Senior GTM Enablement Specialist

Overview

Heads up! This role is based in-person at our office in Fulton Market West Loop area, Chicago.

About Askable – the world’s most loved user research platform, trusted by global brands like Mars, Mastercard, Visa, Pizza Hut, and Accenture. Founded in Australia in 2017, Askable started as an idea scribbled on a sticky note, born out of frustration with clunky, outdated research processes. We set out to build a new way—one that makes quality research accessible to everyone, from Fortune 500s to startups hungry for insights.

By providing seamless access to high-quality participants and Certified Askable Researchers, we enable teams to scale research on demand, deliver insights faster, and build things that matter. Now with offices in Brisbane, London, and Chicago, we’re growing the team to bring Askable’s research power to researchers everywhere, so they can make smarter, user-driven decisions.

Our culture drives everything we do. We live it, breathe it, and work every day to make Askable a place where people can thrive. We believe work should be fulfilling, exciting, and meaningful. Here, you’re not just part of a team. You’re part of a community that cares about what they’re building and how they’re building it. Our Culture Book guides what we stand for, how we work, and the values that unite us—because nothing beats winning with a team you genuinely love working with.

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.

• Design & Scale Onboarding Programs – Craft a structured, multi-week onboarding curriculum that blends live workshops, e-learning modules, and shadowing sessions. Map out every step—from pre-boarding checklists to 30-60-90 day ramp plans—ensuring new hires hit productivity milestones swiftly.
• Develop & Maintain Enablement Content – Own the creation and upkeep of playbooks, battle cards, demo scripts, slide decks, and video tutorials. Partner with Product, Marketing, and Customer Success SMEs to surface new features, competitive insights, and customer stories, then translate those into engaging learning assets.
• Manage Knowledge bases & Tools – Configure and administer our enablement platform, CRM-embedded learning, and content repositories. Upload new materials, set up learning paths and certifications, and troubleshoot access—so every rep has seamless, on-demand access to what they need.
• Lead Live Training & Workshops – Facilitate weekly “Lunch & Learn” sessions and quarterly deep dives on core skills—prospecting, Challenger Sale, objection handling, ROI demos, etc. Incorporate role-plays, peer coaching, and real-time feedback to build both capability and confidence.
• Create Micro-Learning & Certification Paths – Produce bite-sized assets—interactive quizzes, one-pager cheat sheets, infographics, and 3-5 minute explainer videos—that reinforce key concepts. Build certification tracks with assessments to validate proficiency and award badges/certificates.
• Partner with Leadership to Diagnose Gaps – Work with Sales and CS leadership to run regular skills-gap analyses: review call recordings, survey reps, and analyze win-loss data. Translate findings into targeted enablement sprints or “office hours” with SMEs.
• Measure, Report & Iterate – Define success metrics—time-to-first-deal, session NPS, quiz scores, content usage—and build dashboards in Looker (or similar). Present insights monthly, drive continuous improvement cycles, and A/B test new approaches.

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,…