Principal Product Designer

📍 Job Overview

Job Title: Principal Product Designer
Company: Ottimate
Location: United States (Remote)
Job Type: Full-time
Category: Product Design / User Experience
Date Posted: 2025-10-02
Experience Level: 7+ Years
Remote Status: Fully Remote

🚀 Role Summary

• Lead the strategic direction and execution of large-scale product design initiatives, focusing on foundational improvements to user experience and platform consistency.
• Drive the creation and implementation of a comprehensive, company-wide design system to ensure scalability, efficiency, and a cohesive user interface across all Ottimate products.
• Champion a user-centric design culture by conducting in-depth user research and translating insights into actionable, multi-year design roadmaps.
• Foster strong, collaborative partnerships with Product Management, Engineering, and other cross-functional teams to deliver intuitive and powerful B2B SaaS solutions.

📝 Enhancement Note: This role is critical for a rapidly scaling company, requiring a designer who can not only execute but also strategize and influence. The emphasis on a "design system" and "large-scale design initiatives" points towards a need for a Principal-level designer capable of establishing design governance and foundational UX frameworks. The B2B SaaS context, specifically in FinTech, suggests a need for understanding complex workflows and enterprise-level user needs.

📈 Primary Responsibilities

• Spearhead the design and implementation of a company-wide design system, defining standards for UI components, patterns, and brand expression to ensure consistency and efficiency.
• Lead major redesign efforts for the Ottimate platform, focusing on enhancing the overall look, feel, and usability to meet evolving customer needs and business objectives.
• Plan, execute, and analyze comprehensive user research, including interviews, surveys, and usability testing, to uncover deep user insights and inform strategic product decisions.
• Develop and maintain a multi-year design strategy and roadmap, aligning user needs with business goals and technological capabilities.
• Collaborate closely with product managers and engineers throughout the product development lifecycle, from ideation and wireframing to high-fidelity prototyping and final implementation.
• Act as a vocal advocate for user needs and design best practices, influencing product strategy and fostering a user-centric mindset across the organization.
• Mentor and guide other designers within the team, fostering their professional growth and elevating the overall quality of design output.
• Facilitate design reviews and critiques, providing constructive feedback to ensure high standards of quality and alignment with strategic objectives.

📝 Enhancement Note: The responsibilities highlight a blend of strategic leadership and hands-on execution. The expectation to "plan and conduct comprehensive user research" and translate insights into a "multi-year design plan" signifies a strategic component beyond typical senior designer roles. The emphasis on "clear specifications and high-fidelity prototypes" indicates a need for strong visual and interaction design skills.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in Design, Human-Computer Interaction (HCI), or a related field is highly beneficial. Candidates are evaluated primarily on their portfolio and practical experience.

Experience: 7+ years of dedicated experience in product design, with a significant portion focused on complex B2B or SaaS applications.

Required Skills:

• Design Leadership: Proven ability to lead and drive major design projects, including the successful creation and implementation of a design system from inception.
• User Research Expertise: Deep understanding and practical application of various user research methodologies (interviews, surveys, usability testing) to inform strategic design decisions.
• Systems Thinking: Ability to design for scalability and consistency, understanding the impact of a unified design system across a complex product suite.
• Cross-Functional Collaboration: Demonstrated success in partnering effectively with engineering, product management, and other stakeholders in an agile, remote environment.
• Prototyping & Wireframing: Proficiency in creating high-fidelity prototypes and detailed specifications for development teams.
• Communication Skills: Executive-level communication abilities, capable of articulating design strategy, advocating for users, and inspiring cross-functional teams.
• B2B/SaaS Application Design: Experience designing intuitive and effective user experiences for enterprise software.

Preferred Skills:

• FinTech/AP Experience: Prior experience within the accounts payable, procure-to-pay, or FinTech space.
• Design Advocacy: Experience in actively championing and fostering a strong design culture within an organization.
• Mentorship: Experience guiding and mentoring junior designers.
• Global Collaboration: Comfort working with distributed teams across different geographies and time zones.

📝 Enhancement Note: The requirement for "7+ years of experience" and the emphasis on leading "major design projects" and establishing a "design system from the ground up" clearly positions this as a Principal-level role. The preference for FinTech/AP experience is a strong indicator that understanding financial workflows and compliance is a significant advantage.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least two major design initiatives, such as the end-to-end creation of a design system or a comprehensive product redesign.
• Demonstrate a clear understanding of the problem space, user needs, and business objectives for each project.
• Include detailed examples of user research methodologies employed and how insights directly influenced design decisions.
• Present high-fidelity mockups, interactive prototypes, and clear specifications provided to engineering teams.
• Highlight your role and contributions, particularly in leadership, strategic planning, and cross-functional collaboration.

