Senior GTM Enablement Specialist (USA)

Askable•Chicago, IL

17h•Onsite

About The Position

We’re on the hunt for a Senior GTM Enablement Specialist to architect and own our global onboarding and continuous learning programs for Sales and Customer Success. You’ll be the glue between Product, Marketing, and GTM, ensuring every new hire ramps quickly and tenured reps stay ahead of the curve. This role is both strategic and hands-on: you’ll design playbooks, run workshops, and analyse data to refine our enablement engine.

Requirements

To hit the ground running in this role you’ll need at least 3 years experience working in SaaS GTM enablement, Sales Ops, or Customer Success Operations
Proven project management skills—you love juggling timelines, stakeholders, and calendars
Strong content design chops in Google Slides, LMS platforms, and video-editing tools
Comfort with data: you can pull insights from Excel, Looker, or similar BI tools
Excellent communication and facilitation skills, with a knack for making complex topics clear
A self-starter attitude with a growth mindset—thrives in fast-paced, high-growth environments

Responsibilities

Design & Scale Onboarding Programs
Develop & Maintain Enablement Content
Manage Knowledge bases & Tools
Lead Live Training & Workshops
Create Micro-Learning & Certification Paths
Partner with Leadership to Diagnose Gaps
Measure, Report & Iterate

Benefits

Competitive Salary
Generous Paid Time Off (plus extra ‘Askable Days’ – a full day off just for you each month)
Great Health Insurance
Opportunities for international travel, including training in Australia

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