[Hiring] Senior Software Engineer @Pentice

Role Description

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.

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.

Qualifications

• Typically 5+ years of software engineering experience, backend or fullstack with a backend focus.
• Proven ability to ship production systems, frontend and backend, with high uptime and minimal maintenance burden.
• Strong fundamentals in backend systems and API design: versioning, documentation, and modern authentication patterns.
• Experience with TypeScript, Go, or Python is ideal.
• 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.
• Excellent communication: thrive in high-ownership, remote, asynchronous environments.
• Disciplined AI-tool use: Claude Code / Codex in your flow.
• Fluent written and spoken English, with meaningful overlap with the Chicago time zone (Central Time).

Requirements

• Ownership of a technical domain end-to-end.
• 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.
• Ability to ask good questions, make reasonable trade-offs, and move it forward.

Benefits

• Fully remote work.
• US holidays.
• 15 days PTO (grows with tenure).
• Annual compensation review.
• Meaningful equity in a profitable company (not a lottery ticket), granted after an initial 9 to 12 month period once mutual fit is proven.

Company Description

Pentice is a small, AI-native team that builds 4:1 leverage. 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.