Senior GTM Enablement Lead - AI-Driven Training

Juniper Square; Chicago (IL); On-site; USD 116,000 - 145,000; Full time

Benefits offered by this job

Health, dental, vision

Life insurance

Mental wellness coverage

Fertility and family support

Flex Time Off

Annual professional development

Job summary

Juniper Square seeks a builder to shape how go-to-market teams learn, ramp, and improve. This role sits in Revenue Operations and owns GTM Enablement, bridging product updates, pricing, and new sales motions with training, certification, and content.

You’ll design onboarding and ramp programs, partner with Product Marketing, translate positioning into learning, and manage learning systems. Strong communication and CRM analytics are essential.

Qualifications

• 7+ years in Revenue Operations and 3+ years in Sales Enablement.
• Experience in fintech, SaaS, or complex B2B sales motions.
• Ability to translate large amounts of information into clear, actionable content.
• Experience designing and running enablement, onboarding, or certification programs for GTM teams.
• Proven project management and organizational skills; capable of balancing multiple projects.

Responsibilities

• Own and design GTM Enablement, including onboarding, training, and certification for GTM teams.
• Audit rep readiness and drive completion with GTM and RevOps leadership.
• Create onboarding and ramp programs aligned to time-to-productivity benchmarks.
• Collaborate with Product Marketing to translate launches into training content.
• Capitalize on AI to accelerate content creation and learning workflows.
• Build and maintain dashboards connecting enablement activity to GTM performance.

Skills

Revenue Ops

Sales Enablement

AI Proficiency

Sales Analytics

Cross-functional

Education

Bachelor's degree in business

Tools

Salesforce

Tableau

Looker

Job description

Juniper Square seeks a builder to shape how go-to-market teams learn, ramp, and improve. This role sits in Revenue Operations and owns GTM Enablement, bridging product updates, pricing, and new sales motions with training, certification, and content.

You’ll design onboarding and ramp programs, partner with Product Marketing, translate positioning into learning, and manage learning systems. Strong communication and CRM analytics are essential.