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Milestone Inc. is seeking a Principal Product Designer to shape AI-powered enterprise software, beyond a traditional UX role.
You will define how AI-enabled applications feel, behave, and earn user trust, collaborating with Product, Engineering, AI, and Customer Success to simplify complex workflows and build reusable design systems. You will influence product strategy, mentor designers, and help establish design as a strategic capability across the company, driving cross-functional leadership
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
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
Create interaction models that balance automation with user control.
Customer Discovery & Research
Translate insights into product opportunities.
Design Systems
Own and evolve Milestone's design system.
Create:
Ensure consistency across multiple products.
Design Excellence
Raise the quality bar across the organization by
Cross-functional Leadership
A product-focused UX professional passionate about AI, enterprise SaaS, and solving complex problems through elegant, user-centered design.
Required Experience & Qualifications
Technical Skills
Key Focus Areas
Capabilities
KPI and Metrics
Qualifications
Founder-led | AI-first | Award-winning DXP | Global Enterprise Customers