---
title: 'Intermediate Site Reliability Engineer at ContactMonkey'
canonical: 'https://feeny.ai/job/intermediate-site-reliability-engineer-contactmonkey-toronto-1d6gym6j4ccg'
type: 'job'
last_seen: '2026-10-18'
---

# Intermediate Site Reliability Engineer at ContactMonkey

- **Company:** ContactMonkey
- **Location:** Toronto, Canada
- **Posted:** 2026-10-08
- **Last confirmed live:** 2026-10-18
- **Apply:** https://job-boards.greenhouse.io/contactmonkey/jobs/4719230006

## Job description

Hey there! We're ContactMonkey 👋

Our mission is to power measurable employee engagement worldwide, and we're looking for an Intermediate Site Reliability Engineer to join our Engineering team.

## About the job

We’re looking for someone who enjoys running production systems, understands how applications work, and brings practical application security experience.You’ll work closely with our SRE and development teams to maintain our infrastructure, improve deployments, investigate production issues, and address security risks. You’ll also contribute to the technical controls that support SOC 2 audits and GDPR compliance.

Our north star: Become an AI-first engineering team. AI coding agents are a core part of how we build and operate. We use them to write and review Terraform, debug incidents, automate repetitive operational work, and move faster without lowering the bar on quality or security. We’re looking for someone who already works this way, or is excited to: someone who knows how to direct an agent well, check its output with a critical eye, and spot where AI can remove toil from our infrastructure and security workflows. You’ll also help shape how we use AI safely, including guardrails, access controls, and keeping sensitive data protected.

Our environment includes AWS, Kubernetes on EKS, Terraform, Terragrunt, GitHub Actions, Prometheus, Grafana, and CloudWatch. Our applications use Ruby on Rails, Vue.js, and Node.js, with MySQL, PostgreSQL, and Sidekiq supporting the backend.

You’ll take ownership of defined projects and operational improvements, with senior engineers available for guidance and review. There’s room to develop deeper expertise in reliability, infrastructure automation, application security, and AI-assisted operations.

## Your impact

- Infrastructure & reliability: Maintain AWS and Kubernetes environments, troubleshoot production issues, and improve availability, performance, and resource usage.
- Terraform & Terragrunt: Build and maintain infrastructure as code, review plans, manage environment configuration, and address infrastructure drift.
- Deployments & developer experience: Improve CI/CD pipelines, deployment automation, release checks, and rollback procedures.
- Monitoring & incidents: Improve monitoring and alerts, join the on-call rotation, and contribute to incident reviews.
- Application security: Work with developers to assess vulnerabilities, review security risks, and validate fixes.
- CI/CD security: Maintain code, dependency, secrets, container, and infrastructure scanning.
- Cloud security: Strengthen IAM, secrets management, network controls, and Kubernetes security.
- SOC 2 & GDPR: Support technical controls, audit evidence, and personal data protection.
- Recovery: Test backups and recovery procedures, maintain runbooks, and support production readiness.
- Collaboration: Participate in code reviews, document changes, and support application, AI, and data engineering teams.

## About you

- Around 3–5 years of experience in SRE, DevOps, platform engineering, cloud operations, or a related engineering role. Equivalent practical experience is welcome.
- Hands-on experience supporting production workloads in AWS.
- Experience writing and maintaining Terraform modules and Terragrunt configuration, including reviewing plans and working with remote state.
- Experience with Docker and Kubernetes, including troubleshooting deployments, services, health checks, and resource limits.
- A solid understanding of Linux, networking, DNS, HTTP, and TLS.
- Ability to write automation in Python, Bash, Ruby, JavaScript, or another suitable language.
- Experience with Git, pull requests, CI/CD pipelines, and deployment workflows.
- Experience using logs, metrics, dashboards, and alerts to investigate production problems.
- Practical application security experience through vulnerability remediation, secure code review, threat modelling, or security tooling.
- Understanding of common web application risks, including broken access control, injection, authentication weaknesses, and sensitive data exposure.
- Familiarity with IAM, least privilege, secrets management, and encryption.
- Working knowledge of SOC 2 controls and GDPR principles relevant to engineering, including access restrictions, data minimization, retention, and deletion.
- Clear communication skills and good judgment about when to work independently, request a review, or escalate an issue.

