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 delivery.

• Disciplined AI-tool use: Claude Code / Codex in your flow, and the judgment to review, test, and challenge what it produces.

• Fluent written and spoken English, with meaningful overlap with the Chicago time zone (Central Time).

Especially relevant (bonus)

• Experience in fast-paced, high-growth startups where you've worn many hats.

• A track record of prototyping and launching customer-facing products, not just internal tools.

• Designing and operating event-driven architectures.

• Performance profiling, latency reduction, and service-level (SLO/SLA) adherence.

• Reconciliation or operational software · payments (Stripe) or PMS/channel (Guesty-type) integrations · AI agents and automation.

• A genuine passion for building tools, internal or external, that meaningfully improve how people work in hospitality.

Level & scope

We calibrate on demonstrated scope, autonomy, judgment, and impact. This lands mid-senior → senior → lead:

• Mid-senior: owns meaningful systems end-to-end within our architecture; operates what they build.

• Senior: owns technical domains, handles ambiguity, makes sound architectural decisions, understands cross-system consequences, operates independently across product and production.

• Lead (ceiling): the above, plus technical direction across domains and raising the team's effectiveness. Still deeply hands-on, not a people-management role.

High-potential exception: an exceptional mid or early-career engineer who shows senior-level judgment and ownership can enter at the lower end of the range and grow fast. We hire the person, not the years.

Compensation

We publish comp in figures up front. You get all of it before you apply.

• Engagement: Full-time contractor, remote (LatAm-friendly, meaningful Chicago-time-zone overlap).*

• Base: $60,000 to $108,000 USD / year, by level (high-potential mid to lead).

• Performance bonus: quarterly, effective after the initial trial period.

• Equity: meaningful equity in a profitable company (not a lottery ticket), granted after an initial 9 to 12 month period once mutual fit is proven.

• Benefits: fully remote · US holidays · 15 days PTO (grows with tenure).

• Annual compensation review.

Interview process (4 rounds)

Built to resemble the actual work. All rounds are conducted in English.

1. Initial screening: a structured recruiter conversation covering your background, the scope you've owned, how you handle ambiguity, and mutual fit. We confirm basic expectations and salary-range alignment here, before any technical evaluation or code challenge, so no one's time is wasted.

2. Take-home + defense + live coding: a short exercise on synthetic data; then you defend your solution and live-code a change to the same challenge as requirements shift. Not leetcode, but real work on the real problem.

3. System design: a collaborative architecture exercise covering boundaries, data, reliability, failure modes, observability, and trade-offs. We want sound judgment, not the biggest diagram.

4. Founder conversation: with our CEO, covering product thinking, ownership, communication, and mutual fit.

No algorithm trivia. We want to see how you think, build, communicate, and take ownership. Clear our bar, and you'll have real ownership from the first weeks.

For candidates based in Colombia, this can instead be structured as a contrato a término indefinido (indefinite-term employment contract) under Colombian labor law, rather than a contractor agreement, whichever fits you best.

Why Pentice

If you want to own a number, move fast, and build with AI instead of around it, this is the place. Small team, real leverage, high standards, and the people who build the systems get to run them as we scale city by city. If you want a comfortable seat where effort counts more than outcomes, we are not it.

Equal opportunity

Pentice and its operating entities do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.