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Juniper Square

AI Enablement Lead

RemoteCanada only
Published
Experience
Mid
Employment
Full-time
Company size
Mid-size
$130k–$180k/yr
Check eligibility

Open to CA only. Set where you work from to check your eligibility.

No BS summary

AI Enablement Lead to drive internal AI fluency. Design and deliver programs, content, and coaching for AI tools like Claude, Cowork, and Claude Code. Requires daily power user fluency with AI tools and experience in customer education or technical training.

Core skills

ClaudeClaude CodeAI Enablement

Required skills

AI toolstechnical traininglearning and developmentcurriculum designfacilitationpresentation skillswritten communicationtechnical conceptscommand line tools

Optional skills

modern agentic AI tools

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

What they require

  • 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

Benefits

  • 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

Juniper Square is an Operations Partner for private markets, unifying technology, data, and fund administration services into a single platform for GPs.

🇺🇸 United StatesFintechEnterprise
$130k–$180k/yr