Product Design Manager

📍 Job Overview

Job Title: Product Design Manager

Company: Olly Olly

Location: United States

Job Type: FULL_TIME

Category: Product Design Management / GTM Operations

Date Posted: April 08, 2026

Experience Level: 10+ Years

Remote Status: Remote Solely

🚀 Role Summary

• Lead and execute the end-to-end design strategy, encompassing visual language, product experience, and design culture for Olly Olly's platform and brand.

• Drive the development and maintenance of a scalable design system to ensure consistency and efficiency across all product and marketing initiatives.

• Manage and mentor a team of three designers, fostering a high-performance environment focused on craft and velocity.

• Collaborate directly with C-suite executives (CPO, Head of Marketing) to translate business objectives into impactful design solutions.

• Act as a player-coach, balancing leadership responsibilities with hands-on design execution to ensure high-quality output.

📝 Enhancement Note: This role is positioned as a strategic leadership opportunity within a growth-stage company, emphasizing ownership and direct impact on product direction and brand identity. The "player-coach" aspect suggests a need for strong individual contributor skills alongside management capabilities.

📈 Primary Responsibilities

• Own and evolve the comprehensive design system and visual language for both the Olly Olly product and its brand identity.

• Drive the UX/UI design for the core platform, ensuring a seamless and effective experience for thousands of daily SMB clients.

• Oversee external-facing design elements, including the company website, digital collateral, and marketing assets, ensuring brand consistency.

• Provide day-to-day leadership, mentorship, and performance management for a team comprising two product designers and one web/marketing designer.

• Establish and enforce design quality standards and implement robust design QA processes to ensure successful translation of design visions into shipped products.

• Conduct and lead UX research initiatives, including user flows, friction identification, and usability testing, to advocate for end-user needs in product development.

• Translate product strategy into tangible design solutions, focusing on holistic user experiences rather than just feature-level execution.

• Contribute significantly to product roadmap discussions, bringing a strategic design perspective to shape product direction.

• Partner with the Head of Marketing to define and maintain a cohesive brand direction across all customer touchpoints.

📝 Enhancement Note: The responsibilities highlight a dual focus on strategic leadership and hands-on execution, with a strong emphasis on ownership of the design system, user experience, and team performance. The expectation to influence product strategy and collaborate with C-suite indicates a high level of influence for this role.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong educational foundation in Design, Human-Computer Interaction, or a related field is implied by the experience requirements and the nature of the role.

Experience:

• 10+ years of comprehensive design experience, with a minimum of 3 years specifically in a design leadership or management capacity.

• Proven track record of successfully shipping user-centered experiences, demonstrating an ability to move beyond mockups to functional, polished products.

Required Skills:

• Exceptional aesthetic judgment and a high standard of design craft, evident in portfolio and team feedback.

• Strong portfolio showcasing a blend of product design (UX/UI, user flows, systems) and brand/marketing design expertise.

• Deep expertise in leading UX research, usability testing, and translating user insights into actionable product improvements.

• Proven ability to build, scale, and maintain robust design systems that support rapid product development.

• Proficiency in leading and mentoring small, high-output design teams, fostering a culture of quality and velocity.

• Fluency in Figma and other modern design and prototyping tools.

• Strong communication and advocacy skills, capable of positioning design as a strategic function.

• Experience driving wireframing, prototyping, and iterative design processes in close collaboration with engineering and product teams.

Preferred Skills:

• Experience designing for Small to Medium Business (SMB) audiences.

• Background in SaaS product design or digital marketing platforms.

• Familiarity with agency workflows or extensive experience in client-facing web design contexts.

• Exposure to advanced design disciplines such as motion design, interaction design, or mobile-first experience design.

📝 Enhancement Note: The emphasis on "exceptional eye" and "taste" suggests a high bar for creative quality. The "player-coach" dynamic means candidates need to demonstrate both strategic leadership and strong individual design execution skills.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio that clearly demonstrates expertise across both product design (UX/UI, user flows, interaction design, design systems) and brand/marketing design (visual language, collateral, website).

• Case studies that highlight the candidate's leadership approach, including team management, mentorship, and driving design quality and velocity within a team.

• Detailed examples of how user research, usability testing, and customer feedback were leveraged to drive significant product improvements and user satisfaction.

• Evidence of building, scaling, and maintaining design systems, showcasing their impact on development efficiency and product consistency.

