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Sierra has been one of the most interesting AI startups to watch. Founded by Bret Taylor (former Salesforce co-CEO) and Clay Bavor (former Google VP), they're building AI agents for customer service, and they're hiring in Japan and Singapore etc.
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This series collect stories from anonymous candidates to provide real insights regarding software engineer interview process in Japan/Singapore
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The process started with a 30-minute recruiter call. No technical questions here, just a conversation about my background, why Sierra, and what I'm looking for. The recruiter was genuinely curious about my motivation for joining an AI startup versus staying at a bigger company. They also explained the interview process clearly upfront, which I appreciated. No surprises.
One thing worth noting: they asked about my preferred programming language early on. Sierra primarily works in Python and TypeScript, and they want you to interview in one of those. If you're a Java or C++ person, you'll want to get comfortable in Python or TS before the process starts.
This is where it gets interesting. Not LeetCode — it simulates a real scenario you'd encounter working at Sierra. Conducted on CoderPad (sometimes they ask you to share your screen). You'll be given a practical multi-part problem that builds progressively. For example, you might start by calling an API endpoint that fails occasionally but eventually succeeds. After solving that, the response contains a product list with fallback IDs, and you need to iterate through the list and resolve each product's eventual set of IDs into the product objects.
The key here is that each follow-up adds new requirements on top of your existing code. This tests whether you write flexible, extensible code from the start and not whether you memorized a sorting algorithm.
This round was surprisingly fun. You don't need to write a lot of code — you need to understand code.
You're given a small codebase (around 4-5 files) that implements an agent, plus a diagram showing how
the agent should work. The diagram is your source of truth. You can run the agent and iterate on the CoderPad terminal.
At each part, the interviewer describes a scenario they want to test. You need to figure out what's wrong in the code and fix it before moving forward. There were about 3 bugs to find, and if you have time left, they'll ask you to think about how to optimize the code
This is a two-part round and the most unique part of Sierra's process.
Part 1 — Take-home: You receive an API key and a prompt to build an agent that carries out different functions
Part 2 — Onsite presentation (60 minutes): You present your agent to an interviewer who will ask a ton of "why" questions. Why this architecture? Why this approach to tool calling?
Behavioral interview focused on agency and collaboration. You'll be asked about how you've demonstrated ownership and driven projects forward in past roles. How you collaborated with others, handled disagreements, and worked across teams.
They also care about alignment — how this role fits your professional interests and career goals. This isn't a generic "tell me about a time" round. The questions are specific and they dig into details.
Sierra's interview process is practical and well-designed. They test what actually matters for the job: can you write clean, extensible code? Can you adapt when requirements change? Can you reason about data structure tradeoffs? Can you communicate clearly about your past work?
The technical screen with layered follow-ups is the most unique part. It rewards engineers who write flexible, well-structured code over those who memorize algorithms. If you've spent your career building real systems, you'll feel right at home. If you've only been grinding LeetCode, you might struggle with the open-ended nature of the problems.
The whole process took about two to three weeks. Communication was clear throughout. For a startup, they run a tight process.
My biggest takeaway: Sierra interviews like a company that actually cares about hiring good engineers, not good test-takers. Focus your preparation on practical coding, class design, and being able to talk concretely about your past work. That'll get you further than memorizing sorting algorithms.
Want to save your preparation time? Check out https://furustack.com to understand what you need to prepare instead of guessing. Also https://singdev.fyi contains real interview experience with Sierra, so check it out !
