Senior Learning Experience Designer

Twilio Inc.; United States; Remote; USD 113,000 - 141,000; Full time

Benefits offered by this job

Competitive pay

Generous time off

Healthcare

Retirement savings program

Job summary

Twilio Inc. is seeking a Senior Learning Experience Designer to revolutionize how our global sales team learns and performs.

You will bridge instructional design, sales enablement, and AI, creating AI-enhanced learning journeys and performance support tools to shorten ramp times and drive revenue. The role emphasizes agile design, experimentation with AI tools, and collaboration with Sales Leadership and Product Marketing to map learning to strategic methodologies.

Qualifications

• 3–5+ years of experience in instructional design or sales enablement in a fast-paced B2B SaaS environment.
• Expert-level mastery of prompt engineering for curriculum design and content generation.
• Familiarity with AI-enhanced L&D platforms and AI roleplay platforms.

Responsibilities

• Leverage AI tools to rapidly draft and refine learning materials and sessions.
• Build AI-driven roleplay simulations for sales reps to practice conversations.
• Design learning paths aligned to seller competencies and product launches.
• Create just-in-time performance support assets integrated into seller workflows.
• Transform complex product specs into actionable learning experiences.

Skills

Instructional design

Learning design

Prompt engineering

LLMs

Sales enablement

AI tools

Storyline/Rise

Video tooling

Copywriting

Tools

Articulate Storyline

Articulate Rise

Adobe CC

Google Suite

Gong

Synthesia

HeyGen

Midjourney

DALL-E

Runway

Job description

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, 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.

Location

This role will be remote,but is not eligible to be hired in CA, CT, NJ, NY, PA, WA.

Travel

We prioritize connection and opportunities to build relationships with our customers and each other. For this role, approximately 15% travel is anticipated to help you connect in-person in a meaningful way.

What We Offer

Working at Twilio offers many benefits, including competitive pay, generous time off, ample parental and wellness leave, healthcare, a retirement savings program, and much more. Offerings vary by location.

Compensation

*Please note this role is open to candidates outside of California, Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, New Jersey, New York, Vermont, Washington D.C., and Washington State. The information below is provided for candidates hired in those locations only.

The estimated pay ranges for this role are as follows:

• Based in Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, Vermont or Washington D.C. : 106,320.00 - 132,900.00.
• Based in New York, New Jersey, Washington State, or California (outside of the San Francisco Bay area): 112,560.00 - 140,700.00.
• Based in the San Francisco Bay area, California: $125,040.00 - 156,300.00.
• This role may be eligible to participate in Twilio’s equity plan and corporate bonus plan. All roles are generally eligible for the following benefits: health care insurance, 401(k) retirement account, paid sick time, paid personal time off, paid parental leave.

The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.

Applications for this role are intended to be accepted until October 25th but may change based on business needs.

Twilio thinks big. Do you?

We like to solve problems, take initiative, pitch in when needed, and are always up for trying new things. That's why we seek out colleagues who embody our values — something we call Twilio Magic . Additionally, we empower employees to build positive change in their communities by supporting their volunteering and donation efforts.

Updated - Twilio is proud to be an Equal Employment Opportunity employer

We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. Additionally, Twilio participates in the E-Verify program in certain locations, as required by law.

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