Lead Technical Support Specialist

EnrollHere is on a mission to make healthcare enrollment simple, transparent, and accessible for everyone. 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.

Requirements

• 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

Benefits

• 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