Process Documentation:

• For each portfolio project, articulate the design process followed, including discovery, ideation, iteration, and implementation phases.
• Detail how you managed design consistency and scalability, especially if a design system was involved or created.
• Explain how user feedback and data were integrated throughout the design lifecycle to refine solutions.
• Provide examples of how you collaborated with engineering and product management to ensure successful product launches.

📝 Enhancement Note: For a Principal Product Designer role, the portfolio needs to go beyond just showcasing final UIs. It must demonstrate strategic thinking, leadership in process definition (like establishing a design system), and a deep understanding of how user research translates into tangible product improvements within a B2B SaaS context. The ability to articulate process and collaboration is as crucial as the visual output.

💵 Compensation & Benefits

Salary Range: $160,000 USD per year.

Benefits:

• Comprehensive Medical, Dental, and Vision insurance plans, subsidized by the company for employees and their families.
• Employer-sponsored 401(k) plan with a company matching contribution.
• Generous Paid Time Off (PTO) policy, with encouragement for employees to utilize their leave.
• Annual company-wide retreats for team building and strategic alignment.
• Opportunities for professional development and advancement, aligned with a "promote-from-within" philosophy.

Working Hours: Standard full-time hours, estimated at 40 hours per week, with flexibility expected given the remote, globally distributed team structure.

📝 Enhancement Note: The provided salary of $160,000 USD per year is competitive for a Principal Product Designer role in the US, especially for a remote position in a growing FinTech startup. The benefits package is robust, covering essential health services, retirement planning, and work-life balance through PTO and retreats. The mention of flexible hours is typical for remote roles supporting international teams.

🎯 Team & Company Context

🏢 Company Culture

Industry: FinTech / Software as a Service (SaaS). Ottimate operates within the rapidly evolving financial technology sector, specifically focusing on automating accounts payable (AP) processes for businesses. This industry is characterized by innovation, a strong emphasis on security, regulatory compliance, and the drive for efficiency.

Company Size: Ottimate is a growing startup, indicating a dynamic and fast-paced environment. This size typically means more direct impact, fewer bureaucratic layers, and opportunities for individuals to shape processes and culture.

Founded: While the founding date isn't explicitly stated, the company's description as being at a "pivotal moment of scale" suggests it has moved past the early seed stage and is in a phase of significant growth and expansion.

Team Structure:

• The design team is likely small but growing, with this Principal Designer expected to be a key leader.
• Collaboration is expected to be highly cross-functional, with close partnerships between Design, Product Management, and Engineering.
• The team operates in a remote-first or hybrid model, requiring strong asynchronous communication skills and a culture of trust.

Methodology:

• Data-Driven Design: The emphasis on user research and translating insights into strategy suggests a data-informed approach to design decisions.
• Agile Development: The mention of an "agile, and remote environment" implies adherence to agile methodologies for product development and design iteration.
• User-Centricity: A core tenet of the culture is advocating for the user at all stages of product development.

Company Website: https://ottimate.com/

📝 Enhancement Note: The company's focus on AI-powered finance automation in the FinTech space means the design challenges are complex, involving sensitive data, critical workflows, and a need for high trust and reliability. The startup environment at a "pivotal moment of scale" offers both significant opportunity for impact and the challenge of building foundational processes.

📈 Career & Growth Analysis

Operations Career Level: Principal Product Designer. This level signifies a senior individual contributor role with significant strategic influence, ownership of large-scale design initiatives, and leadership responsibilities, including mentorship. It's a step above Senior Product Designer, often involving setting design direction and standards for entire product areas or the company.

Reporting Structure: While not explicitly stated, a Principal Product Designer typically reports to a Head of Design, VP of Product, or a similar senior leadership role. They will collaborate closely with Product Management and Engineering leadership.

Operations Impact: This role has a direct and substantial impact on Ottimate's success by shaping the user experience of its AI-powered finance automation platform. A well-designed, intuitive, and efficient product is critical for customer acquisition, retention, and satisfaction in the competitive FinTech market. The Principal Designer's work will influence how effectively finance teams can cut costs, prevent overpayments, and detect fraud, directly contributing to the company's value proposition and revenue growth.

Growth Opportunities:

• Leadership Development: Opportunity to build and lead a design system, influence product strategy, and mentor other designers, laying the groundwork for future design leadership roles.
• Strategic Impact: Play a pivotal role in shaping the future of Ottimate's product vision and user experience during a critical growth phase.
• Industry Expertise: Deepen expertise in FinTech, AI-driven automation, and complex B2B SaaS design challenges.
• Career Advancement: Potential to move into Head of Design or similar leadership positions as the company scales.

📝 Enhancement Note: The "Principal" title indicates a trajectory towards senior leadership and strategic ownership. The growth opportunities are tied to building out foundational design infrastructure (design system) and influencing company-wide product direction, which are key stepping stones for higher-level design leadership roles.

