Senior Product Designer (Contract)

📍 Job Overview

Job Title: Senior Product Designer (Contract)

Company: Ollie

Location: Remote (U.S. Based)

Job Type: Contract

Category: Product Design / GTM Operations

Date Posted: September 14, 2026

Experience Level: 5-10 Years

Remote Status: Remote Solely

🚀 Role Summary

• This role focuses on delivering high-impact UX and UI execution for critical web and app initiatives within a fast-paced, DTC e-commerce environment.

• The Senior Product Designer will increase design capacity for priority roadmap items, particularly focusing on landing pages, checkout, onboarding, account management, and subscription flows.

• A key aspect involves rapid iteration of concepts, user flows, and prototypes, leveraging existing design systems and research to inform decisions.

• The role requires close collaboration with product management, engineering, and growth teams to translate business goals into polished, development-ready experiences.

• Successful candidates will demonstrate strong visual and interaction design craft, systems thinking, and proficiency in modern design and collaboration tools.

📝 Enhancement Note: While this role is primarily Product Design, its focus on web/app initiatives, checkout, onboarding, and subscription management directly supports Go-To-Market (GTM) operations by enhancing the customer journey and conversion funnel. The emphasis on A/B testing and conversion-focused environments positions it within the broader GTM operations spectrum.

📈 Primary Responsibilities

• Own the end-to-end UX and UI execution for active web and app initiatives, including but not limited to landing pages, checkout funnels, customer onboarding sequences, and subscription management interfaces.

• Act as a force multiplier for the existing product design team, increasing design capacity to ensure priority initiatives meet accelerated year-end roadmap timelines.

• Translate defined product requirements and growth opportunities into polished, user-centric, and development-ready design experiences.

• Develop and rapidly iterate on design concepts, user flows, wireframes, prototypes, and A/B test variants in close partnership with Product Managers, Engineers, and Growth Marketers.

• Leverage existing user research, product strategy documentation, analytics data, and established design system patterns to make informed design decisions and proactively identify potential gaps or risks.

• Produce high-quality design work that is consistently aligned with Ollie's established design system, brand guidelines, and overall customer experience standards.

• Prepare meticulously organized and production-ready Figma files, complete with detailed interaction specifications, responsive design states for various devices, and clear handoff documentation for engineering teams.

• Actively participate in the team's existing planning, design critique, and delivery cadences, with work prioritization being a collaborative effort that adapts to evolving roadmap needs.

• Partner closely with engineering teams throughout the implementation phase, promptly responding to technical questions and conducting thorough design quality assurance (QA) to ensure shipped work meets design standards.

📝 Enhancement Note: The responsibilities emphasize a hands-on approach to execution and a strong collaborative dynamic, typical of contract roles designed to quickly augment existing teams and deliver on specific project milestones within a Go-To-Market context.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent practical experience and design acumen is paramount.

Experience: 5+ years of dedicated product design experience, with a proven track record of senior-level ownership and successful delivery of digital products. Experience in DTC, subscription models, e-commerce, growth marketing, or conversion-focused product environments is highly desirable.

Required Skills:

• Demonstrable strength in visual design and interaction design craft.

• Proven ability in systems thinking and applying design system principles.

• High proficiency in Figma for design, prototyping, and handoff.

• Fluency in Adobe Creative Suite for asset creation and manipulation.

• Experience in translating product and growth opportunities into user-centric designs.

• Ability to work through ambiguity and deliver on tight deadlines.

• Strong understanding of user flows, wireframing, and prototyping methodologies.

• Experience with responsive design principles and implementation.

• Familiarity with design QA processes and collaborating with engineering. Preferred Skills:

• Experience with AI-assisted design tools (e.g., Claude, Figma Make) for concept exploration, prototyping, and accelerating design workflows.

• Familiarity with collaboration tools such as Jira for project tracking and workflow management.

