Head Infrastructure & DevOps (Internal/External Systems)
Location: Toronto, ON (In-office)
Employment Type: Full-Time | Permanent
Mortgage Automator and Lawyer Automator are industry-leading SaaS platforms built to automate and modernize private lending and legal operations. With hundreds of customers across North America and global expansion on the horizon (Australia, New Zealand, and EU), we are scaling rapidly—and need infrastructure to match.
We’re looking for a hands-on technical leader to own the entire IT, DevOps, and Infrastructure function. This includes internal support (devices, networking, permissions), external infrastructure (AWS cloud, CI/CD, uptime), and regulatory compliance (SOC 2, PIPEDA, HIPAA).
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 & Key Responsibilities:
You will be responsible for many critical aspects of our software delivery operations, ensuring our platforms are secure, compliant, and always available to our clients as well as creating efficient, automated development support infrastructure that minimizes bottlenecks and accelerates value creation. You’ll partner closely with Engineering, Operations, and the Executive team to design systems that are scalable, resilient, and secure across global SaaS environments.
This is a builder role: You will implement tools, own processes, and create standards across development, deployment, security, monitoring, compliance, and client-facing infrastructure.
DevOps, Cloud, & Platform Reliability
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.
Help to create secure produciton grade containerized builds for currently traditionally deployed applications.
Ensure high availability and uptime using Site Reliability Engineering (SRE) best practices.
Implement monitoring, alerting, and loging with tools like Prometheus, Grafana, CloudWatch, ELK Stack, or Datadog.
Manage production rollouts, blue/green deployments, canary releases, and rollback strategies.
Security, Compliance, & Risk Management
Work with COO and Operations and assist in the design and implementation of automated controls aligned with SOC 2 Type II, PIPEDA, HIPAA, and GDPR-readiness.
Assist in automating periodic audits, vulnerability scans, access reviews, and policy updates.
Build and maintain secure configurations for cloud and local environments using tools like AWS Config, GuardDuty, Wazuh, or OSSEC.
Collaborate with Operations, Legal, finance, and leadership teams to support third-party security questionnaires and data-sharing agreements.
Collaboration, Support & Client-Facing Reliability
Be the internal point of contact for all production and development infra-related issues, tickets, and escalations.
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.
Create infrastructure dashboards and reports for both technical and non-technical stakeholders.
Suggest overall process improvements to increase develpent throughput and production reliability.
Work with leadership to foster a cultuer “end-to-end” decision making and a shared ownderhip model.
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.
DevOps & Cloud:
AWS (EC2, RDS, IAM, S3, Route 53, VPC, Lambda, CloudFront, CloudWatch)
GitLab CI/CD
Terraform / Open ToFu / AWS CloudFormation
Docker / Podman
Kubernetes (basic knowledge acceptable)
Bash
Monitoring & Observability
Prometheus, Grafana
Kibana, Loki
AWS CloudWatch, New Relic, Monit
Security & Compliance
SOC 2, PIPEDA, HIPAA, GDPR (awareness of requirements)
GuardDuty, Config, IAM policies
Process Knowledge:
Site Reliability Engineering (SRE)
Infrastructure as Code (IaC)
Change Management & Incident Response
Compliance documentation and audit readiness
Agile/Scrum methodologies (used for dev + ops coordination)
Qualifications:
4+ 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.
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
Role Details:
Location: Toronto (In-office)
Type: Full-time, Permanent
Schedule: Monday–Friday
