Customer Success Representative

Summary

Join Bundle as a Customer Success Representative and be the primary point of contact for learners, clients, and trainers. This contract position, working remotely Monday-Friday, 4 PM to 12 AM ET, requires strong communication and problem-solving skills. You will handle inquiries via various channels, troubleshoot issues, collaborate with internal teams, and proactively engage learners. The role involves collecting feedback, reporting insights, and ensuring issue resolution. Flexibility is key, with weekly hours ranging from 30 to 40. Bundle offers a supportive and collaborative remote work environment.

Requirements

• 1–2+ years of experience in customer success, client services, or another learner-facing support role
• Strong written and verbal communication skills, with a natural ability to deescalate, empathize, and build trust
• Exceptional organizational skills and attention to detail—able to manage multiple conversations and priorities with care
• Demonstrated ability to think critically, troubleshoot issues, and contribute to process improvements
• Proficiency with CRM tools (HubSpot preferred), chat systems, and Microsoft Office (especially Excel)
• Tech-savvy and adaptable—comfortable navigating new platforms in a fast-moving, startup environment
• Brings initiative and a learner-centered mindset, with a focus on continually improving the experience for learners and trainers alike
• Must have reliable internet access and a personal laptop with functioning camera and audio capabilities for live communication

Responsibilities

• Serve as the face of Bundle via live chat, email, text, and phone—responding promptly and empathetically to learner and trainer inquiries, feedback, and technical questions
• Troubleshoot and resolve service or product issues by identifying root causes and providing effective, timely solutions
• Collaborate with cross-functional teams—including Learning, Marketing, and Product—to escalate and resolve complex cases
• Proactively engage new and prospective learners to drive activation and utilization across multiple communication channels
• Triage inbound inquiries from the concierge line and coordinate expectations for session requests with both learners and trainers
• Collect and report learner and trainer insights to internal stakeholders to help shape product and experience enhancements
• Ensure consistent follow-up and communication with learners and trainers to verify issue resolution and satisfaction

Preferred Qualifications

• Experience working remotely is a plus
• Associate degree or higher is a plus

Benefits

• Be part of a purpose-driven company focused on skill-building and equity in the workplace
• Thrive in a culture that values creativity, authenticity, and collaboration
• Work with a high-energy team committed to making a real difference
• Enjoy flexible remote work and a team that celebrates wins together