Head of Customer Service

Job description

About Smile

At 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 Role

As 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 You

You 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 important merchant interactions.

What You’ll Need

• 5+ years of experience leading customer support teams, including technical support and cross-functional service roles. You also possess experience in account management, either as a manager or as an individual contributor.
• Tech Know-How - familiarity with tools like Shopify, Intercom, and a willingness to leverage AI for efficiency, and have an opinion around how you see AI advancements in your field. You have led technical support teams, and while not a developer, you have developed a solid baseline of skills along the way.
• A “lead from the front” mindset - comfortable jumping into the inbox, solving merchant issues, and modeling what great looks like.
• Experience working across regions and time zones - with a partnership approach and strong async communication skills.
• Knowledge sharing is in your DNA. You know what it feels like when a customer asks a question and you don’t have the answer at your fingertips, so you prioritize the dissemination of information across your team so that everyone has all of the information that they need to support merchants.
• Coaching instincts - you value reflection, feedback, and ongoing learning, and are committed to helping people grow through thoughtful guidance.
• A track record of delivering high-quality support at a SaaS company, with an eye for detail and a passion for doing right by your customers.
• Operational strength - you know how to drive consistency, use tooling effectively, and maintain balance without over-indexing on headcount.
• Belief in non-linear growth - you support individual contributors developing mastery and advancing without defaulting to management.

Bonus

• Experience managing account managers responsible for the retention and expansion of an assigned book of business.
• Experience working at a SaaS organization with a strong product-led growth (PLG) motion running in parallel to a traditional sales-driven approach.
• If you have experience leveraging AI to improve customer experience outcomes
• Experience within the Shopify app ecosystem - you understand the impact that great customer service has on reviews and ratings, which are essential for company growth in a marketplace environment

Our Commitment to Candidates:

At Smile, we understand that finding a new role is challenging and that self-doubt or imposter syndrome can prevent you from applying to a role, don’t let it! You have a ton to offer and we want you to feel encouraged to apply, even if you don’t check all of the boxes. If you are passionate about eCommerce and helping merchants grow through loyalty and reward, connect with us.

At Smile, we rely on a range of backgrounds, experiences, and ideas. We value diversity, and we’re proud to be an inclusive, equal opportunity workplace. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Smile welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

AI Disclaimer: At Smile, we’re strong advocates for using AI to help speed up iteration, increase productivity, and save our human brainpower for the really challenging problems. While we’re happy for AI to help you generate or tailor your resume, we’d ask that you please refrain from using AI to answer any of the questions on this application form, or to answer questions during the interview process itself.