The Gilbane Advisor

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Box announces general availability of Box Extract

January 15, 2026 /

Box, an Intelligent Content Management (ICM) platform, released Box Extract. Powered by generative AI models from companies like Google, Anthropic, and OpenAI, and combined with agentic capabilities, Box Extract enables enterprises to intelligently and securely pull valuable information from content and save it as metadata in Box. With Box Extract, it is now easier for enterprises to automate workflows, accelerate decision-making, and get faster access to information and insights.

Organizational knowledge resides in the collection of contracts, product specifications, policy documents, charts, and other forms of unstructured content involved in day-to-day business operations. This content provides the critical context AI models and agents require to unlock meaningful business value.

Box’s agentic approach enables Box Extract to understand document structure and meaning, break it down into components, such as paragraphs, tables, or charts, and then pull out the most important information. Teams can create custom Extract Agents tailored to their business needs. These Box Extract Agents give customers the flexibility to store structured data alongside unstructured content as custom metadata, which can also be exported or synced to other systems such as Databricks and Snowflake.

https://blog.box.com/introducing-box-extract-get-actionable-data-enterprise-content-scale

Gilbane Advisor 1-14-26 — Context Graphs, Claude code

January 14, 2026 /

This week we feature articles from Kurt Cagle, and Ethan Mollick.

Additional reading comes from Jacob Steinhardt, Tony Seale, and Tom Krazit.

News comes from Microsoft, Snowflake & Observe, WP Engine & Big Bite, and Squirro.

Our next issue arrives 1/28/26.

All previous issues are available at https://gilbane.com/gilbane-advisor-index

Opinion / Analysis

Context Graphs, Data Traces & Transcripts

Some thoughts on the latest buzzwords

Kurt Cagle: “A knowledge graph is a valuable tool… and a critical part of AI infrastructure moving forward. However, the central idea of context graphs is that you should be able to determine exactly when a decision was made and why, and that is something that a knowledge graph by itself can only give you VERY indirectly…”. 

However, Cagle provides a “stunning” example of context capture with “a graph, a schema, and a bit of a taxonomy.” (15 min)

https://ontologist.substack.com/p/context-graphs-data-traces-and-transcripts

Claude Code and what comes next

With the right tools, AI can accomplish impressive things

With a single prompt, Ethan Mollick asked Claude Code to create an idea for a new business with a working website where you could purchase the product — it took a little over an hour. (Link provided with actual purchase function turned off).

This is an easy, non-technical read that illustrates current AI coding capabilities. (10 min)

https://www.oneusefulthing.org/p/claude-code-and-what-comes-next

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Content Technology News

Microsoft announces agentic AI capabilities for retail

Built for the full retail value chain, Microsoft’s agentic AI streamlines workflows to accelerate decisions by augmenting human expertise across the enterprise.
https://news.microsoft.com/source/2026/01/08/microsoft-propels-retail-forward-with-agentic-ai-capabilities-that-power-intelligent-automation-for-every-retail-function/

Snowflake to acquire Observe

Observe’s observability platform will integrate directly into Snowflake to allow enterprises to ingest and retain all their telemetry data at lower cost.
https://www.snowflake.com/en/news/press-releases/snowflake-announces-intent-to-acquire-observe-to-deliver-ai-powered-observability-at-enterprise-scale/

WP Engine acquires Big Bite

Strategic acquisition of a go-to partner for global publishers adds media industry and technical expertise to provide new solutions to enterprise customers.
https://wpengine.com/blog/wp-engine-acquires-big-bite/

Squirro announces Squirro Release 3.14.4 

Squirro Release 3.14.4 introduces new capabilities designed to close the gap between structured enterprise knowledge and ad-hoc user workflows.
https://squirro.com/news-and-events/new-release-december-2025-enhanced-chat-multimodal-reasoning

All content technology news

The Gilbane Advisor is authored by Frank Gilbane and is ad-free, cost-free, and curated for content, computing, data, web, and digital experience technology and information professionals. We publish recommended articles and content technology news most Wednesdays. We do not sell or share personal data.

Subscribe | View online | Editorial policy | Privacy policy | Contact

Algolia and Microsoft collaborate on retail experiences

January 12, 2026 /

Algolia, an AI Search and Retrieval Platform, today announced a collaboration with Microsoft to provide retailers and brands with greater influence, accuracy, and visibility in AI-driven shopping experiences. The collaboration integrates Algolia’s real-time enriched product attributes (product data, inventory availability, and product pricing) into Microsoft Copilot, Microsoft Bing Shopping, and Microsoft Edge, to help retailers ensure their products appear correctly and competitively across emerging AI discovery surfaces.   

