Senior Lead, Customer Success Training

Jane

Lead and develop customer success training programs at Jane, shaping and supporting a high-performing team. Engage with emerging technology to enhance the learning experience.

Posted 4/14/2026full-timeRemote • 🇨🇦 CanadaSenior💰 CA$110,000 - CA$185,000 per yearWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

comprehensive benefits package

ATS Keywords

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Applicant Tracking System Keywords

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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