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

📌 Digital Customer Success Manager, SMB (Toronto)
🏢 ContactMonkey
📍 Toronto