UI/UX Designer Contractor - Scaled Agile Inc

Overview

piplanning.io is a purpose-built SaaS web application that helps organizations plan and execute at scale, supporting PI Planning and ongoing execution with visual, collaborative workflows with dedicated whiteboard/canvas experiences.

We’re a small, highly accountable product team with end-to-end responsibility for piplanning.io’s success inside Scaled Agile, Inc. (SAI), from discovery and delivery to supporting sales motions and helping customers succeed in the real world. Our work is used in complex, high-stakes enterprise environments, so we care deeply about clarity, reliability, and craftsmanship.

(piplanning.io is part of SAI, the company behind SAFe®, supporting a global community and enterprise customers.)

About the Role

We’re looking for a UI/UX Designer with strong B2B SaaS web-app experience who can own meaningful product areas end-to-end. You’ll work closely with our customers, product, engineering, and go-to-market partners to simplify complex workflows, raise design quality, and ship improvements that customers feel immediately.

What You’ll Be Doing

Own design from discovery to delivery: frame problems, map flows, prototype, design high-fidelity UI, partner with engineers through implementation, and iterate after release.

Design complex B2B workflows and make them feel intuitive, fast, and “obviously correct” for enterprise users.

Push interaction design for our purpose-built whiteboards/canvases: object models, editing states, affordances, spatial navigation, consistency, edge cases, and scalability.

Create strong prototypes in Figma (and beyond when needed) to validate ideas early and align stakeholders.

Contribute to (and evolve) our design system: patterns, components, interaction standards, and documentation that help us ship faster without sacrificing quality.

Collaborate cross-functionally: Product, Engineering, Customer Success, Sales, because in our team, design is part of the full loop (value discovery → delivery → adoption → customer success → value discovery).

Use qualitative + quantitative signals to guide decisions (customer calls, support data, product usage, feedback loops) and make tradeoffs explicit.

And yes, you’ll also use AI not just to work faster, but to create AI-driven capabilities for our users (e.g., smart suggestions, insight generation, automation) that measurably improve planning and execution outcomes.

A successful candidate will have:

Proven product design experience for B2B SaaS web apps, with a portfolio that shows decision-making and outcomes.

Advanced Figma skills and experience contributing to design systems and reusable patterns.

Strong UX fundamentals: Information architecture, interaction design, visual hierarchy, accessibility, and systems thinking.

Confidence in collaborating with engineers, comfortabl