Principal Product Designer

About Milestone:

Milestone Inc. is a leading Digital Experience Software and Services company dedicated to providing comprehensive solutions across every customer touchpoint that enhance engagement and accelerate business growth. Our mission is to pioneer content discovery, personalized digital experiences, and conversions through an AI-powered Digital Experience Platform (DXP).

About Role

We're looking for a Principal Product Designer to help shape the future of enterprise AI software. This is not a traditional UX role.

You'll define how AI-powered enterprise applications should feel, behave, and earn user trust. You'll partner with Product, Engineering, AI, and Customer Success to simplify complex workflows, build reusable design systems, establish design standards, and create experiences customers genuinely enjoy using.

This role will influence product strategy, mentor designers, and help establish design as a strategic capability across the company.

Problems We Area looking to Solve

• Reduce complexity across enterprise workflows
• Build AI-native user experiences instead of simply adding AI features
• Create explainable and trustworthy AI interactions
• Improve adoption through intuitive design
• Design reusable interaction patterns across products
• Build experiences that customers can successfully use from Day 1
• Turn customer feedback into measurable product improvements

Key Responsibilities

Product Design Leadership

• Lead end-to-end product design for major platform initiatives
• Influence product strategy through customer insights and design thinking
• Drive design decisions from discovery through launch and adoption
• Partner closely with Product Managers on problem definition before solutions are built

AI Experience Design

Design experiences across:

• AI Copilots
• AI Agents
• Conversational Interfaces
• Workflow Automation
• Content Generation
• Recommendations
• Explainable AI
• Human-in-the-loop experiences

Create interaction models that balance automation with user control.

Customer Discovery & Research

Lead research activities including:

• Customer interviews
• Journey mapping
• Usability testing
• Design validation
• Concept testing
• Workflow analysis

Translate insights into product opportunities.

Design Systems

Own and evolve Milestone's design system.

Create:

• Components
• Interaction patterns
• AI design guidelines
• Accessibility standards
• Enterprise UX principles

Ensure consistency across multiple products.

Design Excellence

Raise the quality bar across the organization by

• mentoring designers
• reviewing designs
• improving design processes
• establishing best practices
• introducing AI-powered design workflows

Cross-functional Leadership

• Work closely with Product Management, Engineering, Sales & Marketing
• Influence decisions without direct authority.
  

Ideal Candidate Profile

A product-focused UX professional passionate about AI, enterprise SaaS, and solving complex problems through elegant, user-centered design.

Required Experience & Qualifications

• 10+ years of UI/UX or Product Design experience.
• Strong portfolio of B2B SaaS or enterprise products.
• Experience designing AI-assisted experiences.
• Expertise in Figma and prototyping tools.
• Strong understanding of UCD, accessibility and usability.

Technical Skills

• Figma
• FigJam
• Prototyping
• Design Systems
• Information Architecture
• Interaction Design
• Accessibility (WCAG)
• Design Tokens
• Component Libraries

Key Focus Areas

• AI-First Product Design
• Conversational & Multimodal UX
• User Research
• Design Systems
• Enterprise SaaS
• Rapid Prototyping
  

Capabilities

1. Product Design

2. UX Research

3. UI Design

4. AI Interaction Design

5. Conversational UX

6. Design Systems

7. Prototyping

8. Stakeholder Communication

KPI and Metrics

1. Product usability improvements

2. User adoption

3. Reduced task completion time

4. Customer satisfaction

5. Design delivery velocity

6. Accessibility compliance

7. Design system adoption

8. Stakeholder satisfaction

Qualifications

• Bachelor's/Master's in Design, HCI, Computer Science or related field.
• Expertise in Figma, Adobe XD or equivalent.
• Experience with AI-assisted design tools preferred.
• B2B SaaS / Martech / DXP experience preferred.
  
  

What We Offer

• Competitive salary and performance-based incentives.
• Comprehensive benefits package.
• Opportunity to work in a collaborative and innovative environment.
• Career growth and professional development opportunities.
• A chance to be part of a global team that makes a significant impact in the industry.

How to Apply

Interested candidates are invited to submit their resume along with portfolio and a cover letter outlining their qualifications and vision for the role plus previous experience align with key attributes, responsibilities, clear wins or learnings.

Why Milestone

Founder-led | AI-first | Award-winning DXP | Global Enterprise Customers