Lead DevOps Engineer

About Mortgage Automator:

Built by Lenders, Designed for Growth. Mortgage Automator was started in 2013 as a simple document-generating tool for a small private lender in Toronto, Canada. Since then, the software has evolved significantly to encompass every possible feature and account for all the unique lending scenarios. Mortgage Automator is a cutting-edge technology company specializing in providing innovative, automated solutions for the private lending industry.

Our comprehensive product offerings include modules for loan origination, servicing, and administration. The loan origination module automates the entire process from application to approval, ensuring quick and accurate decision-making. Our servicing module streamlines payment processing, accounting, and borrower communications, while our administration tools offer robust reporting, compliance tracking, and portfolio management capabilities, optimizing operations for our clients.

At Mortgage Automator, our mission is to transform the private lending landscape through the power of automation and technology. We are committed to reducing administrative burdens, improving operational efficiency, and enhancing clarity throughout the lending process. By delivering exceptional support and training, we ensure our clients maximize the value of our platform, empowering them to succeed in a competitive market and driving growth and innovation within the industry.

Why Join Us?

• Competitive Compensation & Benefits: Industry-leading pay, full health benefits, generous vacation.
• High Impact: You’ll directly influence and own mission-critical platforms used by hundreds of lenders and legal professionals across North America and beyond. Your work will directly impact client satisfaction, platform reliability, and revenue retention. This is your chance to build and own the entire IT/Infrastructure/DevOps function at two growing SaaS companies.
• Tech-Forward Environment: Work with the latest cloud-native technologies, automation tools, monitoring platforms, and infrastructure-as-code solutions. We embrace modern DevOps practices and encourage technical innovation that improves stability, security, and scalability.
• Industry Momentum: Join a company scaling rapidly in the fintech and LegalTech SaaS space, with expansion into the USA, and international markets. You’ll play a pivotal role in supporting global growth, infrastructure expansion, and evolving compliance requirements across new regions.

Role Overview:

Mortgage Automator is scaling rapidly, and with that comes the need for a dedicated DevOps leader to shape and build our infrastructure and delivery practices. We're looking for a senior DevOps engineer who is passionate about automation, platform reliability, and modern tooling — and who is ready to take ownership of the DevOps function across the company.

As the first dedicated DevOps resource, you'll define our DevOps culture, processes, and tooling from the ground up. You'll play a central role in upcoming initiatives such as containerizing our applications, building robust CI/CD pipelines, adopting Infrastructure as Code, investing in observability, and exploring orchestration tools like Kubernetes. You'll be at the center of these transformations, helping us modernize how we build, release, and operate software.

This is a great opportunity for a senior DevOps engineer with deep hands-on expertise who has led a team before to take the next step in their career — to become the lead DevOps resource for an entire company and drive the company’s DevOps approach from a position of authority.

Primary Job Responsibilities:

• Architect and maintain cloud infrastructure on AWS (EC2, S3, RDS, IAM, CloudFront, VPC, Route 53, CloudWatch, Lambda, etc.).
• Automate environment configurations using Infrastructure as code (IaC) technologies using Open ToFu or AWS CloudFormation.
• Design and maintain CI/CD pipelines using GitLab CI/CD with container-based builds and automated test integration.
• Build secure, optimized, production-grade containers for applications currently deployed in Virtual Machines using multi-stage builds, container security scanning tools, etc.
• Ensure high availability and uptime using Site Reliability Engineering (SRE) best practices.
• Implement monitoring, alerting, and logging with tools like Prometheus, Grafana, CloudWatch, ELK Stack, or Datadog.
• Manage production rollouts, blue/green deployments, canary releases, and rollback strategies.
• Suggest overall process improvements to increase development throughput and production reliability.
• Analyze current technology use and business needs and recommend tools and technologies that can improve efficiency and reliability.
• Work with leadership to foster a culture of “end-to-end” decision making and a shared ownership model.
• Provide support to internal teams (Engineering, Operations, CS, Sales, Product) and external clients when issues impact infrastructure, performance, or uptime.
• Maintain incident response plans and run postmortem reviews related to infrastructure issues.

Anticipated Tools, Platforms & Concepts

While specific tools mentioned below are highly desirable, they are largely examples of the types of tooling we anticipate this position leveraging. However, this position will afford the successful candidate wide latitude in choosing the right tools for the right job.

• AWS (EC2, RDS, IAM, S3, Route 53, VPC, Lambda, CloudFront, CloudWatch)

• GitLab CI/CD

• Terraform / Open ToFu / AWS CloudFormation

• Docker / Podman

• Kubernetes

• Bash

• Prometheus, Grafana

• Kibana, Loki

• AWS CloudWatch, New Relic, Monit

Qualifications:

• 5+ years of experience in IT/DevOps/Infrastructure/Site Reliability roles within a SaaS or tech company.

• Hands-on expertise with AWS, GitLab, and at least one major monitoring suite (CloudWatch, Datadog, etc.).

• Strong scripting and automation skills (Bash, Python, PowerShell).

• Track record of scaling secure and performant systems for customer-facing platforms.

• Excellent interpersonal skills to support internal users and liaise with external clients during infrastructure-related issues.

• Hands-on experience developing Docker Containers and deployment of containers into Kubernetes.

• Experience working in agile teams.

• DevOps leadership / thought-leadership; to include leading small teams, identifying and implementing best practices, researching and selecting the right tools to support engineering and business needs.

Bonus Qualifications (not required):

• AWS Certifications (Solutions Architect, DevOps Pro, etc.)
• Familiarity with supporting compliance efforts (SOC 2, HIPAA, etc.)
• Experience with GitOps practices and tools (FluxCD, etc.)
• Familiarity with expanding multi-region or international cloud infrastructure
• Experience supporting SaaS growth across finance, legal, and lending verticals
• SOC 2, PIPEDA, HIPAA, GDPR (awareness of requirements)
• GuardDuty, Config, IAM policies

Role Details:

• Location: Toronto (In-office)
• Type: Full-time, Permanent
• Schedule: Monday–Friday
• Work Environment: Full Time In Office