• Experience in DTC e-commerce, subscription services, or conversion-rate optimization (CRO) environments.

• Understanding of user research methodologies and how to integrate insights into design decisions.

• Ability to contribute to and maintain design systems.

📝 Enhancement Note: The emphasis on AI tools is a modern requirement, reflecting industry shifts. The preference for DTC/subscription/e-commerce experience directly aligns with Ollie's business model and indicates the need for a designer who understands these specific user journeys and conversion funnels.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated portfolio showcasing at least 3-5 significant product design projects, with a strong emphasis on shipped digital products where you held senior-level ownership.

• For each project, clearly articulate your specific role, the problem you were solving, your design process, the solutions you developed, and the measurable impact of your work.

• Detailed case studies demonstrating expertise in UX/UI execution, user flows, interaction design, and responsive design.

• Evidence of systems thinking, including how you've utilized or contributed to design systems.

• Examples of prototypes and user testing outcomes, if applicable. Process Documentation:

• Within your portfolio, demonstrate a clear and repeatable design process, from discovery and ideation through to detailed design and handoff.

• Showcase how you leverage user research, analytics, and product context to inform your design decisions.

• Include examples of how you have collaborated with product managers, engineers, and growth partners throughout the design lifecycle.

• Provide examples of how you have prepared production-ready Figma files and detailed handoff documentation for engineering.

• Highlight experience with A/B testing design variants and iterating based on performance data.

📝 Enhancement Note: For a contract role focused on rapid delivery, the portfolio needs to quickly demonstrate the candidate's ability to execute efficiently and effectively. Showing a structured process that can be integrated into an existing team's rhythm is crucial. The mention of AI tools suggests a need to showcase how they are integrated into this process.

💵 Compensation & Benefits

Salary Range: As this is a contract role for approximately 20 hours per week over 60-90 days, compensation will likely be offered on an hourly basis. Based on industry standards for Senior Product Designers with 5-10 years of experience in the U.S. market, a rate ranging from $70 to $100+ per hour is a reasonable expectation, depending on experience, specific skill set, and the final agreed-upon scope of work.

Benefits:

• This is a contract position, and standard full-time employee benefits (health insurance, retirement plans, paid time off) are typically not included.

• Potential for conversion to a full-time role at the end of the contract engagement, which would then include a comprehensive benefits package.

• Opportunity to gain experience with a growing DTC pet food company.

• Direct impact on key product initiatives during a critical roadmap period.

• Flexible remote work arrangement within the U.S.

Working Hours: Approximately 20 hours per week for a duration of 60-90 days. Candidates are expected to be available during Eastern Time working hours for collaboration.

📝 Enhancement Note: Salary is estimated based on typical contract rates for senior-level design roles in the U.S. market. Contract roles generally do not include typical employee benefits, but the potential for conversion is a significant factor. The limited weekly hours and contract duration are key details for candidates to consider.

🎯 Team & Company Context

🏢 Company Culture

Industry: Pet Food & Direct-to-Consumer (DTC) E-commerce. Ollie operates in a growing market driven by personalized nutrition and convenience, competing with traditional pet food brands and other DTC players.

Company Size: While not explicitly stated, the description implies a growing team and a need for increased design capacity, suggesting a mid-stage startup or scale-up environment. This often means a dynamic, fast-paced culture with opportunities for significant impact.

Founded: Ollie was founded with the mission of improving the lives of pets and pet parents, focusing on human-grade, tailored nutrition delivered directly to consumers. This mission-driven approach likely permeates the company culture.

Team Structure:

• The Senior Product Designer will be embedded within the digital product team.

• The role reports directly to the Lead Product Designer.

• Close collaboration is expected with Product Managers, Engineers, and Growth Partners, indicating a cross-functional and agile team structure. Methodology:

• Ollie emphasizes a customer-centric approach, focusing on improving the lives of pets and pet parents.

• The company values a culture that cares deeply about its work and team members, suggesting a supportive yet results-oriented environment.

