Sales Development Representative, Mid-Market

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 - Mid-Market Sales Development Representative

We are looking for a high-performing, growth-oriented Sales Development Representative to join our team. This role is pivotal to ContactMonkey’s growth, focusing specifically on Mid-Market accounts (organizations with 1000 to 10,000 employees).

You will work directly with our Director of Sales, playing a foundational role in building and scaling our Mid-Market business development program and driving new pipeline generation. This position requires a strategic mindset to execute targeted Account-Based Marketing (ABM) and sales plays, ensuring we engage the right personas within these complex, high-value organizations to secure meetings and qualify future customers.

Your impact

Building and Executing Outbound

Your primary focus is the strategic creation of new sales opportunities within our defined target market.

Outbound Strategy & Playbook Development

• Program Development: Support the Sales and Marketing Leadership team to optimize the core outbound ABM MM playbook, personalized email campaigns, scripts and ABM Targeted campaigns.

Pipeline Generation & Execution

• Account-Based Marketing (ABM): Execute a targeted, omnichannel ABM approach to optimize conversion rates specifically within Mid-Market accounts.

• Targeted Outreach: Execute sales strategies across multiple channels (Email, LinkedIn, Phone, Video Messaging) to engage, educate, and establish relationships with new prospective clients and key stakeholders.

• Leveraging Tech Stack: Expertly utilize our technology stack (Salesforce, Sales Navigator, Nooks, Salesloft, Gong, Clay, ZoomInfo) to prospect into target accounts, identify key decision-makers, and build a deep pipeline for the sales team.

• Creative Strategy: Actively contribute creative new sales and marketing strategies that help break into complex accounts and redefine our approach to market challenges.

• Core KPIs: You will be working an estimated 800 Accounts Quarterly across 1625 Target Personas and expected to achieve a minimum 5% conversion.

About you:

• Experience: 1+ years of successful, dedicated experience in an outbound sales development capacity.

• Goal Attainment: Proven track record of consistently meeting or exceeding targets (e.g., pipeline or meeting quotas).

• Grit & Drive: Demonstrated relentless persistence and drive to overcome objections, with a natural tendency toward high-quality execution.

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

• Organizational Mastery: Strong organizational skills and acute attention to detail necessary for building repeatable processes and managing outreach volumes.

How you can stand out:

• Building repeatable processes and systems that scale across the organization.

• Selling products that make a positive and lasting difference in people's professional lives.

• Seeking the truth behind customer challenges by asking thoughtful, deep questions.

• Going from zero-to-one in uncharted territory to redefine an industry

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.