AI Enablement Lead

AI Enablement Lead

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.

What You'll Do

• 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

Qualifications

• 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

Compensation

Compensation for this position includes a base salary, equity, and a variety of benefits. The U.S. base salary range is $130,000 - $180,000 USD. Actual base salaries will be based on candidate-specific factors, including experience, skillset, and location, and local minimum pay requirements as applicable.

Benefits include:

• Health, dental, and vision care for you and your family
• Life insurance
• Mental wellness coverage
• Fertility and growing family support
• Flex Time Off in addition to company-paid holidays
• Paid family leave, medical leave, and bereavement leave policies
• Retirement saving plans
• Allowance to customize your work and technology setup at home
• Annual professional development stipend

Your recruiter can provide additional details about compensation and benefits.