Lead Technical Support Specialist

EnrollHere is on a mission to make healthcare enrollment simple, transparent, and accessible for everyone. We partner with organizations nationwide to deliver streamlined technology and exceptional customer experiences, ensuring members can access the coverage they need with confidence. Our fully remote team thrives on collaboration, innovation, and a shared commitment to improving the enrollment journey for all.

The Lead Technical Support Specialist is a senior member of the EnrollHere Support team, responsible for owning frontline support quality, mentoring teammates, and serving as the primary escalation point for technical and workflow-related issues. This role is ideal for someone who has hands-on Intercom experience, understands modern ticketing systems, and enjoys balancing customer-facing support with operational leadership. You’ll work closely with Product, Engineering, and Operations to improve support workflows and customer experience.

• Serve as the primary escalation point for complex Tier 2–3 issues involving platform workflows, integrations, dialer tools, and account configurations.
• Respond to high-impact agent, partner, and internal inquiries via Intercom (chat & email) with speed, clarity, and empathy.
• Ensure SLA adherence and consistent response quality across active conversations.
• Identify patterns in support issues and proactively recommend solutions.

Support Leadership & Enablement

• Act as a day-to-day lead for the support function, helping unblock teammates and setting quality standards.
• Review tickets for accuracy, tone, and technical correctness.
• Assist with onboarding and ramping new support hires.
• Contribute to and refine support macros, workflows, and automations in Intercom.

Technical Troubleshooting

• Diagnose browser-based issues using developer tools, console logs, cookies, network requests, and basic HTML/CSS inspection.
• Clearly document bugs, edge cases, and reproduction steps for Engineering.
• Partner with Product and QA to validate fixes and communicate resolutions back to users.

Documentation & Process Improvement

• Own and improve internal and external documentation using Notion and Intercom Articles.
• Identify gaps in onboarding, help content, and self-service resources.
• Help scale support operations by improving workflows, tagging, reporting, and escalation paths.

• Own and scale technical support operations, including escalations, workflow optimization, and Intercom efficiency.
• Improve documentation, onboarding flows, and self-service resources to reduce repeat issues.
• Act as a strong technical liaison between Support, QA, and Engineering to improve issue resolution and product feedback loops.

• 2–4 years of experience in technical support, customer support, or a similar role.
• Strong hands-on experience with Intercom (Inbox, Articles, automations, macros).
• Experience working in a ticket-based support environment (Intercom, Zendesk,
• Freshdesk, Jira Service Management, etc.).
• Comfortable troubleshooting browser-based applications using developer tools.
• Excellent written communication and a calm, customer-first mindset.
• Proven ability to manage multiple priorities in a fast-paced, remote environment.

We believe in taking care of our team, which is why we offer a comprehensive benefits package that supports your health, wellness, and future:

• Medical: 4 United Healthcare medical plans (including an HSA option)
• Dental: 3 dental plans (Aetna and MetLife)
• Vision: 2 Aetna vision plans
• Wellness & Mental Health: 5 additional Medical Plus benefits, including telehealth support and an annual Talkspace subscription
• Ancillary Coverage: 4 ancillary plans and supplemental life insurance
• Retirement: 401(k) with a 4% match (after a 90-day exclusionary period)
• PTO & Flexibility: Generous PTO and remote work support
• Growth: Learning stipends and opportunities for professional development