Release & Deployment Lead

Job Summary:

Job Description:

Role: Release & Deployment Lead

Department: R&D

Reports to: Manager, Cloud Ops & Security

Location: Stouffville, ON

Salary: $85,000 - $105,000

Who we are:

At Portfolio+, we empower financial institutions with secure, scalable, and customer-first solutions. As a proudly Canadian company, we're at the forefront of open finance, delivering cutting-edge cloud technology that simplifies operations, enhances security, and drives innovation. Our team thrives in a collaborative, growth-oriented environment where ideas matter, and impact is real. If you're passionate about fintech, innovation, and making a difference, Portfolio+ is the place to build your career. 

Who you are:

We're hiring a Release & Deployment Lead to lead the end-to-end software release lifecycle planning, orchestration, deployments, upgrades, and customer migrations. You'll be the connective tissue across Engineering, QA, Product, DevOps, and Customer Success to deliver smooth, reliable, and timely releases with minimal risk and a strong focus on customer experience, security, and service quality. 

What you'll do:

Release Planning & Coordination

• Build and own release calendars, cutover plans, and roadmaps across multiple products/ environments.

• Facilitate go/on-go reviews, CABs, and cross-functional readiness checks.

• Identify dependencies, manage risks, and remove blockers to keep releases on track.

• Drive clear, timely communications to stakeholders and, where applicable, customers.

Deployment & Automation

• Plan, execute, and monitor deployments for dev/test/staging/production.

• Execute deployment scripts, database migrations, configuration changes, and feature flags.

• Ensure robust version control, branching strategies, and rollback/forward-fix procedures.

• Troubleshoot live deployment issues and coordinate rapid incident response with DevOps/SRE.

System Upgrades & Migrations

• Lead infrastructure, platform, and third-party upgrades with zero/low downtime strategies.

• Partner with DevOps/Cloud teams to validate compatibility, performance, and capacity.

• Own contingency, rollback, and validation plans to safeguard reliability.

Customer Migration Support

• Co-design customer migration plans with Customer Success, Product, and Support.

• Sequence migrations to minimize downtime and business impact; coordinate notifications.

• Ensure data integrity, privacy, and security through every migration step.

Risk, Quality & Compliance

• Define and enforce release quality gates, approvals, and change controls ( e.g., CAB).

• Track and report release health ( e.g., change failure rate, MTTR, deployment frequency).

• Lead post- release reviews and root-cause analyses with clear corrective actions.

• Uphold security, regulatory, and company standards throughout the release lifecycle.

Continuous Improvement & Enablement

• Evolve tooling, processes, and runbooks to reduce manual effort and errors.

• Champion best practices in DevOps, observability, and progressive delivery.

• Mentor teams on release hygiene, readiness, and operational excellence.

• Manage the year ahead of releases ( major/minor) for all products.

What you bring:

Technical Skills

• 5+ years in Safe Agile, Release Management, DevOps, SRE, or Software Deployment roles.

• Proven success coordinating complex, multi-environment releases at scale.

• Hands-on experience with enterprise upgrades, data migrations, and cutovers.

• Background in customer-facing deployments and managing change in production.

• Strong CI/CD and automation (e.g., Azure DevOps, GitHub Actions, GitLab CI, Jenkins).

• Containers and orchestration (Docker, Kubernetes).

• Infrastructure-as-Code (Terraform, CloudFormation, Ansible).

• Git proficiency (branching, tagging, release/versioning strategies).

• Database migration tooling and practices (e.g., Liquibase/Flyway or equivalent).

• Scripting (Bash, PowerShell, Python) for automation and tooling.

• Observability and logging (e.g., Prometheus/Grafana, ELK/EFK, OpenTelemetry).

• Solid troubleshooting across application, infrastructure, and network layers.

• Tools: DevOps/Jira, Git, CI/CD (A DO/GitHub/GitLab/Jenkins), Octopus Deploy (or similar), Slack/Teams, observability and incident tools.

• Excellent planning, prioritization, and stakeholder management.

• Clear communicator—able to translate technical detail into actionable updates.

• Calm under pressure; decisive in fast-moving or ambiguous situations.

• Customer-first mindset with strong attention to detail and risk awareness.

Bonus Points if you have the following:

• Degree in Computer Science, Engineering, or related field.

• Certifications (e.g., PMP, ITIL, AWS/Azure/GCP, Kubernetes, SAFe).

• Cloud experience: AWS (EC2, S3, RDS, Lambda, CloudFormation), plus Azure/GCP.

• Configuration management tools and secrets management.

• Experience with feature flagging and progressive delivery.

• Safe Agile Certification is an asset.

Technical Environment

• Database platforms: SQL Server, MySQL, PostgreSQL, Progress OpenEdge

• Scripting: Python, Bash, PowerShell, SQL

• Containerization: Docker, Docker Compose, basic Kubernetes

• Version Control: Git, branching strategies, code reviews

• Operating Systems: Windows Server, RHEL, Ubuntu, CentOS

• Cloud Platforms: AWS, Azure

• Automation: Basic CI/CD pipelines, configuration management

Travel & Work Environment

• Occasional evening/weekend release windows and on-call rotation for major cutovers.

• Be apart of the OnCall Rotation for 24/7 Support

• May require work in various customer environments (data centers, offices, etc.)

We welcome and encourage applications from all qualified individuals who can contribute to the continued diversification of our organization, including those from equity-deserving groups that have been historically underrepresented in the workforce.  

In alignment with the Accessibility for Ontarians with Disabilities Act, 2005, Portfolio+ provides accommodation upon request throughout the recruitment, selection, and assessment process for applicants with disabilities. Please reach out to for any questions or requests. 

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