EnrollHere

Head of Product and Quality Assurance Hybrid Technology Full time Raleigh, North Carolina, United States About the Role EnrollHere is seeking a highly driven Head of Product & Quality to lead product execution, customer engagement, quality assurance, and delivery across our platform. This is a hands-on leadership role responsible for ensuring we build the right products, deliver them quickly, and maintain the highest standards of quality and customer satisfaction. This individual will serve as the bridge between customers, product, engineering, data, compliance, and executive leadership. They must be equally comfortable meeting with customers, writing requirements, testing features, prioritizing roadmaps, and holding teams accountable for execution. Why this Role Matters At EnrollHere, product quality and customer experience are competitive advantages. We are building technology that powers critical business operations for our customers. The right person in this role will directly influence product innovation, customer satisfaction, platform adoption, and company growth while helping ensure we continue to deliver at a pace that sets us apart from the market. About the Culture EnrollHere is not a slow-moving corporate environment. We move fast. We make decisions. We execute. We are obsessed with delivering value to our customers and continuously improving our platform. We believe speed matters, accountability matters, customer engagement matters, and results matter. The ideal candidate thrives in an entrepreneurial environment where priorities evolve, customer feedback drives innovation, and every team member is expected to take ownership. This role is for someone who enjoys being in the trenches, solving problems, engaging with customers, and helping teams deliver exceptional outcomes. Core Values: - Customer First - Ownership Mentality - High Accountability - Bias for Action - Continuous Improvement - Team Before Self - Relentless Execution - Attention to Detail - Strong Communication - Positive Energy and Engagement Requirements Qualifications - 7+ years of Product Management experience in a SaaS environment. - Strong understanding of software development and QA processes. - Highly organized and execution-oriented. - Exceptional communication and customer engagement skills. - Comfortable operating in a fast-paced, high-growth environment. - Willing to be hands-on and deeply involved in day-to-day execution. - Demonstrated track record of shipping products and delivering results. Responsibilities Product Leadership - Meet regularly with customers to understand needs, challenges, and opportunities. - Translate customer feedback into clear product requirements and priorities. - Own product backlog management and roadmap execution. - Write detailed user stories, acceptance criteria, and functional requirements. - Partner closely with Engineering, Data, AI, Compliance, and Operations teams. - Drive feature adoption and customer utilization. Quality Leadership - Build and lead EnrollHere’s quality assurance processes. - Establish release readiness and testing standards. - Perform hands-on validation of critical workflows and features. - Lead user acceptance testing and regression testing initiatives. - Track defects, prioritize fixes, and improve release quality. - Create quality metrics and accountability frameworks. Delivery & Execution - Ensure projects are delivered on time and meet customer expectations. - Coordinate cross-functional teams and remove obstacles. - Hold stakeholders accountable for commitments and deadlines. - Monitor progress and proactively identify risks. - Drive a culture of ownership, urgency, and continuous improvement. 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 90-day exclusionary period)

