Sales Development Representative, SMB

Hey there! We’re ContactMonkey 👋

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

We provide the best-in-class internal communications software, featuring an easy-to-use, customizable drag-and-drop Email Template Builder. Our solution allows Internal Comms teams to create, send, and track engaging HTML emails directly within Outlook or Gmail, providing crucial 2-way feedback and powerful analytics.

Leading organizations, including global brands like Rogers, IKEA, and Ticketmaster, leverage our powerful tech stack to transform internal communications from ignored to impactful.

About the job - Sales Development Representative, SMB

We are looking for a talented and driven Sales Development Representative to join our core sales team. Working alongside our Director of Sales, SDR Manager, and SMB Account Executives, you will be the engine of our growth, focused squarely on the SMB segment (1,000 employees and below).

Your impact

As an SDR focused on high-value accounts, you will:

• Execute Account-Based Strategy: Own and execute the Account-Based Strategy playbook to convert prospects within the defined SMB segment (1000 employees and below).

• Creative Outreach Strategy: Design and launch disruptive, creative outreach strategies using a multi-channel approach (LinkedIn, Email, Video, Cold Calls, Gifting) to engage key contacts within target accounts.

• Outbound Playbook Development: Collaborate with the SDR Manager to continuously A/B test and refine ContactMonkey’s outbound cadences and personalized, targeted email campaigns.

• Qualification & Opportunity Generation: Conduct thorough discovery meetings to contact and qualify prospects, successfully generating Sales Qualified Opportunities (SQOs) monthly for the Account Executives.

• Collaboration & Optimization: Work closely with Account Executives, and Marketing teams to develop strategies, optimize messaging, and continuously improve the sales pipeline and qualification process.

• Core KPIs: You will be working an estimated 2000 SMB Account quarterly, a minimum of 150 dials a day, to drive a minimum of 2% conversion account to demo booked

About you:

• Experience: 6+ months of BDR/SDR experience, ideally within a SaaS environment, with a proven track record of consistently meeting or exceeding targets (e.g. pipeline or meeting quotas)

• Grit & Drive: Relentless persistence and a demonstrated ability to overcome objections and manage complex outreach cycles.

• Communication: Strong written and verbal communication skills, underpinned by an honest and thoughtful approach that inspires confidence.

• Execution & Organization: Strong organizational skills, attention to detail, and a self-starter mentality who actively welcomes and incorporates feedback.

How you can stand out:

• Tool Expertise: Expert proficiency using common SaaS sales tools such as Salesforce, Salesloft (or Outreach), Sales Navigator, and ZoomInfo.

• Curiosity: You enjoy asking the right questions, digging deep to uncover business pain, and building repeatable processes that scale.

• Impact-Driven: You thrive in a dynamic startup environment and are motivated by selling products that make a lasting, positive difference in people's lives.

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 4 weeks per year

💰 Stock option plan for a stake in our success

🏝 Generous vacation package to take well-deserved breaks

📚 Health and Wellness budget to fuel your growth

🧖 One personal day and two 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, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years

• Recognized in 2023, 2024 and 2025 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.