Support Team Captain

ABOUT THE ROLE Hi, I’m Annie https://www.linkedin.com/in/annie-lanari-4264265/, Director of Support here at Jane. I’ve been at Jane for 11 years, and I lead our Support team. Our 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. This work connects directly to Jane’s mission. The better we support our customers, the more time and energy they have to focus on the people who rely on them. I live in North Vancouver and love running, especially when I need space to think through a challenge or reset after a full week. This role is a special one. As a 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 at Jane. 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 in an exciting chapter of growth — including expanding further into the US market — and we're looking for a leader who's energized by what that brings. You'll play a meaningful role in shaping team culture, championing our customers, and helping the people around you do their best work. If you're passionate about developing others, solving real problems, and building an environment where both teammates and customers feel genuinely supported and celebrated, this is the kind of role where you'll thrive. WHAT IMPACT WE'RE LOOKING FOR YOU TO MAKE - Leading, growing and coaching your team. 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. - Coach for demos and account setups. Support the team in delivering polished, confident demos and seamless account configurations. - Identify knowledge gaps and trends to build targeted coaching plans that grow confidence, skill, and team engagement — including helping your team build comfort and curiosity around emerging tools and AI-powered features. - Use support metrics (CSAT, First Call Resolution, and Quality) through weekly quality reviews to guide coaching, track progress, and address performance challenges proactively with thoughtful action plans. - Build an inclusive and trusting team culture — celebrating wins, creating space for open dialogue through regular 1:1s and team meetings, and keeping everyone informed on product updates, company direction, and support goals. - Lead through change with empathy, clarity, and a calm, solutions-focused approach, advocating for your team and your customers across departments. CUSTOMER EXCELLENCE & ESCALATION MANAGEMENT - Handle customer escalations with empathy and urgency, offering real-time backup and coaching team members on how to navigate complex situations with confidence. - Spot trends in escalations and partner cross-functionally with CS Operations, and Content teams to improve workflows, reduce friction, and keep information accurate and current. - Stay up to date on Jane's features, workflows, and best practices — including AI-powered tools like Claude, Fellow — and help your team do the same, so every customer interaction is handled with expertise and care. - Bring genuine curiosity and a growth mindset to technology: comfortable exploring new tools like Claude and other AI assistants, asking questions, and helping your team feel confident in an evolving product landscape. WHAT EXPERIENCE WE NEED - 5 years of leadership experience, leading in a high-touch customer service environment where employee engagement is key! - A strong coach and mentor - you know how to motivate, develop, and retain exceptional people, while holding space for honest feedback and accountability. - You bring ownership to everything you do, taking initiative and following thro