EnrollHere

Own and improve technical support workflows, mentor support team members, and serve as escalation point for complex issues. | Experience in technical support or customer support, hands-on experience with support tools like Intercom, troubleshooting skills, and remote support environment experience. | 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. 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

Own and improve technical support operations, troubleshoot platform issues, and enhance documentation and workflows. | 2-4 years of experience in technical support, hands-on experience with Intercom and ticketing systems, troubleshooting browser-based applications, and excellent communication skills. | 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

Own and expand relationships with telecommunications carriers, oversee trust and reputation management, and align platform capabilities with carrier policies. | Over 8 years of experience in telecommunications or carrier strategy, with direct exposure to Tier 1 carriers, trust frameworks like STIR/SHAKEN, and high-volume outbound environments. | EnrollHere is building the next generation of call trust, identity, and compliance infrastructure for regulated, high-volume outbound communications. We are seeking a VP, Carrier Strategy & Network Partnerships to own and expand EnrollHere’s relationships across the telecommunications ecosystem — including Tier 1 carriers, carrier aggregators, identity providers, and trust networks. This role is responsible for ensuring EnrollHere’s traffic is trusted, authenticated, compliant, and strategically aligned with carrier policy as we scale new products, including branded calling, call reputation intelligence, and marketplace expansion. This is a strategic, externally-facing leadership role with direct impact on product roadmap, carrier risk posture, and platform expansion. Carrier Relationships & Strategy Serve as EnrollHere’s primary executive contact for: Tier 1 carriers (AT&T, Verizon, T-Mobile) Carrier aggregators (Bandwidth, Tata Communications, Telynx, etc.) Identity and trust vendors (Numeracle, Hiya, First Orion, TNS) Build and maintain senior-level relationships within carrier trust, fraud, and abuse teams Establish EnrollHere as a trusted, proactive partner within the carrier ecosystem Carrier Trust, Identity & Reputation Own EnrollHere’s STIR/SHAKEN posture and attestation strategy Align EnrollHere Trust Layer™ capabilities with carrier frameworks and policies Oversee call labeling, reputation management, and remediation workflows Proactively manage carrier risk and escalation paths Product & Platform Enablement Partner with Product and Engineering to: Translate carrier requirements into platform capabilities Pre-clear telecom-dependent product launches Guide implementation of branded calling, call reason metadata, and identity frameworks Ensure telecom dependencies do not create hidden platform risk Regulatory & Policy Interface Work closely with Legal and Compliance teams to: Stay ahead of FCC policy changes Interpret carrier codes of conduct Ensure TCPA/TSR alignment from a network perspective Act as EnrollHere’s internal authority on telecom policy and enforcement trends Commercial & Strategic Expansion Negotiate carrier and vendor agreements, including: Volume pricing Preferred routing Beta and early-access programs Unlock new carrier-supported features and expansion opportunities Support enterprise and marketplace growth initiatives Success Metrics Strong, active relationships with Tier 1 carriers and key aggregators Zero surprise carrier shutdowns or traffic interventions Faster carrier remediation and issue resolution Improved call answer rates and deliverability at scale Carrier buy-in ahead of major product launches EnrollHere participation in carrier roadmap and trust initiatives 8–15+ years in telecommunications, carrier strategy, or network partnerships Direct experience working with: Tier 1 carriers and/or carrier aggregators STIR/SHAKEN, call labeling, and trust frameworks Hands-on exposure to high-volume outbound calling environments Experience interfacing with carrier trust, fraud, or abuse teams 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 Medical Plus benefits, including Talkspace and telehealth 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 time off and remote work support Professional Development: Learning stipends and growth opportunities

Design, develop, and optimize scalable call routing telephony systems with integrations and real-time communications support. | 5+ years software engineering with 2+ years in real-time communications or telephony, proficiency in Go and Python, VoIP protocols, cloud infrastructure, and distributed systems. | 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. We are seeking a Senior Software Engineer to lead the design, development, and optimization of our call routing platform. You will play a critical role in building scalable, reliable, and intelligent telephony solutions that enable seamless customer experiences. The ideal candidate will have deep expertise in VoIP/CCaaS technologies, distributed systems, and cloud-based application development, along with a strong understanding of real-time communications and call routing logic. Responsibilities Product Development & Architecture Design and implement high-performance call routing algorithms and services. Architect scalable, fault-tolerant systems capable of handling large volumes of concurrent calls. Collaborate with product management to translate business requirements into technical solutions. Develop and maintain integrations with telephony providers, CRM systems, and third-party APIs. Implement automated testing strategies for telephony flows and routing logic. Monitor, troubleshoot, and optimize call quality, latency, and system uptime. Conduct performance benchmarking and capacity planning. Mentor junior engineers and contribute to code reviews. Work closely with DevOps and QA teams to ensure smooth deployments and operations. Participate in on-call rotations for production support as needed 5+ years of software engineering experience, with at least 2 years in real-time communications or telephony. Strong proficiency in programming languages such as Go and Python. Expertise in VoIP protocols (SIP, RTP, WebRTC) and telephony platforms (Twilio, Telnyx, Asterisk, etc.). Experience with cloud infrastructure (AWS, Azure, or GCP) and microservices architecture. Solid understanding of distributed systems, networking, and performance optimization. Strong problem-solving and debugging skills. 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