About Me Link to heading

I’m Justin Waltrip, Co-founder & Head of Engineering at Squary AI, an AI platform purpose-built for legal and regulated industries. I work at the intersection of artificial intelligence and the law, building technology that helps legal teams work faster, more accurately, and with greater confidence.

I hold dual degrees in Computer Science and Applied Mathematics & Statistics from Johns Hopkins University, with a focus on Machine Learning.

Current Role: Squary AI Link to heading

Squary AI

I 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 firms across plaintiff, defense, and personal injury practices, Squary AI unifies case documents (pleadings, discovery, medical records, transcripts, spreadsheets, and audio) into a single secure platform.

Key Achievements Link to heading

  • 70% reduction in document review time
  • 80% minimization of case oversight risks
  • 50% acceleration of strategy pivots
  • Millions of pages processed across thousands of 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

Cognistx (May 2021 - Dec 2024) Link to heading

I joined Cognistx, an AI consulting startup, in May 2021 as a Data Scientist. There, I delivered custom AI solutions for over 10 clients across legal, healthcare, and retail. I also co-hosted the AI-Driven podcast, where I discussed enterprise AI innovations with industry leaders.

Squary AI (Jan 2025 - Present) Link to heading

In January 2025, I became Co-founder & Head of Engineering as SQUARE evolved into Squary AI, a product-focused company serving legal and regulated industries. Squary AI was accepted into the Anvil Founder Program in Pittsburgh, a selective accelerator for early-stage technology startups.

Technical Leadership Link to heading

I lead product architecture for Squary AI, managing ingestion and indexing pipelines, model optimization, and scaling for enterprise-grade reliability and security.

I architected the technical foundation of SQUARE (now evolved into Squary AI), an enterprise question answering system that combines 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

Recognition & Talks Link to heading

  • Outstanding New Supplier Award — Duquesne Light Company (Apr 2026)
  • Anvil Founder Coaching Program — Cohort 3, selected for Pittsburgh-based founder program (Jan 2026)
  • Guest, The Dark Arts of the Team Optimization Podcast — Holonic (Apr 2026)
  • Building an Enterprise Question Answering System — Carnegie Mellon, Information Retrieval (Dec 2023)

Beyond Work Link to heading

I am a strong advocate for open-source software and actively contribute to the developer community. I run NixOS on my personal machines and enjoy experimenting with reproducible development environments. Outside of technology, I stay active outdoors with ultimate frisbee, backpacking, and waterskiing.