EnrollHere

EnrollHere

Head of Engineering

Raleigh, North Carolina, United States

Sponsorship not specifiedDetected 48 days ago
Code ReviewGCPKubernetesMachine LearningCybersecurityDetection EngineeringComplianceCadenceHIPAALeadershipCommunication

About the role

  • You are not solely a manager; you are an engineering leader.
  • Additionally, you demonstrate discernment in delegating responsibilities, providing constructive challenges, and knowing when it is appropriate to step back.
  • Artificial Intelligence, automation, and strategic partnerships are primary levers, not afterthoughts.

Responsibilities

  • 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.

Requirements

  • 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.
  • 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 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.
  • 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

Nice to have

  • 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

Benefits

  • 3 dental plans (Aetna and
  • 5 additional Medical Plus benefits, including telehealth support and an annual
  • About EnrollHere EnrollHere is a fast-growing Medicare distribution SaaS platform serving agents, agencies, and carriers.

Company info

  • 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
  • We believe in taking care of our team, which is why we offer a comprehensive benefits package that supports your health, wellness, and future:
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