Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Ajax

Location: New York City, New York, United States

Job Type: FULL_TIME

Category: Product Design / UX/UI Operations

Date Posted: 2026-08-06

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

Remote Status: Hybrid (Primarily in-office, with flexibility)

🚀 Role Summary

• Drive the end-to-end product design process for a SaaS platform solving critical data entry and time-tracking challenges for professional services firms.

• Translate complex, information-heavy workflows into intuitive, delightful, and efficient user experiences, focusing on passive data capture and automated reporting.

• Collaborate closely with engineers, go-to-market teams, and end-users (lawyers, firm administrators) to identify and solve high-impact problems.

• Own the design strategy for core customer trust loops, ensuring seamless integration into daily habits and ultimately eliminating manual timekeeping tasks.

📝 Enhancement Note: While the title is "Senior Product Designer," this role has significant operational impact. The core responsibilities involve optimizing complex business processes (time tracking, data entry, client billing) through design, directly influencing revenue capture and customer retention. Therefore, it aligns with a "UX/UI Operations" or "Product Operations" focus, emphasizing the operational outcomes of design.

📈 Primary Responsibilities

• Conduct in-depth user research by interviewing legal professionals, firm administrators, and internal teams (GTM, Engineering) to deeply understand their workflows, pain points, and needs related to time tracking and client reporting.

• Translate qualitative and quantitative data (e.g., from Posthog, Metabase) into actionable design insights and hypotheses to improve user activation and product adoption.

• Design and prototype intuitive user interfaces and interaction models for capturing, analyzing, and reporting on professional service firm activities, with a focus on passive and automated methods.

• Define and iterate on core user trust loops, ensuring the product reliably captures user activities and generates accurate reports, thereby fostering strong customer retention (aiming for 99% as seen in current metrics).

• Develop strategic design solutions for a "firm intelligence platform" that builds upon the existing time-tracking functionality, enabling richer insights and analytics for clients.

• Actively participate in and contribute to the hiring process for designers and engineers, assessing candidates for technical skill, collaborative potential, and cultural fit.

• Drive the product development lifecycle from problem identification through to shipping and post-launch iteration, ensuring the design is live and delighting users.

📝 Enhancement Note: The "What you'll do" section strongly implies a hands-on role in process definition and problem-solving, extending beyond typical UI design. The responsibilities are framed around understanding and optimizing the operational workflows of client service firms, a key characteristic of operations-focused roles.

🎓 Skills & Qualifications

Education:

• A Bachelor's or Master's degree in Design, Human-Computer Interaction, or a related field is often preferred, though not explicitly stated. A strong portfolio demonstrating equivalent practical experience will be highly valued. Experience:

• Minimum of 5-10 years of professional experience in product design, UX/UI design, or a similar role, with a proven track record of shipping successful products.

• Experience designing complex, information-dense workflows for B2B SaaS products is highly desirable.

• Demonstrated ability to operate independently as a designer and collaborate effectively with engineering teams. Required Skills:

• Portfolio of Shipped Products: A robust portfolio showcasing end-to-end design ownership, from user research and problem definition to final UI implementation and impact.

• User Research & Empathy: Ability to conduct user interviews, synthesize findings, and translate them into user-centered design decisions, particularly within demanding professional environments like law firms.

• Workflow Optimization: Expertise in analyzing, simplifying, and redesigning complex business processes and information-heavy workflows into efficient and user-friendly experiences.

• Interaction Design: Strong skills in designing intuitive user flows, wireframes, and interactive prototypes that enhance usability and user satisfaction.

• Collaboration & Communication: Proven ability to work effectively with cross-functional teams, including engineers, product managers, and go-to-market professionals, articulating design rationale clearly.

• Problem-Solving: A rigorous and brave approach to tackling unsolved problems and a willingness to experiment to find optimal solutions.

Preferred Skills:

• Experience with data analysis tools (e.g., Posthog, Metabase) for hypothesis generation and validation.

• Familiarity with modern front-end technologies (e.g., React) and mobile development frameworks (e.g., Flutter) to understand technical constraints and opportunities.

