Technical Deployment Lead

Overview

Reports to: Manager, Cloud Ops & Security

Location: Stouffville, ON ( Hybrid)

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.

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, Power Shell, 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.
• 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.
• 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 Dev Ops, SRE, Release Engineering, or Deployment-focused roles.
• Strong experience with CI/CD platforms (Git Hub Actions, Git Lab CI, Jenkins, Azure Dev Ops, 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 Power Shell (Bash a plus).
• Experience deploying containerized workloads using Docker and Kubernetes.
• Exposure to infrastructure-as-code concepts (Terraform, Cloud Formation, ARM, etc.).
• 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

• Scripting:
  Python, Bash, Power Shell, SQL
• Version Control:
  Git, branching strategies, code reviews
• Operating Systems:
  Windows Server, RHEL, Ubuntu, CentOS
• Automation:
  Basic CI/CD pipelines, configuration management
• Occasional evening/weekend release windows and on-call rotation for major…