Head of Engineering Hybrid Technology Full time Raleigh, North Carolina, United States Description About the Role This is a foundational leadership role. You will own responsibility for the engineering organization — its people, architecture, delivery, and culture — at a moment when the company has the resources to build something durable and the urgency to build it fast. You are not solely a manager; you are an engineering leader. You work with senior engineers to solve complex issues, establish processes that scale, perform thorough code reviews, and make impactful architectural decisions. Additionally, you demonstrate discernment in delegating responsibilities, providing constructive challenges, and knowing when it is appropriate to step back. The mandate is clear: increase the velocity, quality, and security of product delivery — and do it by building a team and engineering culture that does not depend on heroics. Artificial Intelligence, automation, and strategic partnerships are primary levers, not afterthoughts. The buck stops with you. What You Bring Engineering Credibility As an engineer, you lead by example and are expected to demonstrate proficiency in coding, code review, and active participation in architectural decisions alongside the most skilled members of the team. These capabilities are essential, as any shortcomings will be promptly recognized by the team. A Track Record of Measurable Improvement You do not just adopt new technology — you operationalize it and point to outcomes. You have led engineering organizations through meaningful improvement cycles and have specific results to show for it: delivery velocity, quality metrics, security posture, team capability. Pragmatic Judgement You think strategically but you do not over-build. You know the difference between technical debt that needs to be paid now and technical debt that can be managed. You can sleep at night when the balance sheet is not perfect, as long as you know exactly what is on it and have a plan. Experience in Regulated or Complex SaaS Environments You understand what it means to build software where compliance is real and the cost of getting it wrong is significant. Experience in healthtech, insurtech, or Medicare distribution is a meaningful advantage — not required, but it shortens your ramp and signals you understand the stakes. People Leadership in Complex Team Environments You have inherited teams with existing dynamics, informal power structures, and varying levels of capability. You know how to build culture without blowing up the people who built the product. You lead by example, set clear expectations, and follow through. AI Automation Fluency You have a practical point of view on how AI and automation change the engineering function — and you have put that point of view into practice. You are not chasing hype; you are building sustainable capability. Requirements What You Will Own Engineering Execution - Own end‑to‑end engineering delivery across the full product surface — enrollment workflows, the commission engine, AI‑driven compliance scoring, telephony infrastructure, and the underlying platform that ties it all together - Drive sprint execution, release cadence, and delivery predictability without losing the pace a PE‑backed growth company possess - Establish engineering processes that scale without the bureaucracy that kills momentum — lightweight rituals, clear ownership, and fast decision‑making - Transform the Product Development Lifecycle to incorporate agents and autonomous capabilities driving increased innovation - Build a culture where engineers feel real ownership of outcomes, not just tickets. That means clarity of priorities, transparency around tradeoffs, and a bias (not hard line) toward finishing work, not starting more of it - Set expectations for how the team collaborates: thoughtful code reviews, healthy debate, and a shared commitment to raising the bar on quality and reliability - Create an environment where engineering, QA, and product operate as one delivery unit — aligned on goals, honest about risks, and accountable to the same definition of “done.” - Anchor decisions in customer impact. Engineers should understand how their work shows up in an agent’s workflow, a carrier’s integration, or a beneficiary’s enrollment experience — and use that context to guide tradeoffs, simplify complexity, and eliminate friction - Model the behaviors you expect, such as: direct communication, curiosity, urgency without panic, and a willingness to roll up your sleeves when the team needs it Architecture and Technical Direction - Own technical direction and architectural strategy across the platform - Make pragmatic architectural decisions — right-sized to where the company is today, with a clear-eyed view of where it needs to go - Manage technical debt actively and transparently — it does not need to be zero, it needs to be known, tracked, and directionally improving AI, Automation and Velocity - Identify and implement AI and automation capabilities that materially improve engineering velocity, code quality, and security — not as a pilot program but as a core operating practice - Evaluate and leverage technology partnerships that accelerate capability without creating dangerous dependencies - Build a team that treats AI tooling as a standard part of the engineering workflow - Partner across teams to build an AI innovation roadmap that puts customers first, woven into the product naturally — not bolted on Team Leadership - Lead and develop a team of engineers across varying levels of seniority, experience, and working style that does not compromise the culture, but promotes it - Build a collaborative, entrepreneurial engineering culture — one where ownership is shared, standards are high, and people do their best work without burning out - Hire, develop, and when necessary, make hard calls on team composition or individual performance accountability - Create clarity of role and accountability for senior engineers, including those operating in informal leadership positions Platform Reliability and Security - Own the organization's security posture as an AI-augmented engineering practice, embedding automated code analysis, threat detection and policy enforcement directly into the development and deployment lifecycle - Establish a quality culture reinforced by AI and automation, using intelligent test generation, continuous regression detection, and clear quality gates so reliability and coverage are enforced by default, not inspection - Improve platform resilience through AI‑driven observability and disciplined releases, leveraging anomaly detection and automated root‑cause analysis to reduce incidents and eliminate repeat failures - Ensure regulatory and contractual compliance is engineered into the platform, using automated controls, continuous validation, and auditable enforcement for HIPAA‑adjacent data handling and carrier obligations - Translate compliance requirements into executable, AI‑testable engineering standards in partnership with compliance and operations, ensuring consistency and repeatability across teams and releases - Champion a data‑ and AI‑powered feedback loop across engineering, QA, and production, enabling earlier defect detection, automatic regression prevention, and continuous system‑level learning Qualifications - 8-10 years of progressive engineering experience, with at least 3-5 years in a senior engineering leadership role owning a team and a product - Demonstrated ability to expand engineering capacity through a combination of AI‑native development practices and effective use of off/near-shore or distributed teams, increasing output and leverage without sacrificing quality, velocity, or accountability. - Hands-on engineering capability — you have written production code and can still do it when it matters - Experience leading engineering in a SaaS product company; regulated industry experience (healthtech, insurtech, fintech) strongly preferred - Proven track record of improving engineering velocity, quality, and security with specific, measurable outcomes - Experience with cloud-native platforms (GCP preferred), containerized workloads (GKE/Kubernetes), and modern backend architectures - Familiarity with AI/ML integration in production SaaS environments 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 90-day exclusionary period)

