Support Team Captain - Jane

About the Role

At Jane, our Support team exists to help the helpers — the practitioners and clinic owners running their practices every day. When they’re stuck, stressed, or unsure, we step in to remove obstacles so they can get back to caring for their patients.

As a Support Team Captain, you’ll lead a team of around eight customer support reps and play a direct role in shaping their growth, confidence, and day-to-day experience. You’ll be close to the work — coaching in real time, navigating complex customer conversations, and using insights from quality reviews and metrics to help your team continuously improve.

Jane is expanding further into the US market and looking for a leader who is energized by developing others, solving real problems, and building an environment where both teammates and customers feel genuinely supported and celebrated.

Key Responsibilities

Team Leadership & Coaching

• Lead a team of ~8 customer support reps, using Jane's 4C coaching model to deliver real-time feedback, structured development, and support through tough conversations.
• Support the team in delivering polished, confident product demos and seamless account configurations.
• Identify knowledge gaps and trends to build targeted coaching plans that grow confidence, skill, and team engagement — including building comfort and curiosity around emerging AI-powered tools.
• Use support metrics (CSAT, First Call Resolution, and Quality) through weekly quality reviews to guide coaching, track progress, and address performance challenges proactively.
• Build an inclusive and trusting team culture — celebrating wins, conducting regular 1:1s and team meetings, and keeping everyone informed on product updates and company direction.
• Lead through change with empathy, clarity, and a calm, solutions-focused approach.

Customer Excellence & Escalation Management

• Handle customer escalations with empathy and urgency, offering real-time backup and coaching team members on complex situations.
• Spot trends in escalations and partner cross-functionally with CS Operations and Content teams to improve workflows and reduce friction.
• Stay up to date on Jane's features, workflows, and best practices — including AI-powered tools like Claude and Fellow — and help your team do the same.
• Bring genuine curiosity and a growth mindset to technology, helping your team feel confident in an evolving product landscape.

Qualifications & Experience

• 5+ years of leadership experience in a high-touch customer service environment where employee engagement is key.
• Strong Coaching Skills: Proven ability to motivate, develop, and retain exceptional people while maintaining accountability and honest feedback.
• Ownership & Initiative: Proactive mindset focused on driving tangible outcomes for your team and customers.
• Customer-Obsessed: Passionate about delivering a best-in-class support experience.
• Data-Informed: Skilled at using metrics and insights to identify patterns and inform decisions without losing sight of the people behind the numbers.
• Strong Communication: Clear, empathetic, and confident communicator across 1:1s, team meetings, and written channels (e.g., Slack).
• Distributed Leadership: Experience leading remote or distributed teams with a strong focus on building connection and accountability across distance.

About Jane

Jane is a founder-led, high-growth SaaS company with a remote-first team working across Canada, the US, and the UK. More than 70,000 businesses run on Jane, with 250,000+ practitioners interacting with our platform daily.

Compensation & Benefits

• Salary Range: $75,000 to $120,000 CAD per year.
• Target Salary: For this role, the target benchmark represents an annual salary of $90,000 CAD.
• Regular career development and compensation review opportunities.
• Comprehensive health and wellness benefits package.