This story highlights the effectiveness of apprenticeship programs in diversifying engineering talent. It also provides insights into Airbnb's security engineering culture, specifically how they manage permissions platforms and integrate LLMs while maintaining high security standards.
Jonathan Woodard knows defense. After playing professional football as a defensive end for six years, Jonathan knew he wanted a career where he could always face new challenges, learn new skills, and continue to thrive in high-paced environments. After discovering a passion for programming, Jonathan joined Airbnb’s Connect Engineering Apprenticeship program and excelled; now, we’re lucky to have him on our Secure Development Engineering team. Here’s his story.
Like many kids, I wanted to grow up to become a professional athlete. Playing professional football was my dream, but over the years, it faded into the background because it seemed unrealistic — until it wasn’t.
I was born in California, moved with my family to Maryland and Kentucky, and settled in Tennessee, where I attended middle school and high school. I started playing football in seventh grade, but I didn’t know then how fateful a decision that was. It wasn’t until ninth grade that I really fell in love with the game, and only after my junior year of college that I realized I might be able to play at the professional level.
After being drafted in 2016, I tore my Achilles tendon and missed the entire first season. It felt like my career — my dream — might have ended before it began. Getting that close to my dream was tough. To this day, I have a note I wrote in elementary school about my dreams of playing professionally.
Healing was my priority, but as I recovered, I used my spare time to complete my MBA. Looking back, that decision was almost as pivotal as the one to play football. Little did I know that I would need to practice adapting to new circumstances and making the most of them many more times.
My injury was far from the end for me: From 2016 to 2022, I played for the Jaguars, Falcons, Dolphins, and Bills as a defensive end. But I knew, as many athletes do, that a career in sports is most often just one leg of life’s journey.
So, in 2021, while playing in the Canadian Football League, I started exploring my career options — what I wanted, and what I knew I didn’t want.
My biggest priority was finding a career path that wasn’t just “good enough.” I wanted a career that truly suited me.
That’s when I discovered coding. I taught myself to code during the season, and I couldn’t get enough of it. When I wasn’t practicing, playing, or studying plays, I used my time to dive deeper into coding.
When I retired from football, I knew software was my first choice for the next step in my career. I applied to the Nashville Software School bootcamp, where I took a full-stack web development course. My experience there convinced me I would never get tired of learning more about technology.
There, I learned programming fundamentals, saw the benefits of structured learning over self-study, and transitioned from a mostly active work environment to a more sedentary one. That took some getting used to!
Throughout, I found myself flexing muscles I didn’t know were there. Everywhere I turned, I found new skills and interests I didn’t know I had. Every opportunity to exercise them felt like a chance to grow as a person.
Looking back, it feels like fate, or the best luck of my career: I was scrolling through LinkedIn one day and stumbled on a post about Airbnb’s Connect Engineering Apprenticeship program. I thought, “Why not?”, took a chance, and applied.
On the one hand, I really did think I was a fit; on the other hand, I wondered how stiff the competition was. When the acceptance came through, it felt surreal. I was a fan of Airbnb as a user, and the chance to see how it all worked on the inside, and potentially join the company itself, was beyond exciting.
The program accepted 10 apprentices, including me, and offered a 6-month program split into two phases.
In the learning phase, we heard about the Airbnb tech stack, learned the company’s working methods, and we built and presented projects.
In the team placement phase, each apprentice was matched to an Airbnb team. We worked on projects of gradually increasing complexity until the program culminated in a group presentation and the possibility of conversion to a full-time role.
The apprenticeship program reminded me of how valuable it was to play on a team — and learn from a team — that really has your back.
There were weekly technical mentor meetings where I could ask all sorts of questions, and I had plenty. Some were about corporate operations — norms and expectations that someone who’d worked in corporate for years might take for granted. I had questions about different career paths in tech and how different decisions might play out. And because I had a bootcamp background, I often had questions about computer science fundamentals that my education hadn’t yet covered. My alumni mentor, Jeremiah Boyle, made a particularly big impact. Our conversations helped open my mind to backend engineering, which I hadn’t considered before.
When we started the team placement phase, we each got a team buddy who served as the primary day-to-day point of contact and helped guide the technical work. Kyler Mejia, who’s a Senior Software Engineer and has been at Airbnb for almost 9 years now, was my team buddy and had a tremendous impact on my growth as an engineer.
As we went from phase to phase, the program also provided an alumni host system, which offered peer guidance from people who’d been through the program before me. I had support from every angle, and I flourished, eventually getting the offer to join the company full-time.
Today, I work on the Secure Development Engineering team, which covers cloud and infrastructure protection, vulnerability management, product security, and identity and access management, with my focus on the latter two.
While working on Airbnb’s largest permissions platform, I found the challenge of balancing security and safety with LLM integration, an exciting new dimension of security software engineering. This challenge was exciting to pursue in part because of the engineering culture here. My team is highly collaborative, and everyone at the company prizes transparency and cross-team collaboration.
I remember the day I got accepted into the apprenticeship program, and the day I was offered the chance to work full-time; each time, the reality exceeded my expectations. Airbnb has such a reputation for being creative and collaborative, and the product is a part of so many people’s best memories, including mine. It felt really special, and, as it turned out, it was as great on the inside as it appeared on the outside.
Three years in, I’ve found numerous, sometimes surprising, parallels between football and security engineering.
In football and in security, you will inevitably face intense, high-pressure situations, often with little warning.
In football, that might be the final play that determines the outcome of the game, and in security, that might be a critical incident that threatens security if it’s not addressed. Now that I’m an engineer, I find myself drawing on that high-intensity experience, switching from one pace of work to another to make quick decisions and think on the fly.
Another parallel I’ve found is that a strong team, supported by a leader who knows how to bring out the best in each person while navigating adversity together, can make all the difference. I’ve been fortunate enough to experience that both on the football field and here on the Secure Development Engineering team, led by Kadia Mashal.
But I’ve also had to adapt: Football is a game with a strict set of rules you operate within, whereas the software and security spaces require much more flexibility because there are many more variables to defend against. Football gave me experience to build on, but software has offered me directions for growth.
Now, I can look backward and close the loop on my apprenticeship experience by supporting new apprentices as an alumni host, and look to the future by learning about the evolving ways AI is changing security.
As a defensive end, I frequently ran containment, which prevented other teams from making big gains. Now, I’m part of a team running containment with much higher stakes. I might be behind a keyboard instead of on a defensive line, but every day is still just as exciting.
If you’re from an underrepresented background or are taking an unconventional path into tech, like me, then I highly recommend applying to the Connect Engineering Apprenticeship program. There’s no better way, in my opinion, to make a career transition. And if you’re interested in Airbnb’s approach to security and the opportunity to support a vital function at the company, then check out our openings.
My Journey to Airbnb — Jonathan Woodard was originally published in The Airbnb Tech Blog on Medium, where people are continuing the conversation by highlighting and responding to this story.
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