Sr. Product Designer (Contract)

📍 Job Overview

Job Title: Sr. Product Designer (Contract)

Company: Yolando

Location: United States / Toronto, Ontario, Canada

Job Type: CONTRACT

Category: Product Design / UX/UI Design

Date Posted: April 13, 2026

Experience Level: Mid-Senior Level (5-10 years)

Remote Status: Remote OK

🚀 Role Summary

• Lead the creation of intuitive, user-centric UX and UI designs for a competitive intelligence and Generative Engine Optimization (GEO) platform, directly impacting user experience and platform success.

• Develop and maintain robust, development-ready design components and systems that align with and enhance Yolando's established design system.

• Drive brand design initiatives, ensuring visual consistency and craft across all product touchpoints and external-facing marketing materials.

• Collaborate closely with product management and engineering teams to translate complex requirements into simple, elegant, and actionable design solutions.

• Contribute to a fast-growing, recently funded startup redefining AI search visibility and competitive intelligence for businesses.

📝 Enhancement Note: This role is a contract position with a strong emphasis on product design, UX/UI, and brand consistency. The "Sr." in the title, coupled with the responsibility for design systems and brand contributions, suggests a need for experienced candidates capable of independent work and strategic design thinking. The "GEO" aspect points to a specialized niche within SaaS product design, requiring an understanding of how users interact with AI-generated content and how businesses can optimize their presence within it.

📈 Primary Responsibilities

• Partner with the product manager to conceptualize, wireframe, and prototype user flows and interface designs for Yolando's core platform features.

• Translate complex user needs and business requirements into clear, concise, and actionable design specifications for engineering teams.

• Build, iterate on, and maintain a comprehensive design system, ensuring scalability, reusability, and adherence to brand guidelines.

• Craft high-fidelity UI mockups and interactive prototypes in Figma, demonstrating intended user interactions and visual aesthetics.

• Conduct thorough UX research, including competitive analysis and user testing, to validate design decisions and uncover opportunities for improvement.

• Develop and refine visual identity elements, including logos, typography, color palettes, and iconography, for both product and marketing collateral.

• Ensure all designs adhere to accessibility standards (WCAG) and best practices for responsive design across various devices and platforms.

• Actively participate in design reviews, providing and receiving constructive feedback to elevate design quality and team collaboration.

• Collaborate with developers to ensure accurate implementation of designs, providing detailed specifications and ongoing support.

📝 Enhancement Note: The responsibilities highlight a blend of strategic product design, hands-on UI/UX execution, and brand stewardship. The emphasis on "development-ready" designs and contributing to the design system indicates a need for practical experience in bridging the gap between design and development. The mention of "GEO" and AI search implies a requirement for understanding emerging technologies and their user interface implications.

🎓 Skills & Qualifications

Education:

Experience:

• 5-10 years of professional experience in UX/UI design, with a significant focus on product design for SaaS platforms.

Required Skills:

• Figma Expertise: Advanced proficiency in Figma for wireframing, prototyping, UI design, and component creation.

• UX/UI Design: Deep understanding of user-centered design principles, interaction design, and information architecture.

• Design Systems: Experience building, maintaining, and scaling design systems for consistency and efficiency.

• Visual Design: Strong aesthetic sensibility, with a keen eye for typography, color theory, layout, and visual hierarchy.

• Prototyping: Ability to create interactive prototypes to effectively communicate design concepts and user flows.

• Brand Design: Experience developing and implementing visual identity systems and ensuring brand consistency across digital products.

• User Research: Familiarity with various user research methodologies to inform design decisions and validate solutions.

• Collaboration: Excellent communication and interpersonal skills, with the ability to effectively collaborate with cross-functional teams.

• Problem-Solving: Strong analytical and problem-solving skills, with the ability to simplify complex user journeys.

Preferred Skills:

• Framer Experience: Familiarity with Framer for advanced prototyping or design implementation.

• Automation Tools: Experience designing interfaces for automation builders, user design canvases, or AI agents.

• Marketing Software: Understanding of or experience designing for marketing technology, including email platforms, digital ad tools, or direct mail platforms.

• Startup Environment: Previous experience working in a fast-paced, growth-stage startup.

• Framer Experience: Familiarity with Framer for advanced prototyping or design implementation.

