Overview
At Lupa, we're hiring a Technical Lead for a profitable, bootstrapped company building the world's first AI-native hospitality platform. This is a rare, high-ownership opportunity: you'll take a live, revenue-generating product used by real luxury-rental guests every single day, make it rock-solid, and then architect it into a single unified platform that can scale across buildings and cities.
The software already exists and works — one system screens and checks guests in, another runs the front desk. But it's fragile, split across separate services, and hard to see into when something breaks. Your job is to own that reality: make it reliable, make it observable, then consolidate it into one clean backend built to expand.
This is the senior technical seat. You own the architecture and the reliability number, you write code every day with AI as your multiplier, and you review everything before it reaches a guest. If you love shipping, owning production truth, and turning fragile systems into platforms, this is built for you.
Note: This is an individual-contributor role with architectural authority. It is not a people-management job. If you want to stop coding and run a team, this isn't the seat.
What You'll Do
Own reliability of the guest-facing systems. Both core systems stay up and recover fast. That uptime/incident number is yours.
Own the architecture. One data model, one backend, and the plan to consolidate the separate services without losing data or taking the apps down.
Run the migration. Move live production data carefully, with backups and rollback. No "big bang," no lost bookings.
Set the reliability standard. Error handling, retries, escalation, and observability. You define what "ready" means on this team, and the others build to your bar.
Keep the airplane flying. Guests check in through this software right now — job one is that it doesn't break while you rebuild underneath it.
Write and review code daily. Use Claude Code or Codex as a multiplier, but review and test everything before it hits production.
Tell the engineering truth straight to a non-engineer product owner who needs an honest technical partner.
What success looks like:
Day 30: Both apps audited. One place to see logs, errors, and alerts across them. A written definition of "ready." Baseline reliability numbers set.
Day 90: Reliability is trustworthy enough to expand the front-desk system past the buildings it's stuck at. First service consolidated into the unified backend with a clean, no-downtime migration — without losing velocity.
Month 12: One backend, major services consolidated and observable, platform live across buildings and into new cities. High uptime, low P1 incidents, fast recovery.
Who You Are
Must-haves:
Production systems you personally owned and kept running — bring the reliability numbers. Track record beats resume.
A real migration you ran: live data moved across systems without downtime or loss, and a clear story of how you de-risked it.
Resilience as a reflex — when asked how you'd handle a fetch that fails for a non-error reason, you reach for retries, backoff, escalation, and observability before the question is finished.
Strong full-stack TypeScript: React and Node, in production.
GCP or comparable cloud experience.
SQL and NoSQL, REST/GraphQL, webhooks, and third-party integrations (Stripe, Guesty-type APIs).
Heavy, disciplined AI tool use — Claude Code or Codex in your daily flow — and you never push agent-written code to prod unread.
Fluent English, written and spoken. Decisions get written down here.
This is NOT for you if:
You're an architect who doesn't code — this seat ships.
You only know greenfield. This is live, fragile production, not a blank repo.
"Done" means "it worked on my machine."
You want to manage a team instead of building. The team is small and you're hands-on.
You need a big engineering org to land in. There isn't one yet — you help build it.
What's In It For You
Real ownership of the architecture and the reliability number — the most senior technical seat on the team, reporting directly to the CEO.
A profitable, bootstrapped company with nine years of operating history and genuine product-market fit in a niche. No VC, no runway clock.
AI-native culture where you're expected to move fast with modern tooling as your multiplier.
Remote setup with a distributed team across Chicago and LatAm.
Schedule / timezone: Standard full-time, aligned to a distributed US/LatAm team. Application
Ready to own the engineering truth of a live, scaling platform? Send us three things:
A system you kept alive — one production system you owned, what it did, its scale, its uptime/incident numbers, and the worst outage you handled.
A migration you ran — one time you moved live data across systems, and how you avoided downtime and data loss.
One line — why this role, not another, plus your AI stack and what it does for your output.
Top candidates hear back the same day. The final stage is a single 120-minute working session: you'll design against changing facts, review and build in a seeded local repo, use AI visibly, and work through tradeoffs live with the CEO and founding engineer. No production access or live guest data is used.
Apply through Lupa today — we'd love to see how you keep systems alive.