Head of Engineering

About Enroll Here

Enroll Here 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, Enroll Here 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…