• AI/ML Product Design: Experience designing products that leverage artificial intelligence or machine learning.

📝 Enhancement Note: The requirements emphasize hands-on proficiency with Figma and a strong portfolio as critical. The preference for experience in automation builders, AI agents, and marketing software directly relates to Yolando's product offering, indicating a desire for candidates who can quickly grasp the domain. The "5-10 years" experience level, combined with "Sr." title, suggests they are looking for someone who can operate with a high degree of autonomy and strategic input.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Case Studies: A minimum of 3-5 detailed case studies showcasing your product design process from problem identification to final solution, highlighting your role and contributions.

• Figma Work: Demonstrations of your proficiency in Figma, including complex UI designs, interactive prototypes, and examples of reusable components or design system contributions.

• User-Centricity: Evidence of how user needs and research informed your design decisions, with examples of user flows, wireframes, and usability testing insights.

• Brand Integration: Examples of how you have maintained or developed brand consistency across product interfaces and marketing materials.

• Development Handoff: Clear examples of how you prepare designs for development, including annotations, component specifications, and collaboration with engineering.

Process Documentation:

• Ability to articulate your design process clearly, including discovery, ideation, prototyping, testing, and iteration phases.

• Documentation of how you approach building and maintaining design systems, including component libraries and style guides.

• Examples of how you conduct design research and translate findings into actionable design improvements.

• Demonstrations of how you ensure design feasibility and collaborate with developers to overcome implementation challenges.

📝 Enhancement Note: For this role, the portfolio is paramount. It needs to clearly demonstrate not just creative output but also a structured, user-centric design process. The emphasis on "development-ready" designs and design systems means showcasing practical, implementable work. Candidates should be prepared to walk through their Figma files and explain their design system methodology.

💵 Compensation & Benefits

Salary Range:

• Based on industry benchmarks for Sr. Product Designers with 5-10 years of experience, particularly in contract roles within tech hubs like Toronto and major US cities, a competitive hourly rate or project-based fee would typically range from $60 - $100 USD per hour (or equivalent in CAD). This estimate considers the specialized nature of the role (GEO, AI, Competitive Intelligence), the contract employment type, and the requirement for advanced Figma and design system skills.

• Methodology: This estimate is derived from analyzing contract Sr. Product Designer roles on platforms like LinkedIn, Glassdoor, and specialized design job boards, adjusted for geographic cost of living in Toronto and major US tech markets, and factoring in the startup environment which may offer slightly more flexibility.

Benefits:

• Flexible Freelance Engagement: Opportunity to work on a contract basis, offering flexibility in schedule and project scope.

• Innovative Startup Environment: Exposure to cutting-edge AI technology and a fast-paced, growth-oriented company culture.

• Direct Impact: Significant influence on the product's user experience and brand identity.

• Professional Development: Opportunity to work with a well-funded startup and contribute to a redefining platform.

• Collaborative Team: Work alongside experienced product managers and engineers in a supportive team setting.

Working Hours:

• The role is expected to require approximately 40 hours per week, typical for a full-time contract engagement. However, as a freelance position, there may be flexibility in daily scheduling, provided project deadlines and collaboration needs are met.

📝 Enhancement Note: Salary is estimated due to the contract nature and lack of explicit figures. The range provided is a broad estimate for North America for experienced designers in contract roles. The benefits listed are directly from the job description and are typical for contract positions in startups, emphasizing flexibility and impact.

🎯 Team & Company Context

🏢 Company Culture

Industry: Competitive Intelligence & Generative Engine Optimization (GEO) within the SaaS sector. Yolando leverages AI to help businesses understand and improve their visibility in AI-generated search results.

Company Size: Recently funded startup ($8.5M from Drive Capital), indicating a growing team, likely in the 20-50 employee range, with potential for rapid expansion. This size allows for significant individual impact but also requires adaptability and self-direction.

Founded: Yolando was "born out of BirdseyePost," suggesting a foundation in established marketing technology with a pivot to address the emerging AI search landscape. This implies a blend of practical marketing experience and disruptive technological innovation.

Team Structure:

• Product & Design: The Sr. Product Designer will work closely with a Product Manager, suggesting a collaborative product development process.

• Engineering: Direct interaction with developers for design handoff and implementation is a key aspect.

• Cross-functional Collaboration: While not explicitly detailed, the nature of a startup means designers will likely interact with marketing, sales, and leadership teams to ensure cohesive product and brand strategies.

