[Hiring] Technical Support Specialist @EnrollHere

Role Description

The 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.

Responsibilities

• 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.

What Success Looks Like

• 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.

Qualifications

• 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