Head of Engineering

EnrollHere • Raleigh, NC

3d

About The Position

This is a foundational leadership role at EnrollHere, a fast-growing Medicare distribution SaaS platform. The Head of Engineering will own responsibility for the engineering organization — its people, architecture, delivery, and culture — during a phase of accelerated growth. The role requires not just management but also engineering leadership, including active participation in solving complex issues, establishing scalable processes, performing code reviews, and making architectural decisions. The primary mandate is to increase the velocity, quality, and security of product delivery by building a team and culture that does not rely on heroics, with a strong emphasis on leveraging Artificial Intelligence, automation, and strategic partnerships. The buck stops with this role.

Requirements

• 8-10 years of progressive engineering experience.
• 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.
• 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.
• 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.

Nice To Haves

• Regulated industry experience (healthtech, insurtech, fintech) strongly preferred.
• Experience in healthtech, insurtech, or Medicare distribution is a meaningful advantage.

Responsibilities

• 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.
• Drive sprint execution, release cadence, and delivery predictability.
• Establish engineering processes that scale without bureaucracy, focusing on 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, with clarity of priorities, transparency around tradeoffs, and a bias toward finishing work.
• Set expectations for team collaboration, including 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, ensuring engineers understand how their work affects users and using that context to guide tradeoffs and simplify complexity.
• Model behaviors such as direct communication, curiosity, urgency without panic, and a willingness to roll up sleeves.
• Own technical direction and architectural strategy across the platform.
• Make pragmatic architectural decisions that are right-sized for the company's current state and future needs.
• Manage technical debt actively and transparently.
• Identify and implement AI and automation capabilities that materially improve engineering velocity, code quality, and security.
• 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.
• Lead and develop a team of engineers across varying levels of seniority, experience, and working style.
• Build a collaborative, entrepreneurial engineering culture where ownership is shared, standards are high, and people do their best work without burning out.
• Hire, develop, and make necessary decisions on team composition or individual performance accountability.
• Create clarity of role and accountability for senior engineers.
• Own the organization's security posture as an AI-augmented engineering practice, embedding automated code analysis, threat detection, and policy enforcement.
• Establish a quality culture reinforced by AI and automation, using intelligent test generation, continuous regression detection, and clear quality gates.
• Improve platform resilience through AI‑driven observability and disciplined releases, leveraging anomaly detection and automated root‑cause analysis.
• Ensure regulatory and contractual compliance is engineered into the platform using automated controls, continuous validation, and auditable enforcement.
• Translate compliance requirements into executable, AI‑testable engineering standards in partnership with compliance and operations.
• Champion a data‑ and AI‑powered feedback loop across engineering, QA, and production for earlier defect detection, automatic regression prevention, and continuous system‑level learning.

Benefits

• 4 United Healthcare medical plans (including an HSA option)
• 3 dental plans (Aetna and MetLife)
• 2 Aetna vision plans
• 5 additional Medical Plus benefits, including telehealth support and an annual Talkspace subscription
• 4 ancillary plans and supplemental life insurance
• 401(k) with a 4% match (after 90-day exclusionary period)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed