The AVP Technology Lead – Digital is a strategic technology leader responsible for enabling, scaling, and modernizing our shared digital platforms that support secure, connected, and frictionless Client and advisor experiences. This role provides technology leadership across core digital assets including Secure Web, Public Web, & Secure Mobile, and related enablement platforms such as client identity and access management, and an internal design system.

The role combines strategic leadership, technical oversight, people leadership, delivery execution, operational accountability, and vendor/financial management to drive technology excellence and measurable business value. The AVP partners closely with Product, Client Experience, Architecture, Cybersecurity, Operations, Engineering, and Business leaders to ensure digital assets are resilient, scalable, secure, reusable, and aligned to enterprise priorities.

This role operates in a complex, high-visibility environment where digital platform reliability, modernization, and cross-business enablement are critical to Client outcomes. The leader must be able to bring clarity to a broad mandate, make decisions in ambiguity, and build a high-performing technology organization that balances speed, stability, security, and long-term platform health.

What will you do?

1. Technology Strategy, Platform Enablement & Engineering

- Shape, communicate, and align the digital technology strategy across business units, ensuring it supports near-term delivery commitments and longer-term modernization objectives.

- Partner with Business Leads, Product, Client Experience, Architecture, Cybersecurity, Operations, and Enterprise Technology to define platform roadmaps, OKRs, sequencing, and investment priorities.

- Provide thought leadership on the evolution of shared digital platforms, including identity, web, mobile, integration, data enablement, and reusable digital capabilities.

- Promote technology stack standards, modern engineering practices, automation, and architectural discipline, balancing build vs. buy vs. partner decisions in a complex technology ecosystem.

- Ensure design and engineering decisions account for reusability, scalability, security, maintainability, accessibility, and technical debt reduction.

- Create the conditions for exceptional digital experiences by enabling business and product teams with reliable, scalable, secure, and reusable platforms.

2. Platform Delivery & Execution

- Accountable for end-to-end delivery of digital platform capabilities, including oversight of internal delivery teams, vendors, system integrators, and total cost of ownership.

- Drive delivery excellence by improving velocity, quality, reliability, predictability, and agile maturity across multiple squads.

- Track delivery metrics, identify bottlenecks, and implement targeted productivity and delivery maturity improvements.

- Serve as the primary escalation point for platform, delivery, vendor, and dependency-related issues, enabling rapid resolution in a complex environment.

- Ensure delivery is integrated across product, architecture, engineering, operations, cybersecurity, and business priorities.

- Embed test-and-learn, automation, and continuous improvement practices to improve speed, quality, and sustainability.

3. People Leadership & Capability Development

- Lead, mentor, and develop technology leaders and teams, fostering a collaborative, inclusive, accountable, and execution-focused culture.

- Design and optimize team structures to support clear ownership, delivery outcomes, modernization priorities, and clear accountabilities.

- Partner with Chapter, Engineering, Product, and Business leaders on workforce planning, role clarity, succession planning, and capability development.

- Build internal capability in digital engineering, enablement, agile delivery, vendor management, and operational excellence.

- Coach leaders to manage performance effectively, clarify ownership, and build resilient teams through change and transformation.

- Lead budget management, including annual planning, cost tracking, capitalization, forecasting, and investment prioritization.

- Manage strategic vendor and system integrator relationships, holding partners accountable for delivery quality, outcomes, knowledge transfer, and value realization.

- Drive cost transparency and technology spend optimization across applications, infrastructure, security, vendor, and platform investments.

- Identify opportunities to reduce long-term dependency on external partners while strengthening internal platform ownership and capability.

- Ensure stability, security, technology currency, resiliency, and end-of-life decommissioning for applications within scope.

- Establish governance processes that balance speed of delivery with risk management, audit, regulatory, cybersecurity, and control requirements.

- Partner with Application Operations to ensure effective incident management, change management, disaster recovery, and business continuity planning.

- Proactively manage operational risk, application health, technical debt, and service reliability across shared digital capabilities.

6. Cross-Functional Collaboration & Stakeholder Engagement

- Act as a strategic technology partner to leaders across Product, Client Experience, Business, Operations, Architecture, Cybersecurity, and Enterprise Technology.

- Communicate digital strategy, delivery status, risks, trade-offs, and dependencies with clarity and transparency.

- Represent the Digital technology function in executive forums, bringing enterprise perspective, external insight, and pragmatic recommendations.

- Strengthen alignment between technology investments, business priorities, Client experience outcomes, and enterprise digital strategy.

Accountabilities

- Align digital strategy with business objectives, Client outcomes,



enterprise standards, and shared technology priorities.

