Lead Technical Support Specialist
EnrollHere
Full-time|Remote|Pinehurst, North Carolina, United States At EnrollHere, we are dedicated to transforming the healthcare enrollment experience into one that is straightforward, transparent, and accessible for all. We collaborate with organizations across the nation to provide innovative technology solutions and outstanding customer service, empowering members to confidently secure the coverage they need. Our fully remote team is driven by a culture of collaboration, innovation, and a mutual commitment to enhancing the enrollment process for everyone.The Lead Technical Support Specialist plays a pivotal role within the EnrollHere Support team, taking ownership of frontline support quality, mentoring fellow team members, and acting as the primary escalation point for technical and workflow-related challenges. This position is perfect for someone with practical experience in Intercom, a solid understanding of modern ticketing systems, and a passion for blending customer-facing support with operational leadership. You will collaborate closely with Product, Engineering, and Operations teams to enhance support workflows and improve customer experiences.Key ResponsibilitiesServe as the primary escalation point for intricate Tier 2–3 issues related to platform workflows, integrations, dialer tools, and account configurations.Provide prompt and empathetic responses to high-impact inquiries from agents, partners, and internal teams via Intercom (chat & email).Ensure adherence to service level agreements (SLAs) and maintain consistent response quality across ongoing conversations.Recognize patterns in support issues and proactively propose solutions.Support Leadership & EnablementAct as the daily lead for support operations, assisting teammates in overcoming obstacles and establishing quality standards.Review support tickets for accuracy, tone, and technical correctness.Facilitate onboarding and training for new support hires.Contribute to the development and improvement of support macros, workflows, and automation within Intercom.Technical TroubleshootingIdentify and diagnose browser-based issues utilizing developer tools, console logs, cookies, network requests, and basic HTML/CSS inspection.Accurately document bugs, edge cases, and reproduction steps for the Engineering team.Collaborate with Product and QA teams to validate fixes and communicate solutions back to users.Documentation & Process ImprovementTake ownership of enhancing both internal and external documentation using Notion and Intercom Articles.Identify gaps in onboarding processes, help content, and self-service resources.Assist in scaling support operations by optimizing workflows, tagging, reporting, and escalation procedures.Success MetricsEffectively own and scale technical support operations, including escalation management, workflow optimization, and Intercom efficiency.Enhance documentation, onboarding processes, and self-service resources to minimize recurring issues.Serve as a strong technical liaison between Support, QA, and Engineering to improve issue resolution and facilitate product feedback.
Feb 24, 2026