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 a program that moved more than 600 presales engineers globally toward solution-oriented, architecture-level thinking. Former VMware CTO Ambassador. 2x vExpert.
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 Glean as the company's enterprise AI knowledge management platform, selected after evaluating multiple RAG solutions including Onyx and others. Reached positive ROI in just over two months of real production use, not a controlled pilot, expanding adoption across hundreds of employees with each step justified to the C-suite with data-driven reporting built on internal Glean usage metrics and Forrester's Total Economic Impact analysis of the platform.
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
Partnered with legal and compliance teams to develop company-wide AI policy and usage guidelines covering appropriate use cases, safety boundaries, and data handling standards, using the EU AI Act, GDPR, and emerging global AI regulations as benchmarks regardless of geography. Contributed AI expertise to vendor evaluations against those same standards. Maintains AWS Bedrock governance through per-user and per-function usage dashboards, balancing cost, guardrail enforcement, and usability across teams with different risk profiles.
Agentic AI Adoption
Driving Claude Code adoption across technical teams through usage frameworks, CLAUDE.md standards, and personalized coaching, with the biggest impact in reducing token consumption through deliberate configuration habits. In parallel, building and running production Glean workflow agents that automate daily briefings, meeting prep, and operational workflows across technical, business, and development teams.
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.