10+ years in enterprise software delivery with significant AI development experience
Direct experience in requirements analysis, use case definition, configuration, integration, and testing
Proven track record of implementing AI or automation in delivery organizations
Experience leading initiatives across distributed, multi-region teams
Strong organizational and prioritization skills
Ability to influence adoption across regions without direct authority
Excellent communication, writing, and training skills
Responsibilities
Set the strategy for AI use in the implementation lifecycle
Transform identified AI ideas into practical tools and playbooks
Innovate cost-effective AI solutions for implementations
Establish a governance framework for AI tools and outputs
Drive a 25%+ effort reduction target across projects
Develop reusable AI-assisted workflows for various tasks
Select and develop delivery-supporting tools and create playbooks
Ensure practice remains current with evolving AI models and tools
Deploy standards and playbooks across global delivery regions
Train delivery leads on approved tools and workflows
Audit project teams for compliance with AI standards
Report metrics on compliance and effort reduction to leadership
Manage data handling and IP risks related to AI use
Benefits
Hybrid work model
Opportunity to work with a global team across multiple regions
Access to cutting-edge AI tools and technologies
Professional development and training opportunities
Engagement in innovative projects that shape the future of service delivery
Full Job Description
HYBRID - Montreal, Canada
Role: The Principal Strategist, AI for Services Delivery reports to the Chief Operating Officer. Equisoft implements different solutions for large and complex life and annuity carriers worldwide. This role owns how AI is used across the full implementation lifecycle: requirements analysis, use case definition, configuration, integration, and testing. It is central to Equisoft's objective of maximizing the use of AI across the enterprise, giving delivery teams the tools to accelerate implementations, with a target of 25%+ effort reduction across projects.
Your Day with Equisoft:
Set the approach for using AI in requirements analysis, use case definition, OIPA rules and configuration, integration, and test case generation
Take the AI ideas Equisoft has already identified and turn them into tools, techniques and playbooks ready to roll out across our services and regions
Look for new ways to innovate with AI in implementations, especially around configuration, in a cost-effective way
Build a governance framework: which AI tools are approved, how outputs get reviewed, and where human sign-off is mandatory
Drive the 25%+ effort reduction target on Equisoft/manage and Carbon implementations, and track progress project by project
Develop reusable AI-assisted workflows for generating OIPA rules and complex SQL, drafting user stories, and automating test case creation
Select and/or develop the tools that support delivery, including MCP integrations with Atlassian and Azure DevOps, and turn them into practical delivery playbooks
Keep the practice current as models and tools change: retire what doesn't work, scale what does
Deploy the standards and playbooks across every delivery region: USA, Canada, Caribbean, LATAM, EMEA/APAC, and the India Global Capability Centre (configuration, QA, data migration)
Train delivery leads and practitioners on approved tools and workflows
Adapt the rollout to each region's maturity and workload rather than applying one plan everywhere
Audit project teams against the defined AI standards, and flag and correct deviations
Report compliance and effort-reduction metrics to delivery and executive leadership
Own data handling and IP risk for AI use on carrier-confidential project data, working with Information Security
Work with regional delivery VPs to align the rollout with each region's delivery calendar, and with the enterprise AI and IT teams to stay aligned on direction
Requirements
Technical
10+ years in enterprise software delivery, with meaningful time developing systems using AI
Direct experience across the phases this role covers: requirements analysis, use case definition, configuration, integration, and testing
A track record of introducing AI or automation into a delivery organization, not just piloting it
Experience leading initiatives across distributed, multi-region teams
Soft skills
Strong sense of organization and prioritizing
Ability to influence and drive adoption across regions without direct reports
Analytical and problem-solving skills
Ability to communicate, write and synthesize information, and to train and coach practitioners
Team spirit, tact, diplomacy, autonomy, rigor, and discipline
Nice to haves:
Life and annuity insurance domain expertise
Experience with AI tooling in software delivery: LLM-assisted code and rule generation, automated test generation, MCP-based integrations
Experience standing up AI governance frameworks in regulated or carrier-confidential environments