• The need for rapid execution and delivery implies an agile or iterative product development methodology.

• The use of AI tools suggests an openness to adopting new technologies to enhance efficiency.

Company Website: myollie.com

📝 Enhancement Note: The company culture description highlights a passion for pets, a commitment to quality, and a collaborative spirit. For a designer, this suggests an environment where creativity is valued, but also where practical execution and team alignment are critical for success, especially within a contract engagement.

📈 Career & Growth Analysis

Operations Career Level: This contract role is at a Senior Product Designer level, requiring independent ownership and execution of complex design tasks. While it's a contract position, the experience gained in driving key web/app initiatives and collaborating cross-functionally is valuable for career progression.

Reporting Structure: The role reports to the Lead Product Designer, providing direct guidance and oversight. Collaboration extends across Product Management, Engineering, and Growth teams, offering exposure to various functional areas within the GTM and product development process.

Operations Impact: The designer's work directly impacts key GTM operations by enhancing the customer acquisition funnel (landing pages, onboarding), retention (account management), and revenue generation (checkout, subscription management). Their contributions will be measured by improvements in conversion rates, user satisfaction, and operational efficiency of digital platforms.

Growth Opportunities:

• Immediate Impact & Skill Development: Rapidly contribute to high-priority, time-sensitive projects, honing skills in agile design execution, cross-functional collaboration, and adapting to existing design systems and workflows.

• Potential Full-Time Conversion: A significant growth opportunity exists if the contract converts to a full-time role, offering long-term career development within Ollie.

• Exposure to DTC & Subscription Models: Gain in-depth experience in a thriving DTC e-commerce sector, specifically within the pet industry, which is a specialized and growing niche.

• AI Tool Integration: Opportunity to deepen expertise in using AI-assisted design tools, a critical skill for future-proofing a design career.

📝 Enhancement Note: The contract nature means growth is tied to performance and potential conversion. The focus on DTC and subscription models provides niche experience valuable for future roles in similar industries.

🌐 Work Environment

Office Type: This is a fully remote position, allowing for work from any U.S. location.

Office Location(s): Remote (U.S. Based). While location within the U.S. is flexible, candidates based on the East Coast are preferred, and availability during Eastern Time working hours is required for effective collaboration.

Workspace Context:

• Collaborative Digital Space: Work will be conducted primarily through digital collaboration tools, requiring strong communication and remote work etiquette.

• Tooling and Technology: Access to and proficiency with Figma, Adobe Creative Suite, and potentially AI design tools are essential. Collaboration tools like Jira will likely be used for task management.

• Team Interaction: Regular participation in virtual meetings, design critiques, planning sessions, and stand-ups with the product design team and cross-functional partners.

Work Schedule: Approximately 20 hours per week, with flexibility in scheduling as long as Eastern Time working hours are covered for collaborative sessions. This part-time contract allows for balancing other commitments.

📝 Enhancement Note: The remote-first nature requires self-discipline and excellent asynchronous and synchronous communication skills. The preference for East Coast candidates and ET working hours is crucial for scheduling and team integration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess qualifications and experience.

• Portfolio Presentation/Interview: A session where you will walk through selected projects from your portfolio, discussing your process, contributions, and impact. Expect to be asked about your experience with Figma, AI tools, and DTC/subscription environments.

• Cross-functional Interviews: Conversations with Product Managers, Engineers, or Growth Partners to assess collaboration style, problem-solving abilities, and fit with the team's working rhythm.

• Lead Product Designer Interview: A final discussion with the Lead Product Designer to assess overall fit, design philosophy, and alignment with Ollie's values and project needs.

Portfolio Review Tips:

• Highlight Impact: For each project, clearly quantify your contributions and the resulting business impact (e.g., conversion rate improvements, user satisfaction scores, efficiency gains).

