Greenhouse ·
full-timeSenior Learning Experience Designer
Twilio · Remote - US
Twilio provides a cloud communications platform that lets developers embed messaging, voice and video capabilities into applications. As a Senior Learning Experience Designer on the Learning Experience Design team, you will focus on building AI‑enhanced training for Twilio’s global sales organization. Day‑to‑day work includes using large language models, prompt engineering and AI authoring tools to draft learning materials, creating interactive role‑play simulations where reps practice objection handling and discovery calls, and designing performance support assets such as FAQs and playbooks that sit inside CRM or Slack workflows. You will collaborate with sales leadership, product marketing and revenue operations to map learning pathways to seller competencies, product launches and sales methodologies, and to develop personalized learning paths based on tenure, role and skill gaps. The role also involves implementing AI‑driven feedback loops that assess video pitches and call recordings, researching emerging AI tools for the enablement stack, establishing prompt libraries and best practices, and monitoring metrics like ramp time and quota attainment to optimize programs. The position suits an experienced instructional designer who is comfortable with adult learning theory, adept at modern AI design tools, skilled at cross‑functional collaboration, and able to thrive in a remote‑first environment.
Who we are 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. . Hiring and how we work 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. . See yourself at Twilio Join the team as Twilio’s next Senior Learning Experience Designer. About the job 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. Responsibilities 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. Qualifications 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! *Required: 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,
| Role | Senior Learning Experience Designer |
|---|---|
| Company | Twilio |
| Location | Remote - US |
| Type | full-time |
| Compensation | Not disclosed |
| Posted | 2026-10-08 |
| Deadline | Rolling |
Typical process for this type of role
A general guide — the exact steps for this specific listing may vary; check the original posting for details.
- 1ApplicationSubmit your resume through the apply link.
- 2ScreeningRecruiter reviews your background against the role.
- 3AssessmentA technical test, assignment, or coding round, depending on the role.
- 4Interview(s)One or more rounds with the hiring team.
- 5OfferOffer letter with compensation and start date.
Before you apply
0/4Senior Learning Experience Designer at Twilio: frequently asked questions
- What is the salary for this role?
- Twilio has not stated compensation in the listing. Check the original posting or ask during the application process.
- Is the Senior Learning Experience Designer position remote, hybrid or onsite?
- The listing marks this role as remote, with Remote - US as the location.
- What is the application deadline?
- Twilio has not listed a fixed deadline, so apply early in case the opening is filled.
- How do I apply for the Senior Learning Experience Designer role?
- Use the Apply button on this page. It opens the original listing on job-boards.greenhouse.io, where you submit your application with the company.
More at Twilio
Other jobs at Twilio
- Partner Program Manager · Remote - US
- Americas Sales Business Partner Manager · Remote - US
- Principal Presales Engineer, Product Specialist · Remote - Brazil
- Senior Field Marketing Manager - DACH · Remote - United Kingdom
- Account Executive 4 · Remote - US
Explore Related Placements
// similar opportunities
You might also like
Senior Instructional Designer
Samsara
Who we are Samsara (NYSE: IOT) is the pioneer of the Connected Operations™ Cloud, which is a platform that enables organizations that depend on physical operati...
Learning Experience Designer
Dropbox
Role Description As a Learning Experience Designer within Dropbox’s Customer Advocacy organization, you will create engaging, accessible, and effective learning...
Senior Partner Marketing Manager
Twilio
Who we are 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...
['Full-time remote work schedule', '6–8+ years experience required']
Senior Experience Engineer
Parity
About Us Parity is one of the world’s most experienced companies building the core infrastructure behind blockchain — the system that allows information and val...
Senior Experience Engineer
Parity
About Us Parity is one of the world’s most experienced companies building the core infrastructure behind blockchain — the system that allows information and val...
Sr. Staff Experience Designer
Airbnb
Airbnb was born in 2007 when two hosts welcomed three guests to their San Francisco home, and has since grown to over 5 million hosts who have welcomed over 2 b...