Data & AI Specialist (For independent contractors)

Role Description

As the Data & AI Specialist within Agile@Booking.com, you will hold a twofold mandate. First, you will own the department's data and reporting infrastructure — building the pipelines, dashboards, and measurement frameworks that give leadership and Agile coaches evidence-based insight into the progress and impact of our transformation work.

Second, you will drive the conceptual and practical integration of AI into the department: shaping how Agile coaches themselves use AI in their day-to-day work, and evolving the agile practices we teach so they remain relevant for teams whose product development is increasingly AI-assisted. You will operate as an internal expert, partnering with the Data & AI Lead, Agile coaching leads, and trainers to translate ambition into working systems and adopted practice.

Key Job Responsibilities and Duties

• Build and operate the department's data infrastructure; design and maintain pipelines, data models, and reporting layers that turn engagement, training, and coaching activity into reliable metrics on progress, adoption, and outcomes across the transformation programme.

  
  
  

• Enable insight and evidence-based decision-making; deliver dashboards and analyses that let Agile coaching leads, trainers, and leadership see where teams stand, where interventions are working, and where the programme needs to adjust. Make the data usable, not just available.

  
  
  

• Define measurement frameworks for Agile coaching impact; partner with Agile coaches and leads to translate qualitative coaching outcomes into measurable signals, and evolve these measures as the programme matures.

  
  
  

• Integrate AI into the Agile coaches' workflow; identify, prototype, and roll out AI-assisted tools and practices that make coaches more effective — from preparation and content generation to synthesis of team observations and knowledge sharing across the community.

  
  
  

• Evolve agile practices for AI-assisted product development; research and codify how core agile practices (backlog refinement, estimation, iteration planning, definition of done, quality practices, team topologies) need to adapt when engineering and product teams are working with AI coding assistants and AI-augmented workflows. Translate these insights into training and coaching content.

  
  
  

• Coach the Agile coaches; run enablement sessions and working groups that upskill the department on AI tooling, data literacy, and the changing shape of the teams they coach.

  
  
  

• Partner with trainers and Agile coaches; work closely with trainers to embed AI-related content into baseline training, and with coaches to feed back learnings from the field into how we measure and how we teach.

  
  
  

• Contribute to the wider Agile@Booking.com community; share findings, run experiments in the open, and collaborate with peers to raise the collective capability of the department on both data and AI fronts.

  
  
  

• Engage with the broader Booking.com data and AI landscape; stay connected to internal data platforms, AI enablement initiatives, and the product/engineering communities using AI in practice, so the department's guidance reflects the reality on the ground.

Communication

• Cooperates and shares information frequently with the Data & AI Lead and coaching leads within Agile@Booking.com.

  
  

• Cooperates daily with agile coaches and trainers across the department.

  
  

• Cooperates regularly with Product and Engineering teams and leaders adopting AI-assisted development, and with internal data platform and AI enablement teams.

  
  

• Occasional interaction with senior leadership stakeholders consuming programme reporting, and with external experts in the agile/AI space.

Qualifications & Skills

• Solid hands-on data engineering and analytics experience; comfortable building and maintaining pipelines, modelling data, and delivering dashboards that people actually use (SQL, a modern data stack, BI tooling).

  
  
  

• Working fluency with AI/LLM-based tools and workflows; has moved beyond casual use into designing, prototyping, and rolling out AI-assisted ways of working for others.

  
  
  

• Knowledge of Agile, particularly Scrum and Kanban and DORA metrics. Experience as a Scrum Master or Agile Coach is highly advantageous

  
  
  

• Experience working within agile product development teams; familiarity with iterative development, backlog work, and team events. Genuine curiosity about how agile practices need to evolve for AI-assisted product development teams.

  
  
  

• Proven ability to translate ambiguous, conceptual problems into concrete measurement frameworks, prototypes, or adopted practices.

  
  
  

• Strong facilitation and enablement skills; can teach and coach peers on data and AI topics, adapting to varied levels of technical background across a 100+ person department.

  
  
  

• Ability to work across the boundary between data/engineering craft and organisational change; equally comfortable in a pipeline, a dashboard review, and a coaching community session.

  
  
  

• Familiarity with how AI coding assistants and agentic workflows are changing engineering practice is highly advantageous.

Essential Skills & Highly Desirables

• Essential that the candidate has 5+ in a Software Engineering role

  
  
  

• Essential experience in applying agile ways of working, concepts, practices in software engineering context using data

  
  
  

• Essential skills in applying AI to the above skills

  
  
  

• Highly desirable skills in data products and dashboard building