Senior Product Designer - WorkHero

📍 Job Overview

Job Title: Senior Product Designer
Company: WorkHero (Workshop Venture Partners)
Location: Boston, MA (Hybrid)
Job Type: FULL_TIME
Category: Product Design / GTM Operations Enablement
Date Posted: 2025-10-27
Experience Level: 4+ Years
Remote Status: Hybrid

🚀 Role Summary

• Drive product vision and strategy: Collaborate directly with founders to define and execute the product roadmap for an AI-powered back-office platform targeting the HVAC industry.
• End-to-end design ownership: Lead the entire design lifecycle, from in-depth customer research and problem definition to high-fidelity designs, prototyping, and iterative user feedback integration.
• Deep customer immersion: Dedicate a significant portion of your time (30%+) to direct user research with contractors and office managers, understanding their operational challenges and workflows.
• Design for complex AI workflows: Conceptualize and design seamless integrations between AI agents and human oversight, ensuring automation feels reliable and intuitive for non-technical users.
• Establish design foundations: Develop and maintain design systems, interaction patterns, and quality standards to ensure consistent, high-quality user experiences across the platform as the company scales.

📝 Enhancement Note: While this role is primarily Product Design, its focus on AI-powered back-office operations for skilled trades places it at the intersection of product and GTM Operations Enablement. The designer will be crucial in creating tools that directly impact the operational efficiency and GTM success of WorkHero's target customers. The emphasis on customer research and understanding complex workflows is a direct parallel to operations roles focused on process optimization.

📈 Primary Responsibilities

• Conduct extensive qualitative and quantitative user research, including interviews, surveys, and contextual inquiries, with HVAC contractors and office managers to uncover unmet needs and pain points.
• Translate complex operational workflows, such as invoicing, permit applications, rebate processing, and warranty registration, into intuitive and user-friendly designs.
• Design user interfaces and interactions for a multi-platform product suite, including a contractor-facing mobile application, internal tools for office managers, and AI-driven workflow automation systems.
• Develop and maintain a comprehensive design system, including UI components, style guides, and interaction patterns, to ensure brand consistency and accelerate design and development cycles.
• Create high-fidelity mockups, interactive prototypes, and detailed specifications for engineering teams, ensuring accurate implementation of design intent.
• Partner closely with product management and engineering to define product requirements, prioritize features, and ensure timely, high-quality product releases.
• Champion a user-centered design approach throughout the organization, advocating for user needs and providing data-backed design recommendations.
• Experiment with and design for AI-powered features, focusing on creating trust and transparency for users interacting with automated systems.
• Contribute to shaping the overall product strategy and vision by bringing a user-centric perspective to strategic discussions with leadership.

📝 Enhancement Note: The core responsibility of "designing for AI-enabled workflows" and "understanding complex operational workflows" highlights how this design role directly supports operational efficiency for WorkHero's clients. This requires a deep understanding of business processes, similar to a Business Analyst or Operations Specialist.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's or Master's degree in Design, Human-Computer Interaction, or a related field is often preferred. Equivalent practical experience will be strongly considered.
Experience: 4+ years of professional experience in product design, with a proven track record of delivering end-to-end design solutions for complex digital products.

Required Skills:

• End-to-End Product Design: Demonstrated ability to manage the full design process from user research, ideation, wireframing, prototyping, to high-fidelity UI design and user testing.
• User Research & Synthesis: Expertise in qualitative research methodologies (interviews, contextual inquiries) and the ability to synthesize findings into actionable design insights.
• Prototyping & Wireframing: Proficiency with industry-standard design tools such as Figma, Sketch, Adobe XD, or similar for creating interactive prototypes and detailed wireframes.
• Design Systems: Experience in creating, maintaining, and scaling design systems to ensure product consistency and efficiency.
• AI/ML Product Understanding: Demonstrated curiosity and foundational understanding of AI/ML concepts and how they can be applied to improve user experiences and automate workflows.
• Strategic Product Thinking: Ability to understand business objectives, market dynamics, and translate them into effective design strategies that drive product success.
• Complex Problem Solving: Aptitude for taking intricate, multi-step processes and designing elegant, simplified user experiences.
• Exceptional Communication: Clear and concise verbal and written communication skills, with the ability to articulate design rationale and influence stakeholders.
• Cross-functional Collaboration: Proven ability to work effectively with product managers, engineers, and other cross-functional teams.
• Early-Stage Startup Adaptability: Comfort with ambiguity, a proactive approach to problem-solving, and the ability to thrive in a fast-paced, evolving environment.

