Tisson Mathew
Founder & CEO @ Skypoint
About
Legacy healthcare and senior living software is a database with a UI and an AI sticker. It doesn't reduce labor. It increases it.That's the problem I built Skypoint to solve.Skypoint brings 20+ agentic AI applications that cover the entire healthcare and senior living operation — sales, compliance, workforce, analytics, care management, and data. Every app has skyAgent inside, our AI engine that executes real work. Not suggestions. Finished outputs.$1M net new revenue at Bickford. 1,000s of hours saved per month at Cascadia. 1,100+ communities. 250+ integrations. HITRUST r2 certified.Start with one app. Replace one legacy healthcare or senior living vendor. Expand when ready.
United States
Lake Oswego
Computer Software
Senior Living Communities, Agentic AI Development, AI for Healthcare, Healthcare Information Technology (HIT), Data Warehousing, Large Language Models (LLM), CUDA, Python (Programming Language), SkyPoint AI Platform, SkyPoint Master Data Management (MDM), The Databricks Lakehouse Platform, SkyPoint Customer Data Platform (CDP), SkyPoint Value-Based Care Data Platform (Healthcare), SkyPoint Modern Data Stack Platform (MDSP), SkyPoint Healthcare Data Platform (HDP), SkyPoint Empower - Data Privacy Compliance Software, Tamr, SkyPoint Modern Data Stack Platform, Cloud Computing, Enterprise Software
Experience

Founder & CEO
Portland, Oregon Area
Built Skypoint from zero to replace legacy healthcare and senior living software with agentic AI that actually does the work. Not recommendations. Not dashboards. Work. Deployed at 1,100+ locations. 250+ integrations. 20+ AI-native applications across growth, revenue cycle, operations, workforce, and compliance. HITRUST r2 certified. Growing 3X year over year. The proof is in production. Bickford cut a billing process that required 100+ people down to one. Cascadia saves 100+ hours per community per month. Legacy software is a database with a UI and an AI sticker. We built something different.

Chief Technology Officer
Orange County, California Area
Technology enabled integrated healthcare provider and health plan in Medicare Advantage. Led digital transformation of the company including migration to Microsoft Azure. Member of the Executive Leadership Team.

Chief Information Officer
Cincinnati, Ohio
Member of the executive leadership team at Triplefin business unit. Reorganized and transformed the business with Microsoft azure cloud based technology platform. Revenues grew from $160M to $450M. Exit to H.D. Smith / Eversana.
Tisson Mathew's Contact Information
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