Head of Engineering

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 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 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)