Senior Customer Success Associate, Strategic Markets

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