Product Director Jobs in Chicago, IL

Who we are:

At Preferred Travel Group, we champion the power of travel to inspire meaningful connections and enrich lives around the world. As a global family of brands and programs representing the finest independent hotels and resorts, we are united by a shared belief in authenticity, collaboration, and the value of independent spirit. Our culture reflects our ideology in action: people first, relationships at the center, and a commitment to creating lasting impact for our partners, our global community, and one another. When you join Preferred, you become part of a purpose-driven organization where ideas are welcomed, growth is encouraged, and your work contributes to shaping the future of travel.

Why this role matters:

Preferred Travel Group (PTG) operates a premier hotel loyalty rewards program connecting discerning travelers with a curated portfolio of independent luxury hotels worldwide. Our loyalty platform sits at the heart of everything we do, driving member acquisition, engagement, and retention across a global portfolio of properties. As we accelerate investment in our digital platform, we are adding a Senior Product Manager to own the end-to-end product experience across iprefer.com and the I Prefer mobile application.

We are seeking a strategic, data-driven, and customer-focused Senior Product Manager who can translate vision into execution, leading the delivery of digital experiences that engage travelers, strengthen loyalty, and support business growth. This is a high-impact, highly visible role reporting directly to the Senior Director of Product. You will be the day-to-day product owner for PTG's primary Brand and B2B user-facing digital properties, responsible for roadmap, backlog, and delivery execution. You will partner closely with engineering, design, marketing, and loyalty operations, and you will be deeply embedded in a modern stack that includes a Next.js front end, Hygraph headless CMS, SynXis reservations, and our enterprise loyalty platform. Success in this role comes from delivering digital experiences that increase engagement, personalization, and conversion across PTG's owned channels. The Director will establish a clear and scalable digital product roadmap, ensuring UX and product align to effectively enhance customer experiences, drive revenue growth, and support strategic business objectives.

What you’ll deliver:

• Delivery leadership across web and mobile consumer facing surfaces
  • Own end-to-end delivery planning for the brand and B2B consumer web and mobile releases, including roadmap sequencing, backlog health, sprint readiness, launch coordination, and post-release validation.
  • Partner with engineering and UX to break strategy into well-defined epics, user stories, acceptance criteria, and release plans that keep teams aligned and delivery predictable.
  • Maintain a clear operating cadence for stakeholder reviews, dependency management, and delivery trade-off decisions across web, mobile app, CMS, reservations, and loyalty platform workstreams.
• Primary Product Owner for B2C digital experiences
  • Serve as the primary Product Owner for PTG’s Brand sites, ensuring the digital roadmap reflects member needs, commercial goals, brand priorities, and operational requirements.
  • Drive continuous improvement of discovery, booking, account, offers, and loyalty redemption experiences across responsive web and mobile app surfaces.
  • Translate member insights, business priorities, analytics, and stakeholder feedback into a prioritized roadmap that balances near-term conversion gains with longer-term platform scalability.
• Data-informed decision making
  • Establishing and defining product KPIs, instrument key user flows, and utilizing analytics across the platform to inform prioritization decisions and demonstrate product impact
  • Define and track GEO performance metrics, ensuring application of PTG's methodology for measuring discoverability.
• B2B product oversight and people leadership
  • Provide day-to-day prioritization, coaching, and delivery guidance for the part-time B2B Product Owner, ensuring B2B roadmap execution stays connected to broader digital platform strategy.
  • Coordinate B2B and Brand roadmap dependencies so shared capabilities, content models, integrations, and release timelines are planned holistically and communicated clearly.
• Release execution and delivery governance
  • Lead release readiness for Brand websites and mobile launches, ensuring scope, QA, analytics tagging, content, merchandising, training, and stakeholder communications are complete before launch.
  • Create a clear delivery operating model that defines intake, prioritization, sprint planning, dependency tracking, launch approvals, and post-launch measurement across product, design, engineering, and business teams.
  • Proactively identify risks, blockers, resourcing gaps, and cross-platform dependencies that could affect delivery timelines, escalating trade-offs with clear recommendations.
• Consumer experience optimization
  • Own the ongoing optimization of core Brand consumer journeys across web and mobile, including discovery, hotel detail, booking entry points, account management, loyalty engagement, offers, and redemption flows.
  • Use behavioral data, voice-of-customer inputs, usability findings, and business performance trends to prioritize improvements that increase conversion, engagement, retention, and member satisfaction.
  • Partner with UX, content, CRM, loyalty, and hotel-facing teams to ensure B2C product experiences are intuitive, personalized, commercially effective, and consistent across channels.

