Clayton Gray

Clayton Gray

Founder & CEO @ Kaboodle AI

About

I am a founder and technologist focused on building reliable, real world AI systems that go beyond single model outputs. My work centers on designing multi-model, deliberative architectures that surface disagreement, challenge assumptions, and produce more balanced and trustworthy results in high consequence environments. I am the Founder and CEO of Kaboodle AI, a multi-model AI platform designed for workflows, not one off responses. Rather than relying on a single model, Kaboodle orchestrates multiple large language models to critique, challenge, and refine each other throughout a process. The goal is to support iterative reasoning, multi step problem solving, and real decision making, not just generate an answer and move on. Kaboodle is an official AWS startup partner, with Amazon Web Services supporting the development and scaling of the platform. My work is focused on AI system architecture. This includes designing prompt strategies, orchestrating multi-model workflows, building evaluation and scoring frameworks, optimizing cost and performance, and deploying production grade AI systems on AWS. I also design AI assisted development workflows that intentionally use different models for planning, implementation, critique, and verification so teams can build with more control and fewer missed considerations. I am currently working on provisional patents related to AI system design, model orchestration, and real world reliability. Looking ahead, I am focused on expanding Kaboodle’s role in workflow driven AI and bringing these systems into environments where decisions actually carry weight. What drives my work is a practical understanding of how technology is used under pressure. I focus on building AI systems that are transparent, predictable, and accountable, designed for people who need to trust what they are using. Earlier in my career, I spent over two decades supporting executive teams in high stakes financial environments. That experience shaped how I think about trust, operational risk, and reliability, and it directly informs how I design and evaluate AI systems today.

Country

United States

City

New York

Industry

Information Technology & Services

Skill

Artificial Intelligence (AI), System Architecture, Amazon Web Services (AWS), Enterprise IT Strategy, AI Storytelling, React UI for Interactive Media, GPT-4 / LLaMA / DALL·E Integration, Startup Strategy & Product Design, AWS Bedrock, Prompt Engineering, React.js, Tailwind CSS, AI Product Strategy, Business Ownership, Start-up Leadership, Disaster Recovery, VMware vCenter, Microsoft Teams, Data Centers, Executive Support

Experience

Kaboodle AI

Founder & CEO

Kaboodle AI

LinkedIn
2026-1 - Present · 9 mos

New York, New York, United States

Founder of Kaboodle, a multi-model, deliberative AI platform designed to produce more balanced, trustworthy, and well-reasoned outputs by orchestrating multiple large language models rather than relying on a single system. Kaboodle challenges models against each other in real time to surface disagreements, reduce blind spots, and improve response quality across complex questions. Kaboodle is an official AWS startup partner, with Amazon Web Services investing in and supporting the development of the platform. Current focus includes building a production-ready MVP, scaling secure cloud infrastructure on AWS, and preparing Kaboodle for early users, enterprise evaluation, and investor engagement.

Top US Hedge Fund

Top US Hedge Fund

Top US Hedge Fund

2025-9 - Present · 1 yr 1 mo

New York, United States

Provided desktop and end user support at a top hedge fund, supporting Windows and macOS environments across physical and virtual desktops. Worked extensively with VDI infrastructure using Citrix and XenCenter, managed iOS devices and mobile workflows, and supported Microsoft Intune rollouts for device management and policy enforcement. Involved in day to day user support, system provisioning, and ongoing platform maintenance.

Fortress Investment Group

Senior System Analyst

Fortress Investment Group

LinkedIn
2016-11 - 2025-4 · 8 yrs 6 mos

· Member of small task force to develop and implement AI strategies in MS SharePoint · Part of the AI technology team to roll out Microsoft Copilot to firm · Provide direct dedicated support for Dean Dakolias and Pete Briger, the Co-chairmen of Fortress Credit, as well as all Partners and Managing Directors. · Sole dedicated support for annual partner off-site meetings. · Support of Windows 10 environment including MS Office, Bloomberg, Adobe, Teams, as well as numerous house applications. · Host of multiple weekly partner IC Zoom calls and Monday morning zoom for Credit all (400+ employee’s) · Migrated 100+ users from AirWatch to Intune on iOS and Android devices. · Lead presentations, demos, and is main POC in coordinating file migrations from network share drives to MS SharePoint. · Host presentations and demos for users migrating from Symphony Chat to MS Teams. · Attended ServiceNow, Knowledge 2022 at Javits Center and took several hands-on training labs. · Active Directory support including account unlocks, group management and software deployment. · Support of all Windows PCs and laptops and all iOS devices both iPhones and iPads. This included deployments and upgrades. · Hardware setups including PC config changes of RAM and GPUs. · Physical desk setups including trading floor setups with Bloomberg, standing desks, and numerous multi-monitor configurations. · Travel to remote offices in SF, LA, and ATL to support business as needed. · Provide personal tech recommendations, setups, and deployments to partners and VIPs as needed for WFH.

