Scaled Customer Success Lead

Toronto, ON
Hybrid
Posted Aug 27, 2026
1 position

$80,000–$120,000 / year

Opens an external site

Employment type: Full-time
Experience level: Senior · 5+ years
Posting language: English
Working hours: 40 hours per week
Office presence: 3 days per week

Job summary

Design and operate a proactive, tech-touch engagement motion to drive retention and product adoption across a large SMB portfolio. Own Gross Dollar Retention (GDR) by building automated onboarding, health scoring systems, and AI-assisted workflows.

Job details

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.

What you’ll do

Requirements

Requires a hands-on builder with experience executing scaled, low-touch CS motions in an early-stage SaaS environment. Must be proficient in CS automation tools and capable of integrating AI into operational workflows.