This month, I announced I have resigned my position as a Principal Software Engineer for Amazon Web Services (AWS) and accepted a new role as a Member of Technical Staff with Anthropic. After announcing my transition out, 34 people at AWS scheduled office hours for 1:1 interviews with me, and I got asked a lot of questions. I’m sharing some of the common questions and answers here. Whether my thoughts are actually worth sharing is a question I try not to think about too hard. (Plus, two people specifically asked if I could blog more after I leave. I’m choosing to believe they weren’t being sarcastic.)

Most asked questions

What made you want to leave?

People were implying—and a few said outright—that I had a position too good to give up. I didn’t make this decision in haste. It took months of consideration, during which time I had many chats with my wife, family, managers, mentors, and friends to collect diverse viewpoints. Those conversations helped me identify my motivations.

Ultimately, it came down to 3 factors:

  • Anthropic is on the cutting edge of AI innovation, a technology that I believe is going to transform our economy and society. I’m aligned with the company’s mission and values, and I want to contribute to something meaningful. While the company is a startup and may not end up being profitable, I think their research will outlast the corporate structure. I hope the science it produces benefits humanity.
  • At AWS, I had been on the same team for 6.5 years and was happy with the state of the projects. In 2025 specifically, I received lots of positive feedback that my focus area, a project called Barge, had delivered “best in class” tooling. I would rather leave a project in a good state than one falling apart.
  • Anthropic’s work climate is favorable. By this I mean the combination of compensation and equity, benefits, work-from-home flexibility, in-office perks, and “vibe”. The last part, “vibe”, is important. I want to be in a space where people are excited and thrilled about their work, and not just clinging to a job, hoping they don’t get laid off to boost profits or forced out to meet a quota for unregretted attrition.

What do you recommend for my career?

Many people asked me for my input. Should they stay at Amazon? Would I be able to hire them into Anthropic? How can they get promoted if they stay at Amazon?

While my feedback was adapted to each individual, some common themes emerged:

SDE II (L5) looking for promotion to senior SDE (L6)

I’ll probably need to write a separate post about this one. The promotion to L6 SDE at Amazon is challenging. Many people wait years, eager for the significant bump in pay and the sense of security that comes from the title.

Right now, Amazon is in a period of contraction. They’ve laid off thousands in 2025 alone. In the “before times” when teams were aggressively growing, promotions to L6 seemed to be easier. Because Amazon brought in so many new college hires, it was easier for anyone with experience to guide a team and fulfill the expectations of a senior engineer. Now, however, teams are shrinking, not growing, leaving less space for people to move into a team-lead type role.

My advice to people asking about this was to dig deeper into the problem space. There are countless things that need solving. Perhaps your current team is too heavy on senior engineers to demonstrate next-level work in your current scope—but there are many unsolved problems. If you can find those unsolved areas, and make it clear to your managers and other leaders why those problems need solving AND help guide a team to deliver on it, you may find that’s a path to promotion. That said, it might not work. The other, more likely path, is that a senior/principal engineer leaves a team and you have grown in skill and expertise so you can fill their shoes.

Stay at Amazon or quit?

Once it came out I was leaving, people started sharing with me they were either interviewing, planning to leave, or were strongly considering it. They wanted my input on my own decision-making process to check it against their own.

People had many reasons for considering quitting Amazon:

  • Frustration with bureaucracy and politics or other team dynamics
  • Lack of opportunities for promotion
  • Desire for more flexibility to work hybrid/remote
  • Looking to increase income by moving to companies that pay better
  • Insecurity due to Amazon’s persistent layoffs, and wanting to move first instead of waiting to be cut

As a side note, in my final exit interview, I shared some of these reasons anonymously with my director. He wasn’t surprised at all. I took that to mean these are all common issues a director deals with. New to me, not to him.

Who will replace you?

