Scaled Customer Success Lead

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 role** As the Digital Customer Success Manager - SMB, you will own ContactMonkey's Small & Medium Business book of business, reporting to Sydney Pearson, Sr. Director of Customer Success. This is an individual contributor, a strategy-to-execution role: you'll be responsible for designing and operating a proactive, tech-touch engagement motion that drives retention and product adoption across a large portfolio of SMB accounts. This is not a people management role. Unlike a traditional high-touch CSM role, your impact is delivered through a combination of automation and systems building alongside direct customer management, applying smart systems, data-driven communications, and targeted human intervention at the moments that matter most. You'll be accountable for Gross Dollar Retention (GDR) across the SMB segment, and you'll build the infrastructure that makes that number move. This role is ideal for someone who has personally built and run a scaled CS motion before, someone who thinks in process & systems, acts on data, and understands how to keep a large, diverse book of business healthy without manual hand-holding on every account. **What you'll be doing** - Own customer retention (GDR) as your primary metric, the health and retention of the SMB segment is your responsibility - Design and operate the tech-touch motion: automated onboarding sequences, usage-triggered nudges, health-based alerts, and scaled business reviews - 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 use those insights to continuously improve the playbook and provide provide feedback - Own 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 **Skills and Qualifications** **Hands-on builder** - Experience in an early-stage, SMB-focused SaaS company where efficiency was a necessity, not a nice-to-have - Personally built and executed a tech-touch or low-touch CS motion — not just supported someone else's - Directly owned a GDR or NDR number and can speak to how you moved it - Background as a Customer Success Manager, with direct experience owning a book of business, including renewals, upsell conversations, and account escalations - Comfortable being the primary point of contact for a portfolio of accounts, not just the system behind the scenes **Ops and automation instinct** - You solve problems by automation and/or building systems, not by solving the same thing twice - Have 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 self-generate reporting and insights independently **AI fluency** - You don't just *use* AI tools, you build with them. You've shipped workflows or agents that do real work autonomously - Comfortable wiring AI into a stack: retrieval over a knowledge base (e.g. surfacing the right save play from a playbook library based on account signals), chaining steps, automating against APIs — not just prompting in a chat window - You treat AI as infrastructure for the motion, not a productivity hack on the side - Sharp judgment on where automation earns trust and where a human still has to own the call **About you** - You are proactive by default — you engage customers before problems surface, not after - You are a systems thinker who treats every manual task as a process waiting to be automated - You are data-driven and comfortable pulling your own analysis to inform decisions - You thrive in ambiguity and are energized by building something from the ground up - You understand the difference between SMB and Enterprise Customer Success — and you know why that matters - You're comfortable owning a large book of business directly, building genuine relationships with customers even when the primary engagement model is tech-touch - You enjoy the direct customer-facing side of CS as much as the systems side; you don't see relationship management and automation as a tradeoff **What we bring to the table** 🏥 100% employer-paid benefits & 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 CAD - $120,000 CAD with a variable component. 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 net 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.