Millennium

System Engineer

Millennium

LinkedIn
2016-2 - 2016-11 · 10 mos

First and second level support specialist for 1000+ hedge fund employees with an emphasis on the traders and VDI support. · Supported a robust remote client VM environment with Citrix and RDP using RSA security tokens. · Create/modify user accounts, security groups, and distribution list in Active Directory. · Supported multiple Market Data apps including Bloomberg, Reuters Eikon, FactSet as well as in house applications. · Supported over 1000 Blackberry’s as well as Good MDM on iOS and Android. · Maintained a flexible work schedule working both early and late shifts to accommodate a team of 9 techs.

Taconic Capital Advisors

Desktop Engineer

Taconic Capital Advisors

LinkedIn
2014-12 - 2015-10 · 11 mos

· First and second level support specialist for 100+ hedge fund employees with an emphasis on the traders. · VIP white glove support for management level users, partners, and company founders. · Responsibility to the trading teams including market data (Bloomberg, Advent-Geneva, Markit access), Citrix VDI support. · Activate, deploy, and trouble shoot all iOS, Android, and Blackberry devices including iPads and iPhones. · Configured and managed all mobile devices in MobileIron MDM this included extensive configurations while working directly with MobileIron support. · Add and remove users and devices to various Active Directory groups as well as password resets and account unlocks. · Imaged and deployed desktop, laptops, and thin clients. · Helped in many systems related aspects of company move from 450 to 280 Park Ave.

Charles Schwab

Desktop Support Analyst

Charles Schwab

LinkedIn
2011-8 - 2014-12 · 3 yrs 5 mos

· Provide service plus onsite desktop support to Windhaven & Thomas Partners staff and remote staff. · Primary responsibility to the trading teams including market data (Bloomberg, Portfolio Center, Advent – Moxy, FactSet), and VMware VDI support. · Activate, deploy and trouble shoot all iOS and Blackberry devices including iPads and iPhones using MobileIron MDM. · Image, deploy, and rebuild laptops and desktop computers for employees including the companywide migration to Windows 8. · Install and configure MATLAB - MathWorks for research team. · Account manager for Bloomberg and MathWorks for ordering and transferring licenses. · Handle trading and executive support escalations, I’m the first point of contact for any technical issues. · Submit order request for trading and executives for access related changes. · Help design, test, and support disaster recovery and business continuity plans at SunGard facility. · Preformed and assessed with server maintenance, upgrades, and failures.

Federal Reserve Bank of Kansas City

Information Technology Support Specialist

Federal Reserve Bank of Kansas City

LinkedIn
2008-10 - 2011-8 · 2 yrs 11 mos

· First and second level support specialist for all 12 districts of the Federal Reserve System. · Provide local assistance to Kansas City users. · Deploy, configure, and troubleshoot multiple Blackberry models for all major carriers. · Deploy and rebuild laptops and desktop computers for employees. · Support Lotus Notes 7.5 and 8.5 including the migration from 7.5 to 8.5. · Iron Key admin in charge of deploying new Iron Key devices. · Track and communicate weekly changes to the service desk as well as to other service partners. · Manage and complete user email requests for service desk support. · Identify process/procedure gaps and help create and implement solutions. · Handle executive support escalations. I received multiple achievement awards for providing exceptional customer service. · Worked third party vendor Equant to set up the Asia ebank, an out-hosted environment running on Windows 2000 Advanced Server and Citrix client. · Evaluated and recommended software for the ebank project based on functionality, cost, and support. · Worked as a liaison between Equant and Fleet's systems group to provide access and compatibility for over 100 Foreign Exchange trade applications. · Conducted testing on Citrix servers at Equant headquarters in London, England. Visited and inspected data centers. · Presented product information to Fleet Asia branch locations in Singapore, Hong Kong, Seoul, and Tokyo. · Conducted system inventories at Fleet Asia branch locations in Singapore, Hong Kong, Seoul, and Tokyo. · Documented day-to-day project progress on out-hosted global network, including orders installations and testing results.

Education

The University of Kansas

The University of Kansas

LinkedIn

Geological and Earth Sciences/Geosciences

1990-8 - Present · 36 yrs 2 mos
Harvard Extension School

Harvard Extension School

LinkedIn

Philosophy

2000-2 - Present · 26 yrs 8 mos

Clayton Gray's Contact Information

Email

******@***.com

Phone

(**) *** ****

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