• Experience in the professional services industry (legal, accounting, consulting) or with time-tracking and billing software.

• Design for passive data capture and automated reporting systems.

📝 Enhancement Note: The "Who you are" and "You'll excel here if" sections provide strong indicators for required skills. The emphasis on "shipped products," "operate independently and collaboratively," and "turn dense, information-heavy workflows into delightful, fast experiences" directly informs the required skills. The role demands not just aesthetic design but functional, process-oriented design.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Shipped Products Showcase: A dedicated section highlighting 2-3 significant products or features you've designed and launched, demonstrating your full design lifecycle ownership.

• Process Optimization Case Studies: Detailed case studies that illustrate your ability to analyze complex, information-heavy workflows, identify inefficiencies, and design solutions that improve user experience and operational outcomes (e.g., reduced time spent on data entry, increased reporting accuracy).

• User Research & Problem Definition: Examples of how you've conducted user research, synthesized findings, and used them to define core problems and design requirements for new features or products.

• System Integration Context: Evidence of how your designs integrate with existing systems or workflows, particularly in a B2B SaaS context, and how they contribute to overall business objectives like customer retention and pilot conversion.

Process Documentation:

• Showcase examples of how you document your design process, including user journey maps, wireframes, interactive prototypes, and potentially user testing reports, demonstrating clarity and thoroughness.

• Highlight your approach to iterating on designs based on user feedback and performance data (e.g., A/B testing results, usage analytics from tools like Posthog).

• Demonstrate your understanding of how design decisions impact system performance, such as the "entry in progress" tracker example, which aimed to improve activation by providing real-time feedback on captured data.

📝 Enhancement Note: The job description emphasizes "ownership" and "work is done when it's live and our users are delighted," implying a need for a portfolio that goes beyond static mockups. It needs to showcase the impact of the design, particularly in optimizing business processes and driving user adoption, which is critical for operations-focused roles.

💵 Compensation & Benefits

Salary Range: $210,000 - $270,000 base salary per year.

• This range is wide to accommodate varying levels of seniority within the "Senior" title, reflecting the company's openness to candidates with a broad spectrum of experience. Offers may exceed this range for exceptional candidates. Benefits:

• Equity: .25% - .75% equity stake in the company, offering significant upside potential as the company grows.

• Unlimited PTO: Flexible paid time off policy, trusting employees to manage their time effectively.

• Paid Lunches & Dinners: Company covers meals on Fridays, fostering team connection and a positive work environment.

• Comprehensive Health Coverage: Medical, Dental, and Vision insurance plans to support employee well-being.

Working Hours:

• The job description implies a standard 40-hour work week, but also emphasizes flexibility and an adult approach to work, as seen in the remote work examples. While the primary work arrangement is in-office (5 days/week), there's explicit mention of flexibility for personal needs.

📝 Enhancement Note: The salary range and equity details are explicitly provided. The "wide range" explanation is crucial for candidates to understand the company's flexibility. The inclusion of "Unlimited PTO" and "Paid lunch/dinner on Fridays" are specific benefits that contribute to the overall employee experience, particularly relevant for demanding roles in fast-paced startups.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / SaaS (specifically focused on professional services automation)

Company Size: Small to Medium-sized (12 employees: 5 engineers, 7 Go-to-Market)

Founded: The company has raised $10 million in venture funding, indicating it's a growth-stage startup with significant traction. The exact founding date isn't specified but implies a relatively recent establishment with rapid development.

Team Structure:

• Lean & Agile: The team is small, comprising 5 engineers and 7 Go-to-Market professionals, including this designer role. This suggests a flat hierarchy and a high degree of individual contribution.

• Cross-functional Collaboration: Close collaboration is essential, with designers working directly with engineers, sales, and customer success teams. The provided sprint example highlights this interdependency.

• Mission-Driven: The team is united by a strong mission to solve a critical, unsolved problem for white-collar businesses, particularly client services firms.

Methodology:

• Data-Driven Experimentation: Ajax utilizes data from tools like Posthog and Metabase to form hypotheses, test them, and iterate rapidly. The sprint example is a prime illustration of this approach.

