Product Manager - Proper OS

Proper Hospitality is seeking an experienced Product Manager to join our corporate team in Los Angeles.

What We're Building

Hospitality is one of the oldest, most human industries in the world. It has also barely changed operationally in decades. We're changing that — not with a point tool, not with a clever chatbot, but with a platform that reimagines how an entire property thinks, operates, and serves its guests.

• This is a product, not an internal tool.
• It has to work on day one at a single property and scale cleanly to hundreds.
• Every architectural decision compounds over time.
• Every agent will be onboarded to new properties, new teams, and new data environments.

We are replacing workflows that have been done by hand for decades. Done right, this changes what it means to run a hotel.

What This Is

You are the translation layer. Department heads tell you what's broken in their day. You turn that into a spec the engineering team can ship in a sprint. You validate the output. You run the adoption playbook.

You will get your hands dirty. You'll sit in morning standups at hotels, shadow department heads, build quick prototypes in Claude to test concepts, and write acceptance criteria tight enough that engineering doesn't have to guess. You will work daily with our engineering lead and the Chief of Staff, CEO, President, and COO.

What You'll Actually Do

Requirements & Specs (50%)

• Embed with department heads and Hotel GMs to understand their actual workflows — not what they say they do, what they actually do.
• Write agent specs with clear acceptance criteria ("Proposal agent pulls fact sheet + F&B minimums from wiki, generates draft in brand voice, posts to Teams for DOS review. Acceptance: under 15 min from inquiry to draft, DOS edits < 20% of content.")
• Prioritize the backlog. When leadership sends 14 ideas and engineering has capacity for 3, you decide which 3 and defend the decision with data.
• Run the intake process for new agent requests — triage, scope, estimate, schedule
• Build quick prototypes in Claude or lightweight tools to test concepts before engineering invests real cycles.

Adoption & Feedback (30%)

• Run the 4-week adoption playbook per workflow: build with them (Week 1), validate quietly (Week 2), soft launch (Week 3), expand (Week 4).
• Validate agent output quality before go-live — is the briefing actually useful? Is the proposal actually in brand voice? Would the GM read this before their standup?
• Track adoption metrics: are people reading the briefing? Has anyone muted the Teams channel? Are department heads referencing agent data in their updates?
• Collect and route feedback to engineering. When a GM says "this alert is noise," you figure out why and write the threshold adjustment into the next sprint.

Prototyping & Strategic Input (20%)

• Build working prototypes to test assumptions before committing engineering time.
• Evaluate new AI capabilities weekly — but only deploy what maps to defined operational ROI, not speculative experiments.
• Translate what's happening at the AI frontier into specific, actionable opportunities for luxury hospitality.

Who You Are

• You've been a PM for 3–6 years.
• You've shipped products that non-technical users depend on daily — not just internal tools for engineers.
• You understand LLMs and AI agents at a practical level. You've used Agentic AI tools extensively (Claude, Openclaw, Perplexity computer). You built prompts and understand RAG conceptually. You don't need to write production TypeScript, but you can read a spec and spot when something won't work.
• You've sat with end users and changed a roadmap based on what you learned. Not what the exec suggested — what the user actually needed.
• You write clearly. Agent specs, adoption reports, status updates for the CEO — you're comfortable at every altitude.
• You're comfortable with ambiguity. This isn't a Google PM role with a 6-month planning cycle. It's a startup PM role where you're defining the product while building it.
• You can wire together a prototype before lunch and present the business case after it.
• Bonus: experience with hospitality systems, revenue management, or guest experience platforms. But what matters more is the ability to learn a domain fast and empathize with users who are not technical.

Program Details

• Experience: 3–6 years in product management
• Compensation: $150K–$175K DOE
• Contract-to-hire option available.
• Location: Los Angeles, in-person. You need to be at hotels.
• Access: Direct seat at the table with the CEO, President, COO, and Chief of Staff
• Impact: Your work goes live on-property, affecting real guests and real revenue across 12 luxury lifestyle hotels. This isn't a sandbox.

