Scaled Customer Success 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

Hey there! We’re ContactMonkey

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

About the job - Scaled Customer Success Lead

Join our Customer Success team in a net-new, high-impact IC role where you will work to solve this problem: How can we use data, automation and AI to manage our SMB customer relationships at scale? As our Scaled Customer Success Lead, you won't just drive retention and GDR at the segment level. You’ll develop a deep understanding of the customer journey and lead in building the tech-touch motion behind it, from automations and health signals to AI-assisted workflows, proactive outreach, and scaled engagement.

You’ll report to Sydney Pearson, our Director of Customer Success, and partner closely with Customer Success, Product, Marketing, and Sales Operations to build an SMB program that’s as streamlined as it is effective.

This role is ideal for someone who has personally built and run a scaled CS motion before, someone who thinks in process and systems, acts on data, and knows how to keep a large, diverse book of business healthy without manual hand-holding on every account. A hands-on builder with strong ops and automation instincts, and fluency with AI tools.

Your impact

• Design and execute the tech-touch motion: automated onboarding sequences, usage-triggered nudges, health-based alerts, and scaled business reviews
• Own customer retention (GDR) as your primary metric, the health and retention of the SMB segment globally 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 turn those insights into playbook improvements and feedback for the broader team
• Drive 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

About you

• 5+ years of experience in Customer Success or Customer Operations
• Direct experience owning a GDR/NDR outcomes, as the main point of contact, including renewals, upsell conversations, and account escalations
• Direct experience building and executing a scalable, low-touch CS motion
• Recent experience at an early-stage SaaS business
• 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 generate your own reporting and insights without waiting on an analyst

How you can stand out

• Experience with AI tools that streamline workflows and improve the customer journey

What we bring to the table

100% employer-paid benefits + a 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 $100,000-$120,000 CAD + variable. 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 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

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:

• 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
• Raised $55 million Series A financing in 2023

Diversity is our strength

At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.

AI Disclosure:

We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.