EnrollHere is an AI-powered platform and system of record for insurance distribution serving Medicare Advantage agencies, field marketing organizations, and carriers.
About EnrollHere EnrollHere is a fast-growing Medicare distribution SaaS platform serving agents, agencies, and carriers. The platform combines AI-based compliance scoring, agent enrollment workflows, commission management, and telephony infrastructure into a single operating environment for the Medicare distribution market. Backed by recent private equity investment, EnrollHere is entering a phase of accelerated growth with the capital, commercial momentum, and market position to become the defining platform in its category. 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 seni