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 Director of Product Design is responsible for managing the usability of all products and workflows, ensuring they are intuitive and user-friendly to achieve adoption and business impact. They work through their team to create systems for continuous product research and user feedback, identify and validate high-value problem and solutions, and develop prototypes and high-fidelity designs for production software. The role requires systematic thinking, deep empathy for user needs, and creativity to develop impactful product designs. It is a highly collaborative role that involves influencing cross-functional peers across technology functions, building relationships with cross-functional commercial partners and executives, and managing a high-performing design team.

How You’ll Do It

Lists of responsibilities

Continuous Research & Feedback Systems
- Organize systems for in-depth one-on-one interviews and distribute periodic surveys to gather qualitative and quantitative feedback.
- Organize usability testing sessions and launch beta testing programs to involve users in early-stage product evaluation.
- Implement feedback mechanisms within the product and leverage customer support interactions to capture real-time user feedback.
- Systematize the analysis of usage data and user behavior to identify patterns and areas for product improvement.
- Establish user feedback panels and maintain online forums to facilitate ongoing user input and discussion.
Solution Generation & Refinement
- Define standard processes to quickly create and iterate on design concepts using rapid prototyping and detailed wireframes.
- Define guidelines for building interactive prototypes and high-fidelity mockups to visualize final designs and test usability.
- Lead focused design sprints and collaborative workshops with cross-functional teams to brainstorm and co-create solutions
- Develop user journey and/or empathy maps to understand user interactions and inform design decisions across a broad set of users, workflows, and products
- Implement systems for A/B testing and scenario-based design approaches to tailor solutions to specific user contexts and determine the most effective designs.
People Management
- Attracting, recruiting and evaluating Product, Engineering, and Design talent as part of hiring panels
- Regular meetings with direct reports to provide coaching, feedback, and guidance (1x1s, development meetings, problem-solving sessions)
- Formal performance management processes including calibrations, written performance summaries, etc.
Influencing and Communication
- Building high-trust relationships with senior leaders across the business to serve as a trusted advisor and thought partner
- Evangelizing a compelling vision for continuous product discovery and solution refinement systems that educate and inspire buy-in across the organization
- Distilling complex information across multiple domains into a synthesized, well-supported structure that informs and makes the case for action
- Facilitating or leading large cross-functional meetings with stakeholders of any seniority level

The Right Stuff

10 years experience in overall professional experience working on complex business and/or technology problems
5+ years experience in Product Design, UX/UI, and/or User Research experience working in an agile software development lifecycle (SDLC) environment
3 years managing direct reports performing product design / research / UX related work.
Advanced communication (written, verbal and presentation) skills, to deliver complex information effectively and align people with the needs of the project/team
Advanced problem solving skills, able to manage complex situations with multiple layers, and resolve to solution anticipating needs now and into the future
Advanced understanding of continuous product discovery methodologies, including interviews, ethnographic research, job shadowing, passive feedback collection (e.g., surveys, product usage analytics), prototyping, etc.
Advanced awareness of workflow, and project tradeoffs to make decisions based on needs now and into the future
Advanced leadership knowledge, and ability to build, develop and coach the team and manage the overall group/team workflow to successful deliverables/outcomes
Demonstrated ability to influence strategic direction of major business initiatives and product development lifecycles
Advanced understanding of modern software development tools, processes, and architecture patterns; knows how to strike a balance between usability needs and the back-end software solution complexity
Demonstrated ability to manage multiple project deliverables, making decisions and understanding tradeoffs, and create processes for efficiency and effective product delivery for their team and broader cross-functional delivery coalitions
Demonstrated mastery of synthesizing understanding of a given market in terms of key user segments and value sizing, jobs to be done, competitive offerings, and target opportunities for differentiated value creation.
High level skillset in program management tools, and project mapping
High level technical skills and mastery of the industry to mitigate complicated issues and manage multiple complex deliverables simultaneously
G-Suite Tools, Collaboration tools (slack is preferred), basic office machines, Atalassian SDLC suite (Jira, Confluence, etc.)
Expert with modern product design tools such as Figma and Miro, as well as user ethnography and feedback tools and methods

Base Compensation Range

$175,000 - $220,000 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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Director, Product Design