At Glean:GO 2026, the AI transformation firm argues that escaping “pilot purgatory” requires an operating system for AI-enabled work, not simply more tools pushed into production.
Most enterprise AI programs do not stall because the technology fails. They stall because the organization never builds the machinery to turn a promising pilot into repeatable business impact. That gap between experimentation and operating results is the problem GleekOps Co-Founder Tim Glomb intends to tackle when he takes the stage at Glean:GO 2026.
GleekOps, an AI transformation and implementation firm serving SMBs and enterprise brands, is bringing that message to Glean’s flagship enterprise AI conference, taking place August 26–27 at Fort Mason in San Francisco. The event will also be available virtually at no cost.
“The next phase of workplace AI will be defined by outcomes, not by the number of pilots launched or tools deployed,” said Elisa DeFoe, CEO and Founder of GleekOps. “Organizations that connect AI investments to measurable improvements in speed, capacity, quality, and decision-making will be the ones that create lasting advantage.”
Glomb’s session, “Escape pilot purgatory with Tim Glomb: A practical playbook for AI momentum,” addresses a growing challenge for business leaders: why expanding access to powerful AI technology has not consistently translated into measurable operating impact.
While much of the “AI for work” conversation has focused on moving pilots into production, Glomb argues that pilot success is only part of the challenge. The larger opportunity, he says, is to build an operating system for AI-enabled work, one that connects workflows, enterprise knowledge, governance, ownership, technology, employee behavior, and measurable business outcomes across the organization.
“Pilot purgatory is a symptom, not the disease,” said Glomb. “If every AI initiative has to independently fight through questions of ownership, governance, knowledge access, adoption, and measurement, the organization has not built the infrastructure for transformation. The real opportunity is to create an operating system that allows the business to continuously redesign how work gets done.”
During the session, Glomb will share a practical framework for identifying high-value workflows, establishing clear business ownership, defining proof of value, and creating explicit “kill-or-scale” decisions for AI initiatives. He will also address the organizational capabilities that must develop alongside the technology, including workflow redesign, governance, enterprise context, AI literacy, and platform readiness.
The goal, Glomb argues, is not simply to put more AI into production. It is to give organizations a repeatable way to re-architect work across functions.
“The mistake leaders can make is treating AI like another software deployment,” said Glomb. “AI becomes transformational when organizations start with the work itself. Where are people spending time? Where does knowledge get trapped? Where do handoffs slow the business down? Which decisions can happen faster? Technology is one layer. The operating model around it is what determines whether AI actually changes the business.”
GleekOps works with organizations across AI readiness, transformation, enablement, and implementation. The firm maps existing workflows and systems, identifies opportunities for AI-enabled redesign, establishes governance and operating structures, drives employee adoption, and implements platforms such as Glean, along with the agents, integrations, and enterprise knowledge connections required to support new ways of working.
That approach reflects a broader shift in how workplace AI investments are being evaluated. Rather than focusing primarily on pilots launched, licenses deployed, or tools adopted, GleekOps encourages organizations to measure changes in the underlying work, including employee capacity created, cycle times reduced, manual processes eliminated, and business outcomes improved.
“AI transformation becomes real when it changes the economics, speed, or quality of a workflow,” Glomb said. “The question leaders should be asking is not how much AI they deployed. It is what changed in the business, and whether they now have the ability to repeat that change across the enterprise.”
Glean:GO 2026 brings together AI leaders, builders, operators, customers, and partners to discuss AI adoption, agents, governance, enterprise knowledge, technical architecture, and business outcomes.
Ahead of the conference, GleekOps is offering free access to three “AI for Work” ebooks authored by Glomb, along with free virtual registration for Glean:GO 2026, at gleekops.com/glean-go. Leaders who want help mapping and redesigning their own high-value workflows can reach GleekOps at gleekops.com/contact, hello@gleekops.com, or 610.496.5133.
Glomb’s participation in Glean:GO 2026 reinforces GleekOps’ focus on helping business leaders move beyond isolated AI projects and build the organizational capability to continuously redesign how work happens.
About GleekOps
GleekOps is an AI transformation and implementation firm that turns AI investment into measurable operating impact.
Working across AI readiness, transformation, enablement, and implementation, GleekOps helps organizations identify high-value workflows, redesign how work gets done, establish the governance and operating models required for AI, deploy enterprise AI platforms, build agents and integrations, and drive adoption across the organization.
GleekOps focuses on practical business outcomes, including increased employee capacity, faster decision-making, reduced manual work, improved access to institutional knowledge, and measurable operating leverage.
GleekOps works with companies of all sizes and across industries, including Revenue Analytics and Round Table Resource Group, among others, to set strategy and execute against their AI for Work investments.
For more information, visit gleekops.com.
About Glean:GO 2026
Glean:GO 2026 is Glean’s flagship enterprise AI event, bringing together customers, partners, builders, media, analysts, and enterprise leaders. The event will take place August 26–27, 2026, at Fort Mason in San Francisco, with a virtual attendance option.
Media Contact
Elisa DeFoe
GleekOps
elisa@gleekops.com
gleekops.com