Senior Learning Experience Designer

At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and empower millions of developers worldwide to craft personalized customer experiences.

Our dedication to remote-first work, and strong culture of connection and global inclusion means that no matter your location, you’re part of a vibrant team with diverse experiences making a global impact each day. As we continue to revolutionize how the world interacts, we’re acquiring new skills and experiences th...

We use Artificial Intelligence (AI) to help make our hiring process efficient. That said, every hiring decision is made by real Twilions!

In this role, you’ll:
 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.

Twilio values diverse experiences from all kinds of industries, and we encourage everyone who meets the required qualifications to apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table!
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.