• Demonstrations of successful cross-functional collaboration, particularly with Product Management (CPO) and Marketing (Head of Marketing), and how design influenced strategic decisions.

Process Documentation:

• Examples of established design QA processes and how they were implemented to ensure shipped products met design specifications.

• Documentation or case studies illustrating the process of translating product strategy into thoughtful, end-to-end design solutions.

• Workflow examples showing how wireframing, prototyping, and iteration were conducted in close partnership with engineering and product teams.

• Case studies detailing the evolution of a design system, including its impact on rapid development and scalability.

📝 Enhancement Note: The portfolio is critical for this role, serving as the primary evidence of both leadership capability and individual design excellence. It must showcase a holistic approach to design, from strategic influence to detailed execution and team management.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for a Product Design Manager with 10+ years of experience and 3+ years in leadership, in a remote US-based role for a $25M ARR company, the estimated salary range is $160,000 - $220,000 USD per year. This estimate considers the significant responsibility, strategic impact, and "player-coach" nature of the role.

Benefits:

• Health, Dental, and Vision Insurance: Comprehensive coverage for employees and potentially dependents.

• Stock Options/Equity: Potential for ownership in a growing company, aligning employee success with company growth.

• Generous Paid Time Off (PTO): Likely includes vacation, sick leave, and paid holidays, supporting work-life balance.

• Professional Development Budget: Funding for conferences, courses, workshops, and certifications to support continuous learning in design and leadership.

• Remote Work Stipend: Potential allowance for home office setup, internet, or co-working space costs.

• 401(k) Plan: Retirement savings plan with potential company match.

• Parental Leave: Paid leave for new parents.

Working Hours: Standard full-time hours are typically 40 hours per week. Given the remote nature and the "player-coach" demand, flexibility may be expected, particularly around core collaboration hours with US-based teams and C-suite.

📝 Enhancement Note: Salary is estimated based on the company's reported ARR ($25M), the role's seniority (10+ years experience, 3+ leadership), the remote US location, and the "player-coach" dynamic. Benefits are inferred based on common offerings for growth-stage tech companies in the US.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / Technology, specifically serving the Home Services industry with a platform for SMBs to manage their online presence, lead generation, and customer interactions.

Company Size: Olly Olly is a growth-stage company with $25M ARR. This suggests a team size likely ranging from 50-150 employees, indicating a dynamic environment where roles can have significant impact and individual contributions are highly visible.

Founded: While the founding date isn't explicitly stated, the $25M ARR milestone suggests Olly Olly is an established startup that has achieved significant market traction and is in a scaling phase.

Team Structure:

• The Design team consists of three individuals: two Product Designers focused on the core platform's UX/UI and one Web/Marketing Designer for client-facing creative.

• This role reports directly to senior leadership, likely the CPO (Chief Product Officer) and Head of Marketing, indicating a direct line of influence and collaboration with executive decision-makers.

Methodology:

• Data-Driven Design: The role emphasizes using data, customer feedback, and usability insights to inform and enhance the product experience.

• Agile Development: Comfort in a "fast-moving, growth-stage environment where priorities shift and speed matters" suggests an agile or iterative development approach.

• Strategic Partnership: Design is positioned as a strategic function, not just a delivery layer, implying a proactive and consultative approach to problem-solving.

• Holistic Brand Experience: A focus on the "end-to-end design system and visual language across product and brand" indicates a unified approach to customer perception.

Company Website: https://www.ollyolly.com/

📝 Enhancement Note: The company's focus on empowering SMB home service businesses provides a clear mission. The $25M ARR and growth-stage status suggest an environment ripe for someone who wants to build and shape processes and culture, rather than inherit a mature, established system.

📈 Career & Growth Analysis

Operations Career Level: This role is at a Senior Management / Director level within the Design function. It's a critical leadership position responsible for both strategic direction and team performance. It’s not just about managing tasks but shaping the vision, culture, and output of the design team and its impact on the business.

Reporting Structure: The Product Design Manager will report directly to the CPO (Chief Product Officer) and will also have a close working relationship with the Head of Marketing. This dual reporting/collaboration structure emphasizes the integrated role of design across product and brand strategy.

Operations Impact: The Product Design Manager's impact is substantial, directly influencing:

• Customer Acquisition & Retention: Through effective UX/UI and brand messaging on the website and platform.