Preferred Skills:

• Small Business/Blue-Collar UX: Prior experience designing for small business owners, field service professionals, or blue-collar workers.
• Industry Knowledge: Familiarity with the HVAC, plumbing, electrical, or other home services industries.
• AI Feature Shipping: Experience designing and shipping products with AI-powered features or agent-based functionalities.
• Mobile Design: Proficiency in designing native mobile applications for iOS and Android platforms.
• Previous Startup Experience: Experience working in early-stage (pre-Series A) startups.

📝 Enhancement Note: The emphasis on "designing for complexity" and "AI-enabled workflows" directly relates to operational efficiency. Candidates with experience in designing operational tools or improving business process workflows will have a distinct advantage.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Case Studies: Showcase at least 2-3 comprehensive case studies demonstrating your involvement in the entire product design lifecycle, from initial research to shipped product.
• User Research & Problem Definition: Clearly articulate the user problems you identified and the research methodologies used to uncover them. Highlight how insights directly informed design decisions.
• Design Process & Iteration: Detail your design process, including wireframing, prototyping, user testing, and how you iterated on designs based on feedback.
• High-Fidelity Designs & UI Craft: Present polished, high-fidelity mockups and interactive prototypes that demonstrate strong visual design principles and interaction design expertise.
• System Thinking: Include an example of your work on a design system, component library, or pattern documentation, illustrating your ability to create scalable and consistent design solutions.
• Impact & Outcomes: Quantify the impact of your design work where possible, using metrics related to user adoption, task completion rates, efficiency gains, or business outcomes.

Process Documentation:

• Workflow Mapping: Demonstrate your ability to visually map and analyze complex operational workflows.
• User Journey Mapping: Showcase user journey maps that illustrate the user's experience with a product or service, identifying key touchpoints and opportunities for improvement.
• Design System Documentation: If applicable, provide examples of how you've documented design system components, patterns, and guidelines.

📝 Enhancement Note: For this role, the portfolio should heavily emphasize how the candidate's design solutions directly improved user efficiency, reduced cognitive load, or streamlined complex operational tasks, particularly in the context of AI integration.

💵 Compensation & Benefits

Salary Range: $120,000 - $160,000 USD per year.

Benefits:

• Competitive Salary: A strong base salary commensurate with experience and the impact of the role.
• Meaningful Equity: Significant stock options or equity grants, reflecting the foundational nature of this hire and the company's growth potential.
• Comprehensive Health Benefits: Medical, dental, and vision insurance for employees and dependents.
• Flexible Work Environment: A hybrid work model that balances in-office collaboration with remote flexibility.
• Professional Development: Opportunities for continuous learning, skill enhancement, and attending relevant industry events.
• Mission-Driven Culture: Working with a team passionate about making a tangible impact on small businesses.

Working Hours: Standard full-time hours (approximately 40 hours per week), with flexibility offered due to the hybrid work arrangement. Core collaboration hours are expected.

📝 Enhancement Note: The salary range provided is competitive for a Senior Product Designer role in the Boston area, especially for an early-stage, venture-backed startup. The inclusion of meaningful equity is a significant draw for candidates looking to be part of a company's growth trajectory.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (SaaS), focused on AI and Back Office Operations for Skilled Trades (specifically HVAC).
Company Size: Early-stage startup (likely <50 employees, given recent seed funding). This means a hands-on environment where individuals wear multiple hats and have significant influence.
Founded: 2022 (Workshop Venture Partners is the parent/investor, WorkHero is the product/company being built).

