Program Director / Program Delivery Executive

Shape the future of insurance transformation at some of the industry's most important organisations. As a Program Director/Program Delivery Executive (PDE) you will lead complex, enterprise-wide customer Programmes that sit at the heart of digital and AI-driven change. Partnering with C-suite stakeholders and internal leadership, you'll drive delivery excellence, accelerate customer value, and ensure every project delivers measurable business outcomes.

This is a unique opportunity for a seasoned software delivery leader to combine deep insurance/financial services technology expertise, commercial acumen, and AI-native ways of working to influence both customer success and long-term growth.

You will be a senior delivery leader with deep insurance and financial services fluency, commercial discipline, and the judgement to run complex, multi-workstream Programmes at pace. Accountable for milestones delivered to agreed exit criteria, risks surfaced before they become crises, and a delivery model that shortens customer time-to-value.

Key Responsibilities:

01 - Programme Delivery & Commercial Outcomes

• End-to-end delivery ownership: Leads the full Programme lifecycle from initiation through planning, execution, and closure. Accountable for delivery on time, within scope, and within budget across all workstreams – including platform implementation, integration, data migration, and business change.
• Time to Value: Owns the pace at which the customer realises measurable outcomes. Sets the time-to-value baseline at programme initiation, tracks it at every milestone, and uses delivery decisions to shorten it. Accountable for committed implementation timelines - and for turning outperformance into a commercial conversation.
• AI-led SaaS implementation velocity: Moves Programmes toward faster implementation cycles consistent with an AI-led SaaS delivery model. Understands the configuration-over-customisation discipline and applies it to keep Programmes on the standard implementation trajectory that maximises customer time-to-value.
• Commercial Outcomes – In partnership with Customer Success, owns NRR contribution of the customer portfolio. Knows the expansion levers, drives them, and reports against them.
• Growth - Identifies upsell and cross-sell potential during delivery and converts insight into pipeline opportunities.
• AI-native execution model: Operates a delivery model in which AI handles the execution layer: status tracking, risk summarisation, documentation, meeting outputs, and reporting cadences. Directs AI tools, evaluates their output, and uses them to accelerate Programme pace and free team capacity for judgement-intensive work.

02 - Milestone Management & Exit Criteria

• Milestone ownership: Defines, manages, and tracks Programme milestones with precision. Each milestone has a clear definition of done, an agreed exit criteria, and formal customer acceptance before the Programme advances. This is the primary mechanism for preventing red projects.
• Exit criteria discipline: Works with the customer to agree exit criteria at the start of each phase – not at the end. Any customer request that falls outside accepted exit criteria is a natural change order, not a negotiation. The PDE holds this boundary with clarity and without conflict.
• Milestone-based billing alignment: Ensures that delivery milestones align with commercial billing triggers. Milestone acceptance by the customer is both a delivery gate and a commercial event. The PDE manages both dimensions in coordination with the Customer Success team.
• Risk and dependency management: Maintains a live Programme risk register. Identifies, assesses, and mitigates risks before they become issues. Manages interdependencies across workstreams, vendors, and internal teams. Surfaces conflicts and trade-offs early and drives resolution with pace.

03 – Insurance & Financial Services Industry Fluency

• Domain depth: Builds and maintains a deep understanding of the customer's business - P&L drivers, operating model, competitive pressures, and regulatory environment. Speaks insurance fluently, or has fluency in financial services technology.
• Insurance Ontology and AutonomousInsurer thesis: Carries our internal point of view into every engagement - articulating why a shared data model across the insurance value chain creates structural advantage, and what the AI-native insurance operating model looks like. Uses both to elevate the conversation beyond current project scope.

04 - Proactive Customer Relationship & Escalation Management

• Customer relationship ownership at the Programme level: Holds the customer relationship at the C-suite level on substance and trust. Is the person the customer calls when something genuinely matters.
• Proactive escalation management: Acts ahead of the problem, not in response to it. Reads signals early – customer frustration, delivery drift, scope ambiguity – and raises the difficult conversation before it becomes a crisis. Foresees escalations and prevents them through structured, proactive management.
• Partners closely with the account's Customer Success Manager — the PDE owns delivery execution, CS owns the commercial relationship and expansion. Together they own the Customer Value Journey, with a clean, documented handoff. Customer health is a shared metric.

05 - Resource Orchestration & Team Leadership

• Cross-functional team orchestration: Manages delivery across blended teams: Internal employees, offshore delivery resources, SI partners, and customer-side teams. Ensures alignment, accountability, and pace across all.
• Team leadership and development: Builds capability with intention, treating team development as a commercial lever rather than an HR task. Leads the full talent lifecycle with candour and integrity.
• Leads the Programme's PM team, setting standards and driving accountability. As the account's delivery standard-setter, the PDE defines the level the team performs to.

Desired Skills and Experience:

• 10–15 years of experience leading complex enterprise software Programmes, with at least 5 years in senior delivery leadership. Proven track record managing multi-workstream Programmes in insurance or financial technology environments.
• Deep insurance domain knowledge: Life & Pension, Property & Casualty, or equivalent specialty lines. Familiarity with Policy Administration Systems and the insurance technology landscape strongly preferred.
• Demonstrated expertise in milestone-based delivery governance: exit criteria design, scope control, change order management, and delivery framework design at enterprise scale.
• Experience leading global cross-functional teams including SI partners, offshore delivery resources, and customer-side teams in a matrixed environment.
• AI transformation experience: practical comfort directing AI tools across program management functions, evaluating AI-generated outputs, and operating an AI-native delivery model.
• Program financial management: budget ownership, forecasting, cost-to-serve awareness, and milestone-based billing alignment.
• Excellent communication and stakeholder management skills. Comfortable running steering committees, presenting to senior customer leadership, and managing difficult conversations with clarity.
• Project management certification required: PMP (Project Management Professional), PgMP (Program Management Professional), or PRINCE2 Practitioner certification.
• Preferred: experience with Scaled Agile (SAFe), hybrid delivery models, and SaaS implementation programs. Additional certifications such as SAFe Agilist, Certified ScrumMaster (CSM), or PMI-ACP are a plus.
• Undergraduate degree required. Relevant technical or business post-graduate qualification is a plus.