AI-Driven Scaled CS Lead

Contactmonkey; Toronto; Hybrid; CAD 100,000 - 120,000; Full time

Benefits offered by this job

Employer-paid benefits

Work from anywhere up to 4 weeks

Stock options

RRSP

Generous vacation

Personal development budget

Volunteer days

Birthday off

Health days

Downtown Toronto office

Job summary

ContactMonkey is hiring a Scaled Customer Success Lead to design automated onboarding, health signals, and AI-driven workflows for SMB relationships at scale. You will own retention outcomes and partner with Product, Marketing, and Sales Ops to build a streamlined, data-driven CS program.

This role suits a hands-on builder with ops instincts, experience in a fast-growing SaaS environment, and the ability to drive cross-functional initiatives across a global customer base.

Qualifications

• 5+ years of experience in Customer Success or Customer Operations.
• Own GDR/NDR outcomes including renewals and upsell.
• Build scalable, low-touch CS motions.
• Recent SaaS experience at an early stage.
• Instrument CS health on Gainsight, Vitally, ChurnZero or similar stacks.
• Comfort with Salesforce, Pendo or Gong for health metrics.
• Ability to generate reporting and insights without an analyst.

Responsibilities

• Design and execute the tech-touch motion: onboarding sequences, nudges, health alerts, and scaled reviews.
• Own SMB segment retention as the primary metric globally.
• Extend and iterate health scoring and early-warning systems.
• Lead churn diagnosis and translate insights into playbooks.
• Drive scalable customer communications and proactive outreach.
• Build AI-assisted workflows for reviews, risk summaries, and reactivations.
• Own and refine automated segment health reporting for CS leadership.
• Collaborate with Product, Marketing, Sales Ops to close gaps impacting retention.

Skills

Customer Success

Data-driven

Automation

Operations

AI tools

Cross-functional

Tools

Gainsight

Vitally

ChurnZero

Salesforce

Pendo

Gong

Job description

ContactMonkey is hiring a Scaled Customer Success Lead to design automated onboarding, health signals, and AI-driven workflows for SMB relationships at scale. You will own retention outcomes and partner with Product, Marketing, and Sales Ops to build a streamlined, data-driven CS program.

This role suits a hands-on builder with ops instincts, experience in a fast-growing SaaS environment, and the ability to drive cross-functional initiatives across a global customer base.