- Define and monitor roadmaps, OKRs, modernization priorities, and delivery sequencing.

- Oversee execution across delivery teams, vendors, system integrators, and enterprise partners.

- Establish governance, track delivery metrics, and drive productivity, quality, and reliability improvements.

- Manage budgets, vendor relationships, and cost optimization opportunities.

- Build and sustain a high-performing, engaged, inclusive, and platform-oriented technology organization.

- Ensure digital platforms are secure, scalable, resilient, reusable, and positioned to support future growth.

What you need to succeed?

Qualifications & Experience

- Bachelor’s degree in Computer Science, Engineering, or related field; advanced degree or MBA is an asset.

- 10+ years of experience in senior technology leadership roles with demonstrated success delivering complex, mission-critical digital platforms.

- Experience leading modernization and enablement of digital platforms such as identity, web, mobile, integration, or client/advisor experience platforms.

- Proven ability to lead technology teams through transformation, platform ownership, and operating model evolution.

- Strong financial acumen with experience managing sizable technology budgets, vendor portfolios, and total cost of ownership.

- Strong stakeholder management, executive communication, and organizational leadership skills.

- Experience in regulated financial services is valuable; depth in digital enablement, engineering excellence, and vendor-heavy delivery environments is prioritized.

- As this position is posted in several locations, we specify that bilingualism (French, English, both oral and written) is required for Quebec only for the frequent interactions with English and French-speaking colleagues or internal partners across Canada or worldwide

Mindset & Behaviours

- Decisive leader comfortable operating in ambiguity, complexity, and transformation.

- Strong technical credibility with the ability to challenge architecture, delivery practices, platform decisions, and CI/CD approaches.

- Builder mindset with equal focus on fixing, scaling, enabling, and simplifying.

- Pragmatic, outcomes-driven decision-maker who balances speed, stability, risk, and long-term application health.

- Collaborative leader who builds trust, drives momentum, and creates clarity across complex stakeholder groups.

- Critical thinker who challenges the status quo constructively and drives continuous improvement.

- Strong coaching orientation with a commitment to developing leaders, teams, and internal capability.

Role Summary

The AVP Technology Lead – Digital is a strategic technology leader responsible for enabling, scaling, and modernizing our shared digital platforms that support secure, connected, and frictionless Client and advisor experiences. This role provides technology leadership across core digital assets including Secure Web, Public Web, & Secure Mobile, and related enablement platforms such as client identity and access management, and an internal design system.

The role combines strategic leadership, technical oversight, people leadership, delivery execution, operational accountability, and vendor/financial management to drive technology excellence and measurable business value. The AVP partners closely with Product, Client Experience, Architecture, Cybersecurity, Operations, Engineering, and Business leaders to ensure digital assets are resilient, scalable, secure, reusable, and aligned to enterprise priorities.

This role operates in a complex, high-visibility environment where digital platform reliability, modernization, and cross-business enablement are critical to Client outcomes. The leader must be able to bring clarity to a broad mandate, make decisions in ambiguity, and build a high-performing technology organization that balances speed, stability, security, and long-term platform health.

What will you do?

1. Technology Strategy, Platform Enablement & Engineering

- Shape, communicate, and align the digital technology strategy across business units, ensuring it supports near-term delivery commitments and longer-term modernization objectives.

- Partner with Business Leads, Product, Client Experience, Architecture, Cybersecurity, Operations, and Enterprise Technology to define platform roadmaps, OKRs, sequencing, and investment priorities.

- Provide thought leadership on the evolution of shared digital platforms, including identity, web, mobile, integration, data enablement, and reusable digital capabilities.

- Promote technology stack standards, contemporary engineering practices, automation, and architectural discipline, balancing build vs. buy vs. partner decisions in a complex technology ecosystem.

- Ensure design and engineering decisions account for reusability, scalability, security, maintainability, accessibility, and technical debt reduction.

- Create the conditions for exceptional digital experiences by enabling business and product teams with reliable, scalable, secure, and reusable platforms.

2. Platform Delivery & Execution

- Accountable for end-to-end delivery of digital platform capabilities, including oversight of internal delivery teams, vendors, system integrators, and total cost of ownership.

- Drive delivery excellence by improving velocity, quality, reliability, predictability, and agile maturity across multiple squads.

- Track delivery metrics, identify bottlenecks,



and implement targeted productivity and delivery maturity improvements.

- Serve as the primary escalation point for platform, delivery, vendor, and dependency-related issues, enabling rapid resolution in a complex environment.

