Staff Product Designer

Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.   Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.

The Staff Product Designer is a senior-level role that represents mastery of design craft while developing readiness for design leadership responsibilities. You'll lead design for 1-2 product teams, mentor other designers, and operate with high autonomy across the end-to-end design process. You'll shape design vision and strategy across multiple complex user flows while influencing senior leadership through compelling synthesis of user insights, market trends, and business opportunities. This role requires deep expertise in product domain, sophisticated design judgment, and the ability to drive alignment across complex organizational boundaries.

How You’ll Do It

Design Leadership and Strategy:

• Shape design vision and strategy across multiple complex user flows, identifying opportunities that drive user value.
• Lead scalable design initiatives requiring sophisticated stakeholder alignment.
• Develop measurement frameworks and success metrics that become organizational standards, directly connecting design decisions to business outcomes.
• Influence senior leadership on strategic design direction through compelling synthesis of user insights, market trends, and business opportunities.
• Navigate complex, ambiguous user requirements with consistently sound judgment and strategic insight.

Research and Domain Expertise:

• Guide strategic product design decisions by synthesizing complex technical, business, and user considerations across the organization.
• Pioneer research methods that uncover strategic opportunities, teaching others how to systematically identify high-value problems.
• Define patterns in experience that balance innovation with technical feasibility and scalability.
• Shape experience strategy through deep understanding of market trends, user behaviors, and competitive insights.
• Serve as an organizational authority on user needs, influencing executive decisions and company direction.

Mentorship and Team Development:

• Provide design mentorship that improves design capabilities across the organization.
• Create playbooks for communications centered around design thinking methodologies.
• Develop frameworks for knowledge sharing that elevate design capabilities organization-wide.
• Build centers of excellence and mentorship programs.
• Serve as an inspiration to the team and help attract top talent to the company.

Cross Functional Collaboration:

• Navigate political dynamics and competing priorities at senior levels by nurturing strong inter-departmental relationships.
• Drive alignment across complex organizational boundaries and competing interests.
• Serve as trusted advisor to senior leadership while maintaining strong credibility with broader organization.
• Maintain trust with executives through strategic design thinking, reliable execution and proactive communication.
• Build relationships with senior stakeholders to expand organizational influence and impact.

The Right Stuff

• 8+ years experience in Product Design, UX/UI, and/or User Research working in an agile software development lifecycle (SDLC) environment.
• Demonstrated experience leading design for complex products or systems, preferably in financial services, insurance, or similarly complex domains.
• Proven track record of successfully mentoring and developing other designers.
• Advanced communication skills with demonstrated ability to influence senior leadership and drive strategic decisions.
• Demonstrated mastery in crafting design systems that transform approaches to complex experience problems.
• Experience developing scalable approaches to solution validation that demonstrate clear connection between design decisions and business outcomes.
• Deep understanding of industry trends, user behaviors, and emerging technologies.
• Ability to anticipate design and market industry shifts and shape organizational strategy based on future opportunities.
• Exceptional problem-solving capabilities and ability to navigate ambiguity with consistently sound judgment.
• Expert with Figma, Miro, and other modern design and collaboration tools.
• Proficiency with user ethnography and feedback collection tools and methods.
• Experience with analytics platforms and ability to leverage data in design decisions.
• Understanding of technical constraints and development processes.
• G-Suite Tools, Collaboration tools (Slack is preferred), Atlassian SDLC suite (Jira, Confluence, etc.).

Base Compensation Range$155,000—$195,000 USD

Compensation & Benefits 

• Competitive cash compensation
• A piece of the pie (in the form of equity)
• Comprehensive health plans
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave
• Our core values are more than just a poster on the wall; they’re tangibly reflected in our work 

Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When we’ve identified a talented individual who we’d like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidate’s knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges. 

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information 

Unless otherwise specified, this role has the option to be hybrid or remote. Hybrid work locations provide team members with the flexibility of working partially from our Denver office and from home. Remote team members must live and work in the United States* (*territories excluded), and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

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Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

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