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.

A Senior Product Designer is responsible for driving significant user and business impact through complex design initiatives across the organization's product portfolio. The Senior Product Designer ensures that design solutions not only solve user needs effectively but also align with business goals and technical constraints, while maintaining the quality and consistency of the product experience. Key responsibilities in this position include leading large-scale design initiatives from discovery through implementation, establishing frameworks for measuring product performance, influencing stakeholders across levels to align on design vision, and demonstrating deep product expertise to drive complex design decisions that balance multiple competing factors.

How You’ll Do It

User Research and Analysis:

Synthesize qualitative and quantitative data to uncover deep insights about user behaviors, both internal and external.
Design comprehensive research programs that identify systemic issues across complex user journeys, focusing on high-ROI opportunities.
Translate research findings into actionable specifications that drive design decisions while maintaining clear documentation of insights for broader organizational learning.

Stakeholder Collaboration

Build consensus around design decisions through clear storytelling and data-driven presentations that connect user needs to business outcomes and technical feasibility.
Partner with engineering and product peers and leadership to establish design specifications and technical requirements that ensure successful implementation of complex workflows.
Drive alignment across business units by facilitating design reviews and workshops that educate stakeholders on design thinking methodologies and validate proposed solutions.
Create and maintain transparent documentation around design risks, trade-offs, and dependencies to build trust with cross-functional partners.

Design Strategy And Execution

Drive end-to-end design solutions for complex products from initial concept through successful implementation while managing ambiguity and evolving requirements.
Create and validate design solutions through rapid prototyping, usability testing, and data analysis to ensure high-quality outcomes that balance user needs with technical constraints.
Define success metrics and establish measurement frameworks that demonstrate clear user and business impact.
Contribute to Pie's Design System by contributing new design patterns, documenting implementation guidelines, and insure adherence to component usage.

Design Thinking Influence

Build and maintain business impact dashboards linking design decisions to key insurance metrics and ROI.
Create clear documentation and guidelines for experience patterns, ensuring consistent implementation across products.
Create and maintain a searchable research repository capturing user insights and solution outcomes.
Pioneer innovative approaches to complex workflows through experimentation. While gathering continuous feedback.

The Right Stuff

High school diploma or GED required. Bachelor’s degree preferred.
7 years demonstrated experience successfully shipping multiple complex features that drove measurable business impact through qualitative and quantitative validation.
Strong track record of autonomously owning the design process from discovery through delivery, including conducting user research, iterating on solutions based on data and feedback, and partnering effectively with product and engineering teams to ensure high-quality implementation.
Proven ability to balance speed with quality while navigating ambiguous problem spaces, with a portfolio showcasing your systematic approach to breaking down complex workflows into elegant, user-centered solutions.
Strong communication skills (written, verbal, and presentation) to clearly convey design decisions, collaborate effectively with cross-functional teams, and align stakeholders with user and business needs.
Capable of tackling complex design challenges, managing multiple constraints, and delivering thoughtful solutions that address both immediate and future needs.
Solid experience with continuous product discovery methodologies, including user interviews, Jobs to be Done Frameworks, job shadowing, passive feedback collection (e.g., surveys, product usage analytics), and prototyping to inform design decisions.
Awareness of design workflow and project tradeoffs, making informed decisions that balance user needs, technical feasibility, and business goals.
Ability to influence product and design decisions, working closely with peers, stakeholders, and leadership to ensure alignment and strategic impact.
Strong understanding of modern software development tools, platforms, and processes, collaborating with Product Managers and Engineers to create scalable and technically feasible design solutions.
Experience managing multiple design deliverables, prioritizing effectively, and contributing to process improvements for better efficiency and collaboration.
Ability to research and evaluate industry trends, competitor products, and market shifts to inform design decisions and improve user experiences.
Proficiency in quantitative and qualitative analysis, leveraging user insights and business and platform metrics to drive design and experience improvements.
Proficiency in Figma, FigJam, Adobe Suite, G-Suite, Slack, Atalassian SDLC suite (Jira, Confluence, etc.), Mixpanel and Looker or other relevant analytics tools
Strong time management skills, with the ability to prioritize and balance multiple projects simultaneously while maintaining high-quality design execution and meeting deadlines.
Some Travel (up to 10%) could be required in this position.

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. All AI-reviewed applications are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to it being reviewed using these AI technologies to assist in our evaluation process.

Base Compensation Range

$135,000—$170,000 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.

Pie Insurance participates in the E-Verify program. Please click here,_ here and here _for more information._Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy.

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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