Senior Lead, Customer Success Training
Jane
full-time
Posted on:
Location Type: Remote
Location: Canada
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Salary
💰 CA$110,000 - CA$185,000 per year
Job Level
About the role
- 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.
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.
Benefits
- comprehensive benefits package
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
training program developmentonboarding program designcontent designdata analysisLearning Management System (LMS)performance trend analysislearner feedback analysisAI integration in learningemerging technology applicationinstructional leadership
Soft Skills
team leadershipcoachingcross-functional collaborationcuriositycontinuous improvementfeedback facilitationadaptabilitycommunicationproblem-solvinggrowth mindset