Hey there! We're ContactMonkeyOur mission? To power measurable employee engagement worldwide. And we'd love for you to join us!About the job - Scaled Customer Success LeadJoin 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 impactDesign and execute the tech-touch motion: automated onboarding sequences, usage-triggered nudges, health-based alerts, and scaled business reviewsOwn customer retention (GDR) as your primary metric, the health and retention of the SMB segment globally is your responsibilityOperate, extend, and iterate the existing customer health scoring and early-warning system that surfaces at-risk accounts before they reach the cancellation windowLead 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 teamDrive customer communications at scale, proactive, segmented outreach so no account goes darkBuild and iterate AI-assisted workflows, including business review generation, account risk summaries, and reactivation sequencesOwn and refine automated segment health reporting to CS leadershipWork cross-functionally with Product, Marketing, Sales,



and Support to surface customer insights and close gaps that impact segment retentionAbout you5+ years of experience in Customer Success or Customer OperationsDirect experience owning a GDR/NDR outcomes, as the main point of contact, including renewals, upsell conversations, and account escalationsDirect experience building and executing a scalable, low-touch CS motionRecent experience at an early-stage SaaS businessInstrumented 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 riskAble to generate your own reporting and insights without waiting on an analystHow you can stand outExperience with AI tools that streamline workflows and improve the customer journeyWhat we bring to the table100% employer-paid benefits + a Health Spending Account from day oneWork from anywhere in the world for up to 4 weeksStock option plan—own a piece of our successRRSP Group Savings Plan to plan for your futureGenerous vacation package to recharge and relaxPersonal development budget to fuel your growthOne personal day + two volunteering days to give backYour Birthday off—celebrate on us!Five health days per year to stay at your bestBeautiful downtown Toronto office for hybrid work—fully stocked with all the best snacksCompensation & Work DetailsThe 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 AreImagine 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 companiesRecognized in 2023, 2024 and 2025 Deloitte Technology Rapid 50TM awards for revenue growth over the past four yearsRecognized in 2023, 2024 and 2025 Deloitte Technology Fast 500TM as one of the fastest-growing companies in North AmericaRaised $55 million Series A financing in 2023Diversity is our strengthAt 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.

📌 Scaled Customer Success Lead (Toronto)
🏢 ContactMonkey
📍 Toronto