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Sapiens

Program Delivery Executive (Canada)

Canada

Job type: Full-time
Experience: 10–15 years of experience leading complex enterprise software programs, with at least 5 years in senior delivery leadership.
Posting language: English
Posted: Sep 22, 2026

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Original job description

Programme Director (Program Delivery Executive)

Reports to: VP - Delivery Success

Matrix Reports: Project Managers

Purpose of the Role

The Program Delivery Executive owns the execution and delivery integrity of Sapiens customer programs. This role sits within the Delivery Success team and is the primary accountable leader for program governance, milestone management, and value delivery inside a customer engagement.

The PDE is a senior delivery leader who brings deep insurance industry fluency, commercial discipline, and the judgement to manage complex, multi-workstream programs with clarity and speed. The role is accountable for ensuring that every milestone is delivered to an agreed exit criteria, that every risk is visible before it becomes a crisis, and that the delivery model operates at the pace that shortens time-to-value for the customer.

The PDE operates an AI-native delivery model in which the execution layer is progressively automated, enabling the role to focus on discernment, governance, and the customer relationship. The role works in close partnership with the Customer Success team for the long-term success and value realization of the customer. Commercial outcomes – NRR, ARR, account margin, and customer reference ability – are shared responsibilities.

Key Responsibilities

01 - Program Delivery & Commercial Outcomes

End-to-end delivery ownership: Leads the full program 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 realizes measurable business outcomes from the Sapiens engagement. Defines the time-to-value baseline at programme initiation, tracks progress against it at every milestone and uses delivery decisions to actively shorten it. Where Sapiens commits to a standard implementation timeline, the PDE is accountable for meeting it and where the team beats it, translates that into a commercial conversation with the customer.
AI-led SaaS implementation velocity: Moves programs toward faster implementation cycles consistent with Sapiens’ AI-led SaaS delivery model. Understands the configuration-over-customization discipline and applies it to keep programs 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 summarization, documentation, meeting outputs, and reporting cadences. Directs AI tools, evaluates their output, and uses them to accelerate program pace and free team capacity for judgement-intensive work.

02 - Milestone Management & Exit Criteria

Milestone ownership: Defines, manages, and tracks program milestones with precision. Each milestone has a clear definition of done, an agreed exit criteria, and formal customer acceptance before the program 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 program risk register. Identifies, assesses, and mitigates risks before they become issues. Manages interdependencies across workstreams, vendors, and internal Sapiens teams. Surfaces conflicts and trade-offs early and drives resolution with pace.

03 - Insurance Industry Fluency & Customer Understanding

Insurance domain depth: Develops and maintains a deep understanding of the customer’s business: their P&L drivers, their operating model, their competitive pressures, and their regulatory environment. Speaks insurance fluently – the economics, the operations, and the dynamics that move the industry.
Insurance Ontology and Autonomous Insurer thesis: Carries the Sapiens intellectual point of view into every customer engagement. Understands and can articulate the Insurance Ontology argument – why a shared data model across the insurance value chain creates structural advantage – and the Autonomous Insurer thesis – what the AI-native insurance operating model looks like, and why Sapiens is positioned to enable it. Uses these frameworks to elevate the delivery conversation beyond the scope of the current project.

04 - Proactive Customer Relationship & Escalation Management

Customer relationship ownership at the program 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.
Customer success partnership: Works in close coordination with the Customer Success Manager on the account. The PDE owns delivery execution; the CS team owns the commercial relationship and expansion trajectory. The handoff between these functions is deliberate, documented, and clean. Customer health is a shared metric.