• Product Adoption & Engagement: By ensuring the core platform is intuitive, efficient, and valuable for SMB users.

• Brand Perception & Market Competitiveness: By defining and maintaining a strong, consistent visual language and user experience.

• Development Efficiency: Through a well-maintained and scalable design system, enabling faster iteration and feature releases.

• Team Development: By mentoring and growing a team of designers, building the company's internal design capabilities.

Growth Opportunities:

• Expanded Leadership Scope: Potential to grow into a Head of Design or VP of Design role as the company scales, overseeing a larger design organization.

• Strategic Influence: Deeper involvement in company-wide strategic planning and decision-making, leveraging design thinking to solve broader business challenges.

• Specialization: Opportunity to deepen expertise in specific areas like design systems, UX research leadership, or brand strategy.

• Mentorship & Advocacy: Becoming a key advocate for design within the organization and mentoring future design leaders.

• Contribution to Company Growth: Direct impact on the company's trajectory through effective product and brand design, potentially leading to significant equity growth.

📝 Enhancement Note: This role offers a unique opportunity for impactful leadership in a growing company where design is highly valued. The growth path is tied to the company's success and the individual's ability to scale the design function and its strategic influence.

🌐 Work Environment

Office Type: This is a fully remote position, with the company explicitly stating "Remote (Offshore)" in the job title, and confirming remote status for the United States. This implies a distributed workforce and a reliance on digital collaboration tools.

Office Location(s): While the role is remote within the United States, the company's operations and likely headquarters are in the US, with a focus on serving US-based SMBs. Specific office locations for the company are not detailed, but the remote nature means employees can work from their chosen locations within the US.

Workspace Context:

• Digital Collaboration: The primary workspace will be digital, requiring proficiency in remote collaboration tools (e.g., Slack, Zoom, project management software).

• Design Tooling: Access to and mastery of industry-standard design tools, particularly Figma, is essential. The company likely supports a robust digital toolkit for designers.

• Team Interaction: While remote, the role demands active participation in virtual team meetings, design critiques, and cross-functional syncs, fostering a connected (though distributed) team environment.

• Autonomy and Structure: The role requires self-discipline and the ability to manage one's own time effectively within a remote setting, while also adhering to team processes and project deadlines.

Work Schedule: The role is full-time (40 hours/week). While remote work offers flexibility, the need to collaborate with US-based leadership (CPO, Head of Marketing) and a distributed team suggests that adherence to core working hours or availability during key overlap periods will be important.

📝 Enhancement Note: The remote nature necessitates strong self-management skills and a proactive approach to communication and collaboration. The "Offshore" designation in the job title, combined with US location requirements, might imply a distributed team model where some members are located outside the US but work within US time zones for collaboration, or simply that the company is open to hiring US-based talent regardless of their specific location within the country.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience, leadership capabilities, and design quality. Emphasis on the "exceptional eye" and breadth of portfolio.

• Hiring Manager/CPO Interview: Discussion focused on leadership philosophy, team management approach, strategic vision for design at Olly Olly, and how the candidate aligns with company culture and values.

• Portfolio Deep Dive & Case Study Presentation: A dedicated session where the candidate presents their portfolio, detailing specific projects, their role, challenges faced, solutions implemented, and outcomes. This is where the "player-coach" aspect will be assessed, looking for both strategic thinking and hands-on execution.

• Team/Cross-functional Interviews: Meetings with direct reports (designers) and key collaborators (e.g., Product Managers, Marketing Leads) to assess collaboration style, communication skills, and cultural fit.

• Final Round/Executive Interview: Conversation with senior leadership (potentially CEO or other C-suite) to confirm strategic alignment and assess overall fit for the company's growth trajectory.

Portfolio Review Tips:

• Curate Strategically: Showcase projects that best demonstrate leadership, strategic impact, and a blend of product and brand design. Prioritize depth over breadth if necessary.

• Tell a Story: For each case study, articulate the problem, your role, the process (research, ideation, iteration), the solution, and quantifiable results or impact. Clearly differentiate individual contributions from team efforts.

• Highlight Leadership: Explicitly detail how you managed, mentored, and developed team members. Provide examples of setting standards, driving quality, and improving team velocity.

• Showcase Design Systems: If applicable, present your approach to building and scaling design systems, demonstrating their impact on efficiency and consistency.

