Customer Success Associate

About Caribou 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. Our platform helps care organizations attract, engage, and retain staff through data-driven recognition, rewards, and coordination tools that make caregivers’ lives better — and agencies more successful. On average, our customers grow their staff by 25 % in year one and reduce turnover dramatically. Caribou was recently recognized as one of The Globe and Mail’s Top Growing Companies — #10 in technology, #29 overall — 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 We’re looking for a Customer Success Associate to help launch and support home-care agencies across North America. This is a tremendous opportunity to start on the ground level of Customer Success at Caribou and establish your foundation for a long-term career of rapid growth and impact at one of Healthcare's fastest-growing tech companies. In this role, you’ll work closely with our Customer Success Managers (CSMs) to onboard new small- and mid-market agencies, helping them see early success with Caribou’s platform. You’ll coordinate onboarding tasks, train customers, and ensure smooth hand-offs to their long-term CSMs — all while learning the foundations of customer success in a high-growth SaaS company. This role is ideal for someone looking to break into the technology or healthcare sector who thrives in fast-paced environments, loves solving problems, and wants to make a tangible social impact. With strong performance, you’ll have the opportunity to grow into a Customer Success Manager role , managing your own portfolio of customers and leading strategic relationships. What You’ll Do Own the early stages of the customer journey — from onboarding through initial adoption Coordinate high-velocity agency launches alongside senior members of the Customer Success team Support CSMs in executing onboarding playbooks, configuring accounts, and setting customers up for success Collaborate cross-functionally with Product, Support, and Operations to remove blockers and improve processes Track and report on key onboarding metrics (e.g. launch velocity, activation rates, first-value milestones) Identify opportunities to improve the onboarding experience through better systems, documentation, or templates Champion the voice of the customer — bringing feedback and insights to the broader team The Ideal Candidate 0–2 years of experience in a customer-facing role (internship, customer success, account coordination, or project support) Exceptional organization and attention to detail Excellent written and verbal communication skills Empathetic, humble, and eager to learn Comfortable juggling multiple projects in a fast-moving, high-growth environment Problem-solver with a proactive, resourceful attitude Mission-driven — excited to help improve the lives of caregivers and the care organizations who support them Low ego and humble: Willing to support the team and customer in all ways Want to stand out? The last time we posted a CS entry-level role, we received 1,000 applications. Prove your attention to detail by sending Christian Alaimo a LinkedIn message with one sentence explaining why you're the best candidate for the opportunity. Include the hashtag #TheHerd. Bonus points if you have: Experience in SaaS, healthcare, home care, or other service-driven industries Why You’ll Love Working Here Purpose with impact: Help solve one of society’s most important challenges — the caregiver shortage. Growth environment: We’re scaling fast, and so will you. The right hire will be on track to become a Customer Success Manager within 12–18 months. Award-winning company: Caribou is a Top 10 Fast-Growing Technology Company in Canada (The Globe and Mail 2025). Remote-first culture: Work anywhere in Canada or the U.S. With ocassional in-person trips to Toronto. Compensation & perks: Competitive salary, stock options, performance bonus, and summer half-days. Values-driven team: Low-ego, high-character people who move fast, stay humble, and sweat the details. The Details Compensation: $55 000 – $72 500 CAD (base) + performance bonus + stock options. Pay band variance is based on experience. Reporting to: COO and working very closely with Senior Customer Success Manager and Customer Success Manager Equal Opportunity Employer At Caribou, we value diversity and are committed to creating an inclusive environment for all employees. We welcome applicants from all backgrounds and experiences.