About the company
Twilio is shaping the future of communications, delivering innovative solutions to hundreds of thousands of businesses and empowering millions of developers worldwide to craft personalized customer experiences. Remote-first company with a strong culture of connection and global inclusion.
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 (objection-handling exercises, discovery calls, uncovering use case exercises) where sales reps can practice realistic customer conversations with generative AI personas
- Develop content into enablement driven by adult learning theory
- Collaborate with Sales Leadership, Product Marketing, and Revenue Operations to map learning pathways to seller competencies, product launches, and strategic sales methodologies
- Design just-in-time performance support assets (FAQs, Playbooks) integrated into seller workflows (CRM, Slack/Teams, Sales Engagement platforms)
- Transform complex product specifications and market insights into actionable learning experiences
- Design dynamic, personalized learning paths based on rep tenure, role, performance data, and skill gaps
- Implement AI-based automated feedback loops that evaluate sales reps' video pitches, call recordings, and written communications
- Research, test, and integrate emerging AI tools into the enablement tech stack
- Establish guidelines, prompt libraries, and best practices for ethical and effective use of AI design tools
- Monitor learning metrics, tool adoption, sales ramp time, and quota attainment
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
- 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
- Strong copywriting and visual communication skills tailored to high-performing sales audiences
Conditions
- Remote role, not eligible to be hired in CA, CT, NJ, NY, PA, WA
- Approximately 15% travel anticipated
- Benefits offered