• Defend Your POV: Be prepared to articulate your design philosophy and defend your design decisions with clear rationale, backed by user insights and business objectives.

• Address "Player-Coach": Be ready to discuss how you balance leading a team with hands-on design work, providing examples of both.

Challenge Preparation:

• Design Challenge (Hypothetical): Be prepared for a take-home challenge or a live design exercise that might involve problem-solving for an SMB audience, refining a user flow, or proposing a visual direction for a marketing asset. Focus on demonstrating your thought process, research approach, and ability to translate requirements into thoughtful design.

• Strategy Discussion: Anticipate questions about how you would approach the first 90 days in the role, how you'd assess the current design team and processes, and your vision for elevating design at Olly Olly.

• Data & Metrics: Be ready to discuss how you use data and metrics to measure design success and inform future decisions.

📝 Enhancement Note: The interview process is rigorous, with a strong emphasis on the portfolio as a key evaluation tool. Candidates should prepare to demonstrate both strategic leadership and hands-on design expertise, with a clear understanding of how design contributes to business growth.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: This is explicitly mentioned as a requirement and is the primary tool for UI/UX design, prototyping, and design system management.

• Design System Tools: Likely includes Figma's component libraries, potentially supplemented by tools like Zeroheight or Storybook for documentation and developer handoff.

• Prototyping Tools: Figma's built-in prototyping capabilities are key. Advanced prototyping might involve tools like Principle or ProtoPie for specific interaction needs.

• Wireframing Tools: While Figma can handle wireframing, dedicated tools like Balsamiq or Whimsical might be used for early-stage ideation or flow mapping.

Analytics & Reporting:

• Product Analytics: Tools such as Amplitude, Mixpanel, or Pendo would be used to track user behavior, feature adoption, and identify friction points within the platform.

• Web Analytics: Google Analytics or similar platforms for monitoring website traffic, conversion rates, and marketing campaign performance.

• Data Visualization/BI Tools: Potentially tools like Tableau, Looker, or Metabase for deeper data analysis and dashboard creation, supporting data-informed design decisions.

CRM & Automation:

• CRM: A CRM system (e.g., Salesforce, HubSpot) would be used by Sales and CS teams, and the design team might interact with it for user insights or to understand customer journeys.

• Marketing Automation: Tools like HubSpot, Marketo, or Mailchimp for marketing campaigns, where design plays a role in email templates, landing pages, and collateral.

• Project Management: Tools like Asana, Jira, Trello, or Monday.com for managing design tasks, workflows, sprints, and cross-functional collaboration.

• Collaboration & Communication: Slack for real-time communication, Zoom for meetings, and potentially Confluence for documentation.

📝 Enhancement Note: Proficiency in Figma is non-negotiable. Familiarity with product analytics tools will be crucial for demonstrating data-informed design decisions. Experience with project management and collaboration platforms is expected for effective remote teamwork.

👥 Team Culture & Values

Operations Values:

• Craft & Quality: A strong emphasis on high standards, attention to detail, and delivering polished, user-centered experiences ("an exceptional eye," "know the difference between good and great").

• Ownership & Accountability: Individuals are expected to "own something" – the design system, product experience, design culture – and take responsibility for outcomes.

• Collaboration & Partnership: Design is not siloed; it requires close partnership with CPO, Head of Marketing, Engineering, and other departments, acting as a strategic function.

• User-Centricity: A deep commitment to understanding and advocating for the end-user, using research and feedback to drive improvements.

• Agility & Speed: Comfort and effectiveness in a "fast-moving, growth-stage environment where priorities shift and speed matters."

• Impact & Purpose: A desire to do "work that actually matters," directly contributing to the success of SMB clients.

Collaboration Style:

• Integrated Design: Design is integrated into the product development lifecycle from strategy through execution, not an afterthought.

• Cross-Functional Alignment: Proactive engagement with Product, Engineering, Marketing, Sales, and CS to ensure cohesive strategy and execution.

• Open Feedback Culture: Implicitly, a culture that encourages constructive feedback to elevate the quality of design work and team performance.

• Knowledge Sharing: The "player-coach" model suggests opportunities for senior designers to mentor junior team members and for the team to share best practices.

• Strategic Voice: Design is encouraged to have a "clear point of view" and contribute to shaping product and business strategy, not just execute on directives.

