Are you energized by providing excellent customer experience and sharing your knowledge to help people solve their problems? We’re looking for a Live Chat Support Specialist to join us at Thinkific.

Thinkific’s Support Team is driven by empathy and a genuine commitment to delivering an exceptional customer experience. Every support interaction accelerates each creator’s unique path to success. We live by our mantra, ‘Serve the individual,’ which encapsulates our commitment and focus on providing personalized and tailored support to each creator on an individual level. It emphasizes the importance of understanding and addressing their unique needs, challenges, and goals, just like we recognize each creator’s “unique genius.”

Our newly formed Live Chat Team plays a key role in helping Thinkific deliver exceptional support to our creators. They work directly with our Premium customers through live chat and email, not only answering questions but also helping them maximize Thinkific to achieve their goals.

Live Chat Support Specialists set the standard for outstanding support and embody our core values in every interaction. They play a crucial role in enhancing our processes, knowledge base, and operations, continually improving the support experience. As we expand our Support offerings, this role helps bring that vision to life. We seek curious, resourceful problem solvers who are fanatical about customer success—people who thrive on helping others and delivering exceptional experiences.

Schedule:

Hours: 9:30 AM – 5:30 PM PST

Schedules:

• Monday – Friday
• Tuesday – Saturday
• Sunday – Thursday

During the initial onboarding and training period (approximately the first two months), you’ll work a Monday–Friday schedule 9AM PT – 5PM PT, to ensure consistent coaching, team collaboration, and skill development.After onboarding, you will be assigned to one of our regular rotating schedules, 9:30 AM PT – 5:30 PM PT

Statutory holiday coverage rotates among the team and is scheduled well in advance, allowing you to plan accordingly.

Your goal will be to drive best-in-class customer experiences. Here’s how you’ll accomplish this:

Deliver exceptional real-time support for Thinkific’s Premium customers

• Provide timely, empathetic, and technically accurate responses via live chat and email.
• Own each customer issue from initial report through resolution, coordinating with Technical Support and Product as needed.
• Troubleshoot platform issues such as failed domain connections, checkout or payment errors, video playback issues, and integration timeouts.
• Investigate issues involving Stripe payment processing or SSO and authentication errors, identifying root causes, patterns, or configuration conflicts that impact multiple customers.
• Resolve escalated inquiries with sound judgment and calm professionalism.
• Identify, reproduce, and document bugs or platform issues, ensuring clear hand-offs and visibility for downstream teams.

Help customers get the most value out of Thinkific

• Go beyond troubleshooting—educate customers on best practices, features, and integrations that help them scale their business.
• Collaborate closely with the Customer Success team to share insights, close feedback loops, and ensure a seamless experience across support tiers.
• Spot early churn signals and work with Support, Success, and Product to retain and grow customers.
• Handle internal inquiries from Support peers and cross-functional teams via Slack, providing timely guidance and accurate information.

Continuously improve how we work

• Identify workflow inefficiencies surfaced through chat patterns and propose actionable improvements.
• Create and update training materials, macros, and knowledge-base documentation to enable your peers.
• Participate in feedback loops with Product, QA, and Enablement teams to share customer insights and recurring friction points.
• Experiment with new tools, workflows, and approaches to improve response speed and quality.

The person we have in mind likely:

• Brings 2–4 years of experience in a customer-facing support role (ideally SaaS), confidently managing live chat and email conversations with empathy and precision.
• Communicates complex ideas simply, explaining technical concepts in a way that empowers creators to feel capable and confident using Thinkific.
• Demonstrates technical curiosity and resourcefulness, troubleshooting across browsers, integrations, and app environments.
• Uses tools such as Zendesk, Slack, Asana, and Google Workspace with ease, and adapts quickly to new systems.
• Diagnoses multi-system issues, identifying configuration conflicts, integration errors, or setup challenges that require investigation and collaboration with Technical Support or Product.
• Thinks critically under pressure and makes sound, timely decisions in a fast-moving live chat environment.
• Acts as a trusted peer and knowledge sharer, supporting team learning, surfacing common pain points, and suggesting improvements to tools, workflows, and automations.
• Demonstrates emotional intelligence and professionalism, especially when supporting strategic or escalated customers.
• Embraces a growth mindset, continuously seeking opportunities to enhance both their craft and the overall customer experience.
• Thrives in a collaborative, metrics-driven environment where feedback is welcomed and actioned.
• Provides rotating weekend or holiday coverage to ensure consistent, global support.

These things would also be nice, but you can learn them on the job:

• Have a basic understanding of HTML/CSS, APIs, Webhooks, or SSO (any coding skills are a plus).
• Be familiar with domain hosting and setting up custom domains.
• Understand Stripe payment processing or support customers who use Stripe.

We’re committed to fair and transparent pay that reflects both where you are and where you can grow to. This role has a salary range of $50,000 – $60,000 in Canada, designed to capture the full journey from developing skills to excelling in the position. Most new hires start between the minimum and midpoint, which aligns with being fully capable in the role. Salaries above the midpoint are typically reserved for team members who have demonstrated strong, consistent performance, deep expertise, and a significant positive impact within the role.

For high-demand or hard-to-fill positions like this one, we may hire above midpoint for candidates who bring exceptional experience, skills, or impact potential.

Diversity, Equity, Inclusion and Belonging & Accessibility

This is just our initial idea of who we’re looking for! At Thinkific, we know that people have unique career journeys. If your experience is close to what we’ve described, but you feel that you might be missing a few of the requirements, please still apply!

We’re also committed to providing a comfortable and accessible interview process for every candidate. If there are any accommodations our team can make throughout our hiring process (big or small), please let us know.