• Customer-Centric Development: A core tenet is "customer happiness," driving design and engineering decisions to ensure user delight and high retention rates.

• Ownership & Impact: Emphasis on delivering tangible results and seeing designs live and positively impacting users, rather than just completing engineering-ready specs.

Company Website: https://joinajax.com

📝 Enhancement Note: The company description paints a picture of a fast-paced, mission-driven startup with a strong emphasis on customer impact and data-driven decision-making. The small team size means each member plays a critical role, and cross-functional collaboration is paramount.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor (Product Design). This role is positioned as a key individual contributor responsible for significant product areas. It requires a high degree of autonomy and the ability to influence product direction.

Reporting Structure: While not explicitly stated, in a team of 12 with 5 engineers and 7 GTM, a Senior Product Designer would likely report to a Head of Product, CTO, or CEO, depending on the organizational structure. The emphasis on collaboration suggests direct working relationships with engineering leads and GTM managers.

Operations Impact: The role has a direct and significant impact on the company's operational success. By improving time-tracking accuracy and efficiency for client service firms, the designer directly influences:

• Revenue Capture: More accurate time tracking leads to better billing and increased revenue.

• Customer Retention: Solving a critical pain point for users leads to high customer satisfaction and retention rates (currently 99%).

• Sales Efficiency: A delightful and effective product improves pilot conversion rates (currently 96%).

• Product Strategy: Insights gathered from users will shape the future development of the "firm intelligence platform."

Growth Opportunities:

• Product Ownership: Opportunity to own significant product areas and drive their strategic direction, moving beyond task execution to strategic contribution.

• Skill Specialization: Deepen expertise in designing for complex B2B workflows, passive data capture, and user behavior change within professional services.

• Leadership Potential: As the team grows, there may be opportunities to mentor junior designers or take on design leadership responsibilities. The role also involves interviewing and contributing to team composition.

• Startup Growth Experience: Gain invaluable experience in a high-growth startup environment, contributing to scaling processes, product, and team.

📝 Enhancement Note: The role offers substantial ownership and impact within a growing startup. The "operations" aspect of this design role means success is measured by tangible business outcomes like retention and revenue, providing a unique growth trajectory for a designer.

🌐 Work Environment

Office Type: Primarily in-office, with a stated expectation of working 5 days/week in their Tribeca, NYC office. However, the company emphasizes flexibility and treating employees as adults.

Office Location(s): Tribeca, New York City. This is a prime downtown Manhattan location, suggesting a vibrant and accessible work environment.

Workspace Context:

• Collaborative Hub: The office is likely designed to foster collaboration among the small, cross-functional team. Expect an environment where designers, engineers, and GTM professionals work closely together.

• Tooling & Technology: While specific office tech isn't detailed, the company utilizes modern tools for product development (React, Flutter, Python) and analytics (Posthog, Metabase), suggesting a well-equipped tech environment.

• Team Interaction: The emphasis on in-office work, Friday lunches/dinners, and the described sprint example indicates frequent, informal, and formal team interactions are integral to the daily workflow.

Work Schedule: While a standard 40-hour work week is implied, the company culture values flexibility. The example of Tyler working from home and Nat taking time off suggests a pragmatic approach to work-life balance, provided core responsibilities and team collaboration are maintained.

📝 Enhancement Note: The work environment is a hybrid model, leaning heavily towards in-office presence for collaboration, but with a clear acknowledgment of employee autonomy and flexibility. The Tribeca location adds to the appeal.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application, resume, and most importantly, your portfolio. Be prepared to articulate your design process and impact.

• Design Challenge/Case Study: You will likely be asked to present a portfolio case study or complete a design exercise that demonstrates your ability to tackle complex workflow problems, similar to the examples provided in the job description. Focus on showing your thought process, problem-solving approach, and how you measure success.

• Team Interviews: Interviews with engineers and GTM team members to assess collaborative skills, cultural fit, and how you approach problem-solving within a cross-functional team.

• Final Round: Likely with leadership (CEO/CTO) to discuss overall product vision, strategic alignment, and final fit.

