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 challenges and code. You’ll take on ambiguous problems with incomplete information, discern what truly matters, make reasonable assumptions, build solutions using AI, integrate with real systems (Guesty, Stripe, internal APIs), deploy them, and verify the outcomes. The primary indicator of success is how effectively you convert ambiguity into measurable, working results—not lines of code.
What You’ll Own
The automation workflows that meet operations: guest journey steps, message drafting and review flows, pricing and reporting signals, and current engines that run as separate tools.
The agent systems behind those workflows: prompts, tool usage, structured output, evaluation, observability, and cost management.
The necessary integrations, end to end: webhooks in, actions out, idempotent design, reconciliation, and observability.
The first production version of solutions and their measurement: what changed, by how much, and how results are proven.
What Ownership Means Here
You get a problem and an outcome, not a ticket. You write the specification, choose what not to build, deploy after one review, and operate your shipped work.
If the requirements are off, you raise it and propose what’s correct.
How We Build
Stack: Node, TypeScript, React.
One repository, three environments, staged/gated deploys with receipts.
AI tools in daily engineering, full engineer responsibility for all shipped code.
Written and concise engineering standards.
What We’re Looking For
Two or more concrete examples of: problem → decision → shipped solution → measured impact (with numbers).
Hands-on: you build and ship solutions yourself and have operated your own work.
Experience with integrations: external APIs, webhooks, understanding idempotency and reconciliation.
AI as an engineering tool: agents, structured output, evaluation, and a habit of catching incorrect AI output.
Clear written English: can communicate complex ideas to both CEOs and engineers.
Especially Relevant (Bonus)
Background in hospitality or property operations
LLM observability and evaluation
Event-driven architectures
Experience as a founder or solutions engineer
Level & Scope
Mid to Senior level
Reports to the founding engineer
Works daily with the CEO on key workflows
Compensation
Base: $60,000–$96,000 USD/year (mid-level: $60,000–$78,000; senior: $78,000–$96,000)
In-band moves based on production integrations, AI evaluation, business-facing experience
Quarterly performance reviews post-trial
Equity after 9–12 months
15 PTO days + U.S. holidays
Fully remote, quarterly team gatherings
Colombia contracting available
Your First 90 Days (Sample Project)
Own the end-to-end pre-arrival flow: from building house rules to guest check-in (with quiz and follow-up messages), measured by reduction in parking/check-in inquiries to the front desk.
You author the specification, ship the solution behind one review, and bring measurable results.
Interview Process
Screening: Discussion of one ambiguous business problem you owned, start to finish (20 min + short technical touch).
Forward Engineering Challenge: Build with AI, then defend and adapt live (4h take-home, 90 min live).
System Design with AI: Business scenario with added constraints (60–90 min).
CEO Conversation.
No Loom, no read. Top candidates hear back in 48 hours. Final round is a paid deployment trial with our CEO.
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.
Hands-on engineering with AI tools, experience with external APIs and webhooks, clear written English, and two or more examples of problem-to-shipped-solution with measured impact.
Key Responsibilities
- building automation workflows
- integrating external systems
- deploying and verifying solutions
Skills & Tools
Node, TypeScript, React, Guesty, Stripe, Claude
Job Details
- Category: Software Development
- Seniority: Mid Level
- Commitment: Full Time
- Workplace: Remote — United States or Colombia
- Salary: USD 60,000 – 96,000 / year
- Languages: English
Benefits
- Generous paid time off
About Pentice
An AI-native company building an operating system for luxury high-rise buildings, expanding city by city across the U.S. — Industry: Information Technology