Senior Learning 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 that make work feel truly rewarding. Your career at Twilio is in your hands.

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

Also, while we are a remote-first company, you may be asked to report in person on an ad-hoc basis for team gatherings, functional off-sites or customer meetings.

Join the team as Twilio's next Senior Learning Experience Designer.

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.

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…