Sr. Design Project Manager (For independent contractors)

Role Overview

This role will provide dedicated, full-time program and operations support to UX leadership during a critical period of transformation.

The role brings together three connected workstreams into one coherent scope. First, it will support the continued rollout, onboarding, and change management of the UX Operating Model, ensuring that UX practitioners are successfully onboarded to the new Jira-based ways of working and that adoption is sustained through structured communications, training, support materials, and follow-through. Second, it will lead UX’s participation in the 2027 annual planning cycle across Booking.com’s evolving annual and quarterly planning processes and across all four BUs, while using that hands-on delivery to identify, test, and recommend the right planning model for UX moving forward. Third, it will ensure these two efforts are translated into one practical operating approach, so that the way UX leaders, managers, and ICs plan and run work is better aligned with broader company and BU planning rhythms.

This is a senior individual contributor role focused on independently leading a portfolio of complex initiatives and operational improvements for UX. It is not intended to own department-level strategy or broad cross-department program outcomes in the way a Level G role would. Instead, it is intended to lead delivery, shape recommendations, build operational standards, and help embed a scalable model in partnership with UX leadership and key cross-functional stakeholders.

Program Scope

1. UX Operating Model adoption and rollout

- Drive onboarding, adoption, and change management for the UX Operating Model

- Ensure UX practitioners are able to use the new Jira-based ways of working effectively

- Build the supporting materials, communications, and interventions needed to make adoption stick

2. UX annual planning leadership and model improvement

- Lead UX’s participation in the 2027 annual planning cycle across CBO and all four BUs

- Use delivery of that cycle to identify, test, and recommend the best longer-term model for how UX should operate within annual and quarterly planning processes

- Gather requirements, pain points, and constraints across stakeholders and translate them into a practical improvement plan

- Improve consistency, clarity, and sustainability of planning for UX leadership

3. Integration of planning and the UX Operating Model

- Ensure planning expectations are translated into the way UX managers and ICs actually plan, prioritize, track, and deliver work

- Define how approved improvements should show up in team rituals, planning expectations, Jira usage, and operating guidance

- Help embed those improvements into 2027 ways of working so they can continue beyond the contract period

Key Job Responsibilities and Duties

- Lead change management and onboarding for the UX Operating Model rollout, including stakeholder mapping, communications, training coordination, adoption tracking, and issue follow-up.

- Drive UX Jira onboarding and adoption by coordinating rollout activities, documenting ways of working, supporting teams through transition, and ensuring practitioners can successfully use the new system.

- Create and maintain the core operating materials needed for successful adoption, including playbooks, process guides, training assets, FAQs, intake guidance, and supporting documentation.

- Partner with UX craft leaders and managers to identify friction points, resistance themes, and local adoption gaps, and convert those into targeted interventions.

- Establish and run a clear operating cadence across the contract period, including milestone plans, status updates, risks, dependencies, success metrics, and leadership reporting.

- Assess the current-state UX planning challenge across CBO and the four BUs, including pain points, inconsistencies, planning burden, stakeholder expectations, and gaps in the current model.

- Lead and manage UX’s participation in the 2027 annual planning cycle across the four BUs, including timelines, inputs, documentation, stakeholder coordination, decision tracking, and follow-through.

- Gather and synthesize requirements across BUs and leadership groups related to annual planning, quarterly planning, and operating cadence, and align stakeholders on practical improvements where possible.

- Capture learnings from the 2027 annual planning cycle and translate them into clear recommendations for a more sustainable UX planning approach.

- Shape and document the recommended future-state UX planning approach in partnership with UX leadership and key business stakeholders, including how UX should engage with annual and quarterly planning processes going forward.

Own the connector work between planning and the UX Operating Model, ensuring that leadership planning rhythms are translated into how UX managers and ICs plan, prioritize, track, and deliver work.

- Define and implement updates to operational standards, templates, and guidance needed to connect planning expectations with manager rituals, team planning, intake, prioritization, Jira usage, and ways of working.

- Coordinate planning inputs and outputs across leaders and stakeholder groups so that UX participation in planning is more structured, consistent, and easier to execute.

- Facilitate alignment discussions and working sessions with senior stakeholders to drive clarity on trade-offs, ownership, and next steps.

