indeed
Customer Success Lead, SMB (Tech Touch)
CONTACTMONKEY
Toronto, CAN
Full Time
Mid
Hybrid
1 weeks ago
Customer SuccessTech Touch StrategyAutomationData AnalysisSalesforcePendo
Free
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Customer SuccessTech Touch StrategyAutomation
About the Role
ContactMonkey is looking for a Customer Success Lead to own the SMB book of business, designing and operating a tech-touch engagement motion to drive retention and product adoption.
Key Skills for This Role
Customer SuccessTech Touch StrategyAutomationData AnalysisSalesforcePendo
Responsibilities
- 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
- 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
Requirements
- Experience in an early stage, SMB focused SaaS company where efficiency was a necessity
- Personally built and executed a tech touch or low touch CS motion
- 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
- 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
- Practitioner level command of agentic AI tools applied to software engineering
Full Job Posting
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.
What you'll be doing
- Own customer retention (GDR) as your primary metric.
- 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.
- Lead churn diagnosis for the segment.
- Own customer communications at scale.
- Build and iterate AI assisted workflows.
- Own and refine automated segment health reporting to CS leadership.
- Work cross functionally with Product, Marketing, Sales, and Support.
Skills and Qualifications
- Hands on builder: Experience in an early stage, SMB focused SaaS company where efficiency was a necessity.
- Personally built and executed a tech touch or low touch CS motion.
- Directly owned a GDR or NDR number.
- Background as a Customer Success Manager, with direct experience owning a book of business.
- Ops and automation instinct: You solve problems by automation and/or building systems.
- Have instrumented CS health and risk on a CS platform or a homegrown stack.
- Comfortable with Salesforce, Pendo, Gong, or equivalent tools.
- Able to self generate reporting and insights independently.
- AI fluency: You don't just use AI tools, you build with them.
- Comfortable wiring AI into a stack: retrieval over a knowledge base, chaining steps, automating against APIs.
- Sharp judgment on where automation earns trust and where a human still has to own the call.
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.
- RRSP Group Savings Plan.
- Generous vacation package.
- Personal development budget.
- One personal day + two volunteering days.
- Your Birthday off.
- Five health days per year.
- Beautiful downtown Toronto office for hybrid work.
Compensation & Work Details
- The salary range for this role is CAD 80,000 CAD 120,000 with a variable component.
- 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
- ContactMonkey is changing the way companies connect and communicate with their people.
- Our all in one platform features a drag and drop email builder, engagement tools, and analytics.
- Ranked by the Globe & Mail as one of Canada's fastest growing companies.
- Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50 and Fast 500 awards.
- Raised CAD 55 million Series A financing in 2023.
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