Algolia customers gain greater influence over how their products are represented across Microsoft digital sites. Retailers benefit from enhanced brand control and stronger context awareness within Copilot, Bing Shopping, and Edge, backed by fresher, deeper, and more accurate product data.  

AI-driven discovery becomes shoppable through real-time, retailer-approved data, giving merchants influence over external, “off property” AI surfaces. Retailers can now extend their merchandising strategies into LLM environments that were previously inaccessible. 

Algolia, with the help of Microsoft, is address critical gaps in agentic commerce, more dynamic product storytelling, and deeper insights into how products perform across Microsoft experiences for richer reporting and retail media measurement. 

https://www.algolia.com/about/news/algolia-collaborates-with-microsoft-to-drive-real-time-product-data-to-shopping-experiences

Microsoft announces agentic AI capabilities for retail

January 8, 2026 /

Microsoft announced a set of agentic AI capabilities aimed at supporting automation and decision-making across retail operations, including merchandising, marketing, store operations, and fulfillment. The tools are designed to connect data and workflows so teams can act on context in real time.

Copilot Checkout, now available in the U.S. on Copilot.com, allows shoppers to complete purchases directly within Copilot without being redirected to a retailer’s website, while merchants remain the merchant of record. The service integrates with partners including PayPal, Shopify, and Stripe, and supports participating retailers such as Urban Outfitters, Anthropologie, Ashley Furniture, and Etsy sellers.

Microsoft also introduced Brand Agents for Shopify merchants and a personalized shopping agent template in Copilot Studio. These tools enable conversational shopping experiences using a retailer’s product catalog, with options ranging from turnkey deployment to fully customizable implementations.

In public preview, a catalog enrichment agent template automates product onboarding and categorization by extracting attributes from images and enriching data for search and recommendations.

For physical stores, a store operations agent template provides natural-language access to inventory, policies, and operational insights, helping staff manage workflows, staffing, and day-to-day decisions using internal and external data signals.

https://news.microsoft.com/source/2026/01/08/microsoft-propels-retail-forward-with-agentic-ai-capabilities-that-power-intelligent-automation-for-every-retail-function

Snowflake to acquire Observe

January 8, 2026 /

Snowflake, an AI Data Cloud company, has signed a definitive agreement to acquire Observe, a provider of AI-powered observability. With this acquisition, Snowflake will deliver their next generation of AI-powered observability, built on open standards and designed for the scale, complexity, and economics required by modern AI-driven enterprises. Snowflake and Observe will provide enterprises with: 

  • Agentic AI for faster troubleshooting: The combination of Observe’s AI-powered Site Reliability Engineer (SRE) with data in Snowflake enables a shift from reactive monitoring to proactive, automated troubleshooting. Observe’s AI SRE leverages a unified context graph that correlates logs, metrics, and traces, allowing teams to detect anomalies earlier, identify root causes, and resolve production issues faster.
  • An open-standard architecture built for scale: The acquisition also establishes a unified, open-standard observability architecture based on Apache Iceberg and OpenTelemetry. Enterprises can manage massive telemetry volumes using economical object storage, elastic compute, and interoperable standards.
  • Full telemetry data retention with efficient economics: As AI-driven applications generate volumes of logs, metrics, and traces, enterprises have increasingly been forced to rely on sampling and short retention windows to manage cost. By unifying Observe’s AI-powered observability platform with Snowflake’s scalable data foundation, organizations may eliminate these tradeoffs.

https://www.snowflake.com/en/news/press-releases/snowflake-announces-intent-to-acquire-observe-to-deliver-ai-powered-observability-at-enterprise-scale

WP Engine acquires Big Bite

January 7, 2026 /

WP Engine, a global web enablement company providing products and solutions for websites built on WordPress, today announced its acquisition of Big Bite, an enterprise agency known for the development of advanced editorial tools to improve how global brands and media organizations create and share digital content.

A longstanding WP Engine agency partner, Big Bite has over a decade of experience developing newsroom platforms, publishing workflows, and specialized tools that combine editorial flexibility with technical excellence. Their publishing expertise has helped transform the digital ecosystems of some of the world’s biggest media brands, including The Times, The Wall Street Journal, New York Post, Metro, and Macworld. As part of this transaction, Big Bite’s agency business will be wound down, and its team will transition into WP Engine’s Engineering organization to help build products that enhance publishing solutions for customers and agency partners. 

