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Ai Transformation Leader

Posted on May 27, 2026

Milano, Italy
0 - 0 USD (yearly)

Full Time

Ai Transformation Leader job opportunity

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Description

Core Accountabilities

1. Revenue & Growth

Originate and close large AI transformation programmes (multi-year, multi-function)
Build and maintain a robust AI pipeline across EMEA
Deliver profitable AI-led engagements with clear commercial outcomes
Partner with market leaders to convert demand into revenue

2. Client Transformation

Lead end-to-end AI transformation engagements across:
Pricing optimisation
Underwriting decision support
Claims automation and triage
Reserving and capital monitoring
Ensure AI is embedded into day-to-day client operations, not isolated pilots
Act as a trusted advisor to C-suite clients on AI strategy and execution

3. Integration with Propositions

Embed AI into all core propositions:
Pricing
Underwriting
Claims
Reserving
Capital
Establish and lead AI champions within each practice
Ensure every major client engagement is AI-enabled by design

4. Go-to-Market Leadership

Define and lead the firm’s AI narrative in insurance
Develop flagship use cases that anchor client conversations
Equip colleagues and client leaders with practical AI sales tools and propositions
Elevate the firm’s external position through thought leadership and client impact

5. Technology & Product Evolution

Leverage current AI ecosystem (e.g. LLMs, cloud platforms) to deliver immediate client value using our technology
Feed into the development of proprietary AI-enabled capabilities, based on proven client demand
Ensure technology investment is driven by real client use cases, not internal agendas

6. Internal Adoption & Behaviour Change

Drive AI adoption across the firm
Every proposal includes AI elements
Teams are trained on practical AI application
Remove low-value manual work through AI-enabled delivery
Align incentives to reward AI-led growth and delivery

Qualifications

Success Metrics

AI-driven revenue and bookings
Size and quality of AI pipeline (12–18 months forward visibility)
Number and scale of AI transformation programmes delivered
Reusability and scalability of AI-enabled propositions

Candidate Profile

Experience

Proven track record in selling and delivering large-scale transformation (consulting, technology, or both)
Deep understanding of insurance value chain (pricing, underwriting, claims, reserving, capital)
Experience applying AI / advanced analytics in real business contexts (not theoretical)
Strong commercial instincts with a history of winning and scaling revenue

Capabilities

Combines strategic thinking with execution discipline
Credible at C-suite level with clients
Able to translate between technical teams and business leaders
Builds high-performing, multi-disciplinary teams
Drives change in complex, matrixed organisations

Mindset

Commercially driven, not academically focused
Action-oriented: prioritises delivery over perfection
Pragmatic on technology: uses what works now, builds what is proven
High standards: expects AI to materially improve outcomes, not just processes

Key Relationships

EMEA Market Leaders
Proposition Leaders (Pricing, Claims, Reserving, Capital)
Technology leadership
Strategic clients (C-suite stakeholders)

First 6–12 Month Expectations

Establish AI as a core commercial pillar of the business
Collaborate to define and launch flagship AI propositions
Secure initial transformation deals with priority clients
Build initial AI capability and delivery model
Demonstrate tangible client impact and internal adoption

Bottom Line

This role exists to ensure:

AI is not a capability we talk about — it is how we grow, sell, and deliver.

At WTW, we believe difference makes us stronger. We want our workforce to reflect the different and varied markets we operate in and to build a culture of inclusivity that makes colleagues feel welcome, valued and empowered to bring their whole selves to work every day. We are an equal opportunity employer committed to fostering an inclusive work environment throughout our organisation. We embrace all types of diversity.

We’re committed to equal employment opportunity and provide application, interview and workplace adjustments and accommodations to all applicants. If you foresee any barriers, from the application process through to joining WTW, please email candidatehelpdesk@willistowerswatson.com.

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