Jason Decastro
Technical Cofounder, CTO, CISO
Technical cofounder and CTO/CISO who builds health tech products from 0 to 1. Cofounded a venture-backed virtual dementia care company serving Medicare beneficiaries across 9 states under the CMS GUIDE Model, spanning a proprietary EHR, telehealth, payor integrations, clinical interoperability, and value-based care delivery infrastructure. Led a 22-person technology organization and a $7M+ R&D budget; achieved HITRUST and SOC 2 certifications and maintained zero reportable cybersecurity incidents over 4+ years handling ePHI. Remains hands-on in architecture, AI-native development workflows, and production systems.
Experience
Fractional CTO Innovent Capital
- Operate as fractional CTO across Innovent's product portfolio, owning architecture, shipped product, AI tooling infrastructure, DevOps, and growth engineering
- Built a multi-agent Claude Code development system with 6 specialized sub-agents, git-worktree parallelism, and 134 auto-generated RSpecs, reducing integration defects by ~25%
- Engineered AI-powered matching and workflow systems that improved UX and reduced inference costs by ~50%, including automated deck analysis, match scoring, and lifecycle outreach
Cofounder, CTO, CISO Remo Health
- Cofounded Remo Health and led engineering, platform, data, security, and IT operations for a 22-person technology organization; managed the company's largest departmental budget at $7M+ in annual R&D spend
- Architected and built the healthcare technology stack from zero, including Pathways (our proprietary EHR), a HIPAA-compliant telehealth platform, patient and caregiver portals, and supporting analytics and marketing systems
- Enabled GUIDE-compliant, multi-payor operations serving Medicare beneficiaries across 9 states by building enrollment, claims, and credentialing infrastructure. Integrated key interoperability and revenue partnerships
- Owned security and compliance as CISO; authored and approved 39 security policies and procedures, led HITRUST and SOC 2 Type II certifications and recertifications, achieved 100% coverage on HIPAA security controls, and maintained zero reportable cybersecurity incidents over 4+ years handling sensitive ePHI
- Led near-zero-downtime cloud migration from Aptible/AWS to GCP/GKE, reduced infrastructure spend by ~30% and significantly improved database performance and query latency to under 1 second; forked Medplum and optimized for GCP
- Built the data and analytics pipeline using Particle Health, Segment, and BigQuery, powering board-level reporting, funnel analysis, and conversion metrics
- Built the full clinical product surface for care delivery such as labs, orders, e-prescribing, medication reconciliation, historical patient records via HIEs, scheduling, revenue cycle management, licensing and credentialing, care plans, risk stratification, radiology imaging, charting, among many other features
- Built AI-powered clinical tooling including expert reply generation for the caregiver community, encounter summarization, and a medication risk calculator for dementia patients
- Established DevSecOps and production security practices including GitHub CodeQL, Datadog SAST/SCA/IAST, multi-stage non-root Alpine containers, GPG-signed releases, GCP Secret Manager, and automated E2E testing
CTO Nixstro
- Led product delivery for consultancy clients in real estate and education technology, scoping projects, defining technical architecture, and managing cross-functional delivery teams
- Built a high-throughput MLS API for REBNY, used at scale to power real estate websites that require real-time listing data
- Worked extensively with data for real estate clients who required complex normalization work, using Python and R for processing, D3.js for visualizations, and efficiently indexed PostgreSQL and MongoDB databases
VP of Engineering LG Fairmont
- Led all engineering and product across the company, building and architecting several complex real estate systems and solutions while also creating a positive and highly productive eng culture
- Built a proprietary platform from scratch for searching listings and generating leads; implemented ElasticSearch to support scaling property searches across millions of listings
- Rebuilt the underlying structure of how we collected, parsed, and integrated listings into our product, optimizing speed, design, and performance at every stage of the ingestion pipeline
Software Engineer New York Magazine
- Built interactive articles and digital experiences for clients like CNN and HBO, and created reusable ad units for the ad operations team to sell at scale
- Built the infrastructure required to support video content. Rebuilt the Travel section from legacy tech to a new stack using ES6, Node.js, and Clay (proprietary content management system)
Software Engineer Red Antler
- Built internal products for the ad and sales teams to improve communication and organization around client relations using Node, React, LESS, and Jenkins
Early Career History
-
JPMorgan Chase (Software Engineer, Jun 2015 – Aug 2015)
Worked in Global Technology Infrastructure, one of the engineering teams required to be on-call for emergencies. Built new testing tools using Python, JavaScript, Selenium, Cucumber, and Jenkins while also optimizing existing tooling to improve performance and scalability -
Flatiron School (Software Engineer, Jun 2014 – Jun 2015)
Built data analysis tools using Python and D3.js for aggregating and visualizing student behavior and enabling data-driven product decisions; Served as an assistant instructor where I wrote and improved curriculum and gave lectures to students on web development and computer science
Expertise
Healthcare
CMS GUIDE Model, Medicare, Medicare Advantage, Medicaid, value-based care, FHIR and HL7
interoperability, EHR architecture (Canvas, Medplum, custom), claims submission and
adjudication, revenue cycle management, provider credentialing, patient enrollment, payor
contracting, telehealth platform design, care coordination workflows, caregiver support,
clinical data exchange, Particle Health, Photon, Stedi, Availity, ClaimMD, HealthGorilla,
SMART on FHIR
Security & Compliance
CISO leadership, HIPAA Security Officer, HITRUST CSF certification and recertification, SOC
2 Type II, ePHI handling, vendor security and BAA management, incident response, access
control (RBAC across 50+ systems), 7-year HIPAA audit logging, SIEM (Datadog), MITRE-based
threat detection, Vanta, 1Password, MDM, Zero Trust architecture
AI & Agentic Systems
Claude Code, multi-agent orchestration, MCP servers, custom skills and hooks,
Anthropic/OpenAI Batch APIs, prompt engineering and evaluation, RAG/semantic search,
AI-assisted development workflows, automated code review
Engineering
GCP/GKE, AWS, Kubernetes, Terraform, Docker, React, Next.js, Node.js, Python, Ruby on Rails,
Hotwire/Stimulus, Hasura/GraphQL, PostgreSQL, BigQuery, Elasticsearch, Redis, Datadog,
OpenTelemetry, Cloudflare, GitHub Actions, LaunchDarkly
Corporate IT & IT Services
Apple Business Manager, Kandji MDM, SentinelOne, 1Password enterprise, Google Workspace,
Zero Trust architecture, IT onboarding/offboarding, equipment lifecycle management, vendor
access auditing via Vanta
Leadership
Team building (0–22 engineers), $7.3M budget management, hiring pipeline design,
vendor selection and enterprise partnerships, product strategy, release process
optimization, engineering culture development