About the role

As the SMB Customer Success Lead, 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 $80,000 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.