Senior Lead, Customer Success Training

TL;DR

Senior Lead, Customer Success Training (SaaS): Lead and develop training programs for the Support team with an accent on onboarding new members and cross-functional product knowledge delivery. Focus on integrating AI for scalable personalized learning, fostering continuous improvement, and using data to evolve content and performance.

Location: Remote in a distributed environment (team across Canada, US, UK)

Salary: CA$110,000–185,000 (most new hires at $145,000)

Company

Founder-led high-growth SaaS company building tools for healthcare clinics, with 800+ remote team members across Canada, US, and UK.

What you will do

• Lead and develop a team of trainers while delivering training and building content alongside them.
• Own onboarding programs for new Support team members to ensure they succeed from day one.
• Deliver cross-functional product onboarding for other teams needing deep product knowledge.
• Innovate with AI and emerging tools to make learning scalable and personalized while keeping human focus.
• Foster continuous improvement through feedback, iteration, and data-driven insights.
• Keep training content aligned with evolving product and processes.

Requirements

• 3-5 years in training, L&D, or instructional leadership, ideally in customer support, success, or SaaS.
• Experience leading trainers or facilitators and developing their skills.
• Hands-on delivery of onboarding and product training programs at scale via LMS.
• Enthusiasm and practical experience with AI for learning enhancement.
• Comfort in remote/distributed cross-functional work, familiarity with HelpScout/Talkdesk, data usage.

Culture & Benefits

• Pay for growth with transparent salary bands and regular career conversations.
• Comprehensive benefits package including health, learning opportunities.
• Fast-growing environment emphasizing adaptability, resilience, open communication.
• Embracing AI to work smarter and delight customers.
• Focus on impact, learning agility, humility, and solving problems together.