Head of Customer Service & Technical Support

Our MissionMicromart is redefining convenience - turning any location into a retail opportunity with our Smart Store platform. By combining hardware, software, and data, we’re building a delightful unattended shopping experience for consumers and making operating an unattended Smart Store easy for entrepreneurs.
Our ValuesWe’re driven by ambitious, mission-focused thinking, a deep commitment to earning customer trust, a craftsmanship mindset that prioritizes simplicity and quality, and a culture of shared growth where we support each other and celebrate wins together.
Role OverviewWe are looking for a Head of Customer Service and Technical Support to build, elevate, and scale a world-class support organization to support our B2B customer base (owner/operators, SMBs).
Your mission is to transform every service interaction, whether a question, a failure, or a frustration, into trust-building moments that strengthens loyalty and empowers our customers to run their businesses with confidence.
You will own the full customer support experience across chat, email, and phone, leading a 24/7 support team while partnering with engineering, product, and operations to rapidly resolve issues and continuously improve the customer journey.
Key ResponsibilitiesCustomer Service Leadership

• Build and manage a high-performing customer service and technical support team.
• Review tickets for quality, tone, accuracy, and timeliness.
• Coach, mentor, and train support specialists.
• Implement and manage best-in-class tools and processes
• Ensure customers consistently receive fast, empathetic, accurate service across all channels (chat, email, phone)
• Proactive outreach to customers about issues that may be business impacting
• Maintain high standards for NPS, CSAT, first response time, resolution time, automation rate, and overall support cost
• Structure and refine SLAs, escalation paths, and service policies to deliver consistent, high-quality outcomes.

AI-First, Automation-Forward Support

• Champion AI and automation tools to reduce manual ticket volume, improve response speed while maintaining a high quality of response with 24/7 availability
• Development and continuous improvement of:
• Helpdesk articles
• Training videos
• Macros and snippets
• AI Enabled Agents
• Internal SOPs and troubleshooting guides

Continuous Improvement

• Become a subject-matter expert in our Smart Store hardware and Platform software
• Review support trends and customer requests to provide actionable insights to engineering, product and operations teams to prevent repeat issues and improve the customer experience.
• Escalate issues to internal stakeholders and ensure timely resolution and follow up with customers.
• Balance customer needs with business needs to create scalable, and sustainable policies and processes to scale high quality support across all channels.

Crisis & Escalation Management

• Act as the point of leadership during major outages or high-impact customer issues.
• Set up clear escalation protocols for the team, executives, and customers.
• Remain composed under pressure and communicate promptly, accurately, and transparently.

QualificationsSoft Skills & Mindset

• High empathy - especially toward entrepreneurs and small-business operators.
• Calm under pressure - able to handle emotionally charged conversations with confidence and clarity.
• Relentlessly resourceful - creative problem-solver who provides practical workarounds and keeps customers moving.
• Fast-thinking, relationship-driven, and relentlessly committed to customer success.
• High ownership and agency - takes extreme responsibility and accountability for plans, actions and deliverables

Operational & Leadership Strengths

• 5+ years in customer support or technical support, with at least 2 years leading teams.
• Proven ability to run a multi-channel 24/7 support operation.
• Expert in HubSpot, Intercom, Zendesk, or similar support platforms.
• Strong program & project management skills with a track record of improving SLAs and processes.
• Experience designing escalation frameworks and incident-management playbooks.
• Experience working with or managing support teams overseas, either directly or through a BPO partner.

Technical & Product Skills

• Familiarity and ongoing curiosity in exploring best-in class AI tools for customer service
• Experience supporting connected devices, SaaS, or hardware-plus-software products.
• Proficiency with computer and networking hardware - able to perform basic troubleshooting of routers, computers, monitors
• BONUS: You have been or have served small business owner/operators
• BONUS: Have worked in vending, micro-markets, CPG, retail, or food service environments

What We Offer

• Competitive salary + equity package
• Health, dental, and vision benefits (for employees and dependents)
• Free meals at the office through KitchenMate
• Monthly gym-membership stipend
• Remote flexibility with access to our Toronto office
• Downtown office location next to Union Station with gym, pickleball court, and much more.

Micromart is an equal-opportunity employer and welcomes applicants from all backgrounds.