Because I had stayed in the same team and position for 6.5 years, I accumulated a lot of domain knowledge and understanding of history. But I want to be clear: I’m not special. There are many engineers who know these systems well. I was never a single point of failure—though I did have a unique perspective from a breadth of knowledge across areas and deep insights in a few specific domains.

I don’t feel any guilt about leaving. Amazon is going to be fine. It’s a huge company with enormous resources. The people around me will get to learn and grow in ways they couldn’t have with me always present to answer questions or make calls.

There’s some discomfort in realizing you’re not as essential as you thought. Better to leave before Amazon figures that out too.

I left people a “redirect” table pointing to other managers and engineers taking on leadership of various areas of work. The machine keeps running.

What’s next

Stepping out of the spotlight

Amazon has a culture of high expectations for anyone with principal-level titles. For years they’ve hosted an internal talk series called “Principals of Amazon”. They record the sessions and the content is often used as reference material. In meetings, I found that the principals could often use their influence and title to break ties or make final calls. On more than one occasion, senior managers directly asked “what is your call here, Nate?”. And in my organization, my role extended beyond software engineering into people management: hiring, mentoring, and coaching.

Lalit Maganti recently wrote a post about his experiences as Staff+ at Google on a developer tools and infra team. His post resonated with me because I, like Lalit, was not on a “product” team at AWS where we had direct external customers. That said, there was still some level of spotlight internally. I was involved in giving internal talks to showcase our internal services and tooling. I wrote newsletters and Slack announcements. At Amazon, this “internal marketing” is necessary to raise awareness. The company is so large and filled with so many bright, talented people, that the pace of innovation is breakneck.

In my next role at Anthropic, there is no “principal” in my title. I’m a “Member of Technical Staff”, the same title as all of my peers. I’m eager to see how this changes conversations—it’s been a long time since I was new anywhere. And I’ve found at Amazon that my title was often entering the meeting before me, so anything I said came with an air of authority, regardless of whether my opinion had technical merit or not. Moving out of the spotlight seems refreshing—a chance to ground myself again.

Why Anthropic, why now?

I’ve been cautious about avoiding hype in making this choice. I’d been considering Anthropic, xAI, or OpenAI for over a year. I actually had an application open in 2024 but held off—I needed time to clarify my thinking. At some point in the last year, it became clear a transition was needed. I was either going to change roles internally at AWS or leave.

I spent my last three months at Amazon exploring a new project space, but I’m more excited about what I’ll get to work on at Anthropic. I was able to have several interviews beyond the typical hiring loop to learn about what I’ll be doing there. I’m going to be intentionally vague about the specifics for now, but hopefully I’ll have a chance to blog more in the future.

I’m excited to see how AI models are actually developed. I’ve heard Dario say that a lot of the work to do science comes down to engineering. I want to be part of that.

Work flexibility

I’m also excited to have more flexibility in how I work. There’s an Anthropic office in Seattle, but as I understand it, there isn’t a “badge report” system like Amazon has been using to enforce return-to-office goals—and in some cases, force out people unwilling to comply. Everything I’ve heard indicates people go to the office because they’re genuinely excited to be there, and the atmosphere is vibrant and collaborative.

My office at Amazon had begun to feel empty and hollow. I would drive a long commute to sit in a cubicle and join Zoom calls. I had one of the better cubicles—I had a window—but I often felt isolated from the people around me.

Back to coding

Finally, I’m excited to keep coding. Coding is why I got into this profession.

I’ve enjoyed learning to use AI as a coding assistant. I’ve heard Dario say 90% of Anthropic’s code is written by AI. I was maybe getting 60-70% of that in my work at Amazon, but the spec-driven approach of Kiro didn’t feel quite right—too heavy for small changes. I’m curious to see what Anthropic has developed to make AI-assisted coding even more effective.

I believe AI will transform my profession even more than it already has, and I’m eager to contribute. There’s vast, unlocked potential that’s been too hard to achieve due to the difficult nature of coding prior to AI. I’m excited to see what we—collectively, humanity—are able to do with better technology.