📍 Job Overview
Job Title: Head of Product Strategy
Company: PriceSpider
Location: Remote, US
Job Type: Full-Time
Category: Product Strategy & Leadership (with Design Implications)
Date Posted: 2025-06-09
Experience Level: 8-12+ Years (5+ in Leadership)
Remote Status: Remote Solely
🎨 Role Summary
- Define and execute overarching product strategy, influencing the direction of the user experience and design outcomes across core platforms (WTB, Prowl, Platform).
- Drive the integration of AI and Machine Learning into product capabilities, requiring a strong understanding of how advanced technology impacts user interaction and interface design.
- Lead initiatives focused on modernizing product experiences through automation, personalization, and predictive insights, directly shaping the functional and visual design requirements.
- Develop product leadership, including directors, fostering a culture that values innovative product design and user-centered development methodologies.
🖼️ Primary Responsibilities
- Set and clearly communicate a unified product vision and strategic roadmap that guides design, engineering, and data teams towards cohesive and impactful product development efforts.
- Champion the adoption of AI/ML within both platform infrastructure and customer-facing features, requiring collaboration with Design to ensure AI-driven insights are presented in a user-friendly and actionable manner.
- Identify and prioritize opportunities for automation, personalization, and predictive insight, translating strategic goals into tangible design requirements and feature specifications.
- Manage and mentor Directors and other product leaders, building a strong product team that understands and prioritizes the importance of user experience and design excellence.
- Own the end-to-end product lifecycle management, from discovery and planning through delivery and iteration, ensuring design deliverables are integrated effectively at each stage.
- Forge strong partnerships with GTM (Go-to-Market), Engineering, and Data teams to ensure seamless execution of the product strategy and the delivery of high-impact features with strong design integrity.
- Act as the key product representative in discussions with customers, partners, and internal executives, effectively articulating the product vision, design approaches, and value proposition.
🎓 Skills & Qualifications
Education: While not explicitly stated, a Bachelor's or Master's degree in a related field such as Business, Computer Science, Design, or a technical discipline is typically expected for a role at this level. An MBA or formal strategy/innovation background is preferred.
Experience: 8–12+ years of progressive experience in product management, with a minimum of 5 years in a leadership capacity managing product teams. Demonstrated success in the SaaS or ecommerce platform space is essential. Experience leading initiatives involving AI/ML or advanced data-integrated products is a key requirement. A strong portfolio or track record demonstrating strategic product leadership and successful product launches is highly valuable.
Required Skills:
- Defining and communicating a clear, actionable product vision and strategy that inspires and aligns cross-functional teams, including design.
- Proven leadership and team management skills, with the ability to mentor and develop product professionals while championing a culture of design thinking and user-centricity.
- Deep understanding of AI/ML principles and their practical application in product development, including how they can be leveraged to enhance user experience and deliver predictive insights.
- Extensive experience within the SaaS or ecommerce platform industry, understanding the unique challenges and opportunities in this space, particularly concerning user engagement and conversion through design.
- Exceptional executive-level communication and presentation skills, with the ability to articulate complex product strategies and design rationales to diverse audiences.
- Strong strategic planning and analytical abilities, capable of translating market trends and user needs into a compelling product roadmap that considers design feasibility and innovation.
- Fluency in Agile methodologies and a deep understanding of product discovery and delivery cycles, ensuring design is effectively integrated throughout the development process.
- Experience partnering effectively with Go-to-Market, Engineering, and Data teams to ensure product strategy is executed with technical feasibility and design quality in mind.
Preferred Skills:
- Background specifically within ecommerce, retail tech, or MarTech sectors, bringing domain expertise that can inform product strategy and design decisions.
- Hands-on experience with embedded AI, recommendation engines, or intelligent automation technologies, understanding the design implications of such features.
- Proven experience with Product-Led Growth (PLG) strategies, understanding how product design and user experience can drive adoption and expansion.
- A formal background in strategy or innovation, such as an MBA, which can provide a structured approach to market analysis and competitive positioning, influencing product design direction.