Portfolio Review Tips:

• Highlight Operations Impact: For each case study, clearly articulate the problem, your design solution, and the tangible business/operational outcomes achieved (e.g., improved retention, faster processing, reduced errors). Use metrics where possible.

• Showcase Workflow Transformation: Select projects that demonstrate your ability to simplify complex, information-dense workflows. Explain your process for analyzing existing workflows and designing more efficient alternatives.

• Demonstrate Collaboration: Include examples of how you worked with engineers and other stakeholders. Explain how you incorporated feedback and navigated technical constraints.

• Tell a Story: Structure your case studies as narratives – problem, approach, solution, results. Make it engaging and easy to follow.

• Focus on "Why": Be prepared to explain the "why" behind your design decisions, linking them back to user needs and business objectives.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with the challenges faced by professional services firms regarding time tracking, billing, and client management. Research common pain points.

• Process Mapping: Practice mapping out complex workflows and identifying potential areas for simplification or automation.

• Data Interpretation: Be ready to discuss how you would use data (like from Posthog/Metabase) to inform design decisions and measure success.

• Articulate Trade-offs: Be prepared to discuss design trade-offs and how you prioritize features in a fast-paced environment.

📝 Enhancement Note: The interview process and portfolio review will heavily emphasize the candidate's ability to translate complex operational processes into effective user experiences. Candidates should prepare to demonstrate not just design skills, but also a deep understanding of business impact and process optimization.

🛠 Tools & Technology Stack

Primary Design Tools:

• Figma: As a modern design tool, Figma is highly likely to be the primary platform for wireframing, prototyping, and UI design.

• Prototyping Tools: Beyond Figma's capabilities, dedicated prototyping tools might be used for more complex interactions.

Analytics & Reporting Tools:

• Posthog: Explicitly mentioned for data capture and analysis, used for hypothesis generation and understanding user behavior.

• Metabase: Also explicitly mentioned for data analysis, likely used to query and visualize data to inform product decisions.

Development & Implementation Context:

• React: The front-end framework used by the company, meaning designers should understand its capabilities and constraints.

• Flutter: The framework for their native app, indicating a need for cross-platform design considerations.

• Python: Used for backend development, suggesting an understanding of how data processing and backend logic might influence the user experience.

Other Potential Tools:

• Project Management Software: Tools like Jira, Asana, or Trello are common in agile environments for task tracking.

• Collaboration Tools: Slack or similar for daily communication.

📝 Enhancement Note: The explicit mention of Posthog and Metabase highlights the data-centric nature of this role. Designers are expected to be comfortable using these tools to inform their work, which is a key differentiator for operations-focused design roles.

👥 Team Culture & Values

Operations Values:

• Customer Happiness: This is the primary driver, stated verbatim from their engineer. All design and product decisions should prioritize user satisfaction and delight.

• Ownership: Taking full responsibility for features from conception to live deployment and user impact, not just handing off designs.

• Brave & Rigorous Exploration: A culture that encourages experimentation and learning from failures in pursuit of solving difficult, unsolved problems.

• Efficiency & Automation: A core mission is to free professionals from time-consuming data entry by automating processes, reflecting a value for efficiency.

• Data-Driven Decision Making: Utilizing data from tools like Posthog and Metabase to validate hypotheses and guide product development.

Collaboration Style:

• Cross-functional Integration: Designers work hand-in-hand with engineers and GTM teams, participating in sprints and contributing to problem-solving from ideation to deployment.

• Open Communication: The emphasis on treating employees as adults and the flexible work arrangements suggest a culture of trust and open communication.

• Feedback-Oriented: The iterative nature of their sprint example implies a continuous feedback loop among team members and with users.

• Pragmatic & Impactful: The focus is on shipping impactful solutions that delight users, rather than getting bogged down in process for process's sake.

📝 Enhancement Note: The culture is clearly defined around customer obsession, ownership, and iterative, data-informed product development. This is a crucial aspect for candidates to understand, as it dictates how work is done and how success is measured.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Habit Change: The core challenge is designing a system that users will adopt and integrate into their daily habits, ultimately replacing a deeply ingrained (and often disliked) manual process. This requires deep behavioral design expertise.

