Technical Deployment Lead

Job Summary:

Job Description:

Role: Technical Deployment Lead

Department: R&D

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.)

Worker Sub Type:

Number of Openings Available: