--- title: 'Scaled Customer Success Lead at ContactMonkey' canonical: 'https://feeny.ai/job/scaled-customer-success-lead-contactmonkey-toronto-vnpjp9sfrn30' type: 'job' last_seen: '2026-09-13' --- # Scaled Customer Success Lead at ContactMonkey - **Company:** ContactMonkey - **Location:** Toronto, Canada - **Posted:** 2026-07-10 - **Last confirmed live:** 2026-09-13 - **Apply:** https://job-boards.greenhouse.io/contactmonkey/jobs/4695867006 ## 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 - Scaled Customer Success Lead Join our Customer Success team in a net-new, high-impact IC role where you will work to solve this problem: How can we use data, automation and AI to manage our SMB customer relationships at scale? As our Scaled Customer Success Lead, you won't just drive retention and GDR at the segment level. You’ll develop a deep understanding of the customer journey and lead in building the tech-touch motion behind it, from automations and health signals to AI-assisted workflows, proactive outreach, and scaled engagement. You'll report to Sydney Pearson, our Director of Customer Success, and partner closely with Customer Success, Product, Marketing, and Sales Operations to build an SMB program that's as streamlined as it is effective. This role is ideal for someone who has personally built and run a scaled CS motion before, someone who thinks in process and systems, acts on data, and knows how to keep a large, diverse book of business healthy without manual hand-holding on every account. A hands-on builder with strong ops and automation instincts, and fluency with AI tools. ## Your impact - Design and execute the tech-touch motion: automated onboarding sequences, usage-triggered nudges, health-based alerts, and scaled business reviews - Own customer retention (GDR) as your primary metric, the health and retention of the SMB segment globally is your responsibility - Operate, extend, and iterate the existing customer health scoring and early-warning system that surfaces at-risk accounts before they reach the cancellation window - Lead churn diagnosis for the segment, maintain a data-backed, documented picture of why SMB accounts leave, and turn those insights into playbook improvements and feedback for the broader team - Drive customer communications at scale, proactive, segmented outreach so no account goes dark - Build and iterate AI-assisted workflows, including business review generation, account risk summaries, and reactivation sequences - Own and refine automated segment health reporting to CS leadership - Work cross-functionally with Product, Marketing, Sales, and Support to surface customer insights and close gaps that impact segment retention ## About you - 5+ years of experience in Customer Success or Customer Operations - Direct experience owning a GDR/NDR outcomes, as the main point of contact, including renewals, upsell conversations, and account escalations - Direct experience building and executing a scalable, low-touch CS motion - Recent experience at an early-stage SaaS business - Instrumented CS health and risk on a CS platform (Gainsight, Vitally, ChurnZero) or a homegrown stack (Salesforce + product analytics + automation) - Comfortable with Salesforce, Pendo, Gong, or equivalent tools to instrument health, productivity, and risk - Able to generate your own reporting and insights without waiting on an analyst ## How you can stand out - Experience with AI tools that streamline workflows and improve the customer journey ## 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—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 salary range for this role is $100,000-$120,000 CAD + variable. 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. This is a new position based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x per week to promote collaboration. ## 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 $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 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. AI Disclosure: We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes 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. [ContactMonkey Job Board (Greenhouse)](http://job-boards.greenhouse.io/contactmonkey) ## Other roles at ContactMonkey - [Strategic Account Executive](https://feeny.ai/job/strategic-account-executive-contactmonkey-toronto-zs8jwwst2tcz) — Toronto, Canada