• Balancing Complexity and Simplicity: Translating dense, information-heavy workflows for professional services into intuitive and fast user experiences is inherently difficult.

• Solving an Unsolved Problem: Ajax is tackling a fundamental inefficiency in a large market with novel approaches, meaning there isn't a clear established playbook. This requires significant creative problem-solving and resilience.

• Data Capture Fidelity: Ensuring the passive data capture is accurate and reliable enough to be trusted by professionals who bill by the hour is a significant technical and design challenge.

Learning & Development Opportunities:

• Deep Domain Expertise: Opportunity to become an expert in the operational challenges of legal, accounting, and consulting firms, understanding their specific needs and workflows.

• Product Strategy Influence: Contribute directly to shaping the product roadmap and the strategic direction of a growing SaaS company.

• Advanced UX/UI Skills: Hone skills in behavioral design, complex workflow optimization, and designing for automation in a B2B context.

• Startup Growth Experience: Gain invaluable experience in scaling a product and team from an early stage, understanding the full lifecycle of a startup.

• Mentorship & Leadership: Potential to grow into a design leadership role as the company expands, mentoring other designers and influencing design culture.

📝 Enhancement Note: The challenges are significant but directly tied to high-impact growth opportunities. Candidates who thrive on solving complex, real-world problems will find this role particularly rewarding.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you transformed a complex, information-heavy workflow into a simple and delightful user experience. What was your process, and what was the impact?" (Focus on workflow analysis, design decisions, and quantifiable results.)

• "How would you approach designing a 'firm intelligence platform' that builds upon our existing time-tracking functionality? What key features would you prioritize and why?" (Demonstrate strategic thinking and understanding of user needs beyond basic timekeeping.)

• "Ajax's primary reward function is customer happiness. How do you incorporate this into your design process, especially when dealing with potentially frustrating tasks like time tracking?" (Showcase empathy and a user-centric approach.) Company & Culture Questions:

• "What excites you about Ajax's mission to solve the time-tracking problem for professional services firms?" (Demonstrate research and alignment with the company's purpose.)

• "How do you approach collaboration with engineers and go-to-market teams, especially in a fast-paced startup environment?" (Highlight your teamwork and communication skills.)

• "Given our focus on data analysis (Posthog, Metabase), how do you see yourself using data to inform your design decisions?" (Showcase your data literacy and analytical approach.) Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline the problem, your user research, your design process (wireframes, prototypes), the final solution, and most importantly, the measurable impact.

• Quantify Success: Use metrics like retention rates, pilot conversion improvements, time saved, or error reduction to demonstrate the value of your work. If exact numbers aren't available, use estimations with clear assumptions.

• Show, Don't Just Tell: Walk through interactive prototypes or mockups to illustrate your design. Explain the rationale behind key UI/UX decisions.

• Highlight Collaboration: Specifically mention how you collaborated with engineers and other stakeholders, and how you navigated feedback or technical constraints.

• Connect to Ajax: Relate your experiences and skills back to Ajax's specific challenges and goals (e.g., designing for passive capture, simplifying complex workflows, achieving high customer retention).

📝 Enhancement Note: The interview preparation should focus on demonstrating an understanding of business operations, process optimization, and data-driven design. Candidates need to show they can translate design skills into tangible business outcomes.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your portfolio to highlight projects that demonstrate your experience in designing complex B2B SaaS workflows, process optimization, and achieving measurable user/business impact. Focus on case studies that show your end-to-end ownership from problem definition to shipped product.

• Resume Optimization: Ensure your resume clearly articulates your experience in product design, UX/UI, and any relevant operations or workflow optimization experience. Use keywords such as "workflow optimization," "user experience design," "SaaS," "B2B," and "product strategy." Quantify achievements wherever possible.

• Prepare for Case Study Presentation: Be ready to walk through 1-2 of your strongest case studies in detail, focusing on the problem, your process, the solution, and the quantifiable results. Practice explaining the "why" behind your design decisions and how they align with business objectives.

• Company Research: Thoroughly research Ajax, its mission, its product, and its target market (professional services firms). Understand the pain points of time tracking and data entry in this industry.

⚠️ 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.

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