Director, Technology Delivery

at  Healthcare of Ontario Pension Plan HOOPP

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, and newly extended maternity/parental leave top of 26 weeks)
• optional post-retirement health and dental benefits subsidized at 50%
• yoga classes, meditation workshops, nutritional consultations, and wellness seminars
• access to an annual wellness reimbursement program for health and wellness-related expenses for permanent and temporary employees
• 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, Technology Delivery will provide strategic direction and leadership for a suite of IT platforms and custom-developed applications that support the business objectives of the Investment Solutions Group (ISG) portfolio (e.g., Trading Solutions). This role requires mentoring Senior Engineering Managers, aligning with senior business leaders, and partnering with Product Directors to drive IT controls, custom application delivery, and integration with trading platforms like Bloomberg. The Director is responsible for overseeing platform management, custom development, and delivering innovative, scalable technology solutions.
What you will do:

Team Leadership and Management

• Leads 3-4 development teams (with 2-3 engineering managers) and oversees 20+ Systems Developers.
• Provides direct leadership to Sr. Engineering Managers (M2) and other professionals, ensuring alignment with HOOPP’s Core Values.
• Identifies individual and team strengths and opportunities, creating development plans and performance improvement initiatives.
• Creates and manages succession planning, addressing key person risk and ensuring a strong talent pipeline.

Strategic IT Leadership and Delivery

• Leads the development and execution of 1–2-year IT strategies for business partners at the VP, Senior Director, and Director level.
• Collaborates with Product Directors to define technology strategies and ensure alignment with business objectives across multiple IT platforms.
• Accountable for platform management, prioritization, and delivery results across a portfolio of 20-50 technologies and services.
• Oversees full-stack custom development for trading applications and manages platforms, vision, and service design.
• Develops integrated, aligned platform roadmaps and partners with other senior leaders for cross-departmental initiatives.

Innovation and Platform Management

• Plans and drives innovation within product stacks, balancing time and value to ensure impactful outcomes.
• Manages the prioritization of platform backlogs and work efforts across teams to meet business outcomes and OKRs.
• Leads or supports strategic initiatives, feature implementations, and technology integrations with key platforms in investment, risk, and finance sectors.
• Accountable for driving innovation and delivering integrated roadmaps for platforms/services.

Vendor and Cost Optimization

• Leads and manages vendor strategy, negotiating to optimize costs across the suite of platforms and services.
• Partners with senior divisional executives and vendors to influence, negotiate, and align platform goals with business outcomes.
• Oversees contracts and relationships with external service providers to ensure value and alignment with the organization’s technology strategy.

Resource and Culture Carrier

• Sets team priorities and allocates resources effectively to support platform needs and strategy execution.
• Mentors engineering managers and ensures alignment with value-focused outcomes such as Minimum Viable Products (MVPs) and Return on Investment (ROI).
• Builds a strong organizational culture that attracts, retains, and develops high-quality staff, encouraging innovation, productivity, and growth.
• Advocates for an open and empowering culture where staff can voice opinions, challenge the status quo, and drive innovation.

Executive and Business Partnership

• Develops strong relationships with AVP/VP/Senior Director-level clients in Investment Finance, Investment Risk, and Investment Management.
• Guides clients on effective portfolio-level work decisions, considering various angles and potential outcomes.
• Engages in forward-thinking strategic discussions, advising clients on upcoming technology challenges and solutions.
• Partners with business leaders to ensure delivery aligns with the business objectives of the Investment Solutions Group (ISG).

Our Technology Stack

• Investment Platforms: Extensive experience with platforms such as Bloomberg, Charles River, Blackrock Aladdin, and other similar trading platforms.
• Custom Development: Expertise in scalable FinTech application development and full-stack custom development for investment trading systems, integrating vendor and bespoke solutions.
• DevOps & Agile: Strong knowledge of DevOps and Agile practices, with experience in implementing lean software development methodologies.
• Platform Management: Experience managing multi-product/platform SaaS technology environments for corporate clients, with a deep understanding of front, middle, and back-office workflows.
• Cloud & SaaS: Familiarity with cloud platforms, platform management, and supporting multi-vendor integrations.

What you Bring:

• Education: Bachelor’s degree in Business, Computer Science, Engineering, or related field (or equivalent experience).
• Capital Markets Expertise: 3-5+ years of Capital Markets experience, with deep knowledge of investment platforms (e.g., Bloomberg, Charles River).
• Leadership: 10+ years leading technical teams, including software development, platform management, and infrastructure engineering.
• Customer Focus: Proven ability to implement customer support strategies in multi-platform environments, driving platform innovation.
• Project Management: Experience leading multi-million-dollar strategic projects with a strong ability to balance time constraints and analysis requirements.
• Emotional Intelligence: Strong people leadership and emotional intelligence, fostering a culture of empowerment and innovation within teams.
• Communication & Negotiation: Excellent communication, negotiation, and influencing skills to manage relationships with senior business leaders and external vendors.
• Agile Experience: Experience building and leading teams in Agile Scrum environments, with a focus on continuous improvement and value delivery.

Please refer the Job description for details