About Me Link to heading

I’m Justin Waltrip, Co-founder & Head of Engineering at Squary AI, with a passion for leveraging machine learning and artificial intelligence to address real-world challenges.

My academic journey began at Johns Hopkins University, where I pursued dual majors in Computer Science and Applied Mathematics and Statistics, with a focus on Machine Learning, laying a solid foundation for my career in technology.

Current Role: Squary AI Link to heading

Squary AI

I currently lead engineering at Squary AI, a workflow-driven AI platform for legal and regulated industries. Trusted by leading law firms including Quatrini Law Group, Aldridge Pite, and other plaintiff and defense firms, Squary AI unifies case documents (pleadings, discovery, medical records, transcripts, spreadsheets, and audio) into one secure platform.

Key Achievements Link to heading

  • 70% reduction in document review time
  • 80% minimization of case oversight risks
  • 50% acceleration of strategy pivots
  • 500,000+ pages processed across 1,000+ workflows

Our platform features parallel task execution, attorney-ready outputs, and seamless integrations with SharePoint, Filevine, and Google Drive, delivering source-linked answers that integrate directly into legal workflows.

Career Journey Link to heading

Squary AI / Cognistx (May 2021 - Present) Link to heading

I joined Cognistx, an AI consulting startup, in May 2021 as a Data Scientist, where I crafted bespoke AI solutions for over 10 clients across industries including legal, healthcare, and retail. My role also allowed me to dive into the world of digital media as a co-host for the AI-Driven podcast, exploring the forefront of enterprise AI innovations.

In January 2025, I became Co-founder & Head of Engineering as SQUARE evolved into Squary AI, now a product-focused company serving legal and regulated industries.

Technical Leadership Link to heading

I lead product architecture, ingestion & indexing pipelines powering Squary AI, overseeing model optimization, scaling, and team delivery for enterprise-grade reliability & security.

I spearheaded the technical development of SQUARE (now evolved into Squary AI), an advanced enterprise question answering system that integrates extractive QA with retrieval augmented generation (RAG).

Key contributions included:

  • Automating extraction of critical information from complex documents
  • Designing a robust, multi-tenant serverless AWS architecture
  • Leading development of an evaluation framework for prompt engineering to enhance RAG model effectiveness
  • Building cross-format AI search across text, audio, video, spreadsheets, and complex case materials
  • Implementing seamless integrations with SharePoint, Filevine, Google Drive, and other document management systems

Additional Projects Link to heading

Outside of natural language processing, my work also included:

  • MoleculeAI: Utilized graph neural networks to revolutionize the drug discovery process
  • Product Placement: Used diffusion models to generate realistic backgrounds for retail items

Previous Experience Link to heading

Before Squary AI/Cognistx, I co-founded Nexxt Labs LLC (April 2017 - April 2020), where I gained early entrepreneurial experience in technology ventures.

Beyond Work Link to heading

Beyond my professional endeavors, I’m an advocate for open-source software and continuously explore new technologies. I’m currently developing a local-first recipe management system that I plan to open-source.

As a Linux enthusiast, I enjoy experimenting with NixOS among other distributions. When I step away from the keyboard, I find joy in playing ultimate frisbee, backpacking, and waterskiing, embracing the balance between my digital and outdoor worlds.