Contactmonkey

Contactmonkey

Digital Customer Success Manager, SMB

Toronto

Sponsorship not specifiedDetected 1 day ago
AccessibilityEmail MarketingSalesforceRecruitingCustomer SuccessLeadershipCommunicationMicrosoft Office

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.

Responsibilities

  • 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
  • Work cross-functionally with Product, Marketing, Sales, and Support to surface customer insights and close gaps that impact segment retention
  • You solve problems by automation and/or building systems, not by solving the same thing twice
  • You don't just use AI tools, you build with them.
  • You are data-driven and comfortable pulling your own analysis to inform decisions

Skills

  • 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
  • Comfortable being the primary point of contact for a portfolio of accounts, not just the system behind the scenes
  • Comfortable with Salesforce, Pendo, Gong, or equivalent tools to instrument health, productivity, and risk
  • Able to self-generate reporting and insights independently

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.

Benefits

  • Own customer retention (GDR) as your primary metric, the health and retention of the SMB segment 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 use those insights to continuously improve the playbook and provide provide feedback
  • Own and refine automated segment health reporting to CS leadership
  • Have instrumented CS health and risk on a CS platform (Gainsight, Vitally, ChurnZero) or a homegrown stack (Salesforce + product analytics + automation)

Company info

  • 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:
  • 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.
  • Imagine being part of a team of brilliant minds, all shaping the future of workplace communication.
  • 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
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This listing is sourced directly from Contactmonkey's careers page and normalized into a canonical job model.