- Ensure delivery is integrated across product, architecture, engineering, operations, cybersecurity, and business priorities.

- Embed test-and-learn, automation, and continuous improvement practices to improve speed, quality, and sustainability.

3. People Leadership & Capability Development

- Lead, mentor, and develop technology leaders and teams, fostering a collaborative, inclusive, accountable, and execution-focused culture.

- Design and optimize team structures to support clear ownership, delivery outcomes, modernization priorities, and clear accountabilities.

- Partner with Chapter, Engineering, Product, and Business leaders on workforce planning, role clarity, succession planning, and capability development.

- Build internal capability in digital engineering, enablement, agile delivery, vendor management, and operational excellence.

- Coach leaders to manage performance effectively, clarify ownership, and build resilient teams through change and transformation.

4. Financial & Vendor Management

- Lead budget management, including annual planning, cost tracking, capitalization, forecasting, and investment prioritization.

- Manage strategic vendor and system integrator relationships, holding partners accountable for delivery quality, outcomes, knowledge transfer, and value realization.

- Drive cost transparency and technology spend optimization across applications, infrastructure, security, vendor, and platform investments.

- Identify opportunities to reduce long-term dependency on external partners while strengthening internal platform ownership and capability.

5. Operational Excellence, Risk & Security

- Ensure stability, security, technology currency, resiliency, and end-of-life decommissioning for applications within scope.

- Establish governance processes that balance speed of delivery with risk management, audit, regulatory, cybersecurity, and control requirements.

- Partner with Application Operations to ensure effective incident management, change management, disaster recovery, and business continuity planning.

- Proactively manage operational risk, application health, technical debt, and service reliability across shared digital capabilities.

6. Cross-Functional Collaboration & Stakeholder Engagement

- Act as a strategic technology partner to leaders across Product, Client Experience, Business, Operations, Architecture, Cybersecurity, and Enterprise Technology.

- Communicate digital strategy, delivery status, risks, trade-offs, and dependencies with clarity and transparency.

- Represent the Digital technology function in executive forums, bringing enterprise perspective, external insight, and pragmatic recommendations.

- Strengthen alignment between technology investments, business priorities, Client experience outcomes, and enterprise digital strategy.

Accountabilities

- Align digital strategy with business objectives, Client outcomes, enterprise standards, and shared technology priorities.

- Define and monitor roadmaps, OKRs, modernization priorities, and delivery sequencing.

- Oversee execution across delivery teams, vendors, system integrators, and enterprise partners.

- Establish governance, track delivery metrics, and drive productivity, quality, and reliability improvements.

- Manage budgets, vendor relationships, and cost optimization opportunities.

- Build and sustain a high-performing, engaged, inclusive, and platform-oriented technology organization.

- Ensure digital platforms are secure, scalable, resilient, reusable, and positioned to support future growth.

What you need to succeed?

Qualifications & Experience

- Bachelor’s degree in Computer Science, Engineering, or related field; advanced degree or MBA is an asset.

- 10+ years of experience in senior technology leadership roles with demonstrated success delivering complex, mission-critical digital platforms.

- Experience leading modernization and enablement of digital platforms such as identity, web, mobile, integration, or client/advisor experience platforms.

- Proven ability to lead technology teams through transformation, platform ownership, and operating model evolution.

- Strong financial acumen with experience managing sizable technology budgets, vendor portfolios, and total cost of ownership.

- Strong stakeholder management, executive communication, and organizational leadership skills.

- Experience in regulated financial services is valuable; depth in digital enablement, engineering excellence, and vendor-heavy delivery environments is prioritized.

- As this position is posted in several locations, we specify that bilingualism (French, English, both oral and written) is required for Quebec only for the frequent interactions with English and French-speaking colleagues or internal partners across Canada or worldwide

Mindset & Behaviours

- Decisive leader comfortable operating in ambiguity, complexity, and transformation.

- Strong technical credibility with the ability to challenge architecture, delivery practices, platform decisions, and CI/CD approaches.

- Builder mindset with equal focus on fixing, scaling, enabling, and simplifying.

- Pragmatic, outcomes-driven decision-maker who balances speed, stability, risk, and long-term application health.

- Collaborative leader who builds trust, drives momentum, and creates clarity across complex stakeholder groups.

- Critical thinker who challenges the status quo constructively and drives continuous improvement.

- Strong coaching orientation with a commitment to developing leaders, teams, and internal capability.

Disclaimer:

AI may be used in evaluating candidates.

This posting is for an existing vacancy.

📌 AVP, Technology Lead - Digital (Toronto)
🏢 S.i. Systems
📍 Toronto