Redesigning a Travel Planner with AI

Building Smart Features and Scalable Systems from the Ground Up

AI

Mobile App

[2024]

[2024]

Company / Product Summary

This mobile-first trip planning app serves modern travelers looking for intuitive tools to plan and personalize travel experiences. Initially built as a static itinerary viewer, the app offered limited flexibility. As competition increased and generative AI matured, the team set out to reinvent the product as an intelligent travel assistant capable of dynamically creating itineraries, suggesting experiences, and refining plans through natural conversation.

To support this shift, the product required a complete UX overhaul - not just visually, but structurally. New interaction models were needed to accommodate conversational flows, real-time content updates, and multi-modal navigation across chat, map, and timeline views. At the same time, the design had to remain intuitive for users unfamiliar with AI tools. This meant rethinking how users discover, edit, and trust AI-generated plans - while ensuring the system remains flexible, transparent, and easy to override.

AI Integration

  • Designed UX to support multi-step AI queries, clarifications, and system states (“thinking”, “suggesting”, “fallback”).

  • Aligned UI with AI confidence levels and failure modes.

Component System

  • Built modular Figma components with auto-layout and naming synced to React structure.

  • Maintained parity via Storybook integration.


Tokens & Design System

  • Introduced semantic tokens for color, spacing, motion (e.g., delay.ai-typing).

  • Ensured consistent behavior across chat, map, and card views.


Accessibility

  • Met WCAG AA standards: keyboard nav, screen reader support, contrast compliance.


Testing

  • Prototypes tested via UserTesting.com and staging.

  • Focused on AI reliability, flow clarity, and edge case handling.


Users & Audience

Targeted at independent, experience-driven travelers aged 25–40 — including remote workers, solo travelers, and tech-savvy couples. These users often plan international trips lasting 3–10 days. They want tailored suggestions without spending hours researching or managing spreadsheets. Most are mobile-first users, expect personalization, and are open to AI assistance — but only if it feels trustworthy, optional, and clear.

The Problem

The existing product wasn’t scalable or intelligent - users could manually build trips, but not explore, adapt, or receive suggestions based on context or interest. AI had the potential to unlock hyper-personalized, dynamic planning, but the legacy UX was incompatible. The project aimed to redesign the app to:

  • Seamlessly integrate conversational AI into core user flows

  • Build flexible systems that adapt to AI outputs

  • Create a design foundation that could scale alongside AI capabilities

My Role

As Senior Product Designer, I was hired to lead the integration of AI features and to modernize the entire UX system to support a new planning paradigm. I focused on:

  • Designing all AI-driven experiences end-to-end

  • Auditing and rebuilding the component system from the molecular level

  • Establishing scalable design tokens and accessibility standards

  • Aligning the design with product and AI strategy through weekly working sessions

Collaboration included:

  • Product manager (feature prioritization and AI capabilities)

  • AI integration lead (data flows, prompts, system behavior)

  • Frontend engineers (component integration and accessibility)

  • Researcher (usability testing and behavioral analysis)

  • Design lead (design system alignment)


Discovery & Product Audits

  • Conducted a full UX and flow audit, mapping where users dropped off or hit friction (especially in trip creation, editing, and sharing).

  • Ran a component inventory audit to flag inconsistencies, duplicates, and missing states.

  • Led AI readiness workshops with product and AI leads to understand limitations (e.g., prompt structure, latency, fallback behavior).

  • Mapped current state information architecture, identifying gaps in navigation, state management, and hierarchy.


Testing, Research & Iteration

  • Designed and tested early low-fidelity wireframes using usertesting.com to validate AI chat use cases and edge-case scenarios.

  • Prototyped and tested AI chat interactions to gauge user expectations around tone, transparency, and control.

  • Created variants for visualizing AI outputs (timeline vs. map vs. card format) and tested comprehension and engagement.

  • Facilitated weekly working sessions with engineering and AI teams to align on structure, feasibility, and data states.


64%

🧠 Used AI on First Session

In usability tests, 64% of users engaged with the AI planning assistant during their very first session, indicating high discoverability and perceived value.

Based on heatmaps and session recordings from usability tests and internal pilots. We tracked first-click behavior and flow engagement within the first 5 minutes.

64%

🧠 Used AI on First Session

In usability tests, 64% of users engaged with the AI planning assistant during their very first session, indicating high discoverability and perceived value.

Based on heatmaps and session recordings from usability tests and internal pilots. We tracked first-click behavior and flow engagement within the first 5 minutes.

78%

📍 Preferred Smart Suggestions

78% of participants said they preferred AI-generated suggestions over browsing manually, especially for restaurant picks and day trip routes.

From a follow-up survey after testing three planning paths (manual, search-based, AI-assisted). Users rated AI suggestions as more useful and time-saving.

78%

📍 Preferred Smart Suggestions

78% of participants said they preferred AI-generated suggestions over browsing manually, especially for restaurant picks and day trip routes.

