AI Fellow

Proper Hospitality is seeking an AI Workflow Fellow for a three month, execution focused program embedded with the CEO, President, and Chief of Staff. This role is responsible for building and deploying production ready AI workflows across our hotel portfolio, automating real operational processes tied to clear ROI, and integrating across systems including PMS, Snowflake, Microsoft 365, and guest experience platforms. This is hands on applied AI with live impact on property operations, not research or prototype work.

What This Is

We're not exploring AI at Proper Hotels. We're deploying it. Right now, AI runs our executive briefings, triages guest reviews across 11 properties, automates reporting pipelines, and handles operational workflows that used to eat hundreds of hours. We need someone who can build more of this, faster.

This is a single fellowship seat. You'll work directly with our CEO, President, Chief of Staff and executive team for three months and will be shipping production workflows from week one.

You are the execution engine inside Proper's broader Workflow & AI operating model.

What You'll Actually Do

Building (80%)

Build & Ship

• Design and deploy agent-based workflows that automate real operational tasks (not demos, not prototypes that sit on a shelf)
• Build within clearly defined ROI hypotheses approved by the Head of Workflow & AI (not speculative experiments)
• Wire together APIs across our stack: PMS, Snowflake, Notion, Microsoft 365, Google Workspace, Revinate, STR
• Build multi-agent systems that handle overnight operations, reporting rollups, task accountability, and guest experience triage
• Create tools that General Managers and department heads actually use daily

Identify & Automate

• Audit departmental workflows across the portfolio and find the manual processes burning the most hours
• Build the automation, test it on-property, iterate based on real feedback
• Transition tasks from \"someone does this by hand\" to \"this runs itself\" without losing the human touch that defines Proper

Strategy (20%)

Strategic Input

• Evaluate frontier capabilities weekly, but only deploy those that map to defined operational ROI
• Translate what's happening at the AI frontier into specific, actionable opportunities for luxury hospitality
• Help shape our internal AI skill-building program so the culture evolves with the technology

Who You Are

• You build agents and workflows, not just prompts. Show us something you've built that runs without you babysitting it
• You've shipped applied AI into production environments. Side projects count if they're real and running
• You can wire APIs together before lunch and present to the C-suite after it
• You navigate ambiguity without freezing. If a tool doesn't exist, you build it
• You understand that technology in a hotel should be invisible but felt. \"High Tech / High Touch\" isn't a slogan to you
• You're hands-on with LLMs (OpenAI, Anthropic, open-source), API orchestration, agent frameworks (eg. Openclaw), and data pipelines
• Bonus: experience with hospitality systems, revenue management, or guest experience platforms

Education

CS, Data Science, or MBA with a strong technical background preferred but not required. Non-traditional paths welcome if your portfolio speaks for itself

Program Details

• Duration: 3 months with potential to extend
• Experience: 0-2 years
• Compensation: $7,000 - $10,000/month depending on experience and location
• Access: Direct seat at the table with the CEO, President, and Chief of Staff
• Impact: Your work goes live on-property, affecting real guests and real revenue. This isn't a sandbox.

In your application please include two additional items:

• Something you've built that automates a real workflow (link, repo, or demo)
• A short note on what you'd build first if you had access to a luxury hotel portfolio's entire data stack

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.