🌐 Work Environment

Office Type: This is a fully remote position. The company has a "people-first" approach to culture, emphasizing support and enabling employees to do their best work.

Office Location(s): While the role is remote, the company mentions "global team" and "domestic and international travel for company retreats and team meetings." This suggests Ottimate may have a distributed workforce across the US and Canada (as per the initial note) and potentially other regions, with physical meetups planned periodically.

Workspace Context:

• Remote Collaboration: The environment is optimized for remote work, requiring strong asynchronous communication tools and practices.
• Technology & Tools: Access to modern design and collaboration tools necessary for remote work and complex B2B SaaS design.
• Team Interaction: While remote, there's an emphasis on connection through virtual interactions and planned in-person retreats, fostering team cohesion and aligned collaboration.

Work Schedule: Full-time, with flexibility expected due to the distributed nature of the team. This allows for effective collaboration across different time zones and personal work style preferences, while still ensuring core business hours are covered for critical meetings and support.

📝 Enhancement Note: The remote-first nature of the role necessitates a high degree of self-discipline and excellent communication skills. The planned travel for retreats indicates a commitment to in-person connection and strategic alignment, which is valuable for building strong team dynamics in a distributed setting.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess experience, skills, and alignment with the role's requirements, particularly focusing on B2B SaaS and design system experience.
• Portfolio Presentation & Discussion: A deep dive into your portfolio, where you'll present 1-2 key projects. Expect to discuss your design process, user research findings, strategic decisions, collaboration with engineering, and the impact of your work. This is a critical stage for demonstrating leadership and systems thinking.
• Cross-Functional Interviews: Meetings with Product Management and Engineering leads to assess your collaboration style, communication effectiveness, and ability to integrate design with technical and business realities.
• Design Leadership/Mentorship Discussion: A conversation focused on your approach to design advocacy, building design systems, and mentoring other designers.
• Final Interview: Typically with a senior leader (e.g., Head of Product or CEO) to assess cultural fit, strategic alignment, and overall suitability for the Principal role.

Portfolio Review Tips:

• Focus on Impact: Quantify the impact of your designs whenever possible (e.g., increased user adoption, reduced support tickets, improved conversion rates).
• Showcase Process: Clearly articulate the "why" behind your design decisions, linking them back to user research and business goals.
• Highlight Leadership: Emphasize your role in leading projects, establishing processes (like design systems), and influencing stakeholders.
• Tailor to Ottimate: If possible, subtly reference how your experience with complex B2B SaaS or financial workflows could benefit Ottimate.
• Prepare for Q&A: Be ready to discuss challenges, trade-offs, and how you handled difficult stakeholder feedback.

Challenge Preparation:

• Be prepared for a potential design exercise, which might involve a case study or a problem-solving scenario related to Ottimate's product domain.
• Practice articulating your thought process clearly and concisely, as if presenting to a mixed audience of designers, engineers, and product managers.
• Consider how you would approach building or evolving a design system for a FinTech product like Ottimate.

📝 Enhancement Note: The interview process is designed to rigorously assess not just design craft but also strategic thinking, leadership, collaboration, and cultural fit. The portfolio presentation is a key gate, requiring candidates to clearly articulate their process, impact, and how they operate at a Principal level.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable given industry trends for collaborative design and system building), Sketch, Adobe Creative Suite (Illustrator, Photoshop).
• User Research: Tools for surveys (e.g., SurveyMonkey, Typeform), interview platforms (e.g., Zoom, Google Meet), and potentially dedicated user research platforms (e.g., UserTesting.com, Lookback).
• Collaboration & Communication: Slack, Microsoft Teams, Zoom for daily communication and meetings. Jira, Asana, Trello for project management and workflow tracking. Confluence for documentation.

Analytics & Reporting:

• While not a direct design tool, familiarity with product analytics platforms (e.g., Mixpanel, Amplitude, Google Analytics) is beneficial for understanding user behavior and measuring design impact.
• Dashboarding tools (e.g., Tableau, Looker) might be used by product teams, so understanding data visualization principles is key.

CRM & Automation:

• While this role is in design, an understanding of CRM systems (e.g., Salesforce) and marketing/sales automation tools can provide context for B2B user journeys and business processes.

📝 Enhancement Note: The specific tools are not listed, but given the context of a modern SaaS company, Figma is almost certainly the primary design tool. Strong proficiency in collaboration and project management tools is essential for a remote Principal Designer. Understanding analytics tools is increasingly important for demonstrating design impact.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and advocating for user needs in all design decisions.
• Excellence & Impact: Striving for high-quality design that drives meaningful business outcomes and customer satisfaction.
• Collaboration & Transparency: Open communication, knowledge sharing, and effective teamwork across functions.
• Innovation & Efficiency: Embracing new technologies (like AI) and modern methodologies to solve complex problems and optimize workflows.
• Integrity & Trust: Essential in FinTech, this translates to designing secure, reliable, and compliant solutions.