## How you can stand out

- Supported Ruby on Rails or Node.js applications in production
- Worked with MySQL, PostgreSQL, Redis or Valkey, and Sidekiq
- Experience with GitHub Actions, Argo CD, Helm, Karpenter, or KEDA
- Built useful monitoring with Prometheus, Grafana, or CloudWatch
- Supported services across multiple AWS regions
- Helped remediate penetration-test findings or contributed technical evidence to a SOC 2 audit
- Participated in backup restoration or disaster recovery exercises.
- Familiar with securing AI integrations, agent workloads, or MCP services
- You hold relevant AWS, Kubernetes, Terraform, or security certifications.

Working with the team

You'll work closely with SRE and application engineers, and support AI and data initiatives where they depend on shared infrastructure.

We value people who ask questions, explain their reasoning, and leave systems easier for others to understand. You'll take part in technical discussions and code reviews, share what you learn, and help improve how we operate.

Reducing recurring incidents, unnecessary alerts, and repetitive manual work is part of the role. We want reliable systems and sustainable operations for the people supporting them.

## What we bring to the table

🏥 100% employer-paid benefits and a Health Spending Account from day one 🌎 Work from anywhere in the world for up to four weeks 💰 A stock option plan so you can own a piece of our success 💲 An RRSP Group Savings Plan 🏝 A generous vacation package 📚 A personal development budget 🧖 One personal day and two volunteering days 🎂 Your birthday off 🍎 Five health days per year 💼 A downtown Toronto office for hybrid work, with plenty of snacks

## Compensation and work details

The salary range for this role is $130,000-$150,000 Compensation is based on experience, skills, and our internal compensation framework and equity.

We're happy to discuss compensation throughout the hiring process.

This is a full-time position on our SRE team.

The role includes a shared on-call rotation after onboarding. We'll discuss the schedule, escalation support, and expectations during the interview process.

## Who we are

ContactMonkey helps organizations create, send, and measure internal communications directly within Outlook and Gmail.

Our platform brings together email design, employee engagement tools, and analytics so internal communications teams can understand what reaches their people and what gets a response.

As the product grows, we're investing in reliability, security, and tooling that helps our engineering teams deliver changes confidently.

Diversity is our strength At ContactMonkey, we're building products for diverse organizations, and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

We are committed to an accessible hiring process. If you need accommodations or adjustments during interviews or beyond, please let us know so we can arrange the support you need.

AI Disclosure We use AI to take notes during our interviews. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system uses AI for workflows and hiring process efficiencies.

## About ContactMonkey

## Company Overview
- **One-liner**: ContactMonkey provides an intelligent internal communications platform that enables organizations to design, send, and measure employee emails and newsletters directly from Outlook and Gmail.
- **Entity Type**: Private (Series A)
- **Headquarters**: Toronto, Ontario, Canada
- **Founded**: 2010
- **Founders**: Scott Pielsticker (Founder & former CEO; stepped down March 2026), with Jeff Cates joining as CEO in 2024 to accelerate growth.

## Core Business
- **Primary Industry**: Internal Communications Software / Employee Engagement Technology
- **Target Customers**: Enterprise, mid-market, and growing organizations across sectors including healthcare, finance, insurance, utilities, manufacturing, and food & beverage — primarily B2B internal comms teams.
- **Mission**: Power measurable employee engagement worldwide.

## Products & Services
- **ContactMonkey Platform (Core)**: An intelligent internal email software that integrates directly with Outlook and Gmail. Key features include:
  - **CoAuthor (AI Email Builder)**: An AI agent that writes and designs fully on-brand internal emails for human review in seconds.
  - **ConfidenceCheck (AI Agent)**: Reviews every email before it sends for errors, inconsistencies, and accessibility issues.
  - **Audience Preview**: Previews how different employee groups will receive emails using AI personas.
  - **Analytics & Reporting**: Real-time, segmented analytics (opens, clicks, read time, actions) for every campaign, plus leadership-ready reports.
  - **Employee Newsletters**: Drag-and-drop branded newsletter creation without design skills.
  - **Employee Surveys**: Feedback tools embedded directly into newsletters.
  - **Custom Segments & List Management**: Audience building by department, role, location, seniority.
  - **Bulk Email Sends**: Reach targeted segments at scale.
  - **Seamless Microsoft Integrations**: Send from Outlook, share to Teams and SharePoint.
  - **API Connector & HRIS Integration**: Connects with SAML 2.0 providers and popular HRIS.
  - **Security**: Enterprise-grade, SOC 2 Type 2, GDPR compliant, secure SSO.