Methodology:

• Data-Driven Design: The company's focus on competitive intelligence and optimization implies a strong reliance on data to inform product decisions and measure success.

• Agile Development: Common in startups, likely involving iterative design and development cycles.

• User-Centricity: A stated core principle, focusing on creating simple, intuitive, and user-friendly experiences.

Company Website: yolando.com (Assumed domain based on input)

📝 Enhancement Note: Yolando operates in a cutting-edge niche, blending AI, competitive intelligence, and marketing technology. The culture is likely fast-paced, innovative, and requires individuals who are comfortable with ambiguity and rapid change, common in venture-backed startups. The designer will be pivotal in shaping both the product's usability and its market perception.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a "Sr. Product Designer" on a contract basis. While contract roles may not always offer traditional linear career progression, the "Sr." designation implies significant autonomy, strategic input, and responsibility for key design outcomes. It's an opportunity to act as a lead designer on critical platform features and brand initiatives.

Reporting Structure: The designer will report directly to or collaborate very closely with the Product Manager. They will also interface with engineering teams for implementation. In a startup, this means direct access to leadership and decision-makers.

Operations Impact: The Sr. Product Designer will have a direct and substantial impact on Yolando's success by:

• Enhancing User Experience: Creating intuitive and delightful interfaces that drive user adoption and retention.

• Strengthening Brand Identity: Ensuring a consistent and professional brand presence across all touchpoints, crucial for market perception and trust.

• Improving Product Efficacy: Designing features that effectively help businesses gain competitive intelligence and optimize their AI visibility.

• Driving Adoption: Crafting user journeys that are easy to understand and navigate, reducing barriers to entry for new users.

Growth Opportunities:

• Specialized Skill Development: Deepen expertise in designing for AI-driven products, competitive intelligence platforms, and Generative Engine Optimization (GEO).

• Design System Leadership: Opportunity to significantly influence and expand the company's design system, which can be a valuable portfolio piece.

• Brand Strategy Contribution: Play a key role in shaping the visual identity of a rapidly growing startup.

• Startup Experience: Gain invaluable experience in a dynamic, venture-backed startup environment, potentially leading to future full-time opportunities or roles in other high-growth companies.

• Portfolio Enhancement: The projects undertaken will likely be high-impact, providing strong material for future career endeavors.

📝 Enhancement Note: While a contract role, the "Sr." title and the breadth of responsibilities (product, brand, design systems) offer significant growth and impact. For operations professionals considering this, it's an opportunity to hone skills in a niche, high-demand area and contribute significantly to a company's foundational design elements.

🌐 Work Environment

Office Type: The role is explicitly stated as "Remote OK," with a preference for Toronto-based candidates but welcoming remote applicants. This suggests a distributed or hybrid work model, with a primary office likely in Toronto.

Office Location(s):

• Toronto, Ontario, Canada (primary hub)

Workspace Context:

• Remote Flexibility: Candidates can work from their preferred remote location, offering autonomy and work-life balance.

• Collaborative Tools: Expect to use digital collaboration tools (e.g., Slack, Zoom, Figma) extensively for communication and design reviews.

• Startup Pace: The environment is described as "fast-moving" and "collaborative," indicating a dynamic and potentially intense work atmosphere where quick iteration and communication are key.

• Innovation Hub: Being part of a company focused on AI and GEO places the designer in an innovative tech ecosystem.

Work Schedule:

• The role is described as a contract engagement, with an implied 40-hour work week. While flexibility in daily hours is possible, adherence to project timelines and team collaboration needs is essential. This means being available for key meetings and design reviews during core working hours, regardless of location.

📝 Enhancement Note: The remote flexibility is a key draw, but candidates should be prepared for the fast-paced, collaborative nature of a startup. Effective communication and self-management will be critical for success in this environment.

📄 Application & Portfolio Review Process

Interview Process:

• Application Submission: Submit resume, portfolio, and a brief note of interest.

• Portfolio Review: Initial screening will heavily rely on the portfolio to assess design skills, process, and relevant experience. Expect detailed scrutiny of case studies and Figma work.

• Initial Interview: Likely with a Product Manager or Hiring Manager to discuss experience, design philosophy, and cultural fit. This may include a high-level discussion of your portfolio.

