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 Sales

Join the Sales team, where you’ll have the opportunity to win net new business and be at the forefront of business growth. Our Director of Sales isn’t just closing deals—you're a strategic hunter, driving enterprise growth and building a predictable, scalable revenue engine.

In this role, you’ll report to the VP of Sales and work towards 50% YoY growth alongside the Sales and Marketing, who strive for excellence every day.

Your impact

• Leading BDR and AE teams, who are smart, ambitious, and ready to grow. Your job is to set the bar, keep motivation high, coach them to be their best, and make sure everyone is clear on goals and expectations
• Performance that drives results: you’ll own the key metrics—response times, conversion rates, pipeline impact, quota achievement—and make sure the team is not just tracking to them, but beating them. When something’s off, you’ll spot it fast and get things back on track
• Scaling that works: we’re building for 50% YoY growth, so processes need to be clean, efficient, and repeatable. You’ll bring structure without slowing us down—making smart use of tools like Salesforce, Gong, LinkedIn, Salesloft, Clay, Nooks), to keep the team running smoothly and transparently
• Always testing, always improving: you’ll lead with curiosity—constantly experimenting with what messaging, cadences, and workflows actually move the needle. Work closely with marketing to run tests, learn quickly, and double down on what works
• Sales enablement: You’ll make sure the team is set up to win—designing onboarding tailored to inbound sales, coaching on real call scenarios, and running regular training sessions that sharpen skills to help us move up market to the enterprise space. This means refining qualification criteria for complex buying groups; coaching reps on multi-threading and enterprise messaging; and aligning closely with marketing and sales leadership to prioritize and route high-value accounts effectively. You'll also team up with marketing to keep reps equipped with the right content at the right time, and use frontline insights to keep improving tools and training

About you

• Living in Toronto (GTA) and can commute to our Downtown Toronto office 3x a week
• 8-10 years of experience in B2B software sales - ideally both high velocity as well as enterprise selling success
• 5 years of people leadership experience in B2B sales with at least 1 year managing managers
• You’ve successfully driven net-new business growth across North America through a proactive, outbound sales strategy targeting mid-market and enterprise accounts
• Experience using LinkedIn as a prospecting, lead generation, and communication tool
• Expertise using SaaS tools, such as Salesforce, Salesloft, Gong, Clay, Nooks.
• Experience embracing AI to drive efficiencies in the sales process and scaling sales teams.

How you can stand out

• Previous success a Series A or B scale-up environment
• Previous experience with internal communications tools

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 Fridays in July and August (enjoy that extra long weekend)

🧖 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.