🎨 Portfolio & Creative Requirements
Portfolio Essentials: While a traditional design portfolio isn't required for a Head of Product Strategy role, candidates should be prepared to showcase their strategic thinking and its impact on product outcomes. This can be demonstrated through:
- Case studies detailing product strategies they have defined and executed, highlighting the problems solved, the solutions implemented (including any relevant design components), and the resulting business impact and user outcomes.
- Examples of strategic roadmaps they have developed and managed, illustrating their approach to prioritization, resource allocation, and cross-functional alignment, including how design considerations were factored in.
- Presentations or documentation outlining their approach to integrating new technologies like AI/ML into product offerings, explaining the strategic rationale and the intended user experience implications.
- Examples of how they have fostered a product culture that values user research, design thinking, and iterative development, demonstrating their influence on the creative process.
Process Documentation: Candidates should be able to articulate their strategic process, demonstrating how they move from market analysis and user insights to defining a product vision and execution plan. This includes:
- Describing their methodology for market research and identifying unmet user needs, and how these insights inform product strategy and design requirements.
- Explaining their approach to ideation and strategic prioritization, including how they collaborate with design and engineering to explore potential solutions.
- Detailing their methods for validating product concepts and strategies, including how user testing and feedback are incorporated into the strategic refinement process.
💵 Compensation & Benefits
Salary Range: $200,000 - $235,000 per year. This range is explicitly provided by the company and is based on current market data, varying based on experience, skills, location, and other factors. This range is competitive for a Head of Product Strategy role in the US, particularly in a remote capacity within the SaaS/Ecommerce sector.
Benefits:
- Flexible Work-from-Home Arrangements: Supports work-life balance and autonomy for remote employees, allowing for flexible scheduling that can accommodate creative workflows and focused work periods.
- 401K Match: Provides a retirement savings plan with employer contribution, contributing to long-term financial security.
- Flexible Vacation: Offers autonomy in managing time off, allowing for rejuvenation and personal pursuits which can be beneficial for maintaining creative energy.
- Medical/Dental/Vision: Comprehensive health coverage for employees and their dependents, ensuring access to necessary healthcare.
- 16 Weeks of Paid Parental Leave (US): A generous benefit supporting new parents, demonstrating a commitment to employee well-being and family support.
- Technical Stipend: Provides financial support for necessary equipment or resources to enhance the remote work setup, crucial for effective collaboration and access to tools, including potential design-related software or hardware.
- Professional Development Programs: Opportunities for continuous learning and skill enhancement, supporting growth in product strategy, leadership, and understanding emerging technologies like AI, which is vital in this role.
- Wellness Programs: Initiatives focused on employee health and well-being, promoting a healthy lifestyle and potentially offering resources for managing stress and maintaining productivity in a demanding role.
Working Hours: While not explicitly stated, a full-time Head of Product Strategy role typically involves a standard 40-hour work week, often with flexibility given the remote nature. Due to the leadership and strategic nature, occasional work outside of standard hours may be required for meetings across time zones or critical product initiatives.
🎯Team & Company Context
🏢 Company & Design Culture
Industry: Software Development, specifically focused on Ecommerce Solutions, Retail Tech, and MarTech. PriceSpider operates within the dynamic landscape of online commerce, providing tools that enhance the shopper journey. This context is crucial for a Head of Product Strategy, requiring an understanding of retail trends, consumer behavior, and the competitive landscape, all of which heavily influence product design and user experience. The focus on making the shopping experience "more human" suggests a design culture that values empathy, user understanding, and intuitive interfaces.
Company Size: 201-500 employees (LinkedIn). A company of this size is likely beyond the startup phase but still agile enough for significant impact. For a Head of Product Strategy, this size indicates a need for structured processes and team management, while also offering the opportunity to shape the product direction and culture significantly. It's large enough to have established design practices but potentially still evolving its design maturity.
Founded: 2004 (LinkedIn). Founded over 20 years ago, PriceSpider has a history and established presence in the market. This suggests a level of stability and experience within the ecommerce solutions space. The company's longevity implies an evolution of its product offerings and potentially its design approach over time.
Team Structure:
- The Head of Product Strategy is the top product leader, responsible for managing Directors and developing the product leadership bench. This indicates a hierarchical structure within the product organization.