Team Structure:

• Founders: Direct collaboration with CEO and CTO.
• Core Product & Engineering Team: Small, agile team focused on rapid development and iteration.
• Operations Focus: The company's core mission is to support and optimize the operations of small businesses in the skilled trades.
• Cross-functional Collaboration: High degree of interaction between Product, Design, Engineering, and early Customers/Operations teams.

Methodology:

• Agile Development: Likely employing agile methodologies for iterative product development.
• User-Centric Design: Strong emphasis on understanding and solving customer problems through design.
• AI-Driven Innovation: Leveraging AI as a core technology to automate complex tasks and improve efficiency.
• Data-Informed Decisions: Using data from user behavior and customer feedback to guide product improvements.

Company Website: https://www.workshop.dev/ (This is for Workshop Venture Partners, the investor. WorkHero likely has its own site or will develop one.)

📝 Enhancement Note: As an early-stage company, WorkHero's culture will be heavily influenced by its founders and initial hires. The emphasis on AI and serving small businesses in the trades suggests a culture that values innovation, practical problem-solving, and a deep understanding of customer needs.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a "Senior" Product Designer. It's a foundational hire, meaning the individual will be instrumental in shaping the product's user experience and design processes from an early stage. This offers significant opportunities for growth into a Design Lead or Head of Design role as the company scales.

Reporting Structure: The Senior Product Designer will report directly to the CEO or CTO, indicating a high level of visibility and direct influence on product strategy.

Operations Impact: The designer's work will have a direct and substantial impact on the operational efficiency, profitability, and growth of WorkHero's target customers (HVAC contractors). By creating intuitive and powerful tools, this role enables small businesses to reduce administrative burdens, improve their service delivery, and scale their operations more effectively. This is a critical GTM enablement function.

Growth Opportunities:

• Design Leadership: Potential to build and lead a design team, establish design best practices, and define the design roadmap as the company grows.
• Product Strategy Influence: Deep involvement in product strategy and vision, with the ability to influence the direction of the company's core offerings.
• AI Product Specialization: Gaining expertise in designing for AI-driven products and human-AI collaboration, a rapidly growing field.
• Industry Expertise: Developing deep knowledge of the skilled trades industry and its operational challenges.
• Startup Scaling Experience: Gaining invaluable experience in scaling a technology company from an early stage.

📝 Enhancement Note: The "Operations Impact" section highlights the critical GTM enablement aspect of this design role. The ability to improve a client's operational efficiency is a key metric for success, aligning it closely with operations-focused roles.

🌐 Work Environment

Office Type: Hybrid work environment. While based in Boston, MA, the role allows for remote work with expectations for in-office collaboration.
Office Location(s): Boston, MA, United States.

Workspace Context:

• Collaborative Hub: The office will serve as a hub for in-person collaboration, brainstorming sessions, and team-building activities.
• Tools & Technology: Access to modern design tools (Figma, etc.), collaboration software, and potentially internal tools for AI workflow management.
• Direct Interaction: Opportunities for frequent interaction with founders, engineering, and potentially customer-facing teams to gain insights into operational challenges.

Work Schedule: A flexible hybrid schedule is provided, allowing for remote work days alongside in-office days for key collaborative activities. Employees are expected to manage their time effectively to meet project deadlines and achieve operational goals.