• Showcase Process: Detail your thought process, including how you approached problem-solving, user research integration, iteration, and collaboration. Emphasize your ability to work through ambiguity.

• Figma & AI Proficiency: Be prepared to discuss your workflow in Figma and how you've effectively integrated AI design tools to accelerate your process, while maintaining quality and handling sensitive information.

• DTC/Subscription Relevance: If you have experience in these areas, make sure to highlight it with specific examples of challenges and solutions.

• Conciseness: Given the contract nature and need for speed, be prepared to present your most relevant work efficiently.

Challenge Preparation:

• While a formal "design challenge" might not be assigned, be prepared for in-depth discussions about hypothetical design problems related to Ollie's product (e.g., improving a subscription cancellation flow, designing a new onboarding step).

• Practice articulating your design decisions clearly and concisely, focusing on balancing user needs, business goals, and technical constraints.

• Be ready to discuss how you would approach a new initiative with limited upfront information, leveraging existing resources.

📝 Enhancement Note: The interview process will likely be streamlined for a contract role. The portfolio is paramount, and candidates should be ready to discuss their process and impact in detail, especially concerning the specific technologies and business models mentioned.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for UX/UI design, prototyping, and collaboration. Proficiency in advanced features, component libraries, and auto-layout is expected.

• Adobe Creative Suite: Likely needed for asset creation, image editing, and potentially more complex visual design tasks.

• AI-Assisted Design Tools: Explicitly mentioned are Claude and Figma Make. Candidates should be prepared to discuss their experience and approach to using these tools for concept generation, rapid prototyping, and accelerating design workflows.

Analytics & Reporting:

• Familiarity with analytics platforms (e.g., Google Analytics, Amplitude) is beneficial for understanding user behavior and informing design decisions.

• Experience with A/B testing tools (e.g., Optimizely, VWO) is highly relevant for validating design iterations and optimizing conversion funnels. CRM & Automation:

• While not directly designing within these systems, understanding how product design impacts CRM data integrity and customer lifecycle automation within a DTC context (e.g., impact of onboarding on CRM data) is advantageous.

• Familiarity with project management tools like Jira for workflow tracking and collaboration with engineering teams.

📝 Enhancement Note: The explicit mention of AI tools is a key differentiator. Candidates should be ready to demonstrate practical application of these tools, not just theoretical knowledge. Figma is the core design tool, and mastery is assumed.

👥 Team Culture & Values

Operations Values:

• Keeping Dogs At The Heart: A genuine passion for pets and a commitment to their well-being should resonate. This translates to designing with empathy for both the pet and the pet parent.

• Being Courageous And Kind: Fosters an inclusive environment where open communication, diverse perspectives, and constructive feedback are encouraged. This implies a willingness to speak up, share ideas, and contribute positively to team dynamics.

• Setting New Standards: A drive for continuous improvement, aiming for excellence in product quality, customer experience, and internal processes. This means a proactive approach to identifying areas for enhancement.

• Making Ollie The Best Chapter: A focus on building an impactful business while creating memorable experiences. This suggests a culture that celebrates achievements, learns from setbacks, and values the collective journey.

Collaboration Style:

• Cross-functional Integration: The role requires seamless collaboration with Product, Engineering, and Growth teams, necessitating strong communication and a shared understanding of objectives.

• Agile & Iterative: The fast-paced nature and emphasis on rapid iteration suggest an agile collaboration style, where feedback loops are short and adjustments are made quickly.

• Data-Informed: Decisions are expected to be informed by data and research, implying a collaborative approach that values empirical evidence.

• Open Feedback: The "Courageous and Kind" value suggests a culture where honest feedback is given and received constructively.

📝 Enhancement Note: The company values are clearly articulated and provide insight into the expected behaviors and work ethic. A candidate's ability to align with these values will be assessed during interviews.

⚡ Challenges & Growth Opportunities

Challenges:

• Accelerated Timeline: The primary challenge is delivering high-quality design work within a compressed 60-90 day contract period, requiring efficient execution and prioritization.

