Technical Lead – Fullstack & Automation

About Pentice

Pentice is the operating system behind Cloud9 Windy City: 63 units across 13 Class-A residential buildings in Chicago, turning long-term luxury apartments into hotel-grade short stays and unlocking top-line revenue for the buildings' owners. We are building toward the autonomous operating system for luxury high-rises, and expanding city by city across the U.S.

A small, AI-native team that builds 4:1 leverage. You work alongside Claude every day; AI is a co-pilot, not a buzzword. The team is distributed — some in Chicago, most in Latin America. We move fast, decide fast, and cut politics. We don't hire to fill seats. We hire to pull levers that move numbers. Outcomes beat effort beats intentions.

Every role we post carries its compensation in figures, in the currency you would be paid in. Base is one part. The rest is a quarterly bonus tied to the one number your seat owns. If you move the number you are paid for it, and if the number does not move the bonus does not pay. You get both halves before you apply.

• C Customer Obsession.

• L Leadership Through Ownership.

• O Operational Excellence.

• U Urgency With Intelligence.

• D Do the Right Thing.

• 9 The 9x Mindset.

Three of those decide who lasts here, so read them as warnings rather than slogans.

Leadership Through Ownership. You will be handed a number and very little scaffolding. Nobody will sequence your week for you. If you need a manager to tell you what matters this Tuesday, you will be unhappy here inside a month.

Urgency With Intelligence. We ship, measure, then fix. A good decision today beats a perfect one in three weeks. If you need complete information before you move, this pace will feel reckless to you.

Do the Right Thing. You will get chances to report a number that flatters you. We check. Someone who softens a bad result once does not get a second chance to.

Cloud9 runs luxury short-term rentals across Chicago, and we're turning the operation into a platform (Pentice). The software exists and real guests use it every day:
Lighthouse screens and checks guests in, Glass Bridge runs the front desk. It works. It is also fragile, split across separate services, and hard to see into when something breaks.

We need someone to own that. Make it reliable. Make it observable. Then pull the separate services together into one backend that can run every building and every city we expand to.

This is the senior technical seat. You own the architecture and the reliability number. You work alongside our founding engineer and a junior, and you report to me. You write code every day with AI as your multiplier, and you review everything before it reaches a guest.

This is an IC role with architectural authority. It is not a people-management job. If you want to stop coding and run a team, this isn't it.

Reliability of the guest-facing systems. Lighthouse and Glass Bridge stay up and recover fast. That number is yours. Today it's not good enough to trust, which is the whole reason this role exists.

The architecture. One data model, one backend, the plan to get the separate services there without losing data or taking the apps down.

The migration. Live production data, moved carefully, with backups and rollback. No "big bang." No lost bookings.

The reliability standard. Error handling, retries, escalation, observability. What "ready" means on this team. You set the bar and the others build to it.

Keeping the airplane flying. Guests check in through this software right now. Job one is it doesn't break while you rebuild underneath it.

Day 30. You've audited both apps. There's one place to see logs, errors, and alerts across them. The team…