Senior Learning Experience Designer

Overview

Senior Learning Experience Designer in Twilio's Learning Experience Design team, supporting the GTM organization by designing AI-enhanced learning journeys, simulations and performance support for the global sales team.

What you'll do

• 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.

What you'll need

• 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 (examples of your work required).
• 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.

Details

• This role is remote and is not eligible to be hired in CA, CT, NJ, NY, PA, WA.
• Approximately 15% travel is anticipated.
• Employees may be asked to report in person on an ad-hoc basis for team gatherings, functional off-sites or customer meetings.
• Estimated pay ranges vary by location; the role may be eligible for equity and corporate bonus plans.