Customer Success Manager

Professional Staffing; Toronto; On-site; CAD 65,000 - 90,000; Full time

Job summary

Professional Staffing is seeking an early-career Customer Success Manager for a fast-growing AI software company. You will manage a portfolio of SMB and mid-market clients, guiding onboarding through renewal and helping clients realize measurable value from the platform.

The role is hands-on: own relationships, monitor account health, and identify opportunities to expand. Experience with SaaS CS and daily use of AI tools is preferred in a fast-paced scaling environment.

Qualifications

• 2-4 years in Customer Success, Account Management or 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 work, with examples of time saved or results improved.
• 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.

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.

Skills

Customer Success

Account Management

Communication

Growth mindset

Tools

HubSpot

Salesforce

Gainsight

ChurnZero

Vitally

Job description

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 good 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.