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.

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.

Senior Lead, Customer Success Training

Key skills