Big Bite’s publishing expertise, focused on navigating the rapidly changing digital landscape with innovative solutions, will seamlessly integrate into the premium service WP Engine provides its network of global agency partners.

https://wpengine.com/blog/wp-engine-acquires-big-bite/

Squirro announces Squirro Release 3.14.4

December 15, 2025 /

Squirro, a global supplier of enterprise-grade Generative AI and knowledge graph technology, announced the general availability of its latest Long-Term Support (LTS) platform update. Squirro Release 3.14.4 introduces new capabilities designed to close the gap between structured enterprise knowledge and ad-hoc user workflows.

Most notably, the update includes direct file uploads, multimodal image reasoning, and an enterprise-grade prompt library – features that help organizations extract insights from complex documents, whether stored in enterprise repositories or sitting on a user’s desktop.

The centerpiece of the latest Squirro Platform Release is an enhanced chat experience designed for versatility and depth. Direct file uploads let users bypass traditional indexing workflows by dragging contracts or reports directly into the chat for on-the-spot analysis. For complex long-form content, a new “Chat with Item” agent maintains deep memory context retaining the first 100 pages plus a summary to support Q&A sessions without losing the thread.

Multimodal image reasoning enables the AI to interpret charts, tables, and images contained within documents, while newly introduced table rendering capabilities automatically format structured data outputs into clean, readable tables.

By combining deep context memory, multimodal reasoning, and dynamic ad-hoc analysis, the upgrade enhances reasoning capabilities of auditable agentic workflows.

https://squirro.com/news-and-events/new-release-december-2025-enhanced-chat-multimodal-reasoning

Gilbane Advisor 11-19-25 — AI interviews, benchmarks, coding tools

November 19, 2025 /

This week we feature articles from Nicolas Ethan Mollick, and Dharmesh Shah.

Additional reading comes from Luke Wroblewski, Pete Warden, Jon Udell, and Michael Iantosca.

News comes from Snowflake, Bloomreach, Google, and Sitecore.

Reminder: We don’t publish in December.

All previous issues are available at https://gilbane.com/gilbane-advisor-index

Opinion / Analysis

Giving your AI a job interview

As AI advice becomes more important, we are going to need to get better at assessing it

Ethan Mollick explains why AI benchmarks, while valuable, are in general not sufficient for determining which AI model would be best for your business needs. What to do? Mollick argues that while “vibe benchmarking” can provide some limited insight into model differences,  assessing models for real world applications requires interviewing / testing model skill sets before hiring. Mollick discusses and links to OpenAI’s recent GDPval paper on the topic with examples. (8 min)

https://www.oneusefulthing.org/p/giving-your-ai-a-job-interview

The AI coding tool landscape (and why I just switched tools)

A breakdown of what’s available and what’s actually working

Developer Dharmesh Shah created a helpful table categorizing the different types of AI coding tools. (5 min)

https://simple.ai/p/the-2025-ai-coding-tool-landscape

More Reading

All Gilbane Advisor issues

Content technology news

Snowflake to acquire Datometry Migration Solution

Snowflake enhances data migration with Datometry technology, integrating it into SnowConvert AI to move legacy data faster and reduce costs.
https://www.snowflake.com/en/blog/accelerate-data-migration-datometry-technology/

Google introduces the File Search Tool in Gemini API

File Search accelerates development workflow by handling the complexities of RAG with a user-friendly alternative to a self-managed setup.
https://blog.google/technology/developers/file-search-gemini-api/

Bloomreach launches Personalized Media in-Grid

The new capability unites search, storytelling, and personalization, integrating placement and conversation inside the shopping journey.
https://www.bloomreach.com/en/news/2025/bloomreach-unites-search-storytelling-and-personalization/

Sitecore unveils SitecoreAI

SitecoreAI is the evolution of XM Cloud, unifying content management, customer data, personalization, and search in a single scalable platform.
https://www.sitecore.com/company/newsroom/press-releases/2025/10/sitecore-unveils-sitecoreai-ushering-in-the-ai-first-era-of-digital-experience

All content technology news

The Gilbane Advisor is authored by Frank Gilbane and is ad-free, cost-free, and curated for content, computing, data, web, and digital experience technology and information professionals. We publish recommended articles and content technology news most Wednesdays. We do not sell or share personal data.

Subscribe | View online | Editorial policy | Privacy policy | Contact

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