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Learning Design Specialist

The RealReal -
Greenwich, CT

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Job Details

Full-time
$65,000 - $85,000 a year
3 days ago

Benefits

Paid parental leave
Employee stock purchase plan
Paid holidays
Health insurance
Dental insurance
Parental leave
Vision insurance
401(k) matching

Qualifications

AI models
Rapid prototyping
UX prototyping
Automation
Articulate Storyline
Generative models
Prompt engineering
Canva
Prototype creation
Visual communication design
Developing e-learning programs
Agile
Design thinking
Professional art or design
AI-driven automation
Prototypes
Generative AI
Camtasia
Media editing tools

Full Job Description

About The Role

The RealReal is seeking a creative, disciplined Learning Design Specialist to support the Manager of Learning Design in transforming the employee experience and infusing a high-impact learning culture across the organization. This role treats learning as a premium product—designing self-paced, instructor-led, digital, and micro-learning solutions that eliminate operational friction and drive business results.
As a digital storyteller, prompt architect, and deeply collaborative team player, you will leverage UI/UX design and Generative AI to bypass traditional development bottlenecks. You understand that the best performance solutions are never engineered in a vacuum; you will partner cross-functionally with retail, tech, and operations teams to co-create inclusive learning journeys. By utilizing AI to handle the manual drafting, you maintain a continuous growth mindset to focus intensely on Instructional Integrity, Visual Luxury, and User Psychology—ensuring every touchpoint drives clear business impact and reflects our core values.

What You Get To Do Every Day

Lead the end-to-end digital production of self-paced assets using Camtasia, Canva, and Adobe Creative Suite, ensuring every asset reflects a premium, luxury aesthetic that maintains a consistent "TRR Voice".
Utilize advanced features within Articulate 360 (Storyline and Rise) to build immersive, interactive digital environments where learners actively do and practice rather than just passively watch.
Master Google Gemini and NotebookLM to design sophisticated prompts and automated AI Personas (Gems) to rapidly generate high-quality scripts and asset prototypes
Architect learning journeys that feel invisible by integrating modern performance support tools, job aids, and micro-learning directly into daily workflows to solve business friction at the exact moment of need.
Act as an internal performance consultant and dedicated team player alongside Subject Matter Experts and enterprise leaders, developing positive, cross-functional relationships to rapidly ground learning materials in proprietary technical documentation and transform raw data into actionable tools.
Deploy functional Minimum Viable Products (MVPs) within hours of identifying an operational problem, successfully managing multiple fast-paced project streams independently against firm deadlines.

What You Bring To The Role

Minimum Requirements:

Minimum Requirements:1–3 years of experience in Instructional Design, Digital Experience Design, Learning Technology, or AI engineering within a complex enterprise environment
AI Literacy & Prompt Engineering: Demonstrated capability to integrate Generative AI (such as Google Gemini and NotebookLM) into the instructional workflow for creative brainstorming, script enhancement, workflow automation, and rapid prototyping.
Mastery of ADDIE, Agile, and Performance-Based Design, with the ability to solve business problems through effective instructional architecture.
Performance-First Mindset: A deep understanding of how to solve tangible business problems through technology and workflow-embedded interventions rather than strictly content delivery.
Advanced Portfolio: A demonstrated track record of sophisticated interactivity (specifically within Articulate Storyline/Rise) and high-end visual luxury design.
Creative Tool Mastery: High proficiency in Adobe Creative Suite (Photoshop/Premiere), Camtasia, Canva, and Articulate (Storyline & Rise)

Preferred Requirements:

Experience in Luxury, E-commerce, or Tech-enabled industries.
Strong background in UI/UX Design and digital accessibility standards (WCAG).
Experience administering or architecting content within an Enterprise LMS (Absorb preferred).

Compensation, Benefits, + Perks

Employee Stock Purchase Plan
401K with Company Match
Medical, Dental & Vision Insurance
Paid Parental Leave
9 Paid Company Holidays
Flexible Time Off (With Manager Approval)
Find out more about our Benefits here.

The expected salary range for this role is $65,000.00-$85,000.00. To determine starting pay we carefully consider a variety of factors, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal parity. Additionally, salary is just one component of TRR’s total rewards package. Depending on role, employees may also be eligible for a bonus program, incentive pay and benefits.

The RealReal is the world’s largest online marketplace for authenticated, resale luxury goods, with 40 million members. With a rigorous authentication process overseen by experts, The RealReal provides a safe and reliable platform for consumers to buy and sell their luxury items. We have hundreds of in-house gemologists, horologists, and brand authenticators who inspect thousands of items each day. As a sustainable company, we give new life to pieces by thousands of brands across numerous categories—including women's and men's fashion, fine jewelry and watches, art, and home—in support of the circular economy. We make selling effortless with free virtual appointments, in-home pickup, drop-off, and direct shipping. We handle all of the work for consignors, including authenticating, using AI and machine learning to determine optimal pricing, photographing and listing their items, as well as shipping and customer service.

The RealReal is committed to providing an equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or Veteran status. We will consider qualified applicants for a position regardless of arrest or conviction records. At TRR, People Come First. That’s why diversity and inclusion are vital to our priorities as an equal opportunity employer. You can read about our Diversity Equity and Inclusion program here.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The employee is regularly required to sit; use hands to finger, handle, or feel and talk or hear. The employee is occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell. The employee must occasionally lift and/or move up to 10 pounds. Specific vision abilities required by this job include close vision. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.

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learning specialist jobs in westport, ct

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