• Working Through Ambiguity: As with many startup environments, there may be evolving requirements or less defined problem spaces, requiring the designer to proactively seek clarity and define solutions.

• Balancing Competing Needs: Effectively balancing customer needs, business goals (especially conversion and subscription retention), and technical constraints within tight deadlines.

• Integrating AI Tools Effectively: Learning and applying new AI design tools in a professional, confidential, and impactful manner while maintaining design integrity.

Learning & Development Opportunities:

• Intensive Project Experience: Gain hands-on experience with complex web and app initiatives in a high-growth DTC e-commerce company.

• Cross-functional Exposure: Deepen understanding of how design integrates with product management, engineering, and growth marketing strategies.

• AI Design Tool Mastery: Develop practical skills and a strategic approach to leveraging AI in the design process, a rapidly evolving field.

• Potential for Full-Time Role: Demonstrating strong performance could lead to a permanent position, offering long-term career growth and stability.

📝 Enhancement Note: The challenges are directly related to the contract nature and the dynamic environment. The growth opportunities are significant, particularly in specialized areas like AI design and DTC e-commerce.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to deliver a significant design project under a tight deadline. How did you prioritize, and what was the outcome?" (Focus on your process for rapid execution and decision-making).

• "How do you balance user needs with business objectives, especially in a conversion-focused environment like DTC e-commerce?" (Prepare examples illustrating this balance).

• "Walk us through your process for designing a new feature for a subscription service, from initial concept to handoff." (Detail your methodology, research, iteration, and collaboration). Company & Culture Questions:

• "Why are you interested in Ollie and this specific contract role?" (Research Ollie's mission, products, and recent news. Connect your passion for pets or DTC to your interest).

• "How do you approach working with engineers and product managers to ensure designs are implemented accurately and efficiently?" (Highlight your collaborative approach and communication skills).

• "How do you ensure your designs align with a company's established design system and brand guidelines, especially when working quickly?" (Discuss your systems thinking and attention to detail). Portfolio Presentation Strategy:

• Structure is Key: For each project, clearly outline: Problem, Your Role, Process, Solution, and Impact (Quantify results!).

• Focus on Impact: Select projects that demonstrate your ability to drive business outcomes (conversions, retention, user satisfaction).

• Articulate Your Process: Be ready to explain why you made certain design decisions, referencing research, data, or user needs.

• Showcase AI Integration: If applicable, be prepared to discuss how you used AI tools to enhance your workflow or outcomes in a specific project.

• Conciseness: Given the time constraints, be prepared to present your most impactful work efficiently and answer questions directly.

📝 Enhancement Note: The interview preparation focuses on demonstrating speed, impact, and a collaborative, process-driven approach, all critical for a successful contract engagement. Highlighting specific experience with DTC, subscription models, and AI tools will be advantageous.

📌 Application Steps

To apply for this Senior Product Designer contract position:

• Submit your application through the provided link on Lever.co.

• Curate Your Portfolio: Select 3-5 of your strongest, most relevant projects that showcase your UX/UI execution, systems thinking, and impact in DTC, e-commerce, or subscription environments. Ensure each project clearly articulates the problem, your role, your process, the solution, and measurable results.

• Tailor Your Resume: Highlight your 5+ years of product design experience, specifically mentioning Figma, Adobe Creative Suite, AI design tools, and any experience with subscription models, e-commerce, or conversion optimization. Emphasize your ability to work through ambiguity and deliver quickly.

• Prepare Your Portfolio Walkthrough: Practice presenting your selected projects concisely, focusing on your process, decision-making, and the impact of your work. Be ready to discuss your experience with AI tools and collaborate effectively with cross-functional teams.

• Research Ollie: Understand Ollie's mission, product offerings, and target audience. Consider how your design philosophy and skills align with their values and business goals.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.