Position OverviewThe 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.
Key ResponsibilitiesPlatform Strategy & Architecture- 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 properhotel.com rebuild, properhospitality.com, 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
eCommerce & Site Performance- 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
AI Platform Leadership- 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
Measurement & BI Infrastructure- 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
Dev Team & Vendor Leadership- 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 and scope discipline across all active projects
- Systematize repetitive web operations through workflow automation so the business scales without headcount scaling with it
Cross-Functional Leadership- Serve as the primary web platform partner to Marketing, Revenue, Sales, Operations, F&B, and Property teams - ensuring the site consistently reflects commercial priorities and delivers on guest and customer expectations across the portfolio
- Translate business team needs into clear platform requirements, balancing competing priorities across functions without losing sight of the roadmap or diluting technical standards
- Champion the web platform as a shared business asset, building the relationships and communication rhythms that keep stakeholders informed, aligned, and invested in the platform's success
Qualifications & Experience- 6 to 8 years in technical digital product management or web product ownership, with direct accountability for site conversion and performance outcomes across a multi-site or multi-brand portfolio
- Demonstrated track record of owning a web platform roadmap end to end: from business case through architecture decision through delivery and performance measurement
- Deep expertise in tag management and analytics instrumentation: GA4 event taxonomy, booking funnel instrumentation, GTM container architecture, DebugView troubleshooting, and server-side tracking including Meta CAPI, Google Enhanced Conversions, and deduplication logic
- Proven AI fluency in production - shipped AI-native workflows, not just used AI as a productivity tool; hands-on experience with pipeline design, agent output evaluation, and human-in-the-loop standards
- Actively follows and applies developments in AI search, generative engine optimization (GEO), and LLM citation; translates trends into concrete development and SEO briefs, not slide decks
- Sanity CMS strongly preferred: content modeling, schema design, and how architecture decisions affect SEO and AI crawlability
- Experience collaborating within a high-velocity CRO program: contributing site-side hypotheses, evaluating test feasibility, and prioritizing by revenue impact
- Fluent in managing external development teams and agencies: writes specs, QAs output, and holds partners to timeline and scope
- Luxury, lifestyle, or hospitality background preferred - not required for the right technical operator
Leadership Profile- A systems thinker who builds infrastructure others build on top of, and holds the long view even when short-term noise is loud
- A technically credible operator who earns trust from developers and executives equally, and can communicate complexity without losing either audience
- A commercially-oriented builder who sizes opportunities in dollars, sequences work by impact, and is accountable to outcomes - not just delivery
- An AI-native leader who has shipped real AI workflows in production and understands both the potential and the operational discipline required to make them reliable at scale
- A rigorous analyst who treats data as a primary language and builds measurement infrastructure the rest of the business depends on
- A cross-functional partner who earns influence through clarity, follow-through, and a genuine investment in what other teams are trying to accomplish
Why This RoleThis is a rare opportunity to own a web platform that is genuinely consequential - not a maintenance role with a strategic title. You will be building the infrastructure that scales a 12-property luxury portfolio into its next chapter, at the exact moment AI is reshaping how websites are built, how they are discovered, and what it means to compete for attention and conversion.
The work is cross-functional, highly visible, and directly tied to revenue. You will have a seat at the table with senior leadership and a real mandate to build something that lasts. If you are the kind of operator who gets restless when the platform is not compounding, this role was written for you.
Salary: $165,000-$200,000 BOEProper Perks & Benefits 
