Juniper Square

AI Enablement Lead

Americas (USA or Canada) · Exec · Full-time

Sponsorship not specified$130k-$180kDetected 48 days ago

Agentic AILeadershipCommunicationCollaborationMentoring

About the role

This role requires personal expertise with the tools you teach.
Success is measured by fluency progression and meaningful tool usage across the company.

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
Partner with managers across the company to identify team-level adoption gaps and run targeted enablement against them
Identify high-impact use cases across the organization, document them, and spread them as patterns others can adopt
Partner with AI Guild engineers to onboard employees onto new internal AI tools as they ship
Fertility and growing family support

Proven track record designing and delivering training programs that produced measurable behavior change
Comfort with technical concepts and command line tools, including the ability to use Claude Code and demonstrate its application in real workflows
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
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
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 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.
Annual professional development stipend

Health, dental, and vision care for you and your family
Life insurance
Mental wellness coverage
Flex Time Off in addition to company-paid holidays
Paid family leave, medical leave, and bereavement leave policies
Retirement saving plans
Annual professional development stipend
Lead live training sessions, workshops, and office hours, and produce async learning content for self-paced uptake

This listing is sourced directly from Juniper Square's careers page and normalized into a canonical job model.