Director of Engineering

Pennant Services

8d•Remote

About The Position

Pennant Services is seeking an experienced, hands-on Director of Engineering to lead the Application Development team building products for post-acute businesses, including home health, hospice, home care, and senior living. Reporting to the Senior Vice President of Digital, this role leads the architecture, delivery system, people, and AI-native engineering practice for the software organization. The team uses AI coding agents extensively and integrates with HCHB, Snowflake, Twilio, Microsoft Entra ID, and other systems. The Director owns technical direction across digital products, including service boundaries, data models, integration patterns, and the platform roadmap. The role sets standards for HIPAA-grade engineering and platform operations, including PHI handling, audit logging, least-privilege access, observability, on-call practices, incident response, and cost management. It also makes AI coding agents the default across design, implementation, testing, and review, and develops evaluation suites, automated test generation, CI gates, and review standards to make agent output trustworthy. This leader manages, mentors, recruits, and develops engineers; establishes clear expectations and career paths; and improves output per engineer through tooling and automation. The role represents Application Development with clinical, operational, finance, and IT leaders, partners across Product Management, Data, and Infrastructure, participates in field pilots and rollouts, and contributes to technical strategy and investment cases. The position is remote in the Western US, with travel of approximately 10–15%, including periodic visits to Service Centers and field operations. It is full-time and offers eligibility for an annual bonus and equity.

Requirements

At least 8 years of software engineering experience, including at least 3 years leading engineers as a people manager, with responsibility for 1:1s, performance reviews, hiring, and difficult staffing decisions.
Led engineering at a startup or growth-stage company through adoption of AI-assisted development, with measurable before-and-after results.
Personally built and shipped production software with AI coding agents such as Claude Code, Cursor, Codex, or equivalent within the past 6 months.
Designed and operated a multi-service, cloud-hosted system with a production data layer and third-party integrations.
Established a quality system, including CI/CD, automated testing, code review standards, and incident response, rather than inheriting one.
Experience working under HIPAA, SOC 2, or comparable controls, or a credible plan for establishing PHI handling, audit logging, and access control in new and existing platforms.
Strong written and verbal communication skills, including the ability to explain technical tradeoffs to clinical, operational, and finance leaders.
Bachelor's degree in Computer Science, Engineering, or a related field, or equivalent practical experience.

Nice To Haves

Healthcare operations or EHR integration experience, including HCHB, Epic, eCW, WellSky, FHIR, or HL7.
Built or operated an AI harness layer, such as evaluation suites, agent skills, validation frameworks, or an internal AI developer platform.
Shipped LLM-backed features to end users and evaluated their accuracy and safety in production.
Migrated a product from a low-code or rapid-prototyping platform such as Retool to a durable stack without stopping delivery.
Experience with Go, TypeScript, SvelteKit, Kubernetes (AKS), Snowflake, Temporal, Azure, and Microsoft Entra ID.
Experience working with data scientists and data engineers on a shared platform such as Dataiku, Snowflake, or dbt.
Experience in an internal product group at a larger company after working at a startup.

Responsibilities

Own the technical direction of digital products, including service boundaries, data models, integration patterns, and the platform roadmap.
Support build, buy, and defer decisions and document technical tradeoffs and reversal costs.
Set and enforce standards for HIPAA-grade engineering, including PHI handling, audit logging, least-privilege access, and environment promotion from sandbox through production.
Maintain platform operability through observability, on-call practices, incident response, and cost management.
Make AI coding agents the default for design, implementation, testing, and review, and remove barriers to their effective use.
Build evaluation suites, automated test generation, CI gates, and review standards to make AI agent output trustworthy.
Measure and report delivery metrics, including cycle time, change failure rate, defects reaching the field, and cost per release, including where AI helps or hurts.
Partner with the Data Science team to ship predictive models and LLM features safely into clinical workflows.
Lead, mentor, and develop the development team through weekly 1:1s, clear expectations, performance reviews, career paths, and timely action on underperformance.
Recruit, hire, and retain engineers; own the interview loop and raise the hiring bar.
Grow output per engineer through tooling and automation before growing headcount.
Represent Application Development with clinical, operations, finance, and IT leaders, translating business priorities into engineering plans and engineering constraints into business terms.
Partner with Product Management, Data, Infrastructure, and others to support the success of Digital products.
Participate in pilot and rollout discussions with field agencies and operational partners.
Partner with IT on shared environments, security review, identity, and the boundary between the application platform and enterprise infrastructure.
Contribute to technical strategy and investment cases, including measuring the team's impact on Pennant outcomes.