Customer Support Lead at Jane

About the Role Hi, I'm Annie Lanari, Director of Support here at Jane. I've been with the team for 11 years, and I lead a group that 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. If you'd like to learn more about me, you can find me on LinkedIn [Upgrade to PRO to see link] This is a role for someone who genuinely loves developing people and solving real problems. As a Customer Support Lead, you'll directly lead 6–8 Team Captains, each coaching their own team of up to eight frontline reps — a direct reach of up to 64 people. Your focus is on your Captains: shaping their growth, building their confidence, and setting them up to lead well, because when they thrive, the whole system hums. You'll be close to the work, coaching in real time, helping Captains navigate escalated conversations, and using quality insights and performance data to drive continuous improvement. You see AI as a genuine lever, not a novelty — we use tools like Claude and Fellow to move faster and think sharper, and we're looking for someone already wired that way and excited to push it further alongside us. You'll partner across teams like Market Specialists, Training, and Product, and champion a culture where people feel genuinely valued. This role is for someone who genuinely believes that the people behind the team are just as important as the people in front of it. If you're obsessed with the customer experience and know that starts with how you show up for your team every day — we'd love to meet you. THE IMPACT YOU CAN HAVE: Lead with Heart - You thrive in a people-centric role with a genuine desire to help others succeed — whether that's your team or your customers - You support, coach, and motivate 4–6 Team Captains, investing in each person's growth and understanding what they need to do their best work - You foster an environment where feedback flows both ways, people feel safe to try things, and team morale is something you actively tend to — for you, engagement isn't just a metric, it's a responsibility Coach the Coaches - A big part of this role is developing your Team Captains as leaders — not just evaluating their performance, but building their skills - You conduct regular 1:1s and coaching sessions, equipping them to deliver meaningful feedback and quality coaching to their own teams - You translate data, metrics, and trends into tangible coaching conversations and development plans - When your Team Captains grow, the whole team does — and you know that Own Operational Excellence - You take full ownership of your team of customer support reps, accountable for the health, performance, and continuous improvement of your line of business - You oversee day-to-day operations, queue health, escalation pathways, and workflows, identifying where things can be tightened to reduce friction and lift the customer experience - You leverage AI-assisted workflows to help your team move faster and work smarter Navigate Change and Lead Through It - You're a steady, transparent presence when things shift — helping your team make sense of change, stay grounded, and adapt with confidence - You lead tiger teams and change initiatives with clarity, a positive mindset, and a practical plan - You take a vision, translate it into language that resonates, and turn it into goals your team can actually run with THE EXPERIENCE WE FEEL YOU NEED: Leadership Background - 3–5 years of progressive leadership experience in a customer support or contact centre environment - You've worked the frontline before stepping into leadership — that experience gives you credibility and shapes how your team experiences you as a coach People Development - You've developed team leads or supervisors, not just individual contributors - You know the difference between evaluating performance and actually building someone's capability — and you lean hard into the latter Operational Fluency - Highly organized with the ability to balance competing priorities without losing sight of the bigger picture - Familiar with contact centre software, CRM tools, and AI-assisted workflows like Claude and Fellow (HubSpot is a plus) Tech-Savvy - You're comfortable adopting new technology and pick up products and tools quickly - You use tech intentionally — to enhance customer interactions, support your team, and sharpen how work gets done - Familiarity with contact centre software is expected; curiosity about what's next is what sets you apart here Communication and Problem Solving - Clear and empathetic in how you communicate — whether navigating a tough escalation or steadying your team through uncertainty - You approach ambiguity with a positive mindset and a natural ability to resolve conflict and find solutions under pressure Adaptability - Flexible and fast-moving, you evolve with the environment — and bring the people around you along for the ride - Working shift will be from Monday - Friday; 8:30am - 5:30pm PST More About Jane Jane is a founder-led, high-growth SaaS company born in North Vancouver, British Columbia. We’re now a team of more than 700 people working remotely across Canada, the US, and the UK, united by our mission to help the helpers. We build the products and tools that thousands of clinics rely on every day to run their businesses, care for their patients, and grow their communities. That level of impact means every person at Jane plays an important role in how we show up for our customers. We’re all responsible for being deeply connected to their needs, obsessed with improving their experience, and proud of the difference our work makes in their day-to-day lives. Jane is growing fast, and that growth brings exciting challenges that call for adaptability, resilience, learning agility, and humility. We’re proud of what we’ve built and quick to admit what we don’t know yet. We listen, learn, and adjust as we go. We’re also embracing the possibilities of AI, using it to work smarter, improve our systems, and create even better experiences for our customers and our team. Our goal isn’t just delivery, it’s delight. We move quickly, communicate openly, and solve real problems together. If you’re energized by ambiguity, motivated by impact, and eager to learn with others, you’ll thrive at Jane. Compensation & Benefits At Jane, we’re committed to paying fairly, clearly, and above all, paying for growth. This role has an annual salary range of $75,000 - $120,000. While that is a large range, it is intentional. It reflects the full growth journey someone might take in the role, from developing skills early on to becoming highly proficient and ultimately achieving excellence. Most new hires join at the accomplished stage, which for this role represents an annual salary of $105,000. A starting salary below this typically indicates a candidate with strong potential who is still developing key skills. Salaries above this usually apply to existing team members who have made a significant impact and bring deep Jane-specific knowledge. We believe in paying for growth. You’ll have regular career development conversations with your manager and your compensation will grow as you gain experience and contribute meaningfully to our mission. Paying clearly is one of our compensation fundamentals. Watch this [Upgrade to PRO to see link] short video to learn how our salary bands are set. You’re also encouraged to ask questions about compensation at any point during the interview process. We also offer a comprehensive benefits package, You can learn more about it here [Upgrade to PRO to see link]