Senior Lead, Customer Success Training

Jane

1d • CA$110,000 - CA$185,000 • Remote

About The Position

Hi, I’m Kirsten Stuart, Director of Customer Success Operations. I’ve been at Jane for 8 years, which means I’ve had a front row seat to how our support experience has evolved and scaled alongside our mission to help the helpers.
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 exciting because it sits right at the heart of our impact. You won’t just be delivering training. You’ll be building confidence, shaping how our team grows, and helping Support focus on the most meaningful, human parts of their work. As Jane scales, the way we develop our people needs to evolve with intention - and you’ll help lead that evolution.
What Impact We’re Looking for You to Make
Our training program has a strong foundation - you'll lead the team behind it and drive innovation built on what's already working.

This is a player-coach role. You're not just setting direction from the sidelines — you're delivering training, building content, and doing the work alongside your team. Our primary focus is the customer team — making sure every new Support team member is set up to succeed before they ever take their first interaction. Beyond that, when other teams at Jane need deep product knowledge to do their jobs well, we're there for that too.

Requirements

• 3 to 5 years in a training, learning and development, or instructional leadership role, ideally within a customer support, customer success, or SaaS environment.
• Experience leading or managing a team of trainers or facilitators — you know how to develop the people doing the teaching, not just the programs themselves.
• You're equally comfortable doing the work as directing it — this role needs someone who leads by example, not just by delegation.
• A track record of building and delivering onboarding or product training programs that serve people at different stages and from different contexts.
• Genuine enthusiasm for AI and emerging technology as tools for better learning — with practical experience bringing them into programs in ways that actually work.
• Experience designing content and delivering programs at scale through a Learning Management System.
• Comfort working cross-functionally in a remote or distributed environment, with familiarity in support platforms like HelpScout or Talkdesk, and confidence using data to inform development priorities.

Responsibilities

• Lead and develop a team of trainers, helping them grow in their craft while rolling up your sleeves and contributing directly alongside them.
• Own the programs that prepare new Support team members before they join the floor — this is the core of what your team does, and you're an active part of it.
• Support cross-functional product onboarding for other teams at Jane who need to understand our product deeply to do their work well.
• Bring genuine curiosity and intention to how AI and emerging tools can make learning more scalable, more personalized, and more effective — without losing the human experience at the center.
• Foster a culture of continuous improvement, where feedback is thoughtful, iteration is normal, and growth is something everyone actively invests in.
• Keep training content sharp and aligned — evolving alongside Jane's product and processes so what people learn on day one still holds up on day one hundred.
• Use data with intention — quality insights, performance trends, learner feedback — to keep your programs moving in the right direction.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed