Jonathan Essary

About Jonathan Essary

I am a Senior AI Product Manager and technical product manager who helps teams ship user-centered digital and AI products from conception & discovery through iterative testing & launch across the whole product lifecycle. I integrate LLMs and adjacent AI capabilities into data-informed products, simplifying complex problems, aligning them with user needs and business goals, and driving roadmaps with clear success metrics in close collaboration with business, engineering, design, and data science.At IBM & Dialexa, I have led AI product initiatives and transformation programs, including product leadership for a $1.5B intermodal facility program with six interdependent project workstreams and VP-level stakeholders, alongside GTM strategy and roadmapping for internal AI R&D to create reusable assets. I tailor delivery practices, operating models, and ways of working to each organization\'s maturity and needs.On the AI side, I guide teams in building with LLM architectures, RAG, vector databases, context engineering, and AI agentic workflows. I manage efficient PRDs and backlogs, own product discovery, and use RICE-styled prioritization to balance impact and complexity. As a technical PM, I partner with engineers on retrieval strategies, latency, cost, and LLM evaluation, and define human-in-the-loop workflows and guardrails so AI features are governable and trustworthy. This means evolving from SDLC into spec-driven development and context engineering, where prompts, retrieval design, and evaluation loops are first-class product artifacts.My track record includes an AI-powered tax SaaS that validated product–market fit through a $4M acquisition, and a fundraising platform redesign that delivered 45% revenue growth. I anchor this work in OKRs, KPIs, product analytics, and A/B testing, connecting product decisions to adoption and revenue, not just launch.I actively define, design, and prototype with AI-assisted methods and tools throughout development cycles. This includes context engineering, structuring system prompts and retrieval contexts, and evaluation loops to ensure reliable AI behavior. My foundation is an award-winning design and research background with a Master of Architecture. I bring a fusion of technical understanding, design research, and systems thinking into digital product design and engineering and AI platform design, keeping complex systems grounded in human behavior, which I explore as the Technosapien Condition in The Fusionist and The Short Fuse.I look forward to connecting with you. Stay vigilant, my friend.

Experience

1. IBM

   Present

Education

• The University of Texas at Arlington

  Master of Architecture (M.Arch.), Architecture

  2015 — 2017

• The University of Texas at Arlington

  Bachelor's Degree, Architecture

  2012 — 2014