About the Opportunity Our client is a fast-growing, venture-backed AI software company that automates the paperwork-heavy operations behind financial services. Their platform is an AI operating and decisioning system. It handles data collection, document processing, client onboarding and operational workflows, and plugs into the systems customers already use. Customers include wealth management firms, broker-dealers, insurance carriers and insurance brokers.
They're looking for an early-career Customer Success Manager who is exceptional with AI and already uses it to work smarter every day. This is a great fit for someone with a few years of SaaS customer success under their belt who wants to grow quickly in a high-energy, scaling environment.
The Role You’ll manage a portfolio of SMB and mid-market customers, with accounts typically ranging from $10K-$200K ARR. You’ll guide them from onboarding through renewal and help them get real, measurable value from the platform.
This is a hands-on role: you’ll own your relationships, keep a close eye on account health, and spot opportunities to grow your accounts. You’ll also help shape how the CS team works by finding smart ways to use AI to cut busywork, surface risk early and spend more time with customers.
Key Responsibilities Manage a portfolio of SMB and mid-market accounts ($10K-$200K ARR) from onboarding through renewal.
Run onboarding and training sessions that get new customers to value quickly.
Build strong relationships through regular check-ins and business reviews tied to customer goals.
Own renewals and drive retention, and flag expansion opportunities to grow your book.
Monitor account health,



act early on risk signals and build plans to save at-risk accounts.
Share customer feedback with Product and Engineering to help improve the platform.
AI-Enabled Ways of Working Use AI tools (ChatGPT, Claude, Gemini, Copilot or similar) daily for call prep, account research, summaries, follow-ups and customer communications.
Build simple AI-assisted workflows and automations to save time, for example with Zapier, Make or CRM AI features.
Share prompts and tips that help the wider CS team work smarter.
Use valuable judgment on data privacy, accuracy and when a human touch matters more than automation.
What We're Looking For 2-4 years in Customer Success, Account Management or a similar customer-facing role at a B2B SaaS company.
Experience managing a book of SMB or mid-market accounts, ideally in the $10K-$200K ARR range.
Hands-on, daily use of AI in your work, with examples of how it has saved you time or improved results.
Familiarity with a CRM or CS platform such as HubSpot, Salesforce, Gainsight, ChurnZero or Vitally.
Strong communication skills and confidence running customer calls and training sessions.
A curious, coachable, growth-minded approach, and comfort in a fast-paced, scaling environment.
Experience with financial services, wealth management or insurance customers is a strong asset.
This role is not a support or ticket-handling position. It's for a proactive CSM who drives customer outcomes and uses AI to do it better.
This position reflects a current vacancy with one of our clients. Our Recruiters combine deep market expertise with AI-enabled technology to support a faster, more informed recruitment process.

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📌 Customer Success Manager (Ontario)
🏢 Professional Staffing
📍 Ontario