To power measurable employee engagement worldwide.

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. 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 Work cross-functionally with Product, Marketing, Sales,



and Support to surface customer insights and close gaps that impact segment retention 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 ~ 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 ~ Experience with AI tools that streamline workflows and improve the customer journey 100% employer-paid advantages + a Health Spending Account from day one Generous vacation package to recharge and relax Personal development budget to fuel your growth One personal day + two volunteering days to give back Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks 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. 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.

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; 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.

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. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies. #

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