Sezzle is looking for a Customer Support Representative to handle escalated and complex customer issues requiring in-depth troubleshooting and cross-team collaboration. In this remote role, you will be at the center of technical problem-solving while directly supporting customers.

What You'll Do

Support customers through live chat, email, and occasionally over live video calls.
Resolve complex technical issues, from platform integrations to data syncing challenges, ensuring seamless user experiences.
Use analytical skills and creative problem-solving to make a real impact on customers' day-to-day workflows.
Actively listen and ask the right questions to clarify issues, pinpoint root causes, and provide effective solutions.
Turn customer frustration into confidence by diagnosing problems and communicating solutions.
Stay up to date with product features, integrations, and platform updates through continuous training and hands-on experience.
Grow your expertise at the forefront of evolving technology, sharing valuable insights with both customers and teammates.
Work cross-functionally with internal teams, contribute to training sessions, and provide insights on technical trends and customer pain points.
Shape better processes and improve the customer journey.

What We're Looking For

2–3 years of experience in customer support, technical support, or a related role.
Strong technical troubleshooting and problem-solving skills.
Advanced verbal and written communication skills, with the ability to explain complex technical concepts to non-technical users.
Comfortable meeting with customers over live video calls to troubleshoot in real-time as needed, in addition to live chat and email.
Ability to analyze trends in customer issues and escalate them timely and appropriately.
Experience collaborating cross-functionally with teams such as Product, Engineering, Quality, etc.
Experience working in systems such as Salesforce OneCRM, Slack, Google Workspace, Jira, and Confluence.

Nice to Have

Experience in EdTech (Education Technology), SaaS, or technical support environments.
Experience in API-based integrations, SSO, and data syncing issues.
Familiarity with LMS platforms like Google Classroom, Clever, Schoology, and Canvas.
Understanding of K-12 education technology and classroom workflows.
Experience or familiarity with data analysis and basic scripting for troubleshooting purposes.
Experience with SSO and Identity Management Tools (Clever LMS, Google Workspace/SSO, Classlink LMS), and rostering and identity providers (for example, API & Data Integration platforms or OneRoster and SFTPs).

Technical Stack

Salesforce OneCRM, Slack, Google Workspace, Jira, Confluence
SSO and Identity Management Tools
LMS platforms

Team & Environment

Work cross-functionally with internal teams like Tier 3 and Product.

Benefits & Compensation

Compensation: $53,300 - $61,250 USD
Comprehensive medical benefits with employer contribution to premiums and to HSA accounts.
Additional benefits such as gym reimbursement, pet insurance, free access to the Calm app, Rocket Lawyer and more.
Monthly tech stipend to support WFH needs.
Inclusive benefits to support you and your family, including parental leave, fertility support, adoption, and more.
401(k) plan with employer match.
Flexible PTO, paid sick time off, company holidays plus winter break (Dec 24th - Jan 1st).
Annual learning and development allowance for external training, classes, workshops, conferences, and educational materials.