- The role requires partnering with GTM, Engineering, and Data teams, suggesting a matrixed or cross-functional team structure where product works closely with other departments.
- Collaboration with Design is implicit given the focus on product experience modernization and AI integration, indicating that Design likely reports into Product or has a strong dotted line relationship.
Methodology:
- The job description mentions "Agile fluency" and "deep knowledge of discovery and delivery cycles," indicating that the company likely follows Agile or a similar iterative development methodology.
- The emphasis on identifying opportunities for personalization and predictive insight suggests a data-driven approach to product development and design, likely involving user research and analytics.
- The focus on modernizing the product experience implies an ongoing process of iteration and improvement, potentially involving design sprints or similar rapid prototyping methods.
Company Website: http://www.pricespider.com
📈 Career & Growth Analysis
Design Career Level: This role is a senior leadership position within the Product organization, equivalent to a Director or VP level in terms of responsibility and influence. While not a design role itself, it directly impacts the design function. Success in this role could lead to broader leadership opportunities within PriceSpider or similar strategic roles in larger organizations. For designers, this role represents a key stakeholder and potential reporting line, offering insights into the strategic direction that will shape design projects.
Reporting Structure: The Head of Product Strategy is described as the "top product leader," suggesting they likely report directly to a C-level executive such as the CEO or Chief Product Officer. They will manage Directors within the product team. Design teams typically report into Product at companies like PriceSpider, meaning the Head of Product Strategy would likely oversee the design function or work very closely with design leadership.
Design Impact: This role has significant direct and indirect impact on design. The Head of Product Strategy defines the product vision and strategic roadmap, which dictates the scope and priorities for design projects. Their focus on AI/ML, personalization, and automation will require innovative design solutions. They will influence the design culture by championing user-centered approaches and fostering collaboration between product, design, and engineering.
Growth Opportunities:
- Advancement to a C-level role (e.g., Chief Product Officer) within PriceSpider or another company, leveraging the experience gained in setting and executing company-wide product strategy.
- Increased leadership responsibilities within a larger or more complex product organization, potentially overseeing a broader portfolio of products or a larger team.
- Opportunities to become a thought leader in the ecommerce, retail tech, or AI in product space, through speaking engagements, publications, or industry contributions.
🌐 Work Environment
Studio Type: Remote. This is a fully remote position, meaning the primary workspace is the employee's home office. While there might be occasional travel for team meetings or conferences, the day-to-day work is conducted remotely. This requires strong self-discipline, communication skills, and the ability to collaborate effectively using digital tools, which is also critical for remote design collaboration.
Office Location(s): While the role is remote, PriceSpider has its headquarters in Irvine, CA (LinkedIn), and employees in four countries. This suggests a distributed team environment, which can influence communication practices and meeting schedules to accommodate different time zones. While there is a physical headquarters, this role is explicitly remote US.
Design Workspace Context:
- As a remote role, the individual is responsible for setting up their own workspace. However, the mention of a "Technical Stipend" suggests the company provides support for creating an effective home office environment, which is important for design professionals requiring specific hardware or software.
- Collaboration will rely heavily on digital tools for communication, project management, and potentially shared whiteboarding or design review sessions.
- While there isn't a physical "design studio," the company culture and collaborative tools will define the "creative environment." The focus on making the shopping experience "more human" suggests a culture that values empathetic and user-centered approaches, which are foundational to effective design work.
Work Schedule: The schedule will likely be flexible to some extent due to the remote nature, but will need to align with team meetings and cross-functional collaboration across different time zones, potentially involving early morning or late evening calls depending on the location of colleagues. Managing a global team implies asynchronous communication will also be important.
📄 Application & Portfolio Review Process
Design Interview Process: While this is a Product Strategy role, the interview process will likely involve elements relevant to design and its integration with product strategy. Expect a multi-stage process that could include:
- An initial screening call with HR or a recruiter to assess basic qualifications and fit.
- Interviews with key stakeholders, including C-level executives, engineering leadership, data science leadership, and potentially design leadership, to discuss strategic vision, leadership style, and collaboration approaches.
