind of problematic, I came back to you guys and said, you know, here's what I'm optimizing for. You know, how can we make this work now that I have experience, you know, behind me? And you were great to work with on um, staying true to that. And we had a lot more flexibility because of that. You know, you don't have to get the perfect job right out of your transition because most 99% of the time it's going to be a stepping stone to bigger and better things. And that's really what I learned in retrospect. Now when I think about like what I was optimizing for, I wasn't Optimizing for a stepping stone. I was optimizing for like the perfect job and that just, you know, wasn't realistic. And I'm glad, you know, I have that perspective now because where I'm at is, is exactly where I want to be.
Natalia: Yeah, I think that's such a good point that what you're optimizing for is going to change throughout your lifetime. Right. Like, what's important to you, your priorities, kind of your work life, alignment, it's going to shift and adjust. And so, you know, you called out, you know, and came out of the military, you're like, okay, this is like my checklist of things that I need to make sure happen. And I came to you with a very list of things that you were really open to and you built an amazing career out of being at evolve and in an opportunity that you had never, you never would have considered if you hadn't been open. Right. And then. But I think what has stayed true throughout your career is being really mission oriented. Right. If you came from that service background, supporting the war fighter, like this is something that is true to you and has always been a very fulfilling aspect of your career path. That has been the common thread throughout your professional career, which is something that brings a lot of meaning to you and is a very common thread for our transitioning military and our veterans. Yeah, yeah. You mentioned, you know, Heather. I also got an opportunity to work with Heather. We love working with brake line family and baby Weston will be a future brake liner as well once she's ready for that job search. But to kind of close this out, I'd love for you to share some insights or tips that you have for fellow brake liners. Like what, what are some of those key attributes that have helped you succeed so far in your career?
Jackson Fairburn: A great question. You know, resilience is key, especially like when you're making a transition. I remember mulling over whether I was going to make the jump out of the military, not I loved the military. I was, I was leaving for more personal reasons, you know, and family matters. And it was, it was hard to walk away, especially walking into the unknown. Right. And. But you have to, you have to trust that it's like going to be okay and that everything that you learned in the military about being resilient is going to, is going to course correct you through the process. You know, there are a lot of things that get thrown at you and variables that you can't, you can't predict. But service members are great at resilience and keeping Moving forward, you know, especially in the face of, you know, the face of no. Right. Finding a way. And Breakline helps you break, truly break through and get, and get to a. Yes. From an employer and, and help you to do a lot of things that you, you don't know or can't do. You know, a lot of it is like translating your skills that you've learned from the military and helping you, helping you get to a point of having an effective elevator pitch and being able to storytell and just talk to people without sounding like a robot. Right. You know, there's a lot of that, but ultimately the resilience is what, what will, will get you to where you need to go. I know, I know that, you know, even now in my, in my current role, some other, some other things that I'll say is, you know, I can't, I can't express enough. Like be open to. Yes. And be open to the process of Breakline because it served me well twice. Those that I talk to in the brake line community are those that have embraced, you know, going first during, you know, uh, the lessons or, you know, being, you know, being the ones that, you know, practice their elevator pitch on a walk outside for 30 minutes. Right. With headphones in. You know, you have to, you have to trust the process. Trust the coaches that are giving you the advice, promise you you'll land the role that you want, really do, because it's about, it's about the personal relationships and, and what you bring to the table from your time in the military and, and that's value add to any company.
Natalia: Absolutely. Yes. There's you. You all bring such incredible experience that can often be really hard to translate. Right. And it's like you said, you don't know what you don't know there. This is a, a skill that you must learn, right. Of how to translate your experience, how to make sure that it's a really outcomes oriented trajectory so that you can hit yourself in that role so that they can envision you there. I know that you did that really well throughout your interview process and in some fun and unique ways. And then again, yeah, being open to. Yes. Being open to the possibility. And I think a lot of that comes with, you know, having trust in that process and trust in the brake line team. So we really, really appreciate you giving us that, uh, trust over time and building the community that you have built around you and the other brake liners that have connected with you as well. So we are really excited to hear more in the very near future about how things are going at Swarm Aero. But again, thank you so much for your time.
Jackson Fairburn: Yeah, thanks so much. Appreciate it.
Narrator: Natalia, thanks for joining us for this episode of the Brakeline Arena.
Narrator: If you're a visionary founder building in a mission driven space and want to learn more about our effects based hiring
Narrator: approach, or a purpose driven top performer seeking clarity, community and access to the most ambitious companies in America, join us brakeline.org.