- Build structure and transparency around work in flight by maintaining trackers, dashboards, decision logs, planning documents, and actions needed to keep the work moving.

- Act as a connective layer between leadership intent and day-to-day execution, helping teams understand what is changing, why it matters, and what they need to do differently.

- Identify process improvement opportunities that reduce manual effort, improve consistency, and leave behind reusable systems and assets that can continue beyond the contract.

- Measure and report progress against clear outcomes, especially adoption, readiness, planning delivery quality, recommended improvements, and overall execution.

Success Measures / Expected Outcomes by End of Contract

- A clear and executed change plan for the UX Operating Model has been delivered.

- UX practitioners are substantially onboarded to the new Jira system and ways of working, with known adoption issues identified and addressed.

- Core onboarding and enablement assets are in place, usable, and maintained.

- The current-state planning burden, structural gaps, and cross-BU requirements for UX have been clearly identified and documented.

- UX’s participation in the 2027 annual planning cycle has been successfully managed across the four BUs.

- Key learnings from the 2027 annual planning cycle have been synthesized and turned into a clear set of recommendations for the longer-term UX planning approach.

- A practical and documented approach exists for how the UX Operating Model connects to annual and quarterly planning rhythms, especially for UX managers and ICs.

- Agreed updates to templates, processes, guidance, and Jira ways of working have been identified and implemented where appropriate.

- Risks, dependencies, and key decisions across the work are visible and well-managed.

- The team is left with reusable tools, documentation, governance assets, and operating guidance that support continuation after the contract ends.

Role Qualifications and Requirements

Must-have experience

- Significant experience in program management, UX operations, DesignOps, ResearchOps, ContentOps, or closely related operational delivery roles.

- Proven experience independently leading multiple complex projects or a portfolio of initiatives with multiple stakeholder groups, dependencies, and moving parts.

- Strong experience leading large-scale process change, onboarding, or operational improvement initiatives.

- Strong experience creating and operationalizing repeatable workflows, playbooks, documentation, standards, and governance mechanisms.

- Demonstrated success working across cross-functional stakeholder groups with different goals, incentives, and levels of seniority.

- Experience leading or managing annual planning cycles, quarterly planning, business cadences, or leadership operating rhythms.

- Experience managing complex planning processes with senior stakeholders and multiple cross-functional counterparts.

- Experience supporting UX teams, including Design, Research, and/or Content/Writing, or operating in a similarly craft-adjacent environment where operational decisions affect how creative or product crafts work day to day.

- Strong organizational skills with the ability to manage multiple workstreams, deadlines, dependencies, and stakeholders at once.

- Excellent written and verbal communication skills, with the ability to simplify complex process changes into clear and actionable guidance.

- Comfortable working with Jira, Google Workspace, spreadsheets, presentations, and documentation tools as core operating tools.

- Experience presenting status, risks, trade-offs, and recommendations clearly to senior stakeholders.

- Able to operate with high autonomy, sound judgment, and a practical bias toward execution.

Nice-to-have experience

- Experience in a UX, Product, Design, Research, or Content environment.

- Familiarity with organizational change management frameworks and adoption measurement approaches.

- Experience supporting or improving operating models, ways of working, or portfolio / planning rituals.

- Experience in large, matrixed, international organizations with multiple business units and stakeholder groups.

- Experience facilitating workshops, planning sessions, and leadership working sessions.

- Experience helping define or scale a craft-specific operations capability.

Candidate Profile

We are looking for someone who combines the strengths of a program manager, change lead, and craft-aware operations builder.

They should be highly structured and delivery-focused, but also comfortable with ambiguity and able to influence people who do not report to them. They should enjoy turning unclear or messy processes into practical systems that teams can actually use. They should be strong at follow-through, proactive communication, stakeholder alignment, and converting leadership intent into well-run execution.

The ideal candidate is not just a coordinator. They are someone who can independently spot gaps, design the right operational response, align stakeholders around it, and drive it through to adoption. They should be comfortable representing work status, surfacing risks and dependencies, and helping leaders make decisions about how planning requirements should translate into the UX operating model.

They should also be comfortable operating in a craft environment where success depends not only on program rigor, but on understanding how Designers, Researchers, Writers, managers, and directors actually work in practice.