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Senior Learning Experience Designer

Twilio· Sales Operations
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Hybrid (Remote - US)$106.3k - $156.3kFull-timePosted 1w ago

About the role

Senior Learning Experience Designer to revolutionize how Twilio’s global sales team learns, adapts, and executes with AI-enhanced learning journeys, simulations, and performance support tools to shorten ramp times and drive revenue.

Responsibilities

  • Leverage AI authoring tools, large language models (LLMs), and prompt engineering to rapidly draft, iterate, and refine learning materials, roleplay scenarios, pitch guides, and sessions.
  • Build AI-driven roleplay simulations (e.g. objection-handling exercises, discovery calls, uncovering use case exercise) where sales reps can practice realistic customer conversations with generative AI personas.
  • Develop content into enablement that is driven by adult learning theory; enablement modalities are selected based on what best supports the seller.
  • Collaborate with Sales Leadership, Product Marketing, and Revenue Operations to map learning pathways directly to seller competencies, product launches, and strategic sales methodologies
  • Design just-in-time performance support assets (FAQs, Playbooks) integrated directly into seller workflows (CRM, Slack/Teams, Sales Engagement platforms).
  • Transform complex product specifications and market insights/positioning frameworks into easily digestible, highly actionable learning experiences.
  • Design dynamic, personalized learning paths based on rep tenure, role (AE, SE, SDR, DSR, etc), performance data, and skill gaps.
  • Implement AI-based automated feedback loops that evaluate sales reps' video pitches, call recordings, and written communications.
  • Continually research, test, and integrate emerging AI tools and software into the enablement tech stack to accelerate enablement development cycles, increase outcome quality, and increase enablement impact.
  • Establish guidelines, prompt libraries, and best practices for the team's ethical and effective use of AI design tools.
  • Monitor learning metrics, tool adoption, sales ramp time, and quota attainment to continually optimize enablement programs.

Qualifications

  • 3–5+ years of experience in instructional design, learning experience design (LXD), or sales enablement—preferably within a fast-paced B2B SaaS or technology environment.
  • Expert-level mastery of prompt engineering using LLMs (ChatGPT, Claude, Gemini) for curriculum design, scenario building, and content generation.
  • Intermediate level familiarity/ building with modern AI-enhanced L&D platforms, adaptive learning engines, and/or AI roleplay platforms (e.g., Gong, Articulate 360, Quantified, AI, Allego).
  • Hands-on experience with tools like ElevenLabs, Artlist.Io, RiversideFM, Synthesia, HeyGen, Midjourney, DALL-E, or Runway.
  • Advanced proficiency with authoring tools (e.g. Articulate Storyline/Rise, Adobe CC, Google Suite) integrated with modern AI plugins.
  • A demonstrated ability to create engaging, application-based content.
  • Understanding of the B2B sales cycle, buyer personas, and revenue metrics.
  • Early adopter mentality with a passion for experimenting with emerging tech to automate tedious tasks and maximize creative output.
  • Strong copywriting and visual communication skills tailored specifically to high-performing sales audiences.

Skills

Required:Instructional design / LXDPrompt engineering with LLMsAI-enabled learning platforms

Benefits

  • healthcare
  • retirement savings program
  • paid sick time
  • paid personal time off
  • paid parental leave
  • generous time off
  • wellness leave
Last updated Oct 15, 2026. Interested? Apply on the company site.

About Twilio

Twilio platform for communications and programmable APIs across messaging, voice, video, and AI-enabled workflows.

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