About EnrollHereEnrollHere is building one of the most advanced technology platforms in healthcare distribution, leveraging AI, data, analytics, communications infrastructure, and workflow automation to power the future of insurance and healthcare engagement. As we continue to scale, we are looking for a highly creative, detail-oriented Graphic Designer to join our growing marketing and creative organization. This role will report directly to the Head of Creative and work cross-functionally across marketing, product, sales, executive leadership, events, social media, and partner success teams. We are looking for someone who thrives in a fast-paced environment, understands modern brand storytelling, and can create high-quality visual content that performs across digital and print channels. About the PositionThe Graphic Designer will play a critical role in shaping and elevating the EnrollHere brand across every touchpoint. This individual should possess strong design fundamentals, modern creative instincts, and the ability to execute quickly without sacrificing quality. The ideal candidate has experience supporting high-growth companies, managing multiple creative priorities simultaneously, and creating content optimized for both brand awareness and performance marketing initiatives. In your role, you will: - Design and produce high-quality creative assets across: - Social media - Paid advertising campaigns - Website and landing pages - Sales collateral - Event and conference materials - Executive presentations - Product marketing - Email campaigns - Internal communications - Brand and culture initiatives - Collaborate closely with the Head of Creative to maintain and evolve brand standards across all channels - Support social media content creation and execution, including platform-native creative formats and campaign coordination - Work cross-functionally with marketing, product, sales, compliance, customer success and executive leadership teams - Assist in developing visually compelling campaigns that support customer acquisition, retention, recruiting, and thought leadership efforts - Create creative assets optimized for performance marketing campaigns across platforms such as LinkedIn, Facebook, Instagram, Youtube, Google, etc. - Contribute ideas for improving creative performance, engagement, and brand consistency - Manage multiple projects simultaneously while meeting deadlines in a fast-moving environment - Prepare production-ready assets for both digital and print applications

- 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.

You’ll also help design and manage AI-powered agents that support analytical and forecasting workflows, with a strong emphasis on control, evaluation, and real operational value. This is a hands-on, senior role with clear ownership and accountability. Responsibilities - Build predictive, forecasting, and risk models to support policy decisions, agency strategy, and cash-flow planning. - Own the full production lifecycle of models, including deployment, monitoring, drift detection, and retraining. - Translate model outputs into decision-ready insights for policy, finance, and operations teams. - Partner closely with data engineering and product to ensure models are supported by scalable, reliable data pipelines. - Design and manage AI/LLM-based agents to automate or augment analytical workflows. - Define evaluation metrics, guardrails, and failure modes for agent-driven systems. - Improve model reliability, interpretability, and business impact as the platform scales.

• Lead full-cycle enterprise sales motions with large agency organizations • Sell into agency leadership (owners, CROs, COOs, heads of compliance and sales) • Articulate clear ROI around productivity, compliance, lead monetization, and growth • Manage complex buying groups across sales, compliance, IT, and finance • Partner with Customer Success to ensure smooth onboarding and long-term account growth • Maintain accurate forecasting and pipeline discipline • Contribute feedback to Product and GTM teams based on agency market needs

- Own full-cycle sales for carrier accounts, from prospecting to close - Develop executive-level relationships across product, compliance, operations, and growth teams - Navigate long, complex sales cycles with multiple stakeholders and decision makers - Position platform value across carrier priorities: growth, compliance, efficiency, and reporting - Collaborate with Solutions Engineering, Product, and Customer Success to win and expand accounts - Build accurate forecasts and maintain disciplined pipeline management - Represent the company at industry conferences and carrier-focused events

• Design and execute a comprehensive sales enablement strategy aligned to GTM objectives • Own onboarding, ongoing training, and certification for Sales, SDRs, and Customer Success • Develop and maintain sales content: pitch decks, demos, battlecards, playbooks, ROI tools, and case studies • Partner with Product and Product Marketing to translate features into compelling value narratives • Enable complex deal selling (security, compliance, integrations, procurement cycles) • Drive adoption and optimization of CRM, sales tech stack, and enablement tools • Analyze performance data to identify skill gaps and improve win rates and ramp time • Support new product launches and vertical-specific motions (e.g., Medicare, ACA, commercial lines)