VP, Engineering

Nsight Health• US,

4h•$220,000 - $230,000•Remote

About The Position

Nsight Health is transforming how care is delivered through Remote Patient Monitoring (RPM), Chronic Care Management (CCM), and complex chronic care programs. We empower healthcare providers to manage chronic conditions using real-time data, AI-enabled technology, and 24/7 clinical support. Our HIPAA-compliant platform connects patients and care teams nationwide — improving outcomes, adherence, and peace of mind. Backed by Ciullo Inc., our portfolio spans Nsight Health, Nsure, Nvera, Arryva, and The Sweat Room, with revenue exceeding $100M and a deliberate trajectory toward $1B+. Nsight Health - Where Technology Meets Compassion. We are seeking a first-in-seat engineering executive to serve as VP of Engineering at Nsight Health. This is not an inheritor role — there is no existing engineering organization to slot into. You are building the function from scratch: hiring pipeline, leveling rubric, onboarding, team structure, toolchain, and culture. Reporting directly to the CTO, you are the primary touchpoint for every internal R&D team — translating strategy into execution, unblocking teams, and closing organizational gaps before they become problems. This role operates as a senior peer to the Principal Engineer, Enterprise Architect, and Principal Data Architect. The CTO sets the direction; you make sure it lands. Development is moving fully in-house. Vendor dependencies are being replaced with owned infrastructure. And across everything we build, AI is not a feature — it is the architecture. The people we are hiring now are the ones who make that possible. AI FLUENCY REQUIREMENT - NON-NEGOTIABLE Nsight Health is an AI-first organization. Every member of our leadership and operations team is expected to actively use AI tools in their day-to-day work - not as a novelty, but as a core productivity multiplier. This role requires genuine curiosity about AI, comfort experimenting with tools like Claude, ChatGPT, and workflow automation platforms, and the judgment to know when AI helps and when it doesn't. If AI makes you uncomfortable, this is not the right role.

Requirements

Proven track record leading engineering organizations, ideally in a healthcare or similarly regulated software environment.
Daily, demonstrated use of AI-assisted development tools — this is a hard requirement, not a preference.
Technical credibility in large-scale legacy modernization: you have taken a high-debt codebase and improved quality metrics without stopping the business.
Hands-on enough to review architecture decisions and call technical debt for what it is; strategic enough to sequence remediation against a revenue roadmap.
Experience operating under HiTrust R2, SOC 2, or equivalent compliance frameworks: you know how to ship fast and stay compliant.
Track record of building, integrating, and retaining engineering teams, including across mergers or org transitions.
Clear, direct communicator who writes and speaks like someone who has run engineering reviews.

Nice To Haves

Prior experience as a VP of Engineering or equivalent at a healthcare SaaS company.
Hands-on background as a software engineer or architect: you can read code, review PRs, and contribute credibly in production investigations.
Experience managing DevOps and security engineering functions alongside product engineering.
Familiarity with Remote Patient Monitoring (RPM), Chronic Care Management (CCM), or similarly complex clinical platforms.
Experience building or scaling engineering organizations through M&A or rapid inorganic growth.

Responsibilities

Conduct regular 1:1s with team leads and engineers to track performance, surface blockers, and maintain alignment with engineering direction.
Set and own the operational rhythm of the engineering organization: release cadence, cross-team coordination, and department-level planning cycles.
Monitor KPIs at the department and individual level; hold teams accountable to delivery commitments.
Model and amplify AI-assisted development across the org, embedding those practices into standard workflow.
Build a culture of knowledge sharing: document decisions, cross-train deliberately, and ensure no critical knowledge lives in one person’s head.
Anticipate and communicate engineering org needs to the CTO: forecast hiring demand, identify leveling gaps, surface onboarding friction, and flag cultural drift early.
Collaborate closely with the Principal Engineer, Enterprise Architect, and Principal Data Architect to ensure technical direction translates into execution.
Drive quality standards across every team in the R&D organization, improving consistency and coverage without halting feature delivery.
Set the standard for CI/CD pipelines supporting parallel release streams; define quality benchmarks that enable active development alongside production validation.
Establish and automate CVE detection and remediation workflows, maintaining continuous security posture under HiTrust R2 and SOC 2.
Work within engineering budgets, driving toolchain decisions and vendor relationships in alignment with approved spend.
Partner with the CTO on technical strategy and the path to $1B+.