Director, IT Operations & DevOps

CanadaHelps•Toronto, ON

4d•CA$140,000 - CA$150,000•Hybrid

About The Position

At CanadaHelps we believe in the power of generosity - not just for those who receive it, but for everyone it touches. Every act of generosity sparks connection, inspires change, and brings people together. This is an opportunity to join something bigger: a movement that fuels progress, strengthens communities, and reminds us of what’s possible when we come together. We are a dedicated team of entrepreneurial-minded peers who believe in a world where everyone can thrive. We offer a flexible, inclusive environment built on growth, ambition, and shared success. CanadaHelps provides the most comprehensive and flexible range of giving solutions for donating to any charity in Canada, and we partner with charities of all sizes to ensure they have the tools they need to achieve their goals. Over the past 25 years we’ve helped raise over $3.7B for Canadian charities. Generosity is right here. About the role: We are looking for a full-time Director, IT Operations & DevOp. Reporting to our CTO, the Director, IT Operations & DevOps will lead CanadaHelps’ Infrastructure, DevOps and internal IT functions, helping ensure our technology platforms are reliable, secure, scalable and well supported as the organization continues to grow and modernize. This is a existing vacancy. Reporting to the CTO, this role is responsible for strengthening the operational foundations of the organization through improved processes, automation, service management practices and operational governance. The Director will help drive infrastructure modernization efforts, improve platform reliability and resiliency, reduce operational risk and support the continued evolution of CanadaHelps’ cloud and operational capabilities. This role will work closely with Engineering and business stakeholders to improve how operational services are delivered across the organization. That includes maturing areas such as incident management, change management, operational readiness, monitoring, documentation and disaster recovery practices, while helping reduce reliance on manual processes and operational tribal knowledge. The successful candidate will bring a balance of operational leadership and technical understanding with a strong focus on building internal processes, enabling teams and creating a culture of accountability, continuous improvement and operational excellence. The annual salary range for this role is $140,000 - $150,000. Where an offer falls within this range is determined through the interview process. Candidates are benchmarked by the hiring team based on role scope, relevant experience, skill alignment, and expected impact, using consistent and objective criteria. This position is remote but may require to be in-office in Toronto for team collaborations.

Requirements

10+ years of experience in Infrastructure, DevOps, IT Operations or related technology leadership roles
Experience leading Infrastructure, DevOps and/or IT teams within complex technology environments
Experience improving operational processes, service delivery and organizational accountability
Strong experience with cloud infrastructure environments, preferably Microsoft Azure
Experience leading infrastructure modernization, operational transformation or cloud migration initiatives
Strong understanding of modern DevOps practices including CI/CD, Infrastructure-as-Code, automation and environment standardization
Experience supporting highly available production platforms and improving reliability, monitoring and operational readiness
Experience supporting regulated environments, including security, compliance and audit-related activities (PCI experience is an asset)
Experience with disaster recovery, business continuity and operational risk management
Strong leadership, communication and stakeholder management skills, with the ability to work effectively across technical and non-technical teams
Pragmatic, solutions-oriented mindset with a focus on operational excellence and continuous improvement

Nice To Haves

PCI experience is an asset

Responsibilities

Lead the organization’s Infrastructure, DevOps and internal IT teams
Establish clear and consistent operational practices for incident management, change management, service delivery, disaster recovery and operational readiness
Improve accountability, documentation, ownership and operational consistency across Infrastructure, DevOps and IT
Define and track operational metrics related to platform reliability, service health and operational performance
Establish clear escalation paths, support models and service standards to improve cross-team coordination and delivery
Build a culture of ownership, continuous improvement, operational discipline and automation
Lead infrastructure modernization, cloud operations and environment standardization
Improve platform reliability, monitoring, alerting and incident response capabilities
Partner with Engineering teams to improve CI/CD, environment consistency and developer experience and enablement
Drive Infrastructure-as-Code, automation and repeatable operational practices
Lead capacity planning and platform readiness for Giving Season and other critical fundraising periods
Reduce manual processes, knowledge siloes and legacy operational dependencies through automation, documentation and shared ownership
Support vulnerability management, access management, operational controls and PCI compliance activities
Support audit readiness, disaster recovery and business continuity planning
Reduce infrastructure and operational risk across platforms and third-party services
Ensure operational practices meet security, compliance and risk requirements
Lead internal IT operations including endpoint management, device lifecycle management and internal technology support
Improve IT support processes, service consistency and the end-user experience
Manage IT vendors, licensing and operational technology services
Ensure internal IT services scale effectively as organizational needs evolve