Scaled Customer Success Lead at ContactMonkey in Toronto, ON

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 founding role where you will work to solve this problem: How can we use data, automation and AI to manage our 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 our Senior Director of Customer Success, and partner closely with Customer Success, Product, Marketing, and Sales Operations to build a program that's as streamlined as it is effective. This role is a great fit for someone who has personally designed, built and run a scaled CS motion before. You think in processes and systems, make decisions based on data, and know how to keep a large, diverse book of business healthy without hands-on attention for every account. Above all, you’re a builder at heart who wants real ownership and the chance to make a big impact at an organization on track to double in growth over the next few years. 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 this book of business 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 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 Operations, Digital Customer Success or Customer Experience Direct experience owning a GDR/NDR outcomes 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 $120,000-$150,000 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 abou