Principal Product Designer

Principal Product Designer
Chicago, IL Hybrid (In-office 2–3 days/week) 
Reports to: VP of Product
Salary Range: $163,000–$206,000

ABOUT NEXTPOINT

Nextpoint builds transformative software and services for the legal industry — making eDiscovery, case management, and litigation prep simple, fluid, and affordable for law firms of all sizes. Our secure, cloud-based platform lets teams start document review in minutes, backed by powerful analytics, an intuitive interface, and best-in-class security at every point.

We're problem solvers, simplifiers, and challenge seekers, united by a shared goal: a great team culture and satisfied clients. We're headquartered in Chicago's Ravenswood neighborhood and proud to have been named one of Built In's best startups to work for in Chicago five years running (2022–2026).

ABOUT THE ROLE

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.

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

QUALIFICATIONS

• 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


• Experience with workflows where tech and expert services overlap is a strong differentiator


• Experience in front-end web software development is a strong plus


• 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


• Experience in legal tech, compliance, or document management is a plus — but not required

BENEFITS & PERKS

• 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!

EQUAL OPPORTUNITY EMPLOYER

Nextpoint is an equal opportunity employer. We actively work to build a diverse team and encourage candidates of all backgrounds — including people of color and LGBTQ+ individuals — to apply. All applicants are considered without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, or disability.

Don't see the right role? Apply anyway — we're always looking for high-performing, curious, entrepreneurially-minded people to grow with us. Check out our client reviews on G2 and Capterra.