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Senior AI Product Designer

  • Source: Paylocity
  • Destify
  • Remote
  • Chicago
  • Full-Time
  • Senior

Job Description

Description:

Who You Are:

The Senior AI Product Designer is a high-velocity problem solver. You don’t just design interfaces; you leverage AI-native workflows (think Claude-style rapid iteration and Pencil.dev’s efficiency) to identify and reduce user friction. You are the steward of experience quality, ensuring that our high-speed delivery never compromises our world-class user experience.

  • AI-Native Workflow: You are “AI-pilled.” You use LLMs and AI design tools to automate the mundane, generate rapid variants, and prototype at the speed of thought.
  • Friction Fighter: You are obsessed with data. You identify where users are getting stuck in the funnel and design the path of least resistance.
  • Systems Advocate: You prioritize adopting the Design System to ensure we ship high-quality code, not just high-fidelity images.

Key Responsibilities

1. Design Strategy & Evidence-Based Discovery

  • User Friction Identification: Partner with Product and Engineering to analyze data and identify specific friction points within traveler flows. You translate “The data says users are dropping off here” into “Here is the validated UI solution.”
  • Evidence-Based Approval: Accountable for the “Validation Rate.” You ensure no design moves to production without sufficient user testing or data-backed confidence.
  • Quality Stewardship: Serve as the final point of sign-off for design outputs, ensuring every iteration meets our brand standards and functional excellence.

2. AI-Augmented Engineering Delivery

  • Rapid Prototyping & Iteration: Use AI to shorten the gap between a problem and a testable solution. You focus on “time-to-learning” over “pixel perfection.”
  • Active Delivery Participation: You are a presence in standups and refinements, providing real-time UI/UX guidance to ensure the Definition of Done (DoD) includes visual fidelity and accessibility.
  • Design System Governance: Lead the adoption of the Design System and prevent pattern fragmentation by ensuring we build with existing components first.

3. Cross-Functional Alignment

  • Marketing & Product Bridge: Coordinate with Marketing teams to ensure a seamless brand experience from the first ad to the final booking confirmation. You will leverage attribution data and funnel insights to align the post-click experience with user intent, optimizing conversion pathways within the product to improve guest-level booking outcomes.
  • Funnel Optimization & Guest Conversion: Partner with Marketing to analyze funnel performance and guest behavior data. You will identify friction points within the booking journey to optimize UX priorities, directly supporting guest-level conversion and successful bookings.

Requirements:

Required Qualifications

  • Experience: 5+ years in Product Design, specifically within Traveler sites, B2C, or E-commerce platforms.
  • Proven track record of designing and optimizing conversion-focused user journeys. You must have a strong functional understanding of experimentation (A/B testing), funnel analysis, and user behavior.
  • Demonstrate a workflow that leverages AI (LLMs, generative UI, automated QA) to deliver 2x-3x faster than traditional design methods.
  • Understands the full product lifecycle from discovery to deployment.
  • Driven by a “builder” mindset: you want to see code ship, not just Figma files.
  • High technical aptitude for modern tooling and the EQ to influence Product and Engineering teams without formal authority.
  • High proficiency in Figma and a strong understanding of technical constraints to speak “developer” during ceremonies.
  • Ability to leverage modern tools and lean methods (e.g., unmoderated testing, rapid prototyping, data analytics) to quickly validate insights and iterate based on user feedback.
  • Experience working within the Entrepreneurial Operating System (EOS) is a strong plus.

Why Join Destify

Join a cross-functional team focused on building impactful products and great experiences. This role is about partnership — connecting people, product strategy, and execution to drive growth.

We are looking for the absolute best candidate, regardless of geography. For US-based talent, this range reflects a high-accountability senior role. For LATAM-based talent, we offer top-of-market compensation that reflects the elite nature of this “AI-native” requirement.

  • Flexible Paid Time Off and Paid Parental Leave
  • Caribbean travel…

Skills

  • claude-by-anthropic
  • pencil
  • bridge
  • attribution
  • Figma
  • paylocity
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