- Resource Orchestration & Team Leadership

Cross-functional team orchestration: Manages delivery across blended teams: Sapiens employees, offshore delivery resources, SI partners, and customer-side teams. Ensures alignment, accountability, and pace across all.
Team leadership and development: Treats team development as a commercial lever, not an HR task – holding growth conversations early and building capability with intention. Leads the full talent lifecycle with candour and integrity, from onboarding through to role transitions.
Sapiens ambassadorship: Carries the Sapiens point of view into customer environments. Knows the Insurance Ontology argument, the AutonomousInsurer thesis, and the AI moat – and can hold them in a room.
Project Manager leadership: Directly leads a team of Project Managers across the program. Sets standards, drives accountability, and develops PM capability with intention. The PDE is the delivery standard-setter on the account – the team performs to the level the PDE models and demands.

Desired Skills and Experience

10–15 years of experience leading complex enterprise software programs, with at least 5 years in senior delivery leadership. Proven track record managing multi-workstream programs 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.

Character Dimensions

Delivery discipline: The disposition to hold a program to its commitments – on scope, exit criteria, budget, and quality – with consistency and without compromise. Does not negotiate what was agreed; manages scope through governance.
Judgement under ambiguity: The capacity to make clear decisions when the program environment is unclear. Does not wait for perfect information. Decides, communicates, and adjusts.
Systemic curiosity: The disposition to understand how the customer’s business connects – not just the scope of the current project. Delivery decisions are made in the context of business outcomes, not just technical requirements.
Proactive orientation: Acts ahead of the problem. Reads the signals before they become issues, raises the difficult conversation before it becomes a crisis, and arrives with a solution rather than a problem.
Relational intelligence: The capacity to build trust across difference, ambiguity, and competing interests – with the customer, with the internal team, and with partners. Trust is built through consistency and substance, not through diplomacy alone.
Builder orientation: Energised by complexity and the absence of a clear path. Treats each program as something to be designed and engineered, not just managed.

Key Performance Indicators

The PDE is accountable for the delivery inputs that drive the following outcomes.

KPI

Definition

Time-to-value

Speed from contract signature to customer go-live and first measurable business outcome. The DSM owns the delivery inputs; CS owns the commercial framing of the outcome.

Exit criteria-based milestone billing

Percentage of program milestones delivered with formal customer-accepted exit criteria, on schedule, triggering billing events without dispute.

Program delivery health

Aggregate RAG status across managed programs: on-time, on-scope, on-budget delivery against committed program plan.

Program P&L

Project and Programs account-level gross margin. DSM accountability is cost-to-serve discipline and delivery efficiency; CS accountability is commercial growth.

Net Revenue Retention

Net Revenue Retention contribution from the account, driven jointly by delivery performance (DSM) and commercial expansion (CS). Clean delivery is the foundation of renewal and expansion.

Referenceable C-levels

Named C-level executives (CIO, COO, CTO) at customer accounts willing to act as active references for Sapiens. Earned through delivery excellence, not relationship management alone.

Working Model

Our flexible work arrangement combines both remote and in-office work, optimising flexibility and productivity. Travel to customer sites will be required based on program phase, milestone cadence, and governance requirements.

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More about this job

Responsibilities

The Program Delivery Executive is responsible for the end-to-end execution, governance, and value delivery of complex customer programs. They lead cross-functional teams, manage milestones, and ensure commercial outcomes while driving AI-led implementation velocity.

Requirements

Candidates must have 10-15 years of experience in enterprise software program delivery, with at least 5 years in senior leadership roles. A strong background in the insurance industry, project management certification, and expertise in AI-driven delivery models are required.

Skills

Program delivery
Governance
Milestone management
Insurance industry fluency
Commercial discipline
AI-native delivery
Risk management
Stakeholder management
Customer success
Project management
SaaS implementation
Change order management
Financial management
Team leadership
Cross-functional orchestration

Visa sponsorship

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Keywords

Program Delivery Executive
Insurance
SaaS
AI-native
Governance
Milestone Management
PMP
PgMP
PRINCE2
SAFe
ScrumMaster
Policy Administration Systems
Risk Management
Customer Success
Enterprise Software
Financial Technology
Life & Pension
Property & Casualty
Change Management
Budget Ownership
Stakeholder Management
Cross-functional Leadership
Insurance Ontology
Autonomous Insurer
Time-to-value

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