Back in the Cloud (Again): A Boomerang Story

Introduction

After my first stint at Amazon, I wanted to apply my experience in smaller companies, so I joined Peloton and later a startup. While I was able to put my skills to good use, the tech landscape often felt like a step back in time. At one company, I spent a significant amount of time refactoring a massive monolith to make it scalable, but the bigger challenge was convincing the team why it needed to be done in the first place. On the flip side, I gained hands-on experience with open-source technologies, which were often the most practical and cost-effective choice for our specific use cases.

I also realized that too much time was spent on building basic infrastructure from scratch rather than solving business problems. The startup experience, while unique, was less memorable, though I did gain valuable GCP, ML and AI experience—at the cost of dealing with a fair share of chaos. When it was time for my next move, the choice was clear: big tech. Among multiple offers, AWS was the obvious pick. The role built on my ML/AI background, focusing on using GenAI to improve developer productivity. And it certainly didn’t hurt that I was already familiar with the company and culture.

Coming back as a boomerang felt like picking up right where I left off, but with fresh perspectives, new skills, and a deeper appreciation for what AWS does right.

First 100 Days

The US President is evaluated on their first 100 days. Should the rest of us be judged the same way? The first 100 days in a new job are crucial, setting the foundation for everything that follows. It’s a period of intense learning and adaptation—not just about the technical aspects of the role but also about navigating team dynamics, understanding company culture, and demonstrating value. This is the time to build key relationships, make a strong first impression, and establish yourself as a contributing member of the team. A rocky start isn’t the end of the world, but it can make the road ahead tougher, while a strong start sets you up for long-term success.

Achieving Alignment

Achieving alignment was a critical focus during my initial 100 days at the company. My top priority was identifying what mattered most for the business and the team. My manager facilitated my alignment by providing a well-documented, structured three-month plan, including an onboarding buddy, an advisor, and key stakeholder introductions. The onboarding process was further supported by an SDE bootcamp, split into two sessions over a month, and a library of informative videos covering company-specific topics.

I gained clarity on the team’s long-term vision by attending strategic planning meetings and conducting 1:1s with key stakeholders, enabling me to strategically align my work with their goals. My first project came with a clearly defined team objective that I would own. The description was brief but provided enough context to get me excited about working on GenAI initiatives. I took time to understand the team’s structure, and the unique skills of each member.

Since teams were in the process of defining their annual goals, this gave me valuable insight into the broader strategy and key deliverables for the year. This context helped me see the bigger picture early on, ensuring my contributions were meaningful from the start.

Building Bridges

Credibility is the foundation of trust, influence, and effective collaboration in any professional setting. Early on, I prioritized building relationships by frequently connecting with my manager, who provided a curated list of peers, both within and outside the organization, to engage with. Following my alignment with the team’s objectives and speaking with key individuals, I quickly identified my customers, partners, and stakeholders.

One of the teams I worked closely with had a well-timed off-site, which gave me an opportunity to visit the headquarters. That visit made a world of difference as I got to meet engineers and managers face-to-face, understand their goals, and dive deeper into the tech stack. A single in-person meeting with my colleagues completely changed the dynamic of future interactions, whether in the office or remote. I also focused on fostering strong connections with engineers, ensuring they saw me as a partner in tackling project challenges. I aligned perspectives by documenting my thoughts on key projects following Amazon’s writing culture, inviting feedback and discussion.

Some of my projects intersect with another organization, making cross-team collaboration essential but not always straightforward. Ensuring that my objectives complement, rather than conflict with, their goals has been a priority. My approach is simple: focus on the customer, break down silos, and foster a collaborative mindset. While I hope for the same spirit of cooperation from my partners, I’ve learned that success comes not from expecting reciprocity but from consistently extending a hand. Time will tell how these relationships evolve, but I remain committed to building bridges rather than walls.

Continuous Learning

My focus is on leveraging GenAI to enhance developer productivity across all phases of software development, which is a challenge that is both meaningful and well aligned with my experience. While many competitors exist in this space, Amazon’s unwavering focus on customers sets us apart. Having spent years working with software, I’ve seen firsthand the challenges developers face, and the opportunity to solve these problems excites me. At the same time, AI is evolving rapidly, making it both thrilling and demanding to stay ahead. To keep pace, I’m making the most of Amazon’s internal resources while also enrolling in an online course specializing in Applied GenAI.

The next step in my learning journey is finding a mentor who can provide guidance and serve as a sounding board as I work toward building new products and services in this space. A strong mentor-mentee relationship takes time to cultivate, and I want to ensure it is a valuable and meaningful connection. Until then, I will continue deepening my expertise through books, courses, and hands-on experimentation.

Conclusion

During my first stint at Amazon nearly a decade ago, onboarding felt like a trial by fire. I was thrown into enhancing an audio-related feature on the Kindle Fire HDX just weeks before launch. By the time I hit 100 days, I had shipped a device but lacked a clear understanding of the team’s long-term vision and had not yet built strong relationships with key stakeholders. Before I could fully grasp the bigger picture, reorgs happened, colleagues moved to different teams, and I had to start over with a new set of teammates.

This time around, the experience has been very different. Starting toward the end of the year worked to my advantage—things were slower, giving me time to catch up with people and projects. As I’ve described earlier, building bridges and aligning with team and company goals has made the transition much smoother. Now, I’m eager to dive in, learn fast, and push the boundaries of developer productivity with GenAI, embracing the Amazon way: Work Hard, Have Fun, Make History.