Sasha Caskey Research
Background and Education
Sasha Caskey has over 20 years of experience as a generative AI specialist, speech scientist, software engineer, and entrepreneur, with a Master’s in Science for Natural Language Processing from Columbia University.1 During his graduate studies at Columbia, he was interested in spoken dialog systems, particularly enabling computers to have more complex interactions with users by observing and modeling their interactions, and combining NLP techniques for more powerful human-machine interactions.2 He also studied the feasibility of using spoken dialog systems in hospital domains to aid physicians in cardiac ICUs.
Early Career Path
IBM Watson Research
Before co-founding Kasisto, Sasha was a member of the IBM TJ Watson research team responsible for real-time translation technology and conversational architecture for cars and mobile devices.1 At IBM Research, he led various AI and machine learning projects and contributed to the development of a Real-Time Translation Service for IBM.com.3
Previous Experience
- The MITRE Corporation - Where his passion for conversational systems started3
- ScanSoft International (later Speechworks Intl.) - His first startup experience3
Kasisto Leadership
Company Overview
Sasha is the CTO & Co-Founder at Kasisto, creators of KAI Banking, the leading conversational AI platform for the finance industry.13 Kasisto was founded in 2013 with the vision of enabling companies to engage and transact with their customers through intelligent conversations, anytime, anywhere.4
Notable Clients
Kasisto counts major financial institutions among its customers including:3
- DBS Bank
- JP Morgan
- Mastercard
- Standard Chartered
- TD Bank
- Wells Fargo
Technical Leadership
As Kasisto’s Chief Technology Officer, Sasha drove the architectural design and software development of the KAI platform since it spun out from SRI International in 2014.5 He leads the design and development of integrating KAI’s industry-agnostic, full stack AI technologies:3
- Speech Recognition
- Natural Language Processing
- AI Reasoning
- Natural Language Generation
He created an API-centric architecture optimized for performance, scalability, security and compliance.3
AI Innovation at Kasisto
Sasha leads the design of KAI’s combination hypothesis approach which enables the platform to take advantage of the latest AI technologies as they become available.3 The company has been using Large Language Models (LLMs) since 2018 when they first trained a BERT-based model called KBERT, specialized for banking and financial services use cases.6
Patents and Innovation
Sasha has been awarded over 33 patents for his innovations in AI and conversational technologies.1
Two Sigma Connection
Portfolio Company Relationship
Kasisto appears to be part of the Two Sigma Ventures portfolio company network.7 There was a recent conversation between Two Sigma Ventures and Kasisto’s CTO (Sasha Caskey) about breakthrough use cases for Generative AI, focusing on:6
- Private AI - Fine-tuning LLMs on proprietary data sets for specific institutional knowledge bases
- Personalized, Connected Assistance - Using LLMs to automatically access APIs from private financial data sources for highly personalized insights
Current Status
The search results suggest Sasha may still be primarily associated with Kasisto as of mid-2025, though there are indications of collaboration with the Two Sigma ecosystem. His exact role at Two Sigma may be more recent than available public information, or he may be involved in a consulting or advisory capacity rather than as a full-time employee.
Professional Background Summary
Education:
Core Expertise:
- Generative AI and conversational systems
- Speech science and natural language processing
- Enterprise AI architecture and implementation
- Financial services AI applications
Career Trajectory: MITRE Corporation → ScanSoft/Speechworks → IBM Watson Research → Kasisto Co-Founder/CTO → (Potential Two Sigma role)
Sources
Additional Reference Sources
- Kasisto AI Company Homepage
- Kasisto About Us Page
- Sasha Caskey Author Page - Kasisto
- Sasha Caskey LinkedIn Profile
Research Notes
Note: For the most current information about Sasha’s exact role at Two Sigma, direct verification through LinkedIn or professional contact may be necessary, as any transition may be very recent and not yet reflected in public sources.
Last Updated: August 15, 2025 Research Status: Comprehensive public source review completed
Interactions
2026-03-05
- Sasha shared experiments he’s been working on off my grounding system, calling the project “Forge” - includes a knowledge group and a linter
- Had been working on these experiments for a while before deciding to share
- Mentioned how thorough of a reviewer Wil was, implying he didn’t enjoy the scrutiny
- Dropped 11 comments on his doc regardless
- Reached out to say despite littering his doc with comments, I liked the work and to throw time on my calendar regarding integration
- He booked time for tomorrow (2026-03-06), though he didn’t respond to my comments with the depth I’d like
2026-03-06
- Had a tough call where I told him I wouldn’t integrate his work with grounding because the juice wasn’t worth the squeeze
- Told him the path forward was by increasing the evaluation metrics or adding in complex enough evaluation tasks that showed the additional abilities
- He tried to sell me on just integrating into grounding so he can easily share with others
- I told him that’s what everyone wants and right now it’s not worth it