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EnrollHere

Lead Technical Support Specialist

Sorry, this job was removed at 05:09 p.m. (CST) on Monday, Apr 20, 2026
In-Office
Pinehurst, NC
In-Office
Pinehurst, NC

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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.

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.

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

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

What you need to know about the Austin Tech Scene

Austin has a diverse and thriving tech ecosystem thanks to home-grown companies like Dell and major campuses for IBM, AMD and Apple. The state’s flagship university, the University of Texas at Austin, is known for its engineering school, and the city is known for its annual South by Southwest tech and media conference. Austin’s tech scene spans many verticals, but it’s particularly known for hardware, including semiconductors, as well as AI, biotechnology and cloud computing. And its food and music scene, low taxes and favorable climate has made the city a destination for tech workers from across the country.

Key Facts About Austin Tech

  • Number of Tech Workers: 180,500; 13.7% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: Dell, IBM, AMD, Apple, Alphabet
  • Key Industries: Artificial intelligence, hardware, cloud computing, software, healthtech
  • Funding Landscape: $4.5 billion in VC funding in 2024 (Pitchbook)
  • Notable Investors: Live Oak Ventures, Austin Ventures, Hinge Capital, Gigafund, KdT Ventures, Next Coast Ventures, Silverton Partners
  • Research Centers and Universities: University of Texas, Southwestern University, Texas State University, Center for Complex Quantum Systems, Oden Institute for Computational Engineering and Sciences, Texas Advanced Computing Center

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