ContactMonkey

Scaled Customer Success Lead

ContactMonkey · Toronto

Posted about 3 months ago · $100,000-$120,000

or apply directly on ContactMonkey's site. We never take the application ourselves.

Is this posting real?

This role has been open
80 days
ContactMonkey's roles stay open a median of 80 days
Reposted
No
Salary listed
Yes
100% of ContactMonkey's roles list one
Ghost-job risk at ContactMonkey
high
2 stale, 1 reposted of 3 open
Hiring momentum
4 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-10-22

Measured from postings appearing on and disappearing from ContactMonkey's own greenhouse board since 2026-08-03. Full hiring picture for ContactMonkey.

About this role

As the Scaled Customer Success Lead at ContactMonkey, you will focus on enhancing customer relationships for SMBs through data, automation, and AI. Your responsibilities include designing automated customer interactions, driving retention metrics, diagnosing churn, and collaborating with cross-functional teams to improve customer engagement. This role requires a hands-on approach to building scalable customer success strategies and leveraging technology to streamline processes.

Our read on this posting3.8out of 5
benefits
5/5
freshness
1/5
career value
4/5
role clarity
4/5
pay transparency
5/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of ContactMonkey as an employer.

What you need

  • 5+ years of experience in Customer Success or Customer Operations
  • Direct experience owning GDR/NDR outcomes, 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

Nice to have

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

What you get

  • 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

Worth weighing

  • No specific mention of the tech stack beyond general tools like Salesforce and automation platforms
  • Role is new, which may come with undefined challenges and expectations
  • Salary range provided, but compensation is based on experience and internal equity, which may vary

Summarised from ContactMonkey's posting. Read the full original.

Listed by ContactMonkey on their greenhouse job board, last confirmed open on 2026-10-22. PitchMeAI is not the employer.

More roles at ContactMonkey

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