Sales Development Representative

ContactMonkey Inc.; Toronto; Hybrid; CAD 55,000 - 80,000; Full time

Benefits offered by this job

Employer-paid benefits and HSA

Work from anywhere up to 4 weeks

Stock option plan

RRSP Group Savings Plan

Generous vacation

Personal development budget

Volunteering days

Birthday off

Health days

Downtown Toronto hybrid office

Job summary

ContactMonkey Inc. is hiring four Sales Development Representatives to drive growth. You will be the engine of our expansion, working with Sr. SDR Manager, AEs and Marketing to build pipe and own outbound cadences. This role centers on high-volume calls, multi-channel outreach and rapid qualification of opportunities.

You’ll join a fast-paced, startup environment with strong training, tools and coaching to hit ambitious targets and advance your sales career in SaaS.

Qualifications

• Experience in BDR/SDR roles or customer-facing roles; track record is a plus.
• Strong verbal and written communication; confident on the phone.
• Relentless persistence and ability to handle rejection in long outreach cycles.
• Strong organizational skills, detail-oriented, self-starter mentality.
• Thrives in a fast-paced, high-activity environment with measurable KPIs.

Responsibilities

• Lead with the Phone: make high-volume cold calls and book qualified meetings.
• Execute Account-Based Strategy to engage and convert prospects in defined segments.
• Design and launch multi-channel Outreach to engage targets (LinkedIn, email, video).
• Develop and refine outbound cadences and personalized email campaigns with your manager.
• Run discovery conversations to qualify prospects and generate SQOs for Account Executives.
• Collaborate with Marketing and Sales to sharpen messaging and improve the sales pipeline.

Skills

Cold calling

Communication

Grit

Organization

High velocity

Tools

Salesforce

Salesloft/Outreach

Sales Navigator

ZoomInfo

Job description

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

About the job - Sales Development Representative (SDR)

ContactMonkey is growing and hiring four talented, driven Sales Development Representatives to join our sales team. Working alongside our Sr. SDR Manager and Account Executives, you’ll be the engine of our growth. For many of our future customers, you’ll be their very first conversation with ContactMonkey.

In this role, you’ll report to our Sr. Sales Development Manager and work closely with our Account Executives and Marketing team to build pipeline across our target accounts. We’re a cold-call-driven sales team, so you’ll spend a big part of your day on the phones, backed by the tools, training and coaching you need to hit your targets and grow your career in sales.

Your impact

• Lead with the Phone: Make a high volume of cold calls every day to start conversations with decision-makers, handle objections in real time and book qualified meetings.
• Execute Account-Based Strategy: Own and execute our Account-Based Strategy playbook to engage and convert prospects within your defined segment.
• Creative Outreach Strategy: Design and launch creative, disruptive outreach using a multi-channel approach (cold calls, LinkedIn, email, video and gifting) to engage key contacts within target accounts.
• Outbound Playbook Development: Partner with your manager to continuously A/B test and refine ContactMonkey’s outbound cadences and personalized, targeted email campaigns.
• Qualification & Opportunity Generation: Run thorough discovery conversations to qualify prospects and consistently generate Sales Qualified Opportunities (SQOs) each month for our Account Executives.
• Collaboration & Optimization: Work closely with Account Executives and Marketing to sharpen messaging, build strategy and continuously improve our sales pipeline and qualification process.

About you

• Experience: BDR/SDR experience, ideally in a SaaS environment, is an asset but not a requirement. Some of our best reps have come from hospitality, teaching and other customer-facing roles. If you have a track record of hitting goals and you’re eager to learn, we want to hear from you.
• Cold Calling & Communication: Strong verbal and written communication skills, and you’re confident on the phone. You can think on your feet, build rapport quickly and keep a conversation going with someone who wasn’t expecting your call, all with an honest, thoughtful approach that inspires trust.
• Grit & Drive: Relentless persistence and the resilience to handle objections, bounce back from a “no” and stay motivated through complex outreach cycles.
• Execution & Organization: Strong organizational skills, attention to detail and a self-starter mentality. You actively welcome feedback and put it into practice.
• High-Velocity Mindset: You thrive in a fast-paced, high-activity environment with a high volume of daily dials. Our KPIs and expectations are high, but they’re attainable with the tools and support we provide.

How you can stand out

• 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 a product that makes a lasting, positive difference in people’s working lives.
• Tool Experience: Familiarity with SaaS sales tools such as Salesforce, Salesloft (or Outreach), Sales Navigator and ZoomInfo is a nice to have. We’ll get you up to speed on our stack.

What we bring to the table

• 100% employer-paid benefits + a Health Spending Account from day one
• Work from anywhere in the world for up to 4 weeks
• Stock option plan, so you own a piece of our success
• RRSP Group Savings Plan to plan for your future
• Generous vacation package to recharge and relax
• Personal development budget to fuel your growth
• One personal day + two volunteering days to give back
• Your birthday off. Celebrate on us!
• Five health days per year to stay at your best
• Beautiful downtown Toronto office for hybrid work, fully stocked with all the best snacks

The base salary for this role is $55,000 CAD, with the opportunity to earn an additional $25,000 CAD annually in variable compensation. Compensation is thoughtfully determined based on your experience, skill set and alignment with our internal compensation framework and internal equity.

We’re always happy to answer questions about compensation throughout the hiring process.

These are net new positions based out of our downtown Toronto office at King and Spadina. Our sales team works in the office three days per week (Monday, Tuesday and Thursday) to promote collaboration, learning and a strong team culture.

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, KPMG and countless others use 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 the 2023, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years
• Recognized in the 2023, 2024 and 2025 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America
• Raised $55 million Series A financing 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 let us know 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.

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.