Customer Success Training Program Jobs in Toronto, ON

The global population is aging, and the need for home care is growing each year. Unfortunately, at a time when care is needed more than ever, the home care industry is facing a crisis - a shortage of care workers.

At Caribou, we're on a mission to solve the caregiver crisis. When caregivers feel valued, recognized, and financially secure, they stay longer, deliver better care, and strengthen our communities.

Caribou is building the engagement infrastructure for the home care workforce and the agentic layer for home care operations. Our platform interfaces with office staff and front-line caregivers to facilitate meaningful recognition, stronger relationships, and operational efficiency.

Caribou was recently recognized as one of The Globe and Mail's Top Growing Companies - #10 in technology - and we're just getting started. Join us as we transform how care organizations recognize and retain the people who make care possible.

The Opportunity

This role reports directly into the Head of Strategic Markets. We're looking for a Senior Customer Success Associate to support and eventually lead accounts within our strategic markets portfolio. Strategic Markets includes a range of customer profiles, ranging in size and complexity. Customer Success at Caribou combines consulting, project management, analytics, training, and marketing to care workers. The role is varied and the learning curve is significant.

This is a fit if you're hyper-organized, a strong communicator, highly empathetic, and want to drive results in a customer-facing role. You can work independently and with a team, and you're energized by ambiguity. Experience in consulting, healthcare, account management, or customer success is a plus, but empathy and commitment to your customers matter more.

What You Will Be Doing

• Support Strategic Markets CSMs and the Head of Strategic Markets in servicing a portfolio of enterprise accounts
• Eventually own a growing portfolio of accounts as the primary point of contact
• Build decks and materials, and lead standard customer calls
• Onboard new customers, drive adoption, and manage change throughout implementation
• Deliver product training and coaching across the customer lifecycle
• Monitor usage and engagement metrics, and recommend ways customers can get more value from the product
• Triage and project manage customer issues to resolution
• Partner with teams across Caribou to solve customer problems and unlock value
• Help build and iterate on our enterprise customer success playbook
• Occasional travel to US to meet your customers

About You

• 2+ years professional work experience (customer-facing roles, managing relationships in consulting, high-growth startups, or home care/healthcare a plus)
• Track record of driving results with customers, stakeholders and teammates
• Comfortable working with data and using metrics to draw meaningful conclusions
• Strong problem-solver who can navigate ambiguity and find practical solutions
• Excellent written and verbal communication
• Highly organized with sharp attention to detail and the ability to juggle priorities
• Low ego, strong work ethic, and able to learn independently
• Genuinely motivated by Caribou's mission

Nice to have: SaaS lifecycle knowledge

Compensation

The salary range for this role is $65,000 to $80,000 plus an annual performance bonus.

Why You'll Love Working Here

Purpose with impact: Help solve one of society's most important challenges - the caregiver shortage.

Award-winning company: Caribou is a Top 10 Fast-Growing Technology Company in Canada (The Globe and Mail 2025).

Hybrid work-culture: The team primarily operates out of Toronto with one day a week in-office. Options to work remotely - we just care about getting the best work done.

Compensation & perks: Competitive salary, stock options, and healthcare benefits and summer half-days.

Values-driven team: Low-ego, high-character people who move fast, stay humble, and sweat the details

Interview Process

1. Discovery Call with Roxy - Learn more about Caribou, the role, and share your background, motivations, and career goals.

2. Hiring Manager Interview with Andrew - Dive deeper into your experience and how you've approached challenges, ownership, and collaboration.

3. Leadership Interview with our COO / Co-Founder Christian - Learn more about Caribou's vision, mission, and the journey we're on straight from a Founder. Christian will also explore your experiences through behavioural questions to better understand how you operate, navigate ambiguity, and approach problem-solving.

4. Case Study (Take-Home) - Complete a practical exercise designed to reflect the type of work you'll do at Caribou. We're interested in your problem-solving approach, communication style, and ability to work with data thoughtfully and accurately.

5. Case Study presentation - Present your work to the team! You see some old friends, Andrew, Christian and meet your potential teammate, Laura! This is an opportunity for us to understand how you think, communicate complex ideas, and engage with customers and stakeholders.
6. Background check, references and Offer!

Use of AI: Every application is reviewed by a human, and a member of our team will be present for every interview. Like many companies today, we use AI note-taking tools to help capture conversations accurately, and some interviews may be recorded for training or review purposes. Any use of AI is intended to support our team, not replace human decision-making in the hiring process.
Vacancy Status: This posting is for an existing vacancy.

Equal Opportunity Employer

At Caribou, we understand the value of having a diverse team. We believe in providing equal opportunity employment regardless of race, national or ethnic origin, color, religion, age, sex, sexual orientation, gender identity or expression, marital status, family status, genetic characteristics, disability, and conviction. Please let us know if you require accommodation during the recruitment process. Please contact roxyATcaribou.care if you have any questions or need support in any way.