- A case study or strategic challenge presentation where you will be asked to analyze a business problem or market opportunity and present your proposed product strategy and how it would be executed, including how design would be involved.
- Discussions focusing on your experience leading teams, driving product initiatives, and integrating new technologies like AI/ML, with questions on how you ensure user needs and design principles are incorporated.
Portfolio Review Tips: For this role, instead of a traditional design portfolio, prepare a presentation or document that showcases your strategic product work. Focus on:
- Presenting case studies of products or features where you defined the strategy, highlighting the business problem, the strategic approach, the execution (mentioning collaboration with design), and the outcomes (metrics, user impact).
- Clearly articulating your strategic thinking process, from market analysis and user research insights to defining the product vision and roadmap.
- Demonstrating your understanding of how design contributes to product success and your experience collaborating effectively with design teams.
- If you have experience with AI/ML integration, showcase how you approached the user experience challenges and opportunities presented by these technologies.
Challenge Preparation: If a strategic challenge is part of the process, be prepared to:
- Analyze a given problem or opportunity within the ecommerce or SaaS space.
- Develop a high-level product strategy, including target users, key features (considering design implications), and potential business models.
- Outline a potential roadmap and execution plan, considering cross-functional collaboration with engineering, data, and design.
- Articulate your strategic rationale, defend your decisions, and discuss how you would measure success, including user-centric metrics.
ATS Keywords: Product Strategy, Product Leadership, SaaS, Ecommerce Platforms, AI/ML, Machine Learning, Automation, Personalization, Predictive Insight, Strategic Planning, Executive Communication, Agile, Product Discovery, Product Delivery, Lifecycle Management, Cross-functional Collaboration, Go-to-Market, Engineering, Data, WTB, Prowl, Platform, Retail Tech, MarTech, Embedded AI, Recommendation Engines, Intelligent Automation, Product-Led Growth, Team Management, Mentoring, User Experience (UX), Design Thinking, User-Centered Design, Innovation, Roadmap, Prioritization, Stakeholder Management, Business Acumen, Market Analysis, Competitive Analysis, User Research, Data Analysis, Metrics, KPIs, Remote Work, Global Team.
🛠 Tools & Technology Stack
Primary Design Tools: While this role doesn't directly use design software, the Head of Product Strategy will interact with the outcomes of design tools and potentially participate in design reviews. The design team likely uses industry-standard tools such as:
- Figma or Sketch: For UI/UX design, prototyping, and collaboration. Understanding the capabilities and limitations of these tools can help the Head of Product Strategy better collaborate with the design team.
- Adobe Creative Suite (Photoshop, Illustrator): For visual design, asset creation, and branding elements.
- Prototyping Tools (e.g., InVision, Principle): For creating interactive prototypes to test user flows and demonstrate product functionality.
Collaboration & Handoff:
- Jira or Asana: For project management and tracking product development tasks, including design sprints and deliverables.
- Confluence: For documentation, including product requirements, user stories, and design specifications, facilitating knowledge sharing between product, design, and engineering.
- Slack or Microsoft Teams: For real-time communication and collaboration with cross-functional teams, including quick questions and feedback on design work.
- Zeplin or Abstract: Tools used for design handoff to engineering, ensuring design specifications and assets are accurately implemented.
Research & Testing:
- User Research Platforms (e.g., UserTesting.com, Maze): For gathering user feedback and validating design concepts and prototypes.
- Analytics Tools (e.g., Google Analytics, Mixpanel): For tracking user behavior, measuring feature adoption, and identifying areas for product and design improvement.
- A/B Testing Tools: For testing different design variations and product features to optimize for user engagement and conversion.
👥 Team Culture & Values
Design Values: Based on the company description of making the shopping experience "more human" and helping people "fall back in love with brands," the implied design values likely include:
- User-Centeredness: A strong focus on understanding user needs, behaviors, and motivations to create empathetic and effective product experiences.
- Innovation: A drive to explore new ideas and leverage technology, like AI/ML, to create novel and engaging solutions that differentiate PriceSpider in the market.
