Job Overview
Location
Canada
Job Type
Full-time
Category
Customer Support
Date Posted
March 18, 2026
Full Job Description
đź“‹ Description
- • As a Customer Support Lead at Jane Technologies, you will directly lead 6–8 Team Captains, each coaching their own team of up to eight frontline reps, giving you a direct reach of up to 64 people. Your primary focus is on developing your Captains as leaders—shaping their growth, building their confidence, and setting them up to lead well—because when they thrive, the entire support system hums with efficiency and empathy.
- • Day to day, you will coach in real time, helping Captains navigate escalated conversations, using quality insights and performance data to drive continuous improvement. You will conduct regular 1:1s and coaching sessions, equipping Team Captains to deliver meaningful feedback and quality coaching to their own teams, while translating data, metrics, and trends into tangible development plans.
- • You will take full ownership of your team’s operational health, overseeing day-to-day operations, queue health, escalation pathways, and workflows, identifying friction points and leveraging AI-assisted workflows like Claude and Fellow to help your team move faster and work smarter.
- • You will partner across teams such as Market Specialists, Training, and Product, championing a culture where people feel genuinely valued, and lead tiger teams and change initiatives with clarity, a positive mindset, and practical plans to help your team adapt with confidence during periods of change.
- • Jane is a founder-led, high-growth SaaS company with over 700 remote employees across Canada, the US, and the UK, united by its mission to help the helpers—practitioners and clinic owners who rely on Jane’s tools to run their businesses and care for patients. Your work directly contributes to freeing up their time and energy so they can focus on the people who rely on them.
- • In this role, you will grow as a leader of leaders, deepening your expertise in people development, operational excellence, and AI-augmented support, while contributing to a culture that values delight, open communication, and solving real problems together—preparing you for greater impact within Jane’s evolving support organization.
🎯 Requirements
- • 3–5 years of progressive leadership experience in a customer support or contact centre environment
- • Proven experience developing team leads or supervisors, not just individual contributors
- • Familiarity with contact centre software, CRM tools, and AI-assisted workflows like Claude and Fellow (HubSpot is a plus)
- • Clear and empathetic communication skills, with a natural ability to resolve conflict and find solutions under pressure
- • Comfortable adopting new technology and using it intentionally to enhance customer interactions and team performance
- • Ability to balance competing priorities while maintaining focus on the bigger picture and operational excellence
🏖️ Benefits
- • Annual salary range of $90,000 - $150,000, with most new hires starting at $110,000 based on the accomplished stage of the role
- • Comprehensive benefits package available for review at https://jane.app/documents/hiring/jane_benefits_overview.pdf
- • Commitment to paying for growth, with regular career development conversations and compensation increases tied to experience and meaningful contribution
- • Opportunity to work remotely as part of a distributed team across Canada, the US, and the UK
- • Exposure to and involvement in Jane’s intentional use of AI to improve systems and experiences for customers and team members
Skills & Technologies
Senior
Remote
$90k-150k
About Jane Technologies, Inc.
Jane Technologies operates a cannabis e-commerce marketplace connecting licensed dispensaries and brands with consumers. The platform provides online ordering, delivery, and in-store pickup for cannabis products while offering retailers SaaS tools for inventory management, compliance, and sales analytics. Founded in 2017, the company serves dispensaries across North America.
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