In your application, include:

• A product you shipped where the hardest part was getting non-technical users to adopt it — what broke and how you fixed it.
• A spec or PRD you wrote that you're proud of (can be redacted).
• A short note on how you'd approach your first 2 weeks embedded with a hotel department head you've never met

Proper Perks & Benefits

Compensation & Recognition

• Competitive Salary + Bonus: Rewarding exceptional talent and performance across all levels.
• Recognition Programs: Celebrating achievements big and small through company-wide appreciation and milestone rewards.
• Annual Performance Reviews: Regular opportunities for feedback, growth, and advancement.

Culture of Growth & Belonging

• Culture of Growth: A collaborative, design-forward environment that values creativity, intelligence, and curiosity — where learning and excellence are a daily practice.
• Guided Skills Development: Access to training, leadership programs, mentorship, and cross-property mobility to encourage achievement and discovery.
• Diversity, Equity, Inclusion & Belonging: We honor individuality while fostering a culture of respect and belonging across all teams.
• Community Engagement: Opportunities to give back through local volunteerism, sustainability, and charitable partnerships.

Health & Wellness

• Comprehensive Health Coverage: Medical, dental, and vision plans through Aetna, designed to fit a range of personal and family needs.
• Wellness Access: Company-subsidized memberships with Equinox and ClassPass, plus wellbeing workshops and mental health resources.
• Employee Assistance Program (EAP): Confidential support for emotional wellbeing, financial planning, and life management through Unum.

Time Off & Flexibility

• Paid Time Off: Flexible PTO plus 11 paid holidays each year for corporate team members.
• Paid Parental Leave: Paid time off for eligible employees welcoming a new child through birth, adoption, or foster placement.
• Flexible Work Practices: Hybrid schedules for eligible roles and an emphasis on work-life balance.

Financial Wellbeing & Core Protections

• 401(k) Program: Company match of 50% of employee deferrals, up to the first 4% of eligible compensation.
• Employer-Paid Life & Disability Insurance: Core protections with optional additional coverage.
• Financial Education: Access to planning tools and workshops to support long-term stability and growth.

Lifestyle & Travel Perks

• Hotel Stay Benefits: 75% off BAR (floor of $100) across the Proper portfolio.
• Design Hotels Partnership: 50% off participating Marriott Design Hotels.
• Dining Discounts: 75% off food & beverage at all Proper Hospitality outlets.
• Lifestyle Perks: Complimentary or subsidized parking, cell phone reimbursement, and exclusive hospitality and retail discounts.

Why Join Proper Hospitality

At Proper, we build experiences that move people — and that begins with the team behind them. As a best-in-class employer, we’re committed to creating one of the Best Places to Work in hospitality by nurturing a culture where creativity, excellence, and humanity thrive together.

Everything we do is grounded in the belief that hospitality is more than a profession - it’s an opportunity to care for others and make lives better. Guided by the Pillars of Proper, we show up with warmth and authenticity (Care Proper), strive for excellence in everything we do (Achieve Proper), think creatively and resourcefully (Imagine Proper), and take pride in the style and culture that make us who we are (Present Proper).

We believe our people are our greatest strength, and we invest deeply in their wellbeing, growth, and sense of belonging. From comprehensive benefits to meaningful development programs, Proper is designed to help you build a career, and a life, that feels as inspiring as the experiences we create for our guests.

Our Commitment: Building the Best Place to Work

Our Best Place to Work initiative is a living commitment — a continuous investment in our people, our culture, and our purpose. We listen, learn, and evolve together to create an environment where everyone feels empowered to imagine boldly, achieve confidently, care deeply, and present themselves authentically.

At Proper, joining the team means more than finding a job — it means joining a community that believes in building beautiful experiences together, for our guests and for one another.