From a follow-up survey after testing three planning paths (manual, search-based, AI-assisted). Users rated AI suggestions as more useful and time-saving.

3.5x

📈 More Iterations per Plan

With conversational AI, users iterated on their itineraries 3.5x more than with the legacy flow — exploring more options and customizing trips in real time.

Quantified through prototype analytics and testing logs. Users using AI made more changes and refinements per plan compared to legacy flow users.

3.5x

📈 More Iterations per Plan

With conversational AI, users iterated on their itineraries 3.5x more than with the legacy flow — exploring more options and customizing trips in real time.

Quantified through prototype analytics and testing logs. Users using AI made more changes and refinements per plan compared to legacy flow users.

91%

💬 Found Chat Easy to Use

91% of test users rated the AI chat interface as easy or very easy to use, citing the clear prompts, loading feedback, and undo options as helpful.

Collected via a System Usability Scale (SUS) and open-ended post-test feedback. High scores were linked to clarity of prompts, feedback states, and editability.

91%

💬 Found Chat Easy to Use

91% of test users rated the AI chat interface as easy or very easy to use, citing the clear prompts, loading feedback, and undo options as helpful.

Collected via a System Usability Scale (SUS) and open-ended post-test feedback. High scores were linked to clarity of prompts, feedback states, and editability.

Design System: Foundation & Integration

1) Introduced molecular design principles to rebuild the UI from the ground up:

  • Atoms: Color tokens, type scale, spacing, shadows, interactive states

  • Molecules: Input groups, trip cards, filter chips, chat bubbles

  • Organisms: Day planners, editable itineraries, map views, AI response threads

2) Created a robust design token system:

  • Semantic tokens for accessibility (e.g., color-bg-surface-primary, color-text-muted)

  • Sizing tokens with mobile-first breakpoints

  • Motion tokens to standardize loading, transitions, and chat feedback

3) Integrated all new components into Figma libraries and built a centralized documentation hub using Notion + Storybook references.

4) Collaborated with devs to implement Figma ↔️ code parity for consistent naming, props, and states.


Designing AI Experiences

1)Designed multi-modal AI interactions, allowing users to plan via chat, card selection, or map overlays — depending on their preference.

2)Built flexible flows for:

  • “Start from scratch” trip planning via chat

  • “Add to trip” using AI suggestions contextualized by location and preferences

  • Iterative refinement (“Make this day more relaxing”)


3)Designed AI feedback patterns:

  • System typing indicators and “thinking” states

  • Explanation layers (“Why this recommendation?”)

  • Undo, refine, and escalate controls


4) Created error and fallback UX to handle AI limitations (e.g., ambiguous requests, timeout, unsupported destinations).


Vahan Kirakosyan

Sr. Product Designer

If you like what you see or have any questions, feel free to send me an email anytime.

Vahan Kirakosyan

Sr. Product Designer

If you like what you see or have any questions, feel free to send me an email anytime.

Vahan Kirakosyan

Sr. Product Designer

If you like what you see or have any questions, feel free to send me an email anytime.

Accessibility Improvements

  • Updated color palette to pass WCAG AA contrast standards.

  • Ensured all interactive components were:

    • Keyboard navigable

    • Properly labeled with aria-roles

    • Compliant with focus management and screen reader structure


  • Introduced dynamic text resizing, voiceover testing, and ensured all animations could be disabled for motion-sensitive users.


Outcomes & Learnings

Quantitative Results:

  • AI chat usage grew to 65% of all planning sessions within 30 days

  • 42% decrease in average time-to-itinerary compared to the legacy flow

  • 35% reduction in front-end bugs related to inconsistent component states

  • Achieved full WCAG AA compliance for all new screens


Qualitative Learnings:

  • AI wasn’t just a feature, but it changed how users thought about planning. We had to reframe the app around “conversational exploration” instead of “task completion.”

  • Trust and transparency were essential - users needed to feel they could challenge or refine AI suggestions at any time.

  • The modular design system allowed the dev team to ship new features 2x faster and reduced regressions significantly.

  • Accessibility and performance improvements were not just compliance efforts: they led to visibly improved usability for all users.

  • Working sessions between design, AI, and engineering led to fewer handoff delays and stronger technical alignment across sprints.


TL;DR – What I Brought to This Project:

  1. Led AI integration for the entire product UX, from conversation logic to fallback flows

  2. Rebuilt the product’s design system using molecular principles, scalable tokens, and documentation

  3. Conducted audits, testing, and collaboration rituals that made the product more intelligent, inclusive, and scalable



Selected work

[2022 -2025]

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Redesigning a Travel Planner with AI

Building Smart Features and Scalable Systems from the Ground Up

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Los Angeles

Available for work

Let’s create something great together.

I'm not just here to design products; I'm here to connect with people.

Los Angeles

Available for work

Let’s create something great together.

I'm not just here to design products; I'm here to connect with people.

Available for work

Let’s create something great together.

I'm not just here to design products; I'm here to connect with people.