Customer Success Representative

Company Overview

Bundle is the only 1:1 live skills development solution that specializes in human-centered skills, designing and delivering curated content facilitated live by experts and driven by interactive instruction. Bundle training programs weave together the techniques and perspective learners need to step forward with confidence. The future of learning is human.

As a Customer Success Representative, you will be the first point of contact for Bundle’s learners, clients, and trainers—playing a critical role in ensuring every interaction reflects our commitment to exceptional service. This contract position requires availability Monday through Friday from 4 PM to 12 AM Eastern Time. Weekly hours will range between 30 and 40, depending on client demand, so flexibility within that time frame is essential.

What You’ll Do

• 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.
  
  
  

What You Bring

• 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.
• Experience working remotely is a plus.
• Associate degree or higher is a plus.
• Must have reliable internet access and a personal laptop with functioning camera and audio capabilities for live communication.
  
  
  

Why Join Bundle?

• 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.
  
  
  

Did you know that Bundle is a Certified Great Place to Work?