Sr Lead, AI & Automation - Customer Support at Jane in Canada

ABOUT THE ROLE Hi, I'm Kirsten Stuart https://www.linkedin.com/in/kirsten-stuart-9433861a6/, Director of Customer Success Operations, and I've been at Jane for 8 years. Our Customer Success Operations team is the engine behind one of the most celebrated support experiences in healthcare tech. We sit at the intersection of technology, people, and purpose, building the systems, tools, and intelligence that allow our Support team to show up for healthcare practitioners in a way that feels genuinely human and consistently delightful. From knowledge ecosystems to real-time operations, we're shaping what world-class support looks like as Jane grows. On a more personal note, when I'm not thinking about support strategy, you can usually find me working out or walking my dog. Movement helps me reset, stay curious, and show up with energy, something I try to bring to my work every day. This role is a hybrid builder-and-leader position. You'll be hands-on, designing and shipping agents that remove friction from our team's workflows, while also leading a small team and partnering closely with stakeholders across the Customer Team and AI Transformation Team to make sure the tooling actually lands. The goal is simple but meaningful: free our teams from manual, high-friction work so they can spend their time on the relationships and high-value work that matter most. WHAT IMPACT WE’RE LOOKING FOR YOU TO MAKE 🤖 AI & Agent Building - Design, build, and ship agents that solve specific friction points in the Customer Team workflows, architecting how they work rather than just configuring off-the-shelf tools. - Continuously identify where friction lives across the support organization (repetitive tasks, slow lookups, manual handoffs) and turn that into an agent roadmap. - Own performance and quality of AI tooling in production: accuracy, tone, resolution rates, and where a human needs to step back in. - Stay close to what's emerging in LLMs, agent frameworks, and semantic search. 🔗 Cross-Functional Partnership - Work with the AI Transformation team to align on architecture, capability, and what's feasible now versus later. - Partner with Support stakeholders and the team themselves to understand where the real friction is. - Bring in subject matter experts across Support Ops to validate agent behaviour in their domain before it ships. - Represent Support's needs in company-wide AI conversations, and bring company AI direction back to Support. 📚 Knowledge Foundation - Own the knowledge base and internal documentation, keeping it accurate and well-governed as the substrate agents and Drivers both rely on. - Build content and taxonomy practices that make information usable by both humans and AI, not just searchable. - Use support data and agent performance to find and close knowledge gaps. 🎯 Customer & Prospect Self-Service Experience - Own how customers and prospective customers find answers to their questions, end to end, across guides and the AI answer tool. - Set and hold the exceptional quality bar for those answers: accuracy, tone, and whether the response actually resolves the question. Ensuring results are as good as our world class team. - Analyze what customers and prospects are asking (queries, search terms, unresolved questions) to surface patterns worth acting on. - When the answer is missing or wrong, that's a knowledge or content gap to close. When the real fix is in the product itself, that's feedback to route to Product. - Partner with Product and Product Marketing so recurring "not yet customer" questions inform what we build and how we message it, not just what we document. ⭐ Team Leadership - Lead a small team of knowledge and AI enablement experts: set priorities, run 1:1s, and grow their skills, including agent-building capability. - Build a team that can move between deep AI/technical work and the people side of Support without losing either. 📈 Impact & Measurement - Track quality metrics for AI-assisted and self-service answers, including accuracy and CSAT, to make sure automation holds the same bar as our team. - Track efficiency metrics, including deflection rate, average handle time, and Driver time saved, to show where friction has actually been removed. - Track downstream business impact, including retention and conversion, to connect AI/automation work to outcomes beyond Support. - Present findings and roadmap to leadership regularly; make the case for where to invest next. WHAT EXPERIENCE WE NEED - 5+ years in AI/automation implementation, support enablement, or knowledge/content strategy, ideally with hands-on agent or LLM tooling experience rather than just oversight of it. - Comfortable being the builder: you can actually construct an agent or automation workflow, not just spec one for someone else. - Experience mentoring or leading others, formally or informally. - Strong systems thinker: you see friction and think in workflows, not just documents. - Genuinely cross-functional: you're as comfortable in a room with AI engineers as you are with frontline Drivers. - Experience owning a self-service or customer content program, ideally where you were accountable for both the quality of the answers and what customer questions revealed about product gaps. - Familiarity with tools we use (Hubspot, Help Scout, Talkdesk, Claude, Gumloop etc.) and a real appetite for AI/automation tooling. If you don’t meet every single qualification but are excited about this role, we’d still love to hear from you. MORE ABOUT JANE Jane is a founder-led, high-growth SaaS company with a remote-first team working 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. More than 70,000 businesses run on Jane which has 250,000+ practitioners interacting with our product on a daily basis and growth is continuing to accelerate. 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. No matter your role or team, we expect every Janer to be curious, experimenting, and finding new ways to build with AI. We'll make sure you have the tools, support, and space to explore, learn, and share what you discover along the way. 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. This role has an annual salary of $115,000 to $160,000. While that is a large range, it is intentional. It reflects the full journey someone might take in the role. 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. 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 https://vimeo.com/880258361 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 https://jane.app/documents/hiring/jane_benefits_overview.pdf! Jane takes job scams and candidate fraud seriously. Jane will only contact you from an @jane.app http://jane.app email address. We'll never contact you from a personal email, ask for payment, or request purchases during the hiring process. If something doesn't seem right, please reach out to us at hiring@jane.app before sharing any personal information.