• Design Challenge/Exercise: A practical design exercise or case study presentation may be assigned to evaluate your problem-solving skills, design process, and ability to create development-ready outputs. This could involve analyzing a specific user problem or refining an existing flow.

• Technical/Team Interview: Discussion with engineering or design team members to assess technical proficiency, collaboration style, and understanding of design-to-development workflows.

• Final Interview: Possibly with company leadership to discuss overall strategy, impact, and long-term engagement.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest, most relevant case studies that demonstrate your product design, UX/UI, and brand design capabilities.

• Highlight Process: For each case study, clearly outline the problem, your role, your design process (research, ideation, wireframing, prototyping, testing), and the final outcome/impact. Use visuals effectively.

• Showcase Figma Mastery: Include examples of your Figma work – interactive prototypes, well-structured components, and design system elements. Be prepared to share your Figma files or walk through them.

• Quantify Impact: Where possible, use metrics to demonstrate the success of your designs (e.g., improved conversion rates, reduced user errors, increased engagement).

• Address "Development-Ready": Explicitly show how you prepare designs for developers, including annotations, specifications, and collaboration examples.

• Brand Consistency: If brand design is a focus, ensure your portfolio includes examples of cohesive visual identity application.

Challenge Preparation:

• Understand the Product: Research Yolando, its mission, target audience, and competitive landscape. Understand the core problem they solve (AI search visibility, competitive intelligence).

• Focus on GEO: If a challenge is given, consider how you would design for "Generative Engine Optimization." Think about the user's goals when interacting with AI-generated content.

• Design System Thinking: Be ready to discuss how you would approach building or expanding a design system for a product like Yolando.

• Edge Cases & Scenarios: Practice thinking through complex user flows, edge cases, and error states, as this is a stated requirement.

• Present Clearly: Prepare to articulate your thought process and design rationale concisely and convincingly.

📝 Enhancement Note: The interview process will heavily weigh the portfolio. Candidates should prepare to not only show their designs but also explain the "why" behind them, demonstrating strategic thinking and a robust, user-centered process. The "development-ready" aspect is critical and should be a recurring theme in portfolio examples and interview discussions.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core design tool for wireframing, UI design, prototyping, and component creation. Advanced proficiency is essential.

• Prototyping Tools: While Figma includes prototyping, familiarity with other tools like InVision or Adobe XD might be beneficial for broader context, though likely not required if Figma is mastered.

• Collaboration Tools: Slack (for communication), Zoom/Google Meet (for virtual meetings), Asana/Jira (potentially for task management integration).

Analytics & Reporting:

• Analytics Platforms (e.g., Google Analytics, Mixpanel, Amplitude): While not directly a design tool, understanding how design impacts user behavior tracked by these platforms is crucial for data-informed design.

• Data Visualization Tools (e.g., Tableau, Looker): Familiarity with how data is presented can inform dashboard design or reporting interfaces.

CRM & Automation:

• CRM Systems (e.g., Salesforce, HubSpot): Understanding how product design can integrate with or impact CRM data and workflows.

• Marketing Automation Platforms: As mentioned in "Bonus," familiarity with platforms like HubSpot, Marketo, or similar is a plus, as Yolando operates in the marketing tech space.

• Framer: Mentioned as a bonus, indicating potential for more advanced interactive prototyping or even light code-based design elements.

📝 Enhancement Note: Figma is the non-negotiable tool. The other tools listed are either context for the product domain (marketing tech, AI) or standard collaboration/analytics platforms that any experienced product designer would likely encounter or understand the implications of.

👥 Team Culture & Values

Operations Values:

• Innovation & Proactivity: Encouraging new ideas and solutions, with a proactive approach to identifying and solving design challenges.

• User-Centricity: A deep commitment to understanding and serving user needs, ensuring simple, intuitive, and delightful experiences.

• Craftsmanship & Quality: A dedication to creating best-in-class interfaces and maintaining brand consistency with attention to detail.

• Collaboration & Communication: Fostering an environment where open communication, feedback, and teamwork are valued.

• Efficiency & Agility: Embracing a fast-paced startup environment that requires quick iteration and adaptability.

Collaboration Style:

• Cross-Functional Partnership: Designers will work closely with Product Managers and Engineers, requiring strong communication and the ability to translate needs across disciplines.

