Principal Designer

📍 Job Overview

Job Title: Principal Designer

Company: Modern Life

Location: New York, NY

Job Type: Full Time

Category: Design Operations / GTM Design

Date Posted: 2026-11-05

Experience Level: 8+ Years

Remote Status: Hybrid (4 days/week in office)

🚀 Role Summary

• Lead end-to-end design strategy and execution across product, brand, and marketing initiatives, ensuring a cohesive and high-quality user experience.

• Establish and maintain design standards, including the development and governance of a comprehensive Figma library and design system to ensure consistency and scalability.

• Manage and direct a bench of specialty design contractors (brand, illustration, graphic, UI/UX) by effectively scoping projects, providing clear briefs, and conducting thorough reviews.

• Shape the collaboration model between design, product, and engineering teams, defining best practices for user research and design integration into the product development lifecycle.

• Champion the adoption and innovative use of AI-native tools for rapid prototyping and pushing the boundaries of design capabilities.

📝 Enhancement Note: This role is positioned as a foundational, individual contributor (IC) role for the initial 6-12 months, with a strong emphasis on "doing the work" and establishing core design infrastructure. The "Principal" title signifies seniority and the expectation of strategic influence and ownership, rather than direct people management at this stage. The core focus is on building the groundwork for a future design team.

📈 Primary Responsibilities

• Own the complete design lifecycle for all digital products, brand assets, and marketing collateral, from initial user research and conceptualization through to final shipped work.

• Define, document, and enforce design quality standards, best practices, and guidelines across all touchpoints, ensuring alignment with Modern Life's brand identity and user experience goals.

• Oversee the creation and maintenance of a robust design system within Figma, ensuring its usability, scalability, and adoption across the organization.

• Lead the strategic direction and day-to-day management of external design contractors, including project scoping, creative brief development, feedback provision, and quality assurance to ensure successful delivery of specialized design work.

• Collaborate closely with Product Management and Engineering leads to refine the product development process, integrating user-centered design principles and establishing efficient workflows for user research, usability testing, and design iteration.

• Actively explore and implement AI-native design tools and methodologies to accelerate prototyping, enhance creative exploration, and drive innovation in design workflows.

• Translate complex insurance industry workflows and B2B/B2C interactions into intuitive, user-friendly interfaces for both advisors and end clients.

• Contribute to strategic decision-making by articulating the business value of design initiatives and aligning design outcomes with key business objectives and company growth targets.

• Build the foundational processes, documentation, and team collaboration frameworks that will serve as the blueprint for a future, scaled design team.

📝 Enhancement Note: The emphasis on "product depth and visual and brand range" indicates a need for a versatile designer capable of both strategic UX/UI thinking and strong visual/brand identity development. The "AI-native tools" aspect suggests a forward-thinking company looking to leverage emerging technologies in their design process.

🎓 Skills & Qualifications

Education:

• While no specific degree is mandated, a Bachelor's degree in Design, Human-Computer Interaction (HCI), Graphic Design, or a related field is often preferred for senior design roles. Equivalent practical experience will be strongly considered. Experience:

• Minimum of 8 years of progressive experience in digital product design, with a significant portion spent in senior or lead individual contributor roles.

• Demonstrated experience working within or leading small, agile teams, or specifically as a solo designer responsible for broad design ownership.

• Proven track record of successfully managing and directing external design contractors or vendors, including scoping, briefing, and quality control.

• Experience in setting design standards, developing design systems, and establishing design best practices within an organization. Required Skills:

• Product Design: Deep expertise in user-centered design methodologies, wireframing, user flow mapping, prototyping, and usability testing for complex digital products.

• Visual & Brand Design: Strong aesthetic sensibility and proven ability to develop and maintain a compelling visual identity, including typography, color theory, and layout.

• Design Systems & Figma Proficiency: Advanced skills in creating, managing, and scaling design systems within Figma, including component libraries, style guides, and documentation.

• User Research: Experience planning, conducting, and synthesizing qualitative and quantitative user research to inform design decisions and validate solutions.

• Contractor Management: Ability to effectively scope design projects, provide clear creative briefs, manage timelines, and deliver constructive feedback to external design partners.

• Prototyping Tools: Proficiency with modern prototyping tools (e.g., Figma, potentially tools like Framer, ProtoPie) and an eagerness to explore and leverage AI-native design tools.

• Cross-functional Collaboration: Excellent communication and interpersonal skills to partner effectively with product managers, engineers, marketing, and leadership.

Preferred Skills:

• B2B / Fintech / Insurance Workflow Experience: Prior experience designing solutions for complex business-to-business environments, financial technology, or the insurance sector.

• AI-Native Design Tool Proficiency: Hands-on experience with emerging AI tools for design ideation, content generation, or workflow automation.

• Design Leadership Acumen: While not a people management role initially, experience in mentoring junior designers or leading design initiatives is highly valued.

• Strategic Planning: Ability to contribute to product strategy and roadmap development from a design perspective.

📝 Enhancement Note: The requirement for "8+ years" and "Principal Designer" title strongly suggests an expectation for strategic thinking, ownership, and the ability to operate with significant autonomy, akin to a senior leader even in an IC capacity. The mention of "AI-native tools" is a key differentiator, indicating a company that embraces technological innovation.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing a minimum of 8 years of professional design work, with a clear emphasis on digital product design and brand development.

• Demonstrate depth in product design, including case studies detailing problem definition, user research methodologies, design process, iterations, and measurable outcomes.

• Exhibit breadth in visual and brand design, presenting examples of brand identity development, marketing collateral, and campaign design.

• Include examples of experience setting design standards, developing design systems, or managing design quality across multiple projects or platforms.

• Showcase experience in directing or managing external contractors, with examples of project scoping, briefing, and quality assurance processes. Process Documentation:

• Case studies should clearly articulate the design process followed, from initial problem identification and research through to final implementation and impact assessment.

• Demonstrate a structured approach to user research, including methodologies used, participant recruitment, and how insights were translated into design solutions.

• Provide evidence of experience in establishing or contributing to design systems, detailing the components, