Technical Deployment Lead

Job Summary:

Job Description:

Role: Technical Deployment Lead

Department: R&D

Reports to: Manager, Cloud Ops & Security

Location: Stouffville, ON

Salary: $85,000 - $105,000

Number of Openings: 1

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 hands-on Technical Deployment Lead to design, execute, and own production deployments across cloud-based, customer-facing platforms. This role requires strong technical depth in CI/CD, cloud infrastructure, scripting, and Git-based workflows, combined with the ability to lead high-risk deployment and cutover activities. You will be directly involved in building and running deployment pipelines, executing production releases, validating outcomes, and responding to issues in real time. Experience as a Release Manager or Release Train Lead is a strong asset, but this role is first and foremost technical and execution-driven.

What you'll do:

Hands-On Deployment Execution

• Build, run, and troubleshoot CI/CD pipelines supporting application and infrastructure deployments.

• Execute and lead production deployments, cutovers, and rollbacks across multiple environments.

• Run deployment bridges and act as the technical authority during release windows.

• Perform post-deployment validation using logs, metrics, monitoring, and synthetic checks.

• Investigate and resolve deployment failures, pipeline errors, and environment issues.

CI/CD & Automation

• Develop and maintain deployment automation using Python, PowerShell, Bash, or similar scripting languages.

• Improve pipeline reliability, speed, and safety through automation and standardization.

• Integrate CI/CD pipelines with testing, security scanning, and approval gates.

• Reduce manual deployment steps and operational toil.

Cloud & Platform Deployments

• Deploy and operate applications in cloud environments (AWS, Azure, or GCP).

• Execute deployments on containerized platforms (Docker, Kubernetes, ECS, EKS, AKS).

• Coordinate application, infrastructure, and platform upgrades.

• Validate capacity, performance, and resiliency during deployments.

Git & Release Engineering Practices

• Use Git-based workflows (branching strategies, tagging, release branches) to manage releases.

• Ensure versioning, artifact traceability, and reproducible builds.

• Partner with engineering teams to enforce release hygiene and deployment standards.

Database & Configuration Changes

• Execute and validate database migrations and schema changes as part of deployments.

• Coordinate configuration and secrets updates safely across environments.

• Ensure rollback and backward-compatibility strategies are in place.

Incident Response & Operational Ownership

• Act as the deployment incident lead when issues arise during releases.

• Analyze logs, metrics, and traces to diagnose production issues.

• Coordinate rapid mitigation, fixes, or rollbacks under live conditions.

Continuous Improvement & Enablement

• Identify systemic deployment issues and personally implement improvements.

• Improve runbooks, scripts, and tooling used for production changes.

• Standardize deployment practices across teams and services.

• Mentor engineers on CI/CD, deployment safety, and production readiness.

What you bring:

Technical Skills

• 5+ years in hands-on DevOps, SRE, Release Engineering, or Deployment-focused roles.

• Strong experience with CI/CD platforms (GitHub Actions, GitLab CI, Jenkins, Azure DevOps, or similar).

• Solid cloud experience in AWS. Azure or GCP is a plus.

• Experience with Ansible and Terraform

• Proficiency in Git (branching, tagging, pull requests, release strategies).

• Strong scripting skills in Python and/or PowerShell (Bash a plus).

• Experience deploying containerized workloads using Docker and Kubernetes.

• Exposure to infrastructure-as-code concepts (Terraform, CloudFormation, ARM, etc.).

• Experience executing production database migrations.

• Proven ability to execute high-risk production deployments with minimal customer impact.

• Strong understanding of monitoring, logging, and alerting during deployments.

• Comfortable operating in high-availability or regulated environments.

• Calm, decisive, and accountable during production incidents and cutovers.

Bonus Points if you have the following:

• Experience as a Release Manager, Release Lead, or Release Train Lead who remained hands-on.

• Experience with feature flags, blue/green, canary, or progressive delivery.

• Background in financial services, SaaS, or regulated industries.

• Certifications: ITIL, SAFe, PMP, cloud certifications.

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.

At Portfolio Plus, we use AI-enabled tools to help support parts of our recruitment process, such as creating job descriptions, assessments, and scheduling automations. These tools help us work more efficiently and consistently as we grow. AI supports our hiring teams, but it does not replace human judgment. All hiring decisions are made by people, and AI is never used as the sole decision-maker.

If you have questions about our hiring process, how AI is used, or if you require accommodation at any stage, please reach out to our People & Culture team ([email protected]) and we will be happy to answer any questions you have.

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 [email protected] for any questions or requests.

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