Director of AI at 11:11 Systems · Enterprise AI Adoption · Change Management
AI reaches production when the organization is ready for it. Getting organizations there is the hard part.
I lead AI strategy, governance, and adoption at 11:11 Systems. Ten years as a presales Systems Engineer (SE), ten more in technical enablement. That combination is what makes the programs I build reach production rather than stall in pilot.
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About Me
I'm Joshua Liebster, Director of AI at 11:11 Systems, leading company-wide AI strategy, governance, and adoption across sales, customer experience, finance, and operations. Twenty years at the intersection of presales engineering and technical enablement.
Most enterprise AI deployments don’t fail because of the technology. They fail because nobody planned for the humans. That’s been my core thesis for the past decade, and the reason the programs I build make it from proof of concept to production.
I spent my first ten years as a presales Systems Engineer (SE) at VMware, which taught me what good enablement actually needs to accomplish. The past ten years I’ve been building on that — first in partner technical enablement at Apple, then as Technical Enablement Manager at 11:11 Systems. That role is what put me in position to build the AI program from the ground up.
I hold a Stevie® Award for Excellence in Training, served as VMware CTO Ambassador, and earned the vExpert designation twice.
The mission underneath all of it is simple: make people more capable than they were before they met me.
Key Achievements
Enterprise RAG Deployment
Deployed a Retrieval-Augmented Generation (RAG) platform on Glean that reached positive ROI in just over two months of real production use, not a controlled pilot. Expanding adoption across 1,000+ employees, each step justified to the C-suite with data-driven reporting.
AI Adoption Program
Built and runs a company-wide AI enablement program spanning org-wide training, open office hours, and personalized advisory and coaching for individual contributors through the C-suite. Developed parallel guidance for safe general AI use beyond Glean, keeping customer data and company IP out of public models while giving employees effective tools.
AI Governance Framework
Led authoring of policy and usage guidelines that ensure responsible AI adoption and compliance.
Agentic AI Adoption
Driving Claude Code adoption across technical teams through usage frameworks, CLAUDE.md standards, and personalized coaching. Built on direct experience with the tools, not vendor marketing materials, with the biggest impact in helping teams perform efficiently by reducing token consumption through settings, configuration, and deliberate habits.
Presales Onboarding Excellence
Redesigned Solution Architect onboarding, reducing ramp-up time to 60 days and boosting quota attainment by 25%.
Automated Interactive Demos
Implemented Walnut to deliver guided demos, cutting live demo time in half as well as reaching thousands of top-of-funnel prospects via the public website.
Core Competencies
Thinking About Enterprise AI Adoption?
Exploring AI strategy, presales enablement, or how to make the business case for AI investment? I’d love to connect.
Phone number intentionally omitted for privacy.