• Lead the ground-up modernization of a mission-critical EHR and billing platform serving pediatric therapy practices. • Join at the start of an aggressive growth plan: the goal is to 10x the software business over five years through organic growth and acquisition, backed by committed PE capital. • Own the multi-year technology vision while remaining hands-on—perfect for a director-level (or rising senior manager) leader ready for the top seat. • Work directly with a product-led CEO and a seasoned senior designer; inherit two eager engineers who know the codebase cold and are hungry for mentorship. • Shape engineering culture, hiring roadmap, and best practices from Day 1 in a high-trust, low-bureaucracy environment. • Build HIPAA-compliant AI features (ambient documentation, treatment-plan recommendations, smart scheduling) that clinicians will love—and competitors will chase. • Define and socialize a phased modernization plan aligned to product, clinical, and business goals. • Advise the CEO and Board on architecture, AI adoption, and cloud investment decisions. • Upgrade the legacy .NET platform to modern .NET 8/9+ and retire end-of-life dependencies without disrupting active clinical workflows. • Replace embedded legacy UI with a WCAG 2.1 AA-compliant modern front-end (React, Vue, or Angular)—and write some of that code yourself. • Launch companion mobile apps (leading the work, not necessarily building it) that improve clinician usability and patient workflow efficiency. • Own HIPAA Security Rule posture and drive SOC 2 Type II readiness, executing a security roadmap with third-party audit support. • Bring security intuition to product and design decisions—MFA, encryption, secure-by-default patterns. • Ship clinician-facing AI features by integrating best-in-class models and vendors—applied AI, not custom model development. • Mentor and grow the existing engineers into a high-performing team; recruit as the roadmap demands. • Represent technology with customers, partners, auditors, and the Board.

• Own the stability of a system where millions of users post within the same two minutes, every day • Run 12 squads across three codebases: release discipline, feature flags, platform, developer experience • Own infrastructure cost as a P&L line: GCP, Cloud Spanner, media delivery at scale • Complete our Node.js to Go migration without slowing delivery • Hire exceptional engineers, develop them, and hold the bar high • Set technical strategy with the CEO and product leadership

• Provide strategic guidance on industry trends, technology, and market opportunities • Support evaluation of potential investments and emerging startups • Introduce high-quality founders, investors, and ecosystem partners • Mentor and advise founders within the 16VC portfolio • Contribute to the development of 16VC’s investment theses and ecosystem initiatives

• Set and execute engineering strategy aligned with company goals, product vision, and roadmap. • Lead, mentor, and manage four director-level direct reports across engineering, quality assurance, DevOps, and IT/Cybersecurity. • Build and sustain a high-performing, remote-first engineering culture grounded in our core values, with a strong emphasis on ownership, accountability, and continuous improvement. • Translate product vision and roadmap into executable engineering plans with clear milestones and trade-off decisions. • Ensure engineering decisions proactively enable — rather than constrain — future product possibilities. • Drive adoption of AI-assisted development workflows — including AI coding tools, automated testing, and code review — to measurably improve team velocity and quality. • Provide technical oversight and strategic direction for the company’s data warehouse, including schema design and ETL/ELT pipelines. • Drive a culture of frequent, reliable software delivery while reducing cycle time and deployment friction through CI/CD improvements.