Vice President of Information Technology
Top Benefits
About the role
Confidential Search - VP of IT (Legacy Modernization & Architecture - Azure/.NET) Location: Downtown Toronto (100% in-office, non negotiable)
Compensation: Base Salary of up to $250,000 (no bonus/stock - salary reflects this)
Work Authorization: Must be eligible to work in Canada
Industry: Insurance / Financial Services
About the Role
We've partnered with a well-established and globally recognized financial services organization undergoing a major technology transformation. This is a key executive hire that will sit at the intersection of technology strategy, infrastructure modernization, and application delivery.
As the incoming VP of IT , you'll play a critical role in modernizing a complex legacy application environment (currently built in .NET and C++ ) into a future-state microservices-based architecture -primarily leveraging Microsoft Azure . You'll work closely with the current VP of IT (set to retire in 2 years) and report directly to the CFO .
This is a rare opportunity to architect and lead a full-stack transformation within a highly stable and well-capitalized organization, backed by one of the most trusted names in global finance.
What You'll Do
- Lead the strategic redesign and modernization of a legacy tech stack to a microservices-based, cloud-native architecture
- Oversee application development, platform engineering, DevOps, cybersecurity, data governance, and IT compliance
- Work closely with internal stakeholders to define long-term technology roadmaps aligned to risk, operational efficiency, and growth
- Mentor and build high-performing technical teams across application development, cloud infrastructure, and data
- Provide architectural oversight on system design, modernization approaches, tooling, and security posture (ISO 27001, NIST, OSFI B13, etc.)
- Participate in vendor evaluations, budget planning, capacity management, and resource strategy
What We're Looking For
- Proven experience leading modernization efforts from legacy systems (C++/.NET) to modern, microservices-based cloud architectures
- Deep hands-on knowledge of Azure , with strong understanding of modern DevOps practices, CI/CD, and cloud security frameworks
- Experience overseeing or building out hybrid infrastructure environments with a strong application development component
- 7+ years of experience leading cross-functional technology teams (application, cloud, architecture, governance, security, and data)
- Experience working within highly regulated environments (reinsurance, life insurance, or financial services preferred)
- Strong understanding of security and compliance standards: ISO 27001, NIST, OSFI B13, NYDFS, GDPR, etc.
- Excellent communication skills; capable of engaging both technical teams and executive stakeholders
Why This Role
- Executive visibility
- reports directly to CFO, with a clear succession plan as the current VP of IT prepares to retire
- High impact
- you'll lead the end-to-end transformation of an entire tech stack, setting the tone for the next 5-10 years
- Well-funded, stable org
- backed by one of the most reputable brands in the world, with long-term capital and a patient innovation strategy
- Competitive compensation
- $250K base salary (reflecting no bonus/stock) in a senior-level leadership role
About Vaco
Vaco Holdings is a leading provider of consulting, managed services and talent solutions. As a global professional services organization, Vaco Holdings is dedicated to supporting and transforming organizations in the core areas of accounting, finance, technology and digital. With a team of over 10,000, operating in more than 100 countries, Vaco Holdings provides business-critical services to a diverse and demanding client base through a distinct portfolio of brands: Vaco specializes in talent solutions, managed services and executive search; MorganFranklin Consulting specializes in finance, technology and business services; Pivot Point Consulting is a Best in KLAS healthcare IT consulting leader; Focus Search Partners specializes in retained and interim executive search services; and BUILT specializes in digital services focused on software, cloud, data and AI solutions. In addition to being named to Inc. magazine’s list of the fastest-growing private companies for the past 17 years, Vaco was named to Newsweek’s America’s Greatest Workplaces for Diversity and America’s Greatest Workplaces for Remote Work in 2023.
Vice President of Information Technology
Top Benefits
About the role
Confidential Search - VP of IT (Legacy Modernization & Architecture - Azure/.NET) Location: Downtown Toronto (100% in-office, non negotiable)
Compensation: Base Salary of up to $250,000 (no bonus/stock - salary reflects this)
Work Authorization: Must be eligible to work in Canada
Industry: Insurance / Financial Services
About the Role
We've partnered with a well-established and globally recognized financial services organization undergoing a major technology transformation. This is a key executive hire that will sit at the intersection of technology strategy, infrastructure modernization, and application delivery.
As the incoming VP of IT , you'll play a critical role in modernizing a complex legacy application environment (currently built in .NET and C++ ) into a future-state microservices-based architecture -primarily leveraging Microsoft Azure . You'll work closely with the current VP of IT (set to retire in 2 years) and report directly to the CFO .
This is a rare opportunity to architect and lead a full-stack transformation within a highly stable and well-capitalized organization, backed by one of the most trusted names in global finance.
What You'll Do
- Lead the strategic redesign and modernization of a legacy tech stack to a microservices-based, cloud-native architecture
- Oversee application development, platform engineering, DevOps, cybersecurity, data governance, and IT compliance
- Work closely with internal stakeholders to define long-term technology roadmaps aligned to risk, operational efficiency, and growth
- Mentor and build high-performing technical teams across application development, cloud infrastructure, and data
- Provide architectural oversight on system design, modernization approaches, tooling, and security posture (ISO 27001, NIST, OSFI B13, etc.)
- Participate in vendor evaluations, budget planning, capacity management, and resource strategy
What We're Looking For
- Proven experience leading modernization efforts from legacy systems (C++/.NET) to modern, microservices-based cloud architectures
- Deep hands-on knowledge of Azure , with strong understanding of modern DevOps practices, CI/CD, and cloud security frameworks
- Experience overseeing or building out hybrid infrastructure environments with a strong application development component
- 7+ years of experience leading cross-functional technology teams (application, cloud, architecture, governance, security, and data)
- Experience working within highly regulated environments (reinsurance, life insurance, or financial services preferred)
- Strong understanding of security and compliance standards: ISO 27001, NIST, OSFI B13, NYDFS, GDPR, etc.
- Excellent communication skills; capable of engaging both technical teams and executive stakeholders
Why This Role
- Executive visibility
- reports directly to CFO, with a clear succession plan as the current VP of IT prepares to retire
- High impact
- you'll lead the end-to-end transformation of an entire tech stack, setting the tone for the next 5-10 years
- Well-funded, stable org
- backed by one of the most reputable brands in the world, with long-term capital and a patient innovation strategy
- Competitive compensation
- $250K base salary (reflecting no bonus/stock) in a senior-level leadership role
About Vaco
Vaco Holdings is a leading provider of consulting, managed services and talent solutions. As a global professional services organization, Vaco Holdings is dedicated to supporting and transforming organizations in the core areas of accounting, finance, technology and digital. With a team of over 10,000, operating in more than 100 countries, Vaco Holdings provides business-critical services to a diverse and demanding client base through a distinct portfolio of brands: Vaco specializes in talent solutions, managed services and executive search; MorganFranklin Consulting specializes in finance, technology and business services; Pivot Point Consulting is a Best in KLAS healthcare IT consulting leader; Focus Search Partners specializes in retained and interim executive search services; and BUILT specializes in digital services focused on software, cloud, data and AI solutions. In addition to being named to Inc. magazine’s list of the fastest-growing private companies for the past 17 years, Vaco was named to Newsweek’s America’s Greatest Workplaces for Diversity and America’s Greatest Workplaces for Remote Work in 2023.