Senior Director, Product Design
About Us
Pearl is AI for professional services at global scale—combining advanced AI with verified human expertise to deliver help that’s accurate, accountable, and fast. Since 2003, our network has connected millions of customers with licensed professionals across 196 countries, making real expertise available anytime, anywhere.
Our Values
- Data driven: Data decides, not egos
- Courageous: We take risks and challenge the status quo
- Innovative: We're constantly learning, creating, and adapting
- Lean: We focus on customers, using lean testing to learn how to serve them best
- Humble: Past success is not a guarantee of future success
Why this role exists
Pearl is transforming professional services through AI + human expertise. As AI reshapes how products are imagined, built, and delivered, Design must evolve from crafting screens to orchestrating intelligent experiences.
We are seeking a Senior Director, Product Design to transform Design for the AI age, elevating taste, redefining the role of designers, and building a practice that combines human judgment with AI leverage to create world-class experiences at unprecedented speed.
This leader will define what remains human, what becomes AI-accelerated, and how Pearl delivers intelligent, trustworthy, and emotionally resonant experiences at scale.
Your Mandate
You’ll modernize how Pearl designs and ships experiences, raising the bar on taste and trust while building an AI-native design practice that increases velocity without sacrificing quality. This is a hands-on leadership role (part creative director, part systems builder, part org multiplier), setting the standards for design while building the systems that scale great design across Pearl.
- Transform design into an AI-native practice: define where human judgment matters most and where AI can accelerate workflows from discovery to delivery.
- Set the bar for taste and trust: establish a design standard that ensures experiences feel coherent, credible, and distinctly human as we scale with AI.
- Build an AI-enabled design system: evolve our system into reusable components + patterns + prompts that scale quality and enable safe creation beyond the design team.
- Lead and grow a high-impact team (~20+): coach, develop, and raise the team’s AI fluency while preserving what already makes Pearl design great.
- Ground design in real human insight: deepen customer and expert research, leverage AI to surface behavioral patterns and intent, and ensure experiences reflect how people actually think, decide, and act.
- Drive experience strategy upstream: strengthen research and system-level experience thinking, and partner across Product, Eng, Content, and ML to deliver outcomes, not just interfaces.
The leader we’re looking for
This role calls for a rare blend of creative vision, systems thinking, and AI fluency. The right leader will raise the bar for design while building the practices that allow great work to scale.
Design Authority & Taste Leadership - You possess exceptional design judgment and set a high bar for clarity, coherence, and usability. You understand what makes experiences feel credible, premium, and human.
Systems Thinker & Builder - You design systems, not just screens, building frameworks, tools, and workflows that scale quality and speed.
AI-Native Practitioner - You understand how AI changes the design process and can translate emerging capabilities into practical workflows that amplify human judgment.
Research-Driven Experience Leader - You believe great design begins with understanding people. You integrate research, behavioral insight, and real-world signals into experience decisions.
Experience & Qualifications
- 10+ years in product design, experience design, or related leadership roles
- Proven leadership of multidisciplinary design teams at scale
- Track record elevating design quality and organizational design maturity
- Experience building or evolving design systems used across complex products
- Deep partnership with Product and Engineering to deliver customer-facing experiences
- Demonstrated integration of AI into design workflows, prototyping, or product development to improve velocity, insight, or consistency
- Strong judgment in distinguishing where human craft is essential and where AI can accelerate quality and speed
Strong plus:
- Experience in marketplace, SaaS, platform, or two-sided ecosystem environments
- Experience building rapid prototyping and discovery practices
- Experience scaling design through systems, automation, or tooling
What Success Looks Like in 12–24 Months
- Design operating model transitioned to an AI-native workflow from discovery through delivery
- Measurably improved design velocity without degradation in quality, usability, or customer trust
- AI-enabled design system adopted across Product & Engineering with clear governance standards
- User research and behavioral data embedded at the core of design decisions, with continuous insight loops informing product evolution
- Elevated design maturity across the organization, with cross-functional partners citing Design as a strategic driver of outcomes
- Team AI fluency materially increased, with repeatable workflows and playbooks embedded into daily practice
Remote From these States
California, Florida, Georgia, Idaho, Illinois, Massachusetts, Michigan, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Texas, Virginia, Washington, and Wisconsin.
Pay Transparency
Pearl will provide pay transparency information upon application to those in qualifying jurisdictions.
Employment is with JustAnswer LLC, a Pearl company.
Our Commitment to an Inclusive Workplace
We welcome people from all backgrounds who seek the opportunity to help build a future where professional services are readily available to all. If you have curiosity, passion, and a collaborative spirit, come work with us. Pearl is committed to an inclusive workplace. Pearl is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, disability, age, or other legally protected status.
AI Disclosure & Informed Consent
Artificial intelligence (AI) technology may be used during the hiring process to record, transcribe, analyze, and rank interview responses. By submitting your application and participating in the interview process, you acknowledge and consent to the use of AI technology in the hiring process. For more information see our AI Disclosure and Consent Policy.
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