Instructional Designer & AI Learning Specialist

Who we are...

AvantStay delivers exceptional, unique stays for group travelers. We’re a tech-enabled hospitality brand redefining the short-term rental experience for the modern generation. Venture-funded and rapidly growing in the $100+ billion short-term rental market, we’re setting a new standard for group travel.

About the role

As the Instructional Designer & AI Learning Specialist, you will design, scale, and modernize the learning infrastructure for our short-term rental (STR) field and executive operations. You will sit at the intersection of operational excellence, adult learning theory, and cutting-edge artificial intelligence.

In this role, you will partner closely with Subject Matter Experts (SMEs)—including Regional Directors of Operations, Area Managers, Guest and Owner Relations Leads—to unpack complex operational workflows and translate them into rapid, high-impact training programs. By leveraging generative AI and automation tools, you will accelerate content development, allowing us to deploy just-in-time microlearning, field-friendly SOPs, interactive scenario simulations, and onboarding paths across our growing portfolio.

Key Responsibilities

SME Engagement & Course Requirements Gathering

• Partner with operational SMEs across Market Management, Guest Services, Maintenance, and Homeowner Relations to capture tacit operational knowledge and define clear learning objectives.

• Conduct Needs Assessments (GAP analysis) across frontline roles (e.g., maintenance technicians, area managers) to pinpoint friction points in guest review scores, SLA compliance, and onboarding speed.

• Translate complex, technical, or multi-step operational tasks (e.g., deep-reset audit protocols, de-escalation frameworks) into structured curriculum maps and learning journeys.

AI-Driven Content Strategy & Development

• Utilize generative AI tools (ChatGPT, Claude, Midjourney, Synthesia, ElevenLabs, Articulate 360 AI, etc.) to rapidly draft course outlines, script scenarios, build audio/video avatars, and generate contextual imagery.

• Design engaging, multi-modal learning assets—including interactive e-learning modules, microlearning videos, quick-reference field checklists, roleplay simulations, and digital job aids.

• Establish AI prompt libraries and standardized content generation workflows 

Curriculum Architecture & Deployment

• Build, organize, and maintain our enterprise Learning Management System (LMS) / Learning Experience Platform (LXP).

• Tailor learning experiences for a hybrid workforce—balancing mobile-first, field-accessible resources for on-the-ground technicians/cleaners with desktop-based leadership modules for Market Directors.

Qualifications & Experience

• Instructional Design Foundations: Experience in instructional design, adult learning, curriculum development, or corporate training, ideally within hospitality, short-term rentals, real estate, property management, or field logistics.

• AI Expertise: Demonstrated, hands-on experience using generative AI platforms (text, image, audio, video generation) to produce, iterate, and streamline instructional content.

• SME Collaboration: Proven track record of interviewing busy operational leaders and synthesizing fragmented ideas into clear, structured training materials.

• STR / Operational Mindset: Familiarity with short-term rental operations, turnover cleaning dynamics, field maintenance, guest messaging cadences, and owner relations is a major plus.

Core Competencies

• Rapid Prototyping: Ability to quickly move from an initial SME interview to a functional course draft using AI tooling.

• Agile Project Management: Capability to manage multiple course development sprints simultaneously across different operational domains.

• Field Focus: Ability to design content that resonates with diverse adult learners—from frontline cleaners in the field to C-suite executives.

• Analytical Thinking: Passion for measuring learning outcomes and connecting training completion to business KPIs (RevPAR, guest review scores, owner retention).

Perks and Benefits

• Competitive compensation, paid twice a month - dependent on experience & location

• Flexible workplace - work from anywhere outside the US

When you join AvantStay…

You’ll be doing work that matters alongside an experienced and dynamic team, transforming the way people travel and vacation.  Your place within the colossal travel and real estate industries will leave you with a wealth of opportunities to feel both challenged to innovate and rewarded for your efforts. Of course, we will offer you pay and benefits, but we’re about more than that. AvantStay is a place where you can craft your own path to greatness. Whether you think in code, words, pictures or numbers, find your future at AvantStay. 

Equal Employment Always...

We're proud to be an equal opportunity employer and we celebrate our employees' differences, including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, and Veteran status. Different makes us better.