Director, Web Product & Experience

Pay or shift range: $165,000 USD to $200,000 USD. The estimated range is the budgeted amount for this position. Final offers are based on various factors, including skill set, experience, location, qualifications and other job-related reasons.

Proper Hospitality operates a growing portfolio of luxury and lifestyle hotels, restaurants and bars, and membership clubs. Our web presence is our digital storefront — the place where every paid channel, CRM flow, and direct booking converts. As we scale across 12 properties and beyond, this platform becomes more complex, more consequential, and more central to how we grow.

The Director, Web Product & Experience will own that platform end to end. This is a technical product leadership role accountable for the strategy, architecture, performance, and AI-native evolution of our entire web presence. The right person thinks in systems, leads with data, and builds infrastructure that compounds over time — with deep fluency in how AI is reshaping both how websites are built and how they are discovered.

This role reports directly to the Chief of Staff and operates as a cross-functional leader across Marketing, Revenue, Sales, and Property teams. It sits at the intersection of our digital storefront and Proper OS — our internal data, automation, and agentic platform — ensuring every platform decision advances business objectives while delivering exceptional experiences for guests and customers across every touchpoint.

• Own the long-term vision and roadmap for how our digital storefront evolves across all current and future properties, with every investment sequenced by revenue impact and a clear business case behind it
• Lead the evaluation and evolution of the web stack as the portfolio scales; ensure infrastructure decisions today support 20+ properties tomorrow without rebuilding from scratch
• Drive scope, accountability, and delivery on the  rebuild, , and all Collective property migrations; own the Figma-to-Sanity pipeline and developer sign-off
• Build and maintain a new-property launch playbook so each opening is faster, cleaner, and more consistent than the last

• Lead the full picture of site performance across the portfolio: conversion rate, funnel health, page speed, uptime, booking engine stability, and downstream channel impact
• Own daily and hourly monitoring with defined triage paths when performance drops; resolve issues before they touch revenue
• Partner with the Growth and CRO team to surface site-side hypotheses, prioritize tests by revenue impact, and ensure the platform is always removing friction and enabling faster test execution
• Define and lead how AI operates across the web product: agentic content workflows, automated publishing pipelines, AI-assisted QA, and LLM-native site architecture built to earn citation in AI-driven search
• Set the standard for human-in-the-loop design as the platform scales, ensuring AI automation is reliable, auditable, and aligned with brand standards at every stage
• Translate emerging AI search, GEO, and LLM citation trends into concrete implementation briefs — keeping site architecture ahead of the curve, not reacting to it
• Own the web product’s role within Proper OS, ensuring tracking architecture, CMS infrastructure, and site-side data quality feed reliably into the broader agentic platform

• Own the full reporting stack from tracking implementation through to the dashboards leadership relies on; one source of truth across all 12 properties, updated in real time
• Architect and maintain GA4 event taxonomy, booking funnel instrumentation, GTM container architecture, and server-side tracking including Meta CAPI, Google Enhanced Conversions, and deduplication logic
• Size web opportunities in dollars, build the business case, and be held to the outcome
• Own day-to-day prioritization, technical specs, and QA across the external development team and agency partners; hold all vendors to outcomes, not activity
• Write clear, complete specs and manage delivery from brief through sign-off; maintain timeline…