📝 Enhancement Note: The hybrid nature of the work environment for a design role focused on operational efficiency implies a need for structured in-office days for deep collaboration and ideation, while remote days can be used for focused design work and research synthesis.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter or hiring manager to assess basic qualifications and cultural fit.
• Portfolio Presentation & Discussion: A dedicated session where you'll walk through your portfolio, focusing on 2-3 key case studies. Be prepared to discuss your design process, research insights, decision-making, and the impact of your work. Expect questions on how you'd approach designing for AI and complex operational workflows.
• Design Challenge/Take-Home Assignment: You may be given a design problem (e.g., designing a key feature for the contractor app, or an AI workflow interface) to assess your problem-solving skills, design craft, and ability to work within constraints.
• Founder/Team Interviews: In-depth discussions with the CEO and CTO, focusing on strategic thinking, product vision, collaboration style, and alignment with the company's mission. You'll also likely meet with engineering leads to discuss technical feasibility and collaboration.
• Final Round: Potentially a discussion with advisors or key stakeholders.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the business and user impact of your designs. Quantify results whenever possible.
• Showcase Process: Detail your thought process, research methods, and how you navigated challenges and iterations.
• Highlight AI & Complexity: For this role, specifically emphasize any experience designing for AI, automation, or complex, multi-step operational processes.
• Tell a Story: Structure your case studies as narratives with a clear problem, your solution, and the outcome.
• Be Prepared for Deep Dives: Expect detailed questions about your design decisions, user research, and how you collaborate with engineering.

Challenge Preparation:

• Understand the User: Research the HVAC industry and common operational pain points for contractors and office managers.
• Think AI-First: Consider how AI can solve specific problems and how to design for user trust and transparency with AI.
• Prioritize & Scope: Understand that in a startup, you'll need to make trade-offs. Be prepared to discuss how you'd scope a solution and prioritize features.
• Communicate Clearly: Practice articulating your design rationale and presenting your solutions concisely and effectively.

📝 Enhancement Note: The emphasis on AI and complex operational workflows in the interview and portfolio review process means candidates should prepare specific examples of how they've tackled similar challenges, even if not directly in the HVAC industry.

🛠 Tools & Technology Stack

Primary Design Tools:

• Figma: The industry standard for UI/UX design, prototyping, and collaboration. Essential for this role.
• Sketch: Another popular design tool, though Figma is increasingly dominant.
• Adobe Creative Suite (Illustrator, Photoshop): Useful for asset creation and image editing.

Prototyping Tools:

• Figma Prototyping: For creating interactive prototypes directly within Figma.
• InVision, Principle, ProtoPie: May be used for more advanced or specific prototyping needs.

User Research & Collaboration Tools:

• Miro or Mural: For collaborative whiteboarding, journey mapping, and brainstorming.
• UserTesting.com, Lookback, or similar: For remote usability testing.
• Google Workspace (Docs, Sheets, Slides): For documentation, presentations, and data analysis.
• Slack: For team communication and collaboration.

AI Considerations:

• While not a direct tool requirement for the designer, familiarity with AI concepts and potential AI platforms or APIs that could be integrated into the product would be beneficial.

📝 Enhancement Note: Proficiency in Figma is paramount. The ability to use collaborative tools like Miro/Mural is also crucial for a hybrid/remote team environment focused on complex problem-solving and operational workflow design.

👥 Team Culture & Values

Operations Values:

• Customer Obsession: Deeply understanding and prioritizing the needs of small business owners in the skilled trades.
• Impact-Driven: Focusing on delivering tangible value and operational improvements for customers.
• Innovation & AI-Forward: Embracing cutting-edge technology, particularly AI, to solve complex problems.
• Simplicity & Ease of Use: Making powerful technology accessible and effortless for non-technical users.
• Collaboration & Ownership: Working together effectively and taking responsibility for outcomes.
• Integrity & Trust: Building reliable systems and fostering trust with customers and team members.

Collaboration Style:

• Cross-functional Partnership: Working closely with founders, engineering, and potentially operations specialists to ensure a holistic product approach.
• Open Communication: Encouraging direct and honest feedback to drive continuous improvement.
• User-Centric Decision Making: Basing product and design decisions on user research and feedback.
• Iterative Development: Embracing a cycle of building, testing, and refining based on real-world usage.

📝 Enhancement Note: The "Impact-Driven" value directly aligns with operations and GTM goals. The emphasis on "Simplicity & Ease of Use" for complex operational tasks is a key design challenge that resonates with operations professionals.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for a Diverse User Base: Catering to the needs of small business owners who may have varying levels of technical proficiency and operate in diverse environments.
• Integrating AI Seamlessly: Creating intuitive interfaces for AI-powered workflows that build trust and ensure reliability for users who might be skeptical of automation.
• Balancing Complexity and Simplicity: Designing for intricate back-office operations (invoicing, permits, etc.) while maintaining a simple, user-friendly experience.
• Early-Stage Ambiguity: Navigating a rapidly evolving product roadmap and evolving business needs common in early-stage startups.
• Establishing Design Foundations: Building a robust design system and processes from the ground up in a fast-growing company.