## Market Standing
- **Valuation / Market Cap**: Not publicly disclosed (Private company).
- **Key Metrics**:
  - **Annual Revenue**: USD $15.0 million *(LinkedIn estimate)*
  - **Total Funding**: ~USD $40.5 million
    - Seed Round (March 2012)
    - Venture Round (June 2025) – led by CIBC Innovation Banking
    - Series A (December 2023) – **$40.5M** led by **Updata Partners** [contactmonkey.com](https://www.contactmonkey.com/about)
  - **Customers**: 1,000+ enterprises worldwide, trusted by 10k+ communicators.
  - **Website Visits**: 1.6M+ monthly.
- **Notable Investors/Partners**: Updata Partners (lead Series A), CIBC Innovation Banking (venture round).
- **Growth Signals**:
  - Ranked by **The Globe & Mail** as one of Canada’s fastest-growing companies.
  - **2023 Deloitte Technology Fast 50™** (highest revenue growth over four years).
  - **2024 Deloitte Technology Fast 500™** (innovation and customer impact).
  - 49% employee growth in 2024 (though overall headcount saw a recent -7.3% YoY dip per LinkedIn).
  - 93% GlassDoor rating, 4.2 overall score.
  - 53% female leadership in management.
  - Expanded to operate in 7 countries (Canada, US, UK, Brazil, Australia, Spain, Ireland).

## Competitive Advantages
- **Direct Inbox Integration**: Works natively inside Outlook and Gmail — users don't need to learn a separate platform or HTML.
- **AI-Powered Efficiency**: CoAuthor and ConfidenceCheck significantly reduce creation time and error rates for internal comms teams.
- **Measurable ROI**: Deep analytics that show engagement metrics (opens, clicks, read time) — a differentiator from traditional email tools that lack internal comms tracking.
- **Security & Compliance**: SOC 2 Type 2, GDPR, secure SSO — critical for regulated industries (healthcare, finance, insurance, utilities).
- **Hundreds of Customers**: 1,000+ enterprises already using the platform, creating a strong network effect and customer data moat.

## Strategic Focus
- **Scaling the Platform**: The $55M total funding (led by Updata Partners and CIBC Innovation Banking) is fueling product innovation, team growth, and global expansion.
- **AI Innovation**: Continued investment in AI capabilities (CoAuthor, ConfidenceCheck, Audience Preview) to automate more of the internal comms workflow.
- **Global Reach**: Expanding into new markets (UK, Brazil, Australia, Spain) to serve multinational customers.
- **Enterprise Depth**: Deepening integrations with HRIS, Microsoft Teams, SharePoint, and enterprise SSO to become the central hub for internal communications.

## Why Work Here
- **Culture & Values**: "Making work more human" – emphasizes collaboration, curiosity, ownership, customer love, and playfulness. "The best ideas win" and "Bias for action" are core tenets.
- **Work Model**: **Hybrid** — most team members hit the downtown Toronto HQ weekly for collaboration and team bonding. Also offers up to **four weeks a year to work from anywhere** (beachside, mountainside, etc.).
- **Compensation & Benefits**:
  - Competitive salaries, **performance-based bonuses**, **stock options** (employee ownership).
  - **100% employer-paid health & dental** with extended mental health coverage, wellness and health spending accounts.
  - **4 weeks paid vacation**, **5 health days**, **1 personal day**, **2 volunteer days** per year.
  - **Parental leave top-ups** for all employees.
  - **Personal development budget** for skills growth.
  - Internal promotions and career growth are a priority.
- **Diversity & Inclusion**: 53% female leadership; employees across 7 countries; 17% of employees promoted internally in 2024.
- **Engineering Culture**: 18% of staff is in technical roles; Senior Software Developer salary ~CAD $114k; active hiring for a **Principal Software Engineer** and **Senior AI Engineer** as of mid-2025.
- **Awards & Recognition**: Deloitte Fast 50 & Fast 500, Globe & Mail fastest-growing company — signals a high-growth, high-impact environment.

## Sources
1. [ContactMonkey Official Website](https://www.contactmonkey.com/)
2. [ContactMonkey Careers Page](https://www.contactmonkey.com/careers)
3. [ContactMonkey About Page](https://www.contactmonkey.com/about)
4. [ContactMonkey LinkedIn Page](https://ca.linkedin.com/company/contactmonkey)
5. [ContactMonkey Job Board (Greenhouse)](http://job-boards.greenhouse.io/contactmonkey)

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