Senior Learning Experience Designer

Twilio

2d•$106,320 - $156,300•Remote

About The Position

This position is needed within our Learning Experience Design team which is the engine that helps our GTM organization achieve their revenue goals. We are seeking an innovative Senior Learning Experience Designer to revolutionize how our global sales team learns, adapts, and executes. In this role, you will bridge instructional design, sales effectiveness, strategic priorities, and cutting-edge artificial intelligence. You won't just create training modules—you will design high-impact, AI-enhanced learning journeys, a range of modalities to match the sellers’ needs, interactive simulations, and performance support tools that shorten ramp times and drive revenue. The ideal candidate is an agile instructional designer who actively tests, adopts, and masters modern AI design tools (generative text, AI video, code blocks, voice synthesis, automated assessments, and interactive simulation builders) to multiply design output quality and speed.

Requirements

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 (we’ll want to see examples of your work!).
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.

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, etc.) 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.