--- title: 'Sales Development Representative at ContactMonkey' canonical: 'https://feeny.ai/job/sales-development-representative-contactmonkey-toronto-4806jmke3mfe' type: 'job' last_seen: '2026-10-18' --- # Sales Development Representative at ContactMonkey - **Company:** ContactMonkey - **Location:** Toronto, Canada - **Posted:** 2026-10-06 - **Last confirmed live:** 2026-10-18 - **Apply:** https://job-boards.greenhouse.io/contactmonkey/jobs/4719034006 ## Job description 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 - 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](https://www.linkedin.com/in/ianmaningas/) 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 As an SDR focused on high-value accounts, you will: - 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. Not sure you check every box? Apply anyway! ## 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 ## Compensation & Work Details 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. ## About ContactMonkey ## Company Overview - **One-liner**: ContactMonkey provides an intelligent internal communications platform that enables organizations to design, send, and measure employee emails and newsletters directly from Outlook and Gmail. - **Entity Type**: Private (Series A) - **Headquarters**: Toronto, Ontario, Canada - **Founded**: 2010 - **Founders**: Scott Pielsticker (Founder & former CEO; stepped down March 2026), with Jeff Cates joining as CEO in 2024 to accelerate growth. ## Core Business - **Primary Industry**: Internal Communications Software / Employee Engagement Technology - **Target Customers**: Enterprise, mid-market, and growing organizations across sectors including healthcare, finance, insurance, utilities, manufacturing, and food & beverage — primarily B2B internal comms teams. - **Mission**: Power measurable employee engagement worldwide. ## Products & Services - **ContactMonkey Platform (Core)**: An intelligent internal email software that integrates directly with Outlook and Gmail. Key features include: - **CoAuthor (AI Email Builder)**: An AI agent that writes and designs fully on-brand internal emails for human review in seconds. - **ConfidenceCheck (AI Agent)**: Reviews every email before it sends for errors, inconsistencies, and accessibility issues. - **Audience Preview**: Previews how different employee groups will receive emails using AI personas. - **Analytics & Reporting**: Real-time, segmented analytics (opens, clicks, read time, actions) for every campaign, plus leadership-ready reports. - **Employee Newsletters**: Drag-and-drop branded newsletter creation without design skills. - **Employee Surveys**: Feedback tools embedded directly into newsletters. - **Custom Segments & List Management**: Audience building by department, role, location, seniority. - **Bulk Email Sends**: Reach targeted segments at scale. - **Seamless Microsoft Integrations**: Send from Outlook, share to Teams and SharePoint. - **API Connector & HRIS Integration**: Connects with SAML 2.0 providers and popular HRIS. - **Security**: Enterprise-grade, SOC 2 Type 2, GDPR compliant, secure SSO. ## Market Standing - **Valuation / Market Cap**: Not publicly disclosed (Private company). - **Key Metrics**: - **Annual Revenue**: USD $15.0 million *(LinkedIn estimate)* - **Total Funding**: ~USD $40.5 million - Seed Round (March 2012) - Venture Round (June 2025) – led by CIBC Innovation Banking - Series A (December 2023) – **$40.5M** led by **Updata Partners** [contactmonkey.com](https://www.contactmonkey.com/about) - **Customers**: 1,000+ enterprises worldwide, trusted by 10k+ communicators. - **Website Visits**: 1.6M+ monthly. - **Notable Investors/Partners**: Updata Partners (lead Series A), CIBC Innovation Banking (venture round). - **Growth Signals**: - Ranked by **The Globe & Mail** as one of Canada’s fastest-growing companies. - **2023 Deloitte Technology Fast 50™** (highest revenue growth over four years). - **2024 Deloitte Technology Fast 500™** (innovation and customer impact). - 49% employee growth in 2024 (though overall headcount saw a recent -7.3% YoY dip per LinkedIn). - 93% GlassDoor rating, 4.2 overall score. - 53% female leadership in management. - Expanded to operate in 7 countries (Canada, US, UK, Brazil, Australia, Spain, Ireland). ## Competitive Advantages - **Direct Inbox Integration**: Works natively inside Outlook and Gmail — users don't need to learn a separate platform or HTML. - **AI-Powered Efficiency**: CoAuthor and ConfidenceCheck significantly reduce creation time and error rates for internal comms teams. - **Measurable ROI**: Deep analytics that show engagement metrics (opens, clicks, read time) — a differentiator from traditional email tools that lack internal comms tracking. - **Security & Compliance**: SOC 2 Type 2, GDPR, secure SSO — critical for regulated industries (healthcare, finance, insurance, utilities). - **Hundreds of Customers**: 1,000+ enterprises already using the platform, creating a strong network effect and customer data moat. ## Strategic Focus - **Scaling the Platform**: The $55M total funding (led by Updata Partners and CIBC Innovation Banking) is fueling product innovation, team growth, and global expansion. - **AI Innovation**: Continued investment in AI capabilities (CoAuthor, ConfidenceCheck, Audience Preview) to automate more of the internal comms workflow. - **Global Reach**: Expanding into new markets (UK, Brazil, Australia, Spain) to serve multinational customers. - **Enterprise Depth**: Deepening integrations with HRIS, Microsoft Teams, SharePoint, and enterprise SSO to become the central hub for internal communications. ## Why Work Here - **Culture & Values**: "Making work more human" – emphasizes collaboration, curiosity, ownership, customer love, and playfulness. "The best ideas win" and "Bias for action" are core tenets. - **Work Model**: **Hybrid** — most team members hit the downtown Toronto HQ weekly for collaboration and team bonding. Also offers up to **four weeks a year to work from anywhere** (beachside, mountainside, etc.). - **Compensation & Benefits**: - Competitive salaries, **performance-based bonuses**, **stock options** (employee ownership). - **100% employer-paid health & dental** with extended mental health coverage, wellness and health spending accounts. - **4 weeks paid vacation**, **5 health days**, **1 personal day**, **2 volunteer days** per year. - **Parental leave top-ups** for all employees. - **Personal development budget** for skills growth. - Internal promotions and career growth are a priority. - **Diversity & Inclusion**: 53% female leadership; employees across 7 countries; 17% of employees promoted internally in 2024. - **Engineering Culture**: 18% of staff is in technical roles; Senior Software Developer salary ~CAD $114k; active hiring for a **Principal Software Engineer** and **Senior AI Engineer** as of mid-2025. - **Awards & Recognition**: Deloitte Fast 50 & Fast 500, Globe & Mail fastest-growing company — signals a high-growth, high-impact environment. ## Sources 1. [ContactMonkey Official Website](https://www.contactmonkey.com/) 2. [ContactMonkey Careers Page](https://www.contactmonkey.com/careers) 3. [ContactMonkey About Page](https://www.contactmonkey.com/about) 4. [ContactMonkey LinkedIn Page](https://ca.linkedin.com/company/contactmonkey) 5. 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