In a strategic push to cement its leadership in enterprise-ready artificial intelligence, Iterate.ai has raised $6.4 million in funding. The round is led by Auxier Asset Management and includes distinguished investors Peter Cobb, Mike Edwards, and Dave Zentmyer—all former board members of eBags, the $1.65B online travel retailer co-founded by Iterate CEO Jon Nordmark.
This high-profile reunion isn’t coincidental. The founding team behind Iterate has long demonstrated an uncanny ability to anticipate digital trends before they peak. In 2015, they added “.ai” to their name—seven years before ChatGPT pushed AI into the mainstream. That very same foresight now powers Generate Enterprise, Iterate’s privacy-first, locally-deployable AI assistant, and Interplay, its patented low-code AI development platform. Together, they’re reshaping how enterprises adopt and scale intelligent software—securely and without vendor lock-in.
A Pragmatic Vision for the Way forward for Enterprise AI
said investor Peter Cobb, who previously co-founded eBags and served on the board of Designer Brands (DSW).
This philosophy is at the guts of Generate: a local-first AI platform designed to run Retrieval-Augmented Generation (RAG) workflows on devices like AI PCs or point-of-sale terminals. Unlike typical cloud-based solutions, Generate performs all language model inference, document search, and automation locally—enhancing each privacy and performance. Its no-internet-needed architecture makes it ideal for sectors like retail, healthcare, and government where data sensitivity and latency are critical.
The Infrastructure for Agentic AI
Iterate’s flagship platform, Interplay, complements Generate by offering a visible, drag-and-drop development environment for constructing AI workflows, often called agentic systems. These aren’t static chatbots—they’re autonomous agents that may follow logic trees, perform context-aware tasks, and chain together actions across internal documents, APIs, and enterprise databases.
Agentic AI workflows inbuilt Interplay depend on a spread of machine learning models—from lightweight Small Language Models (SLMs) optimized for embedded hardware to advanced Large Language Models (LLMs) able to nuanced language understanding. Interplay also integrates a vector database layer for semantic search and RAG pipelines, ensuring fast and accurate access to unstructured information like contracts or financial filings.
Behind this innovation is Iterate’s co-founder and CTO Brian Sathianathan, a former Apple engineer and certainly one of the unique members of its Secret Products Group—the elite team that developed the primary iPhone. His experience in hardware-software optimization is clear in how Interplay adapts to diverse chipsets, from Intel CPUs and AMD GPUs to NVIDIA CUDA cores and Qualcomm’s edge processors.
A Legacy of Constructing and Scaling
Investor and former Staples executive Mike Edwards—who led eBags as CEO after Nordmark—emphasized the trust and track record shared by the founding team.
Zentmyer, formerly of Lands’ End, praised the team’s diligence in securing critical hardware and distribution partnerships.
Built for Scale, Designed for Security
Security and data sovereignty are emerging as make-or-break aspects in AI adoption. With its air-gapped deployments, role-based access controls, and on-prem inference engine, Iterate gives enterprises complete control over where and the way their data is processed. That’s why many purchasers are selecting Generate and Interplay to run AI across secure government installations, financial institutions, and privacy-conscious retailers.
And in contrast to traditional AI stacks that require custom fine-tuning or extensive GPU provisioning, Iterate’s platform relies on modular components and zero-trust architecture to deploy rapidly—with or without cloud access.