Learning & Development Opportunities:

• AI Product Design Specialization: Deepening expertise in designing for AI-driven products and human-AI interaction.
• Industry Expertise Acquisition: Becoming a subject matter expert in the operational challenges of the HVAC and skilled trades industries.
• Leadership Development: Opportunities to grow into a design leadership role, mentor junior designers, and shape the future of the design function.
• Startup Scaling Experience: Learning firsthand how to build and scale a technology company, contributing to product strategy and business growth.
• Advanced Design Methodologies: Exploring and implementing cutting-edge design research and prototyping techniques.

📝 Enhancement Note: The challenge of "Integrating AI Seamlessly" is a critical operational enablement task. Designing for trust and reliability in automation is key to driving adoption and efficiency gains for WorkHero's clients.

💡 Interview Preparation

Strategy Questions:

• Scenario-Based: "Imagine a contractor is struggling to understand why an AI-generated invoice is incorrect. How would you design an interface that helps them quickly identify the discrepancy and resolve it?" (Focus on error states, transparency, and user control).
• Product Vision: "How would you approach designing the core experience for a contractor who needs to manage permits for multiple jobs simultaneously, considering AI assistance?" (Focus on workflow, prioritization, and AI integration).
• Process Optimization: "Describe a time you designed a solution that significantly improved the efficiency of a complex user workflow. What was the process, and what were the results?" (Prepare a case study focusing on operational efficiency).

Company & Culture Questions:

• Mission Alignment: "Why are you excited about WorkHero's mission to serve small businesses in the skilled trades?"
• AI Curiosity: "What are your thoughts on the role of AI in back-office operations, and how do you see it impacting the future of trades businesses?"
• Startup Fit: "How do you typically approach working in an ambiguous, fast-paced startup environment?"

Portfolio Presentation Strategy:

• Start with the "Why": Clearly articulate the problem you were solving for the user and the business.
• Show, Don't Just Tell: Use visuals, prototypes, and user flows to illustrate your solutions.
• Emphasize Your Role: Be specific about your contributions, especially in collaborative projects.
• Quantify Impact: Present metrics and outcomes that demonstrate the success of your designs.
• Discuss Trade-offs: Explain the decisions you made and why, including any constraints or compromises.
• Tailor to WorkHero: Frame your case studies in a way that shows how your skills are directly applicable to WorkHero's challenges (AI, operational efficiency, small business users).

📝 Enhancement Note: Candidates should prepare specific examples of how they have designed for efficiency, automation, or complex operational tasks, even if the industry differs from HVAC. Highlighting experience with AI integration or user trust in automated systems will be particularly valuable.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Ashby.
• Portfolio Customization: Ensure your portfolio prominently features 2-3 detailed case studies showcasing end-to-end product design, user research, and ideally, experience with complex workflows or AI integration. Tailor your presentation to highlight how your skills address WorkHero's mission.
• Resume Optimization: Update your resume to clearly articulate your 4+ years of product design experience, focusing on achievements related to user research, problem-solving, design systems, and driving impact. Use keywords relevant to product design, AI, and operational efficiency.
• Prepare Your Story: Practice articulating your design process, your approach to user research, and how you translate complex needs into intuitive solutions. Be ready to discuss your experiences with AI and your understanding of small business operations.
• Research WorkHero: Familiarize yourself with WorkHero's mission, the HVAC industry's operational challenges, and the potential of AI in back-office automation. Understand Workshop Venture Partners' approach to investing in early-stage companies.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and industry-standard assumptions to provide a comprehensive overview. All details should be verified directly with WorkHero (Workshop Venture Partners) during the application and interview process.