Customer Support Team Lead - Remote Eligible

Customer Support Team Lead

Join Our Mission: Help the Helpers with Jane

Let's kick things off with a quick intro. Jane is a team that's all about fostering growth, spreading delight, and serving our healthcare community. We're on the hunt for people ready to jump in and join us while we simplify the lives of healthcare practitioners and patients daily. And guess what? Jane is a remote-first company, meaning every role at Jane, including this one, is remote - giving you the freedom to work from any corner of Canada.

We're founder-led, which means we live our values while maintaining a clear vision for the future. Our product enables the likes of physiotherapists, mental health counsellors, chiropractors, and other allied health practitioners to run their practices in a digital-first way through features such as online booking, charting, scheduling, telehealth, secure payments and billing along with an evolving library of features. You can see more of them here.

There is often a high bar set, not just for the quality of work, but for the care we show for each other and our customers. And it's our customers raising that bar, never standing still and continually improving which keeps us on our toes. It's not just about what you've done before or how quickly you work; it's about your curiosity and drive to solve the right problems and your agility in learning new ways of thinking.

No doubt, Jane's a special place to work. There is autonomy and flexibility to help integrate work into your life in a way that makes sense for you. Need to block out time to pick up the kids? Go for it. That's normal here. And yes, we have a Slack channel for parents, but we've also got channels dedicated to plants, furry friends, food, pride, wellness - you get the idea! While we love to connect virtually, the Jane team also connects in person throughout the year. That comes in the form of departmental get-togethers, company retreats, or possibly a conference or two across North America if you're keen to learn more about our community of healthcare providers. We're on the search for folks who are ready to dive in and become part of our journey toward making healthcare professionals' lives easier every single day.

In short, if you're excited by our growth, ready to contribute to a challenging yet rewarding environment, and eager to be a disruptor alongside a team of talented individuals, we'd love to hear from you!

Your Role in Our Journey

At Jane, our Support Team is at the heart of what we do.

We're on the lookout for a Customer Support Team Captain to coach, empower, and inspire a team of Drivers, who play a critical role in delivering delightful, human-centred support to the healthcare practitioners who rely on Jane every day.

Jane isn't just about answering customer questions; we take support to the next level by providing thoughtful guidance, proactive problem-solving, and relationship-driven customer interactions. Our Drivers don't just respond to inquiries; they educate, troubleshoot, and onboard customers, helping them make the most of Jane's platform.

As a Customer Support Team Captain, you will focus on coaching and developing your team, ensuring they feel motivated, engaged, and equipped to provide top-tier support. You'll foster a culture of open communication and collaboration, ensuring your team has the tools and support they need to thrive. You'll also implement strategies that enhance the customer experience, drive quality, and ensure meaningful results that make a real impact.

If you're a customer-obsessed leader with experience managing a high-functioning support team, we'd love to hear from you!

Coaching, Developing & Engaging Your Team

• Lead a team of ~8 Drivers with support, coaching, and growth opportunities.
• Identify knowledge gaps and trends, and create coaching plans to build confidence and skill.
• Use Jane's 4C coaching model to provide real-time feedback and structured development.
• Build an inclusive and trusting team culture where everyone feels valued and heard.

Performance Management & Driving Success

• Conduct weekly quality reviews to highlight strengths, surface patterns, and drive continuous improvement.
• Use support metrics (like CSAT, First Call Resolution, and Quality) to guide coaching and track team progress.
• Address performance challenges proactively with thoughtful action plans.
• Celebrate wins, big or small, to maintain high motivation and engagement.

Communication & Feedback: The Backbone of Great Leadership

• Keep your team informed on product updates, company direction, and support goals.
• Create space for open dialogue through regular 1:1s and team meetings.
• Advocate for your team and the needs of our customers across departments.
• Lead through change with empathy, clarity, and a calm, solutions-focused approach.

Product Knowledge & Training Support

• Stay up to date on Jane's features, workflows, and best practices, and help your team do the same.
• Monitor quality reviews to identify training opportunities and knowledge gaps.
• Encourage proactive problem-solving and support team confidence in complex situations.
• Collaborate with the Product, Marketing, and Content teams to ensure information is accurate and current.

Managing Escalations & Customer Issues with Confidence

• Handle customer escalations with empathy and urgency.
• Coach Drivers on how to navigate tough conversations and resolve complex issues.
• Offer real-time support when team members need backup.
• Spot trends in escalations and partner cross-functionally to improve workflows and reduce friction.

What We're Looking For

• 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 through to drive real outcomes for your team and our customers.
• With a customer-obsessed mindset, you're passionate about delivering a best-in-class experience and helping others do the same.
• You use data and insights to understand patterns, inform decisions, and guide improvements, without losing sight of the people behind the numbers.
• You're a confident communicator who fosters open, honest conversations across 1:1s, team meetings, and Slack, and you know how to influence and align others toward shared goals.
• You're curious, collaborative, and always looking for ways to improve how we work to create better experiences for customers, your team, and peers.
• Strong problem-solving skills and sound judgment help you navigate ambiguity and make thoughtful, timely decisions.
• Adaptability and resilience, you stay steady through change and know how to support others in uncertain or fast-paced environments.
• You've led remote or distributed teams and understand how to build connection and accountability across distance.

Compensation & Benefits

Jane's committed to paying our team members fairly, clearly, and above all, paying for growth. This role has a minimum annual salary of $75,000 and maximum annual salary of $105,000. As you may have noticed, this salary range is quite large, and this is intentional to account for the growth someone will experience in the role throughout their time at Jane (i.e., from building the skills, to accomplished, to highly proficient, all the way to achieving excellence in the role).

Paying clearly is one of our compensation fundamentals to help folks build trust in the compensation process at Jane. Watch this short video to learn how our salary bands are set. We also welcome you to ask as many questions as you'd like about compensation throughout the interview process to ensure you feel confident and build trust through the process.

At Jane, we're committed to fostering an environment that allows you to come to work as your truest self. We believe it's important to actively recognize, embrace, and celebrate our differences in order to make Jane an inclusive, equitable, and diverse workplace. We want to build a team of people who make conversations rich with perspective and experience. We are committed to listening to every voice in order to learn and grow because doing this will allow us to meet the needs of the diverse community