Director of Engineering

Hey there! We’re ContactMonkey 👋

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

About the job - Director of Engineering

Join the Engineering team, where you’ll have the opportunity to lead our Engineering department. Our Director of Engineering doesn’t just run the day-to-day of our Engineering department, we drive strategic innovation, streamline operations, and align technology initiatives to accelerate business growth and efficiency.

In this role, you’ll report to our Chief Product and Technology Officer and work towards optimizing our product for the enterprise market alongside the Product and Engineering teams, who strive for excellence every day.

Your impact

• Strategic leadership: Own and drive the engineering strategy that powers 30% YoY growth and keeps us aligned with the product roadmap. You'll be a trusted technical voice at the leadership table, guiding decisions around infrastructure, scaling, and what’s next for our platform
• Team management & development: Lead and grow a stellar, cross-functional engineering team (frontend, backend, DevOps—you name it). Foster a culture of ownership, collaboration, and continuous improvement where people do their best work and have fun doing it
• Technical excellence & delivery: Ship high-quality, scalable, and secure products—on time and on point. You’ll keep the bar high and the releases rolling
• Cross-functional collaboration: Work hand-in-hand with Product, Design, Support, and other teams to make sure we’re building the right things in the right way for our customers and the business
• Process & efficiency: Level up our tools, workflows, and agile practices (think: sprint planning, retros, CI/CD) to boost team productivity and keep things running smoothly.
• Innovation & scalability: Keep an eye on the future—explore emerging tech (like AI) to help us scale smartly and keep our platform blazing fast
• Security & compliance: Make sure we’re rock-solid on security, compliant with standards like SOC 2 and GDPR, and consistently delivering reliable, high-performing systems

About you:

• Based in Toronto (GTA), you’re a seasoned engineering leader with at least 8+ years in SaaS and 5+ years leading teams
• Experience working in B2B enterprise scale software
• Have seen through the start up to scale up journey before (ideally at the same org) i.e. experience building software from the ground up but also have experience scaling and maintaining successful software
• You’ve led Engineering orgs of 30+ (4-5 pods + managers) and know how to connect the dots between technical execution and business impact. You coach managers and teams to think big and take ownership

How you can stand out

• Exposure to AI/ML technologies with a demonstrated ability to initiate and deliver successful AI-driven projects
• Comfortable working across cloud platforms such as AWS, Google Cloud, or Azure, and adaptable to shifting infrastructure needs
• Familiarity with Microsoft tools and technologies, while maintaining flexibility and openness to varied technology stacks based on business and product requirements
• You’ve built and scaled engineering orgs that are collaborative, accountable, and high-performing
• You’re not afraid to dive in when things need realigning—setting clear priorities and rallying the team
• You’re curious, bold, and energized by fast-paced environments where learning and experimentation are the norm
• Able to work in a hybrid or DT in-office setting as required
• Computer Science degree or similar

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 6 weeks

💰 Stock option plan for a stake in our success

🏝 Generous vacation package to take well-deserved breaks

📚 Personal development budget to fuel your growth

☀️ Summer flex days in July and August

🧖 One personal day and one volunteering day to give back to the community

🍎 Five health days per year

💼 Beautiful downtown Toronto office for hybrid work—stocked with all the best snacks

Who We Are

Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.

Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.

We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:

• Ranked by the Globe & Mail as one of Canada’s fastest-growing companies
• Recognized in 2023 Deloitte Technology Fast 50™ awards for the highest revenue growth over the past four years
• Recognized in 2023 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America
• Raised a record $55 million Series A financing for a Canadian tech company in 2023

Diversity is our strength

At ContactMonkey, we are building diverse products 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 creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.