Director, Employee Experience & AI Productivity

Priceline • Norwalk, CT

2d • $185,000 - $230,000 • Hybrid

About The Position

This role is eligible for our hybrid work model: 2 days in-office. Our People & Culture and Legal teams make sure we provide a highly ethical working environment where everyone at Priceline can bring their whole selves to work and deliver their very best each day. We want you to thrive – to feel safe, supported, valued, and growing to your highest potential! Why this job’s a big deal: Priceline runs on an AI-driven productivity and automation stack that thousands of employees touch every day — across Priceline, our parent company Booking Holdings, and the BHI centers of excellence. The tools are in place. What we need now is a leader who treats that stack as a product, treats our employees as its customer, and is relentless about turning capability into everyday habit. This isn't a "tool admin" job. We need an employee experience leader who is technically sharp enough to sit down with a software engineer or a finance analyst, understand their workflow, and then tailor our systems to make their lives easier. You'll set the vision for our productivity platforms, own adoption from start to finish, and lead the talented engineering and support teams that keep the engines running. This is your chance to own how an entire enterprise works with AI — and to be judged on whether people actually do more because of it. The platforms are modern and expanding, the mandate spans the whole company plus its parent, and the role carries the seniority and direct executive visibility to set direction rather than react to it.

Requirements

• Experience & Leadership: You've led employee-facing tech or productivity teams before and have a proven record of getting people to actually use (and like) new systems.
• AI fluency: hands-on experience putting AI tools into enterprise workflows, a working grasp of prompt engineering and agentic patterns, and the judgment to evaluate tools critically and reason about AI governance.
• You're comfortable leading technical teams and can hold your own in an architecture discussion with engineers.
• Strong command of a modern productivity and AI stack — Atlassian, an enterprise AI search platform such as Glean, automation tooling such as Workato, Google Workspace, and enterprise AI assistants.
• How You Operate: An employee-experience focus — you think in terms of friction, onboarding, and adoption, and you have used journey mapping or similar methods to understand how people work.
• Proven change-management ability across rollouts, migrations, and deprecations, including building champions and managing the human side of transitions.
• You're an excellent communicator who can translate technical jargon into business value for executives.
• Illustrated history of living the values necessary to Priceline: Customer, Innovation, Team, Accountability and Trust. The Right Results, the Right Way is not just a motto at Priceline; it’s a way of life.
• Unquestionable integrity and ethics is essential.

Nice To Haves

• Travel, e-commerce, or other high-scale consumer technology experience.
• Multi-brand or multi-entity enterprise IT background.
• Familiarity with AI workflow automation or MCP integrations.
• Experience building an adoption or enablement program from the ground up.

Responsibilities

• Set Strategy & Product Direction: Own AI productivity as a product: define what good looks like, decide what we invest in and what we retire, and be accountable for whether the workforce is genuinely getting more done. You'll be measured less by uptime and ticket counts and more by adoption, the friction you remove, and the value employees draw from the tools in their hands. Build a clear roadmap for our stack (Jira, Confluence, Glean, Workato, Gemini, ChatGPT, Claude) that actually matches how we do business. Make the hard calls on what to keep and what to retire, using data and real employee feedback to back up your decisions. Keep a pulse on new AI trends and agentic tools, figuring out what's worth a pilot and what's just noise.
• Drive Adoption & Employee Experience: Figure out how different departments work, find where they're getting stuck, and design the onboarding and support that makes our tools indispensable. Run the programs that drive real use — like user groups and office hours — so new features actually get used. Define the metrics that matter (active use, time saved, capability uptake by function) and hold yourself and the team to them.
• Lead Change Management: Manage the human side of software updates and migrations. Communicate early and often to bring people along on the journey. Treat every launch like an internal campaign: be clear about what's changing, why it's better, and how we'll support people if things get bumpy.
• Lead the Team & Set Technical Direction: Lead a distributed team of engineers and partner with our help desk to make sure access and support are seamless. Bring strong architecture leadership to the team, helping our engineers solve the tough problems and growing our solution-design capabilities. Mentor your people: help them grow their technical skills and create paths for senior engineers to take on more leadership.
• Partner Across the Enterprise: Operate across the whole business. This team serves all of Priceline plus BHI North America, our COEs, and BHI BV user populations. Partner with Security to make sure our AI tools are safe, and with Enterprise Engineering to keep our Google Workspace environment running smoothly. Partner closely with the developer experience team who are building these features for the technical staff. Collaborate with HR, Legal, and Brand leaders to represent the productivity agenda at the highest levels of the company.
• Champion Responsible AI: Set up sensible guardrails for AI use that keep us secure and compliant without slowing the company down.

Benefits

• Health & wellness coverage including medical, dental, vision, and mental health resources
• Generous time off including PTO, holidays, a company-wide Priceline Pause reset week, and paid volunteer days
• Work/life support including the ability to work up to 4 weeks per year from anywhere, parental leave, dependent care and family support resources, Summer Fridays, and office perks like stocked kitchens and catered meals (varies by location)
• Financial security programs such as retirement plans with company contributions, life and disability coverage, and tax-advantaged accounts
• Signature travel perks including employee-only discounts on hotels and flights, VIP deals, and Big Deal Bucks credits
• Additional perks & discounts like travel and partner discounts, tuition support, legal support, and pet benefits
• A people-first culture with Employee Resource Groups (ERGs), social events, recognition programs, and service awards that help you connect, grow, and celebrate together

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed