Customer Success Lead, ContactMonkey
SMB, Tech Touch
CA$80-120k
+ Stock option plan
3 days a week in office
Internal communications platform
Open for applications
Internal communications platform
21-100 employees
Open for applications
CA$80-120k
+ Stock option plan
3 days a week in office
21-100 employees
Company mission
To build a highly-engaged, connected, and productive workforce.
Role
Who you are
- This role is ideal for someone who has personally built and run a scaled CS motion before, someone who thinks in process & systems, acts on data, and understands how to keep a large, diverse book of business healthy without manual hand-holding on every account
- Experience in an early-stage, SMB-focused SaaS company where efficiency was a necessity, not a nice-to-have
- Personally built and executed a tech-touch or low-touch CS motion — not just supported someone else's
- 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
- Comfortable being the primary point of contact for a portfolio of accounts, not just the system behind the scenes
- You solve problems by automation and/or building systems, not by solving the same thing twice
- 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
- You don't just use AI tools, you build with them. You've shipped workflows or agents that do real work autonomously
- Comfortable wiring AI into a stack: retrieval over a knowledge base (e.g. surfacing the right save play from a playbook library based on account signals), chaining steps, automating against APIs — not just prompting in a chat window
- You treat AI as infrastructure for the motion, not a productivity hack on the side
- Sharp judgment on where automation earns trust and where a human still has to own the call
- You are proactive by default — you engage customers before problems surface, not after
- You are a systems thinker who treats every manual task as a process waiting to be automated
- You are data-driven and comfortable pulling your own analysis to inform decisions
- You thrive in ambiguity and are energized by building something from the ground up
- You understand the difference between SMB and Enterprise Customer Success — and you know why that matters
- You're comfortable owning a large book of business directly, building genuine relationships with customers even when the primary engagement model is tech-touch
- You enjoy the direct customer-facing side of CS as much as the systems side; you don't see relationship management and automation as a tradeoff
What the job involves
- 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
- Unlike a traditional high-touch CSM role, your impact is delivered through a combination of automation and systems building alongside direct customer management, applying smart systems, data-driven communications, and targeted human intervention at the moments that matter most
- You'll be accountable for Gross Dollar Retention (GDR) across the SMB segment, and you'll build the infrastructure that makes that number move
- 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 and provide provide feedback
- 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
Our take
Internal communications are vital for informing employees and keeping them engaged with the wider business. However, stagnant and boring emails are often left unread, creating a disconnect between workers and their employers and peers.
ContactMonkey supplies a platform to supercharge internal communications, enabling management to create, send, track, and measure engagement through Outlook and Gmail. The offering consists of an email builder, through which users can create custom email templates, feedback features such as pulse surveys, plus a centralized communication hub and metrics tracking capabilities.
Boasting a host of integrations to facilitate easy adoption, it is no surprise that ContactMonkey's solution has been well-received and recognised by the industry - one case study in particular highlights 50% more time saved by using the platform. An injection of funding in 2023, to the tune of $55 million, supports the company to bring this success forward as it scales to meet rising demand for its products.
Steph
Company Specialist at Welcome to the Jungle
Insights
Company
Funding (2 rounds)
Dec 2023
$55m
SERIES A
Mar 2012
$0.8m
SEED
Total funding: $55.8m
Company benefits
- Hybrid Work
- Bi-weekly Lunch & Learn
- Monthly Team-building Activities
- Employee Stock Options
- Health & Dental Coverage
- Bonus Opportunities
- Extended Vacation Days (34 days of vacation annually, with summer Fridays, and more)
- Personal Development Budget
Company HQ
Fashion District, Toronto, ON
Leadership
Scott Pielsticker
(Founder & Director)Founded Blueback in 2002 and was CEO there for 6 years. Then founded ContactMonkey in 2009, and has been CEO ever since.
Jeff Cates
(CEO)Member of the Board of Advisors at WethosAI. Previoulsy CEO at Achievers, President and CEO at Intuit Canada, and General Business Division Manager at Apple Canada.
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