Principal Product Designer

Nextpoint•Chicago, IL

6d•$163,000 - $206,000•Hybrid

About The Position

We're building the next generation of Nextpoint — a self-service platform designed to serve the full breadth of high-stakes litigation work, alongside a services-led advanced offering that thoughtfully integrates human expertise with technology. Both require the same thing: sharp product design. That's why we're hiring a Principal Product Designer. This is a high-impact role — operating at the intersection of strategy, craft, and execution. You'll define intuitive workflows for some of the most complex user journeys in legal tech, and you'll design systems that span the full service-to-software spectrum. You also know how to use AI. The right Principal Designer who's fluent in modern AI tooling enables us to move at a pace that previously required large teams. This role has the opportunity to shape the future of the Nextpoint product, and you'll have the empowerment and visibility to make it count.

Requirements

10+ years of product design experience, including 2+ years operating at a principal or staff level
A portfolio demonstrating end-to-end ownership of complex, shipped B2B SaaS products and AI-powered experiences
Proven track record designing multi-step workflows and data-heavy applications in B2B, legal, or regulated domains
Proficiency with Figma and modern AI-assisted design tooling; comfort using AI to accelerate research synthesis, prototyping, and development
Ability to communicate design decisions clearly to non-designers, including executive stakeholders

Nice To Haves

Experience with workflows where tech and expert services overlap is a strong differentiator
Experience in front-end web software development is a strong plus
Experience in legal tech, compliance, or document management is a plus — but not required

Responsibilities

Strategic design leadership (approximately 20%) Architect a long-term vision connecting user behavior, legal workflows and market dynamics.
Lead high-impact initiatives that unlock new value by delivering powerfully simple experiences for our users.
Establish intuitive AI design patterns for high-stakes legal workflows. Define guardrails for control, confidence, transparency, privacy, and security
Translate user research, market signals, and product strategy into coherent experience frameworks that guide near- and long-term development
Partner with Product and Engineering executive leadership to frame tradeoffs, anticipate risks, and influence product direction
Design & prototyping (approximately 50%) Design intuitive multi-step workflows for attorneys, paralegals, and litigation support professionals
Build workflows, information architectures, and component-level patterns that scale across the platform
Use prototyping as a primary communication tool — for internal alignment, stakeholder review, and user validation
Develop and maintain design system standards that ensure simplicity and consistency without sacrificing flexibility
Lead org-wide AI design tooling (Figma, Figma Make, Claude, and similar), processes, and standards to scale Product Design’s impact and accelerate iteration
Design for accessibility and responsiveness across desktop and tablet environments
Research & craft (approximately 30%) Conduct or direct user research with legal professionals to stay grounded in real workflow needs
Analyze user behavior data, support tickets, and feedback to identify usability gaps and high-value opportunities
Establish design quality standards and serve as the internal bar-raiser for craft across the product

Benefits

Competitive Pay Commensurate with Experience
Flexible Hybrid Schedule (2–3 Days Onsite)
Comprehensive Health Coverage — Medical (BCBS PPO and HDHP/HSA Options), Dental and Vision (Guardian)
Health, Dependent, and Transit FSA
Generous PTO, Paid Holidays, Flexible Summer Hours, Quarterly Mental Health Days, and Floating Holidays
Annual Professional Development Stipend
Monthly Flexible Benefit Stipend
401(k) with Company Match
Free In-office Lunch Tuesday–Thursday
And More!