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Head of Customer Service, North America
SmileAtlantic Standard TimeRemotefull_timeVerifiedPosted 13 Jun 2025
About the role
About SmileAt Smile, we don’t just build loyalty programs - we create growth engines for ecommerce merchants. With over 100,000 merchants worldwide, we’re already the largest loyalty program provider on the planet. But we’re just getting started.
Our team is globally distributed but closely connected. Collaboration isn’t just a buzzword here; it’s our way of doing business. If you’re looking to be part of a culture where growth for customers, the company, and for you - is the goal, you’re in the right place. We know that Smile.io as a business is in constant evolution - the same is true of our people. We’re here to support each other in our growth, so we talk openly about our career & personal goals.
Smile.io is a fully remote company looking to hire within Canada for this remote role. Overlap with core EST working hours is required.
About the RoleAs Head of Customer Service, North America, you'll lead a cross-functional support team that combines technical excellence, merchant empathy, and operational discipline. You will coach your team to meet their review generation targets and partner closely with your APAC counterpart to deliver 24/7 support, ensuring that every merchant, whether on our core plans or our growing Plus (Enterprise) tier, receives timely, thoughtful, and high-quality care.
This is a hands-on leadership role. You'll set the tone by jumping in when needed, whether it's helping during high-volume periods, covering for a team member, or leading a call with a merchant personally. You jump in with two feet and lead through example, not just direction, taking pride in getting close to the work and continuously raising the bar through real-time coaching and reflection.
You act with a sense of ownership and constantly strive to solve new challenges or help the team develop. You will influence the wider customer service motion at Smile and collaborate with other leadership to adapt it over time to embrace technological advancements and weave in operational efficiencies that support our lean, bootstrapped way of running the business.
This is a full-time, remote position with required hours Monday to Friday, 8am - 4pm Atlantic Time +/- 2hrs. (7am-3pm Eastern Time).
About YouYou have at least 5 years of experience leading customer support teams, including technical support and cross-functional service roles. You know SaaS, ideally in the ecommerce space, and are ready to push boundaries and drive innovation. You believe that the future of customer service is becoming AI-first over time as technologies develop, and as a result, you have a strong familiarity with AI technologies and promote their adoption within an organization. You have a refined sense of communication, knowing exactly what to say and when to say it, ensuring that all messaging aligns with our brand identity and the ideal experience you want for our customers (merchants).
Everyone at Smile is driven by these core values:Be Humble - think of the team before thinking of yourself. We have no room for massive egos.Be Hungry - set hard goals, ask lots of questions and learn every day.Be Human - show empathy towards others, consider the impact of your decisions on other teams.
Our team is globally distributed but closely connected. Collaboration isn’t just a buzzword here; it’s our way of doing business. If you’re looking to be part of a culture where growth for customers, the company, and for you - is the goal, you’re in the right place. We know that Smile.io as a business is in constant evolution - the same is true of our people. We’re here to support each other in our growth, so we talk openly about our career & personal goals.
Smile.io is a fully remote company looking to hire within Canada for this remote role. Overlap with core EST working hours is required.
About the RoleAs Head of Customer Service, North America, you'll lead a cross-functional support team that combines technical excellence, merchant empathy, and operational discipline. You will coach your team to meet their review generation targets and partner closely with your APAC counterpart to deliver 24/7 support, ensuring that every merchant, whether on our core plans or our growing Plus (Enterprise) tier, receives timely, thoughtful, and high-quality care.
This is a hands-on leadership role. You'll set the tone by jumping in when needed, whether it's helping during high-volume periods, covering for a team member, or leading a call with a merchant personally. You jump in with two feet and lead through example, not just direction, taking pride in getting close to the work and continuously raising the bar through real-time coaching and reflection.
You act with a sense of ownership and constantly strive to solve new challenges or help the team develop. You will influence the wider customer service motion at Smile and collaborate with other leadership to adapt it over time to embrace technological advancements and weave in operational efficiencies that support our lean, bootstrapped way of running the business.
This is a full-time, remote position with required hours Monday to Friday, 8am - 4pm Atlantic Time +/- 2hrs. (7am-3pm Eastern Time).
About YouYou have at least 5 years of experience leading customer support teams, including technical support and cross-functional service roles. You know SaaS, ideally in the ecommerce space, and are ready to push boundaries and drive innovation. You believe that the future of customer service is becoming AI-first over time as technologies develop, and as a result, you have a strong familiarity with AI technologies and promote their adoption within an organization. You have a refined sense of communication, knowing exactly what to say and when to say it, ensuring that all messaging aligns with our brand identity and the ideal experience you want for our customers (merchants).
Everyone at Smile is driven by these core values:Be Humble - think of the team before thinking of yourself. We have no room for massive egos.Be Hungry - set hard goals, ask lots of questions and learn every day.Be Human - show empathy towards others, consider the impact of your decisions on other teams.
What You'll Do
- Obsess about performance metrics that speak to the impact and success of the team across multiple angles - review generation, response times, SLOs, retention, efficiency per employee, and more - as you guide a world-class team and help them reach new heights.
- Lead a cross-functional support team that spans technical, billing, and frontline service responsibilities, with a strong commitment to collaboration and shared goals.
- Jump in when needed - responding to merchants directly when volume spikes or coverage is needed, and showing your team that no task is beneath leadership.
- Partner with APAC leadership to manage round-the-clock global support, ensuring consistency in quality and experience regardless of time zone. (Note: this may require some schedule flexibility to accommodate)
- Coach through context - Review team interactions regularly, give timely feedback, and use real examples as learning tools to build confidence, judgment, and excellence.
- Drive operational clarity - including clear expectations for performance, quality, and tone, especially when engaging our Plus (Enterprise) merchants.
- Strengthen the connective tissue between frontline and Plus (Enterprise) teams through shared standards, supportive workflows, and unified growth paths.
- Lay the foundation for future evolution - including role specialization and key skill certifications that reward deep expertise and build trust and confidence in handling our most im
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