📝 Enhancement Note: The culture appears to value high performance, strategic contribution, and a genuine desire to build a valuable product for a specific customer segment. The "player-coach" dynamic suggests a culture where leadership is hands-on and collaborative.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Leadership and Execution: Effectively managing a team while also contributing hands-on design work requires excellent time management and prioritization skills.

• Scaling Design in a Growth Environment: Maintaining design quality and consistency at speed as the company grows and product complexity increases.

• Defining and Evolving the Design System: Ensuring the design system remains scalable, up-to-date, and effectively adopted by product and engineering teams.

• Advocating for Design: Continuously reinforcing the strategic value of design within a fast-paced startup environment, especially when priorities shift.

• Remote Team Management: Building strong team cohesion, fostering collaboration, and ensuring consistent performance across a distributed team.

Learning & Development Opportunities:

• Strategic Influence: Direct opportunity to shape product strategy and company direction through design leadership.

• Building a Design Function: Chance to build and scale a design team and its processes from a strong foundation in a growing company.

• Deepening SMB/SaaS Expertise: Gaining specialized knowledge in designing for SMB audiences and the SaaS domain.

• Leadership Development: Opportunities to refine management skills, mentor designers, and potentially grow into higher-level leadership roles.

• Impactful Product: Working on a product that has a tangible, positive impact on the livelihoods of small business owners.

📝 Enhancement Note: The challenges are inherent to a growth-stage company and a leadership role bridging individual contribution and team management. The opportunities are significant for someone looking to make a substantial impact and grow their career in a dynamic environment.

💡 Interview Preparation

Strategy Questions:

• "How would you approach establishing or refining a design system for a growing SaaS product targeting SMBs?" (Focus on scalability, adoption, governance, and impact on development velocity).

• "Describe how you would balance your responsibilities as a player-coach, ensuring both team development and hands-on design contribution." (Provide specific examples of time management, delegation, and personal contribution).

• "Walk us through a time you had to advocate for a design decision that faced resistance. How did you approach it, and what was the outcome?" (Emphasize data-driven arguments, user empathy, and stakeholder management).

Company & Culture Questions:

• "What excites you most about Olly Olly's mission and product?" (Demonstrate research into the company and its customers).

• "How do you foster a collaborative and high-performing culture within a remote design team?" (Discuss communication strategies, feedback mechanisms, and team building).

• "How do you measure the success of design initiatives, both in terms of user experience and business impact?" (Prepare to discuss relevant metrics and KPIs).

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline the problem, your specific role and responsibilities, the process undertaken (research, ideation, iteration), the solution, and the measurable outcomes or impact.

• Highlight Leadership and Collaboration: Explicitly call out instances of team leadership, mentorship, cross-functional collaboration, and how you influenced strategic decisions.

• Showcase "Player-Coach" Balance: Be ready to detail how you contributed individually while also guiding and empowering your team.

• Demonstrate Design Systems Expertise: If presenting a design system project, clearly articulate its architecture, benefits, and how it was implemented and adopted.

• Defend Your Taste and POV: Be prepared to articulate your design philosophy and the rationale behind your aesthetic and UX decisions, connecting them to user needs and business goals.

• Tailor to Olly Olly: Where possible, draw parallels between your past work and the challenges/opportunities at Olly Olly, showing how your experience is relevant.

📝 Enhancement Note: Preparation should focus on demonstrating a strategic mindset, strong leadership capabilities, a clear design vision, and the ability to execute effectively in a fast-paced, remote environment. The portfolio is the central piece of evidence.

📌 Application Steps

To apply for this Product Design Manager position:

• Submit your application through the provided Ashby link, ensuring your resume and portfolio are uploaded.

• Portfolio Customization: Curate your portfolio to prominently feature projects demonstrating leadership, strategic impact, a blend of product and brand design, and experience with design systems. Prioritize case studies that align with Olly Olly's SMB focus and SaaS environment.

• Resume Optimization: Tailor your resume to highlight leadership experience, quantifiable achievements in design quality and team velocity, and proficiency in Figma and other relevant tools. Use keywords from the job description.

• Interview Preparation: Practice presenting your portfolio, focusing on storytelling, articulating your design POV, and detailing your leadership approach. Prepare to discuss how you would address the challenges and opportunities specific to Olly Olly.

• Company Research: Deeply research Olly Olly's product, target market (SMB home service businesses), mission, and recent news. Understand their competitive landscape and how design can be a key differentiator.

⚠️ 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.

---