Collaboration Style:

• Partnership-Oriented: Working as a close partner with Product Management and Engineering to co-create solutions.
• Data-Informed: Relying on user research and product analytics to guide design direction and validate ideas.
• Iterative & Agile: Embracing an iterative design process that aligns with agile development sprints.
• Advocacy & Influence: Proactively championing design best practices and user needs within the organization.

📝 Enhancement Note: The company emphasizes a "people-first approach" and empowering employees. For a design leader, this translates to an environment where they can influence culture, drive strategic initiatives, and feel supported in their work. The FinTech context adds a layer of responsibility regarding security and compliance in collaborative efforts.

⚡ Challenges & Growth Opportunities

Challenges:

• Establishing a New Design System: Building a design system from the ground up for a complex B2B FinTech product requires significant strategic planning, buy-in, and ongoing maintenance.
• Balancing Innovation with Stability: Implementing AI-driven features while ensuring the core AP processes remain robust, secure, and compliant.
• Remote Collaboration at Scale: Maintaining strong team cohesion, effective communication, and consistent design quality across a distributed and growing team.
• Influencing Cross-Functional Teams: Advocating for design-centric approaches and ensuring user needs are prioritized alongside technical and business constraints.

Learning & Development Opportunities:

• Design Leadership Track: Opportunity to refine leadership skills through mentorship, strategic planning, and potentially building out a design team.
• FinTech & AI Specialization: Deepen expertise in the unique design challenges and opportunities within the FinTech and AI automation space.
• System Design Expertise: Gain extensive experience in designing, implementing, and governing enterprise-level design systems.
• Strategic Product Influence: Contribute significantly to company-wide product strategy and vision.

📝 Enhancement Note: The challenges presented are typical for a Principal-level role in a scaling startup, particularly in a complex domain like FinTech. The growth opportunities are directly aligned with the responsibilities of establishing foundational design processes and influencing product strategy.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the creation of a company-wide design system. What were the biggest challenges, and how did you overcome them?" (Focus on process, adoption, and governance.)
• "How would you approach redesigning a core workflow in our AP automation platform to improve efficiency and user satisfaction?" (Demonstrate your strategic thinking, research approach, and problem-solving skills.)
• "Imagine you have conflicting priorities between engineering constraints and user needs. How do you navigate this to achieve the best outcome?" (Highlight your negotiation, collaboration, and user advocacy skills.)

Company & Culture Questions:

• "What excites you about Ottimate's mission in finance automation?" (Show you've researched the company and understand its market.)
• "How do you foster a user-centric culture within product teams?" (Relate your experiences to Ottimate's stated values.)
• "How do you approach mentoring junior designers and elevating the design quality of a team?" (Connect your mentorship style to Ottimate's "promote-from-within" philosophy.)

Portfolio Presentation Strategy:

• Structure: Begin with the business problem and user need, then walk through your research and ideation process, present key design solutions and their rationale, detail your collaboration with engineering, and conclude with the impact and learnings.
• Quantify Impact: Use data and metrics wherever possible to demonstrate the success of your projects.
• Highlight Leadership: Clearly articulate your role in leading the initiative, making strategic decisions, and influencing outcomes.
• Be Prepared for Deep Dives: Expect detailed questions about your process, decisions, and challenges faced.

📝 Enhancement Note: The interview preparation should focus on demonstrating strategic thinking, leadership in process definition (especially design systems), and a deep understanding of user research and collaboration within a B2B SaaS context. Candidates should be ready to discuss their impact quantitatively and articulate their process with clarity.

📌 Application Steps

To apply for this Principal Product Designer position:

• Submit your application through the provided link on Workable.
• Curate Your Portfolio: Select 1-2 of your most impactful B2B SaaS or complex application design projects that highlight your experience with design systems, user research leadership, and strategic influence. Ensure your portfolio clearly articulates the problem, your process, your solutions, and the measurable impact.
• Tailor Your Resume: Emphasize your 7+ years of experience, specific accomplishments in leading design initiatives, building design systems, and collaborating with cross-functional teams in an agile, remote environment. Integrate keywords such as "Product Design," "Design Leadership," "Design Systems," "User Research," "B2B SaaS," and "FinTech."
• Prepare Your Narrative: Practice articulating your design philosophy, your approach to user-centricity, and your experience in mentoring and advocating for design. Be ready to discuss your strategic vision for a design system and how you would contribute to Ottimate's culture.
• Research Ottimate: Understand Ottimate's product, target market (finance teams, AP departments), and their AI-driven approach to finance automation. Familiarize yourself with their company culture and values as presented on their website and job description.

⚠️ 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.