Lead Technical Program Manager (Director level, individual contributor)

Lead Technical Program Manager

The Lead (Director level) Technical Program Manager (TPM) will be the lead point of contact on assigned initiatives that require delivery of end-to-end technology solutions. The TPM will work closely with the business initiative owner to align the technology services and capacity needed to deliver on the technology commitments. TPMs will work with the business to understand program requirements, manage different phases of development and testing plans, and ensure that projects are delivered on time and within budget.

Office location: Boston - USA, Toronto - Canada, Waterloo - Canada.

Work arrangement: Hybrid - 3 days in office, 2 days from home; remote option is not available.

Position Responsibilities:

• Initiative management: Overseeing the entire lifecycle of an initiative including initiating programs, driving delivery, and providing support when issues arise
• Initiative Delivery: Responsible and accountable for ensuring all aspects of delivery of technology services including Initiation, Planning, Execution, Monitoring/Controlling, Closure, and Post initiative evaluation activities to deliver on scope, budget, and schedule for technology commitments.
• Technical expertise: Using their background in understanding software engineering and technology to implement technology strategies and ensure effective software delivery
• Cross-functional leadership: Providing cross-functional leadership and building alignment for efforts such as product architecture and synchronizing the ask with the IT organization service areas to deliver services. Technical risk management: Identifying and mitigating technical risks that could impact project success
• Value Creation: works closely with Business Initiative lead to build schedule, milestones, goals, and scope by aligning and incorporating technology aspects from components, solutions, feasibility and delivery.
• People & Culture: Foster a culture of innovation, collaboration, while actively driving alignment and productivity for aligned Team

Technical and Architectural Depth

• Strong foundation in software engineering, systems engineering, solution architecture, or technical product leadership, with the ability to review and challenge system designs, APIs, integrations, data flows, deployment models, test strategies, and non-functional requirements.
• Deep understanding of enterprise architecture, platform modernization, cloud adoption, security, data, DevSecOps, observability, operational resilience, and architectural trade-offs across legacy and modern technology stacks.
• Strong knowledge of current-state technologies, including.NET Framework, VB.NET, C#, WinForms, ASP.NET Web Forms, IIS, SQL Server, ETL, batch processing, reporting, legacy calculation engines, document generation, and point-to-point integrations.
• Strong knowledge of target-state technologies and patterns, including modern.NET, ASP.NET Core, RESTful APIs, modular monoliths, microservices, event-driven architecture, React, Angular, TypeScript, relational and NoSQL platforms, containers, orchestration, Python, automation, and AI-assisted engineering.
• Ability to engage credibly with architects, engineering leads, developers, quality engineers, infrastructure teams, security partners, vendors, and senior leaders to guide migration strategies that balance business outcomes, risk, cost, maintainability, performance, and delivery timelines.

Life Insurance and Illustration Domain Knowledge

• Deep understanding of life insurance product structures and calculation drivers across Term, Whole Life, Universal Life, Indexed Universal Life, and Variable Universal Life, including premiums, charges, interest or crediting assumptions, guarantees, loans, withdrawals, cash values, riders, and regulatory illustration requirements.
• Knowledge of insurance illustration engines, including inputs, assumptions, product rules, calculations, ledger generation, scenario management, disclosures, output generation, and reproducibility.
• Understanding of producer point-of-sale and quote-to-submission workflows, including integrations with product and rate sources, CRM or portals, e-signature, case management, new business, underwriting, and policy administration.
• Experience partnering with Product, Actuarial, Compliance, Legal, Distribution, Operations, and Technology to translate product and regulatory changes into traceable technology outcomes.
• Knowledge of controls and evidence required for calculation validation, illustration compliance, releases, assumption changes, effective dating, and auditability.

Leadership and Program Management Skills

• Demonstrated ability to lead large initiatives and multiple interdependent workstreams across teams, platforms, vendors, and organizational boundaries.
• Strong strategic thinking, structured problem solving, judgment, negotiation, facilitation, conflict resolution, and executive communication.
• Ability to influence and drive execution without direct management authority.
• Ability to create clarity in ambiguous situations, frame options and recommendations, and drive timely decisions.
• Experience managing scope, schedule, budget, capacity, dependencies, risks, quality, release readiness, and value realization using appropriate delivery methodologies.
• Ability to communicate technical vision, modernization strategy, delivery confidence, business impact, and risk to both technical and non-technical audiences.
• People leadership experience or demonstrated capability to coach, mentor, align, and motivate cross-functional teams.

Required Qualifications:

• 8+ years of progressive experience delivering complex technology programs in insurance, financial services, or another highly regulated industry.
• 5+ years leading large, multi-year, cross-platform technology initiatives involving multiple engineering teams, business functions, vendors, and senior stakeholders.
• 5+ years of life insurance technology experience strongly preferred, with direct exposure to product development, actuarial or calculation capabilities, illustrations, point-of-sale, new business, underwriting, policy administration, or related distribution platforms.
• Prior experience in software engineering, solution architecture, systems analysis, technical product ownership, engineering leadership, or another technically intensive role strongly preferred.
• Experience leading modernization involving one or more of the following: VB.NET to C#, .NET Framework to modern.NET, desktop to web, monolithic to API-driven architectures, on-premises to cloud-enabled environments, or replacement of legacy and end-of-life components.
• Proven delivery experience across large application ecosystems consisting of desktop, web, services, APIs, databases, batch, reporting, document generation, and external integrations.

Preferred Qualifications:

• Bachelor's degree or higher in computer science, software engineering, information systems, business administration, or a related field, or equivalent relevant experience.
• Experience implementing or governing modern engineering practices, including CI/CD, automated testing, DevSecOps, observability, infrastructure automation, and AI-assisted software delivery.
• Experience with test governance for calculation engines, including actuarial validation, parallel testing, defect triage, regression evidence, and formal sign-off.
• Experience leading regulated releases involving product, rate, assumption, disclosure, or effective-date changes while coordinating technology and business readiness.
• Excellent communication, presentation, documentation, relationship-management, and executive stakeholder skills.
• Highly adaptable, resilient, and effective in a dynamic environment with competing short-term commitments and long-term transformation objectives.

When you join our team:

• We'll empower you to learn and grow the career you want.
• We'll recognize and support you in a flexible environment where well-being and inclusion are more than just words.
• As part of our global team, we'll support you in shaping the future you want to see.