AI Enablement Lead

Juniper Square•,

1d•$130,000 - $180,000•Hybrid

About The Position

We are hiring an AI Enablement Lead to drive internal AI fluency across Juniper Square. You will design and deliver the programs, content, and coaching that move employees up the fluency ladder, from first exposure to confident daily use to advanced application of Claude, Cowork, and Claude Code. This role pairs program design with hands-on delivery. You will build the curriculum, create the materials, lead the sessions, and coach individuals and teams directly. You will partner with managers across the company to identify adoption gaps, target interventions, and measure outcomes. This role requires personal expertise with the tools you teach. You will be a daily power user of Claude, Cowork, and Claude Code, and your own fluency will set the standard for the organization. Success is measured by fluency progression and meaningful tool usage across the company. You will own the enablement function end to end and contribute the patterns you develop back to the broader AI Guild.

Requirements

3 to 7 years of professional experience in customer education, technical training, learning and development, or a related field
Strong personal fluency with Claude and modern agentic AI tools, with demonstrated daily use as a power user
Proven track record designing and delivering training programs that produced measurable behavior change
Curriculum design experience, including segmenting audiences, defining learning outcomes, and building progression paths
Strong facilitation and presentation skills across live and async formats
Excellent written communication skills for non-technical audiences
Comfort with technical concepts and command line tools, including the ability to use Claude Code and demonstrate its application in real workflows
Ability to measure learning outcomes and adoption metrics, and iterate programs based on data
Proven ability to partner with senior stakeholders and influence adoption across organizational lines

Responsibilities

Design and deliver AI enablement programs across the full fluency ladder, from foundational onboarding to advanced practitioner training
Develop curriculum, content, and reference materials covering Claude, Cowork, and Claude Code
Lead live training sessions, workshops, and office hours, and produce async learning content for self-paced uptake
Partner with managers across the company to identify team-level adoption gaps and run targeted enablement against them
Coach individuals and teams one-on-one to unblock specific workflows and accelerate fluency growth
Identify high-impact use cases across the organization, document them, and spread them as patterns others can adopt
Measure fluency progression and meaningful tool usage, and report adoption outcomes to leadership
Partner with AI Guild engineers to onboard employees onto new internal AI tools as they ship
Stay current on the Anthropic product stack and translate new capabilities into accessible training and guidance