Senior GTM Enablement Specialist (USA) at Askable Chicago, IL

Comunidade Metodista; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Competitive Salary

Generous PTO

Great Health Insurance

International travel opportunities

Job summary

Askable in Chicago, IL is looking for a Senior GTM Enablement Specialist to architect global onboarding and ongoing learning for Sales and Customer Success. You will bridge Product, Marketing, and GTM, ensuring rapid ramp for new hires and ongoing rep growth from our Fulton Market office.

The role blends strategy and hands-on work: design playbooks, run workshops, analyze data, and refine the enablement engine to drive performance across the org.

Qualifications

• 3+ years in SaaS GTM enablement, Sales Ops, or CS Operations.

Responsibilities

• Design & scale onboarding programs with multi-week curriculums.
• Develop and maintain playbooks, battlecards, scripts, decks, videos.
• Manage enablement platform, learning paths, certifications, access and issues.
• Lead weekly trainings and quarterly deep dives on core skills.
• Create micro-learning assets and certification tracks with badges.
• Diagnose gaps with leadership and run targeted enablement sprints.
• Measure impact with dashboards and monthly insights, iterate.

Skills

onboarding design

content design

knowledge bases

live training

micro-learning

performance analysis

facilitation

Tools

Looker

CRM platforms

Google Slides

LMS platforms

video editing

Excel

Job description

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

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About Askable

Hey there! We’re Askable – the world’s most loved user research platform, trusted by global brands like Mars, Mastercard, Visa, Pizza Hut, and Accenture.

Founded in Australiain 2017, Askable beganas an idea scribbled on a sticky note, born out of frustration with the clunky, outdated research processes we’d experienced firsthand.

By providing seamless access to high-quality participants and Certified Askable Researchers, we enable teams to scale research on demand, deliver insights faster, and, ultimately, 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.

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Our culture

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.

In fact, we take culture so seriously that we wrote a book on 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.

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About the role

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—all from our Brisbane office.

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What you’ll do

• Design & Scale Onboarding Programs
  Craft a structured, multi-week onboarding curriculum that blends live workshops, e-learning modules, and shadowing sessions. You’ll 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, battlecards, 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 hand-in-hand 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.

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Skills and experience you’ll bring

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
  

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The mindset you’ll need

• Winning with your team : You’ll be proud of the individual work you do, but find winning as team ultimately more fulfilling. This includes having the emotional maturity to give and receive constructive feedback to better the team as a whole.
• Independence and curiosity : You won’t find cabinets full of step by step instructions at Askable. You’ll need to think on your feet, manage your own workflow, problem-solve roadblocks, proactively ask questions, and take responsibility for the goals you set.
• Growth focussed: You’ll enjoy the idea of a stretch goal and always be looking for opportunities to improve yourself, your team, and the business.
• Quick to learn: You’ll bring an ability to quickly learn and understand our product solutions and features, and keep up to date as our offerings evolve.
  

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Perks and benefits

Your excitement about the role itself is what matters most to us. Perks are just the icing on the cake—but let us share a few to whet your appetite.

• 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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Before you go...

Research shows many people (especially women and minority groups) hesitate to apply unless they meet every single requirement. At Askable, we’re committed to building diverse teams with unique perspectives. If you’re excited about this role but your experience doesn’t align perfectly, we’d still love to hear from you.