What Would Make You Stand Out:

• Working knowledge of consent and privacy requirements as they land on the front end (GDPR, CCPA, CMP integration, cookie and tracking governance) and how consent state changes what a page or app is allowed to personalize.
• Experience with GEO, AEO, or structured data strategy for AI and search discoverability, including schema markup, entity-based content models, and how page architecture affects citation and crawl behavior.
• Familiarity with headless CMS platforms and how content modeling decisions affect editorial velocity, component reuse, and front-end delivery across web and app.
• Experience in travel, hospitality, e-commerce, or loyalty, with exposure to search-to-booking funnels, multi-currency and multi-language delivery, or membership and rewards experiences.
• Track record shipping to WCAG 2.1/2.2 AA and treating accessibility as a launch requirement rather than a remediation project.

What you’ll bring to the team:

• 6+ years in consumer product management, with at least 3 years owning customer-facing web and native mobile experiences end to end.
• Demonstrated ownership of a native mobile app lifecycle: release trains, phased rollouts, App Store and Play review, version deprecation, feature flagging, and crash and performance monitoring.
• Practical understanding of modern composable front-end architecture: headless CMS, API-first and BFF patterns, server-side and edge rendering, design systems and component libraries, to make credible tradeoffs with engineering.
• Fluency in web performance and its commercial consequences: Core Web Vitals, page weight, third-party script load, and the conversion cost of each.
• Experience running experimentation programs including A/B and multivariate tests, holdout design, baseline establishment, and using conversion, engagement, and retention data to decide what ships next.
• Experience turning personalization inputs (unified profiles, segments, behavioral signals) into concrete on-surface treatments, and defining the measurement that proves they worked.
• Proven partnership with UX and design teams or agencies: shaping research, pressure-testing flows, and holding a consistent experience across surfaces without becoming the designer.
• Demonstrated ability to translate technical tradeoffs into business value including conversion lift, booking revenue, engagement, and loyalty impact, for non-technical executive audiences.
• Comfort operating in ambiguity with an entrepreneurial mindset: prototyping rapidly, defining metrics where none exist, and pivoting based on data.

Where you’ll thrive:

• You are comfortable operating in a rapidly evolving technology landscape, thrive on continuous learning, and bring a proactive approach to identifying opportunities for automation and efficiency.
• You enjoy leading multiple priorities in a fast-paced environment, balancing strategic thinking with disciplined execution.
• You are confident making well-informed decisions, taking calculated risks, and driving results with a strong sense of ownership and accountability.
• You communicate with clarity and conviction, working independently while maintaining strong follow-through and attention to detail when coordinating with others.

Our Working Culture:

With our in-office philosophy, our associates are expected to be in the office at least three days per week, supporting a healthy balance between in-person collaboration and flexible remote work. We take pride in our vibrant and inclusive culture, which thrives on meaningful connection, shared purpose, and cross-functional teamwork. In-office engagement plays a vital role in fostering spontaneous collaboration, accelerating innovation, and strengthening relationships across teams. It also provides valuable opportunities for mentorship, professional development, and a deeper sense of community.

Please note: While the current expectation is a minimum of three days per week in the office, this may evolve over time in alignment with business needs and our continued commitment to culture-building

Disclaimer - This description reflects the general nature and level of the role. It is not intended to be an exhaustive list of responsibilities or requirements.

Salary

$155,000 - $175,000, actual compensation within this range will be determined by multiple factors including candidate experience and expertise.