Forward 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.

Forward Engineer

The Role

The Forward Engineer bridges the gap between business problems and working code. You’ll tackle ambiguous issues with incomplete information, identify what matters, make reasonable assumptions, build AI-powered solutions, integrate real systems (Guesty, Stripe, internal APIs), ship the solution, and verify it delivers business results. The strength of your impact isn’t measured by code volume, but by how effectively you turn ambiguity into a working outcome.

What You’ll Own

• The operational workflows at the intersection of automation and business—guest journey steps, message drafting with human review, pricing and reporting signals, and workflow engines currently run as separate tools.

• The agent systems powering these workflows: prompt design, tool use, structured outputs, evaluation, observability, and cost tracking.

• End-to-end integrations: webhooks in, actions out, ensuring idempotency, reconciliation, and observability.

• The first production version and related measurement: what changed, by how much, and how you know it worked.

What Ownership Means Here

You receive a problem and a target outcome—not a ticket queue. You write the specification, determine priorities, ship work behind a single review, and own what you build in production. If requirements are off, you identify it and propose an alternative.

How We Build

• Node, TypeScript, React

• Single repo, multiple environments, gated deploys with receipts

• Daily use of AI tools (with engineers responsible for every line in production)

• Clear, concise engineering standards

What We’re Looking For

• Two or more real examples of going from problem to decision to shipped solution—told with numbers

• Hands-on experience: you’ve built, shipped, and operated your own solutions

• Integrations with external APIs and webhooks, with an understanding of idempotency and reconciliation

• AI as an engineering tool: agents, structured output and evaluation, ability to catch and correct issues

• Clear, concise written English for both technical and executive audiences

Especially Relevant (Bonus)

• Experience in hospitality or property operations

• LLM observability and evaluation

• Event-driven systems

• Founder or solutions engineer background

Level & Scope

Mid to senior level. Reports to the Founding Engineer; works daily with the CEO to define workflow requirements.

Compensation

• Base: $60,000–96,000 USD/year ($5,000–8,000/month)

• Salary movement based on shipped integrations, production experience, AI evaluation/observability expertise, and business-facing track record

• Quarterly performance reviews following the trial period

• Equity after 9–12 months

• 15 days PTO plus US holidays

• Fully remote with quarterly team gatherings

• Colombia contracting is available

Your First 90 Days (Example)

End-to-end ownership of the pre-arrival flow: translating building house rules into a guest check-in experience, including quizzes and follow-up messages, measured by reduced parking or check-in support calls. You’ll write the spec, ship it behind a single review, and be measured on outcomes.

Interview Process (4 Rounds)

1. Screening: One ambiguous problem you owned, start to outcome (20 min + a brief technical touch)

2. Forward-Engineering Challenge: Build with AI, then defend and adapt the solution live (4 hours take-home + 90 min review)

3. System Design with AI: Live business problem with shifting constraints (60–90 min)

4. CEO Conversation

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.