Posted 4 months ago
Scaled Customer Success Lead
@ ContactMonkey
Toronto, Ontario
Overview
ContactMonkey is hiring a Scaled Customer Success Lead, a founding role based in downtown Toronto, reporting to the Senior Director of Customer Success. The work centres on designing and running a tech-touch customer success motion, including automations, health scoring, churn diagnosis and AI-assisted workflows, with GDR as the primary metric. The posting states a salary of $120,000 to $150,000 CAD plus variable, hybrid work three days per week in the office, and 100% employer-paid benefits.
Responsibilities:
- Design and run the tech-touch customer motion and automations
- Own GDR as the primary retention metric for the book of business
- Operate and extend customer health scoring and early-warning alerts
- Lead churn diagnosis and turn insights into playbook improvements
- Drive proactive, segmented customer communications at scale
Requirements summary:
- 5+ years in customer operations, digital CS or customer experience
- Direct experience owning GDR or NDR outcomes
- Experience building a scalable, low-touch CS motion
- Recent experience at an early-stage SaaS business
- Hands-on use of Gainsight, Vitally, ChurnZero or Salesforce-based stack
- Comfortable with Salesforce, Pendo or Gong
Tools & skills
Benefits mentioned
Source and dates
Employer career site / ATS feed · greenhouse
- Employer posting date
- 2026-07-10
- First seen by our source
- 2026-10-08
- Source record updated
- 2026-10-19
These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.
Job details
| Seniority | Senior |
| Department | Customer service |
| Experience | 5+ years |
| Work setting | Office |
| Position | Mostly sitting |
| Physical demands | physical low · computer high |
| Languages | English |
| Encouraged to apply | People with disabilities |
| Perks mentioned | Generous paid time off, Retirement plan, Stock or equity |
Summary and details written by AI from the posting; the employer’s posting is the authority.
ContactMonkey
Saved company profile
Historical company information from a saved The Jobs API profile (LinkedIn/Crunchbase fields). It is not live-verified; figures may have changed. Missing values remain unknown.
A new way to track employee communications. Create, send, track, and measure through Outlook and Gmail.
Full company description
ContactMonkey is an internal email software that integrates with Outlook, Gmail, Microsoft Teams, HRIS, and SMS, allowing communicators to create and send engaging employee emails in minutes. Our solution not only frees up valuable resources for strategic initiatives, but also provides powerful tracking and analytics tools, offering deeper insights into employee engagement, needs, and preferences. With real-time data at their fingertips, communicators can optimize their messaging and make informed decisions to better connect with their workforce—all with ongoing support from our team.
- LinkedIn followers
- 13,955
- People associated on LinkedIn
- 100
- Reported office locations
- 468 King St W, 5th floor, Toronto, Ontario M5V 1L8, CA
- Business categories
- Human Resources
- Information Technology
- Productivity Tools
- Software
- Internet
- Email Marketing
- Other recorded names
- ContactMonkey
- Specialties
- Email Tracking
- Salesforce
- Productivity
- Mail Merge
- Outlook
- HTML in Outlook
- Internal Communications
- Employee Engagement
- Email Template Builder
- Email Template Designer
- Internal Email Tracking
- Office 365
- and Outlook for Mac
- Profile identifies a recruitment agency
- No
- Reported total investment
- 40,450,546
Currency and observation date were not supplied; this is not a current valuation or a funding round.
ContactMonkey is an internal email software that integrates with Outlook, Gmail, Microsoft Teams, HRIS, and SMS, allowing communicators to create and send engaging employee emails in minutes. Our solution not only frees up valuable resources for strategic initiatives, but also provides powerful tracking and analytics tools, offering deeper insights into employee engagement, needs, and preferences. With real-time…
| Field | Value |
|---|---|
| Industry | Technology, Information and Internet |
| Company size | 51-200 employees |
| Headquarters | Toronto, Ontario |
| Organization type | Privately Held |
| Year founded | 2010 |
| Specialties | Email TrackingSalesforceProductivityMail MergeOutlookHTML in OutlookInternal CommunicationsEmployee EngagementEmail Template BuilderEmail Template Designer |
| Open jobs on Jobsy | 5 |
| View page |
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 founding role where you will work to solve this problem: How can we use data, automation and AI to manage our 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 our Senior Director of Customer Success, and partner closely with Customer Success, Product, Marketing, and Sales Operations to build a program that's as streamlined as it is effective.
This role is a great fit for someone who has personally designed, built and run a scaled CS motion before. You think in processes and systems, make decisions based on data, and know how to keep a large, diverse book of business healthy without hands-on attention for every account. Above all, you’re a builder at heart who wants real ownership and the chance to make a big impact at an organization on track to double in growth over the next few years.
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 this book of business 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 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 Operations, Digital Customer Success or Customer Experience
- Direct experience owning a GDR/NDR outcomes
- 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 $120,000-$150,000 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.
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