Olya Ossipova

Building the trust layer for AI: marketplace for evals to benchmark model performance and safety, with tools for generating evals.

• Market: Identified critical gap in AI evaluation ecosystem—fragmented, proprietary evals limit transparency and slow AI adoption; built platform to democratize access to high-quality benchmarks.
• Pain Point Analysis: Recognized that teams waste months building custom evals, lack standardized metrics, and struggle to compare models across vendors; created marketplace to accelerate evaluation cycles.
• Product Vision: Designed marketplace model connecting eval creators with teams needing benchmarks, plus tooling to generate evals programmatically—addressing both supply and demand sides of the market.
• Technical Strategy: Building platform to support diverse eval types (safety, performance, domain-specific), with versioning, reproducibility, and integration capabilities for ML teams.
• Market Opportunity: Positioned to become the standard for AI evaluation as model deployment scales, addressing critical need for trust, safety, and performance validation across industries.

Independently built end-to-end HIPAA compliant, multi-tenant AI platform for healthcare operations & government compliance automation. Owned entire stack (FE, BE, Infra, AI pipelines).

• Vision & Road-mapping: Conducted user research with large ($100M to $40B ARR) healthcare organizations and former government commissioners; defined MVP.
• Architecture: Designed + created scalable HIPAA compliant + multi-tenant schema (Postgres/ pgVector + AWS) + integrated APIs (Twilio/Sendgrid, OpenAI, Langchain).
• AI Product Development: Built multi-lingual voice AI, SMS + email parsing agents; eForms with eSignature; and RAG-to-rules driven compliance workflows; created evals.
• Go-to-Market: Positioned Carelink's compliance engine for local/state/federal rule automation and audit readiness; partnering with leading EHR vendors.

AI product development and strategic consulting for companies ranging from startups & funds to Fortune 500 companies. Select engagements:

Restructured product + operations for $38M ARR telecom + delivered new customer platform.

• ML Analytics: Built machine learning powered analytics for churn, ARPU + collections.
• Product Redesign: Shipped redesigned telecom platform to 40K+ users, reducing support tickets by 20%.
• Strategy: Cut call center costs by 45%, restructured billing team + deployed ML analytics; explored satellite & router supply chains.

Spent six months across Southeast Asia, Australia, and the Middle East.

• Studied solar supply chains, grid failures and recovery, solar integration into national grids, and emerging battery technologies.

• Playbook & Partnership: Defined venture studio model and established partnership with McKinsey FUEL, academic institutions (e.g. Cleveland Clinic) & co-investors.
• Focus Areas: B2B, climate tech, healthtech, insurtech & biotech.
• Execution: Identified & incubated product/venture concepts for portfolio company spin outs in highly regulated sectors.

• Platform Direction: Conducted market research for multi-year vision; created growth narratives & board communications.
• Cross Functional Leadership: Partnered with C-suite to align stakeholders, streamline operations, and champion new strategic direction.

First hire in healthcare. Built healthcare & life sciences practice at no-code unicorn Unqork ($2B+ valuation, $207M series C, Investors: CapitalG, BlackRock & Goldman Sachs).

• Client & Team Management: Managed matrixed product/engineering/GTM/UX teams + McKinsey, Deloitte, KPMG, EY + Cognizant partners; coaching rotating teams of 10-20.
• Market Research: Identified market opportunities; acted as corporate venture capital partner to enterprise executives, leading complex client discovery, builds + deployments.
• GTM & Operations: Grew healthcare/government vertical form 0 to $20M+ ARR, training & leading sales, product & engagement teams, establishing operational best practices.
• Product Definition: Authored PRDs, personas, workflows, architecture diagrams + specs.
• Product Build & Deployment: Led strategic highly regulated 0-1 product builds, such as:
  • NYC COVID-19 Apps: Ideated on + led build of UberEats equivalent enabling delivery of 100M meals in 3 months, keeping TLC drivers employed, featured in WSJ/NYT.
  • Hospital Patient Portal: Patient portal + intake/scheduling system used by millions of patients and hundreds of doctors in NYC. Presented at Beckers Hospital Review.
  • Other: Other engagement with federal HHS led to FedRAMP certification for the company, also led teams for Merck, CVS, Aeon + other product engagements.

Built + directed consulting practice across healthcare, public sector + digital transformation for MSP. In parallel, led operations for the company, as director of operations under the CEO.

• Team Management: Managed team of ~30 (product, technical + consultant teams)
• Consulting: Led strategy for client transformations, analytics tool & integration builds
• Growth Strategy: Built public sector practice with MWBE certification + managed government contract bids + contract teams
• M&A: Led competitor acquisition/integration; consolidated systems, employees, accounts
• Branding: Led business rebranding + website overhaul to create modern digital footprint

Founding product manager for IT ticketing system and healthcare integrations.

• Product Management: Defined requirements, feature roadmap + managed sprints
• Project Management: Oversaw budgets, timelines + vendor coordination
• Consulting: Delivered EHR integrations + digital transformation projects for clients

• Started first healthcare cybersecurity research pod at the University.
• Led research on smart contract medical device monitoring and cohort analysis of medically underserved populations.

“Government Operations Reimagined: Productivity with GenAI”

Whitepaper with IBM Research & ECNY, 2024

“Healthcare Blockchain Systems Using Smart Contracts for Secure Automated Patient Monitoring”

Journal of Medical Systems, 2018