• Iterative Design: A culture of continuous improvement, where designs are regularly reviewed, tested, and refined based on feedback and data.

• Open Feedback: Willingness to give and receive constructive criticism to elevate design quality and foster team growth.

• Shared Ownership: In a startup, team members often feel a sense of shared ownership over the product's success, leading to a collaborative and results-oriented environment.

📝 Enhancement Note: The culture is geared towards innovation and rapid execution, common in funded startups. The designer needs to be comfortable with ambiguity, proactive problem-solving, and contributing to both product usability and brand integrity.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for a Nascent Field (GEO): The Generative Engine Optimization space is relatively new, requiring designers to navigate evolving user expectations and technology capabilities.

• Balancing Product & Brand: Simultaneously driving complex product features and maintaining a cohesive brand identity across diverse touchpoints can be demanding.

• Startup Pace & Ambiguity: Working in a fast-growing startup means adapting to changing priorities, tight deadlines, and evolving requirements.

• Development Handoff Complexity: Ensuring seamless translation of intricate designs into functional code, especially with new technologies.

Learning & Development Opportunities:

• AI/GEO Specialization: Become an expert in designing for AI-powered products and the emerging GEO market.

• Design System Expansion: Contribute significantly to and potentially lead the growth of Yolando's design system.

• Brand Strategy Influence: Gain experience shaping the brand identity of a funded startup.

• Startup Operations: Develop a deep understanding of how product, design, and business operations intersect in a high-growth environment.

• Networking: Connect with experienced professionals in the AI and SaaS industries.

📝 Enhancement Note: The challenges are framed as opportunities for growth. Candidates who thrive in dynamic environments and are eager to learn about cutting-edge technology will find this role particularly rewarding.

💡 Interview Preparation

Strategy Questions:

• "Describe your process for designing a complex user flow, from initial concept to final implementation. How do you ensure it's intuitive and handles edge cases?" (Focus on logical flow design, research, and development readiness.)

• "How do you approach building or contributing to a design system? What are the key principles for making it scalable and developer-friendly?" (Highlight component strategy, documentation, and collaboration with engineers.)

Company & Culture Questions:

• "What interests you about Yolando's mission and the GEO space? How do you see your design skills contributing to our success?" (Showcase research and genuine interest in the company's niche.)

• "How do you handle constructive feedback on your designs, especially in a fast-paced startup environment?" (Demonstrate adaptability, collaboration, and a growth mindset.)

Portfolio Presentation Strategy:

• Storytelling: Frame your case studies as narratives, explaining the problem, your journey, and the impact of your solutions.

• Visual Clarity: Use high-quality visuals (wireframes, mockups, prototypes) to illustrate your points. Ensure your Figma work is well-organized and easy to navigate.

• Focus on Process & Rationale: Be prepared to explain why you made specific design choices, referencing user research, design principles, and business objectives.

• Highlight "Development-Ready": Explicitly point out how your designs are structured for efficient developer handoff, including component usage and annotations.

• Conciseness: Be mindful of time during presentations. Practice delivering your key messages efficiently.

📝 Enhancement Note: The interview process will likely be a deep dive into your portfolio and design process. Be ready to articulate your strategic thinking, demonstrate practical skills, and show how you collaborate effectively. Understanding Yolando's specific niche in GEO and AI will be crucial.

📌 Application Steps

To apply for this operations position:

• Submit your resume, portfolio, and a brief note of interest through the provided application link.

• Portfolio Customization: Ensure your portfolio clearly showcases your Figma expertise, user-centric design process, and experience with design systems. Tailor your case studies to highlight projects that demonstrate your ability to create "development-ready" UX/UI.

• Resume Optimization: Highlight keywords such as "Sr. Product Designer," "UX/UI Design," "Figma," "Design Systems," "Brand Design," "Competitive Intelligence," "GEO," and "SaaS." Quantify achievements wherever possible.

• Interview Preparation: Practice articulating your design process, rationale, and how you handle collaboration and feedback. Be ready to present your portfolio and discuss specific projects in detail, focusing on the impact and user-centricity of your work.

• Company Research: Thoroughly research Yolando, its product (GEO platform), its funding, and its market niche. Understand the challenges businesses face in AI search visibility and how Yolando addresses them. This will help you tailor your application and interview responses.

⚠️ 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.