- Collaboration: A commitment to working closely with cross-functional teams (Product, Engineering, Data, GTM) to ensure design is integrated seamlessly into the product development process.
- Impact: A focus on creating designs that not only look good but also drive measurable business outcomes and enhance the user's shopping journey.
Collaboration Style:
- Given the remote nature and global presence, the collaboration style likely emphasizes clear and asynchronous communication, leveraging digital tools effectively.
- The need to partner with GTM, Engineering, and Data suggests a collaborative environment where different disciplines work together towards shared goals.
- A Head of Product Strategy role requires strong leadership and the ability to influence and align diverse teams, implying a collaborative style that encourages open dialogue, feedback, and shared ownership.
⚡ Challenges & Growth Opportunities
Design Challenges: While this is a Product Strategy role, the challenges faced will have significant implications for design. These might include:
- Translating complex AI/ML capabilities into intuitive and user-friendly interfaces that provide clear value to users without overwhelming them.
- Designing personalized experiences at scale across different platforms (WTB, Prowl, Platform) and for diverse user segments.
- Ensuring design consistency and a cohesive user experience across a growing product portfolio and potentially through acquisitions or integrations.
- Balancing innovation and the adoption of new technologies with the need for stability, usability, and accessibility in design.
Learning & Development Opportunities:
- Opportunities to deepen expertise in AI/ML and their application in ecommerce and product development, staying at the forefront of technological advancements.
- Development of strategic leadership skills, including managing and mentoring a team of product professionals and influencing across a matrixed organization.
- Exposure to the complexities of a global business operating in multiple countries, providing experience in adapting product strategy and design approaches for different markets.
- Opportunities to shape the product culture and processes within a growing company, leaving a lasting impact on how product development and design are conducted.
💡 Interview Preparation
Design Process Questions: While you won't be asked about your personal design process in detail, be prepared to discuss your approach to integrating design into the product development lifecycle. Questions might include:
- How do you ensure user needs and design considerations are central to your product strategy? Be prepared to discuss your experience with user research and how it informs your strategic decisions, and how you empower design teams to conduct effective user research.
- How do you collaborate with design teams throughout the product lifecycle, from discovery to delivery? Provide examples of successful collaborations and how you address potential challenges in cross-functional teamwork.
- How do you evaluate the success of product features from a user experience and design perspective? Discuss the metrics you use and how you incorporate user feedback into iterative improvements and future strategy.
Company Culture Questions: Demonstrate your understanding of PriceSpider's mission and values, particularly as they relate to creating "human" shopping experiences. Questions might include:
- How do your leadership style and values align with PriceSpider's focus on creating a human-centered shopping experience?
- How do you foster a collaborative and inclusive environment within your product team and across functions, including working effectively with design?
- How do you approach risk-taking and innovation within product strategy, and how do you encourage creative problem-solving within your teams?
Portfolio Presentation Strategy: As mentioned, focus on presenting case studies of your strategic product work. Structure your presentation to tell a compelling story:
- Start by clearly defining the problem you were trying to solve and the market opportunity.
- Explain your strategic approach and the rationale behind your key decisions, including how you considered the user experience and design implications.
- Detail the execution process, highlighting how you collaborated with engineering, data, and design teams.
- Present the outcomes and impact of your strategy, using relevant metrics (e.g., user engagement, conversion rates, revenue growth).
- Be prepared to discuss challenges you faced and how you overcame them, demonstrating your problem-solving skills.
📌 Application Steps
To apply for this design position:
- Submit your application through this link
- Tailor your resume and cover letter to highlight your experience in product strategy, leadership, and working with cross-functional teams, particularly emphasizing any experience with AI/ML and the ecommerce/SaaS space. Use relevant ATS keywords throughout your application materials.
- Prepare case studies or a presentation that clearly articulate your strategic thinking, the impact of your product decisions, and your experience collaborating with design and engineering teams to bring product visions to life.
- Research PriceSpider's products, target market, and recent news. Understand their position in the ecommerce solutions space and how your strategic vision aligns with their goals.
- Practice discussing your leadership style, experience managing teams, and your approach to fostering a collaborative and innovative product development environment.