Director, Pension Application Development

Why you’ll love working here:

• high-performance, people-focused culture

• our commitment that equity, diversity, and inclusion are fundamental to our work environment and business success, which helps employees feel valued and empowered to be their authentic selves

• learning and development initiatives, including workshops, Speaker Series events and access to LinkedIn Learning, that support employees’ career growth

• membership in HOOPP’s world class defined benefit pension plan, which can serve as an important part of your retirement security

• competitive, 100% company-paid extended health and dental benefits for permanent employees, including coverage supporting our team's diversity and mental health (e.g., gender affirmation, fertility and drug treatment, psychological support benefits of $2,500 per year, parental leave top-up, and a health spending account).

• optional post-retirement health and dental benefits subsidized at 50%

• yoga classes, meditation workshops, nutritional consultations, and wellness seminars

• the opportunity to make a difference and help take care of those who care for us, by providing a financially secure retirement for Ontario healthcare workers

Job Summary

The Director, Pension Application Development provides strategic leadership, technical direction, and operational oversight for HOOPP’s Pension Application Development portfolio within the Pension Solutions Group. This role is accountable for the delivery, support, and evolution of pension administration applications that directly enable HOOPP’s pension operations, member services, and long-term strategic objectives. 

Working in close partnership with Plan Operations, Product Management, and IT colleagues, the Director ensures the application development function delivers secure, resilient, cloud-native solutions that enhance operational efficiency, amazing digital experiences for Members and Employers and support member self-service and enable HOOPP to deliver pension administration at the lowest possible cost. This role plays a critical technology development leadership function in advancing HOOPP’s long-term strategy through technology modernization, agility, and operational excellence. 

What you will do:

• Overall success, reliability, and alignment of pension application development solutions within PSG 

• Leads a team of 5-7 multidisciplinary application development professionals 

• A hands-on leader that ensures the development and delivery of secure, scalable, and cost-effective web application solutions integrated with the core pension record-keeping platform 

• Alignment of application roadmaps with business strategy, operational priorities, and enterprise architecture standards 

• Budget, resource, and technology tool management for the application development portfolio 

• Compliance with audit, risk, governance, security, and regulatory requirements 

• Operational stability, business continuity, and disaster recovery readiness for supported systems 

Leadership & People Management 

• Lead, coach, and develop a high-performing application development team aligned to HOOPP’s core values 

• Support career development, performance management, and employee engagement 

• Develop and maintain succession plans to ensure sustained capability and resilience 

Strategy & Delivery 

• Provide technical and delivery leadership for non-core pension administration applications 

• Partner with Product Management and Plan Operations to develop annual roadmaps and long-term application strategies 

• Drive Agile delivery practices, including sprint planning, reviews, and continuous improvement 

• Assess and recommend new technologies, development practices, and architectural approaches 

Operations & Governance 

• Ensure operational support, uptime, and service-level adherence for supported applications 

• Partner with Security, Risk, and Governance to embed compliance into application design and delivery 

• Support audit, governance, and regulatory activities 

• Ensure business continuity and disaster recovery plans meet established service levels 

Stakeholder & Vendor Management 

• Build strong partnerships with internal stakeholders and external vendors 

• Collaborate with enterprise architecture and IT partners to align solutions with standards 

• Support contract negotiations and vendor performance management 

• Prepare executive, steering committee, and board-level reporting as required 

 Measures of Success 

• Providing secure, dependable, and exceptional web experiences through high-performance web-based applications. 

• Achievement of delivery timelines, budgets, and operational service levels 

• Positive stakeholder feedback from business and IT partners 

• High team engagement (have fun!), retention, and leadership readiness 

• Reduction of technical debt 

• Sustaining and introducing modern app development practices- infusing AI 

• Successful audit outcomes and sustained compliance posture 

What you bring:

• Proven leadership experience delivering complex application development initiatives 

• Deep understanding of pension or insurance record-keeping platforms 

• Expert in cloud-native application architecture, microservices, event-driven and distributed systems, with strong skills in designing resilient, scalable, fault-tolerant, and highly available transactional systems. 

• Microsoft application development stack proficiency – Strong working knowledge of .NET / .NET Core, RESTful API design, secure API authentication and authorization, and integration of custom applications with enterprise and vendor-provided platforms. 

• DevOps, CI/CD, and automation leadership – Demonstrated experience establishing and governing CI/CD pipelines, infrastructure-as-code practices, automated testing, release management, and environment promotion strategies in regulated environments. 

• Security, risk, and compliance by design – Demonstrated ability to integrate security, access controls, monitoring, and audit readiness into cloud apps using secrets management, logging, and operational controls that meet regulatory standards. 

• Operational reliability and resilience engineering – Led teams managing production systems, overseeing SLA/SLOs, monitoring, incident response, performance tuning, and continuity/disaster recovery planning. 

• React & React Native delivery leadership – Proven experience leading teams building modern web and mobile front ends using React and React Native, with strong understanding of component-based architecture and performance optimization. 

• UI/UX execution & design systems – Ability to translate UX designs into scalable, accessible, and consistent user interfaces using enterprise design systems and modern front-end practices. 

• Front-end tooling & cloud integration – Experience with TypeScript, automated front-end testing, CI/CD pipelines, and secure API integration within cloud-native (Azure) application environments. 

• Financial and business acumen, including budgeting and vendor management 

• Ability to influence and partner effectively with senior leaders 

• Comfort operating in a fast-paced, operationally critical environment 

Required Tools & Technology (Must-Haves) 

• Microsoft Azure Platform Services – Azure App Services, Azure Functions, Azure Kubernetes Service (AKS), Azure Virtual Machines, Azure Storage, and Azure SQL, with experience selecting the right service based on scalability, cost, and operational requirements. Microsoft-based development stacks (e.g., .NET, SQL Server) 

• Azure Identity & Security Tooling – Microsoft Entra ID (Azure Active Directory), Role-Based Access Control (RBAC), Managed Identities, Azure Key Vault, and Azure Policy to enforce secure, compliant access and configuration standards. 

• Experience using ADO and infusing AI into the development pipeline 

• DevOps & CI/CD Tooling – Azure DevOps and/or GitHub Copilot, Ai Dev and Tools (Claude or others) including pipelines, repos, work item tracking, automated testing, and release management in regulated environments.