Waypoint AI

Waypoint AI is building Chip - the AI Support Engineer. Chip autonomously triages, routes, and resolves complex support cases. Chip also answers technical support questions, generates post mortems & surfaces insights for engineering, support, product & revenue teams.

We are a Czech-American B2B startup. We raised CZK 60M earlier this year and already work with leading enterprises in production including Volvo, ClickHouse & Kpler.

About the Team

We’re a small team doing big things — tackling hard problems, exploring new ideas, and working with people who care about both the craft and each other.

We’re enthusiastic about AI and treat it as a daily collaborator: we have good experience with vibe coding and pair-programming with AI, using it for code review, debugging, and design exploration, and actively experiment with how AI can make us faster and better engineers. We treat AI as a multiplier—not a substitute for good engineering judgment. We’re opinionated but curious, and we value thoughtful discussion over ego.

What you’ll do

Own vertical slices end‑to‑end with a backend emphasis.
Operate background work with Dramatiq (idempotency, retries, scheduling) to power durable workflows and integrations.
Design and build typed HTTP APIs; keep them fast, well‑documented, and maintainable.
Evolve Postgres schemas safely (migrations, data backfills) with a focus on correctness and transactional integrity.
Measure what matters: logs/metrics/tracing and reliability.
Keep things secure and privacy‑aware by default.
Ship changes through CI/CD pipelines and take responsibility for production behavior.
Collaborate with product & design; build minimal UIs when it unblocks learning.
Use AI pair‑programmers (Cursor, Claude Code) to move fast, but we value correctness, refactoring, and sustainable pace.

You might be a fit if you

Have strong backend foundations (HTTP, SQL, transactions, indexing, caching) and sound engineering judgment.
Have experience or eagerness with Django/Ninja, Postgres, typed Python, and pytest.
Are comfortable in containerized dev flows and automation (Makefiles, Docker Compose); CI/CD experience.
Care about high-level system architecture and long-term system evolution.
Have clear written communication; you document decisions and think in small, shippable slices.

Nice to Have

Redis and search basics; realtime experience (Channels/WebSockets) when needed.
IaC and cloud familiarity.
You are comfortable overlapping into modern frontend when needed (React/Next/TS/Tailwind) and product‑minded decision maker. Frontend work is pragmatic and purpose-driven—not pixel-perfect UI ownership.
LLM product experience: evaluations, cost and latency controls; vector search, knowledge graphs.
You enjoy domain modeling (DDD) and clean boundaries - domain‑driven design instincts: good naming, boundaries, and evolution over time.
“You build it, you run it” mentality.
Exposure to or interest in event sourcing architecture.

Why Waypoint

Real ownership across APIs, data, and background jobs; measurable impact, fast feedback loops.
We’re at the stage where early architectural decisions matter, and you’ll help shape the system before habits calcify.
Sharp, kind teammates who value craft and pragmatism.
Flexible location/hours: We have a beautiful office space at Prague 7 (Holešovice) in a modern quiet area with the possibility to work remotely.
Competitive compensation (aligned with senior CZ market) and meaningful equity.

How to Apply

Send us:

Your application together with a CV or a link to your LinkedIn profile.
A project or feature you shipped end‑to‑end, or your personal github repository.
A brief note on how you use Cursor or Claude Code in your daily work routine.