Senior Software Engineer

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.

HOW WE WORK

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.

HOW WE PAY

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.

WE RUN ON C.L.O.U.D.9, OUR CULTURE OPERATING SYSTEM

• C · Customer Obsession. If they're not raving, we missed it.

• L · Leadership Through Ownership. No passengers, only drivers.

• O · Operational Excellence. How we do one thing is how we do everything.

• U · Urgency With Intelligence. Act now, iterate later.

• D · Do the Right Thing. Character over convenience.

• 9 · The 9x Mindset. 10% better is safe; 9x better is unforgettable.

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.

THE ROLE

The software is live (real guests check in through it daily), and parts of it are fragile because we've moved fast. That's the opportunity: you'll own making it reliable, observable, and world-class, and set the engineering standard as we scale. You'd be one of a handful of builders, with real scope from week one, working directly with the Founding Engineer.

This role is for you if you want deep ownership in a real, profitable business over lottery-ticket odds at a hyped startup, and you'd rather define the standard than inherit one.

WHAT YOU'LL OWN

A technical domain end-to-end. You own a domain, not a queue of tickets:

• Core operational workflows: reservation, turn, and guest-service logic.

• External integrations, synchronization, and reconciliation (Guesty, Stripe, and more).

• Pricing and operational logic; agent-driven workflows and automation.

• APIs, data models, and event-driven systems.

• Monitoring, reliability, and failure recovery, plus the production systems that run it.

With the Founding Engineer, you'll shape the shared backbone: system boundaries, operating records, events, permissions, auditability, security, and reliability.

WHAT OWNERSHIP MEANS HERE

You get a problem, not a ticket (e.g. "reliably synchronize this workflow across several external systems"), and drive it end to end:

understand → question assumptions → design → implement → test → deploy → observe → operate.

Requirements won't always be complete. Ask good questions, make reasonable trade-offs, and move it forward. Don't wait for every decision to be made for you. Shipping isn't the end of ownership; production is part of engineering. Over time you own a domain independently and know enough of the platform to operate confidently when others are unavailable.

HOW WE BUILD

• Backbone, not bureaucracy. Some foundations we can't skip: data ownership, boundaries, permissions, auditability, security, reliability. We don't build enterprise architecture for problems we don't have.

• Pragmatism over purity. What's the actual risk? The simplest thing that works? What must be correct now? What stays reversible?

• Direct communication. Surface risks and disagreements early, including with the Founding Engineer or the CEO. Disagree clearly; change your mind on new evidence.

WHAT WE'RE LOOKING FOR (THE BAR)

We hold a high bar and calibrate on demonstrated capability, not a specific stack. Our stack today is TypeScript / Node + React, but we hire for capability, not a stack. You have:

• Typically 5+ years of software engineering experience, backend or fullstack with a backend focus. We calibrate on demonstrated scope, not years, so an exceptional high-potential engineer with less can still clear the bar.

• Proven ability to ship production systems, frontend and backend, with high uptime and minimal maintenance burden. You built it, shipped it, and owned it when it broke.

• Strong fundamentals in backend systems and API design: versioning, documentation, and modern authentication patterns. Experience with TypeScript, Go, or Python is ideal (capability over a single language).

• Fluency with relational databases and SQL (PostgreSQL a plus); familiarity with a major cloud platform (GCP, AWS, or comparable) and modern observability tooling.

• Clean-code discipline and automated testing: quality is a habit, not a phase.

• Product sense and an MVP mindset: balance technical quality with speed and user value; scope a milestone, ship it, learn, iterate. You push back when something doesn't feel right.

• Excellent communication: you thrive in high-ownership, remote, asynchronous environments, and collaborate across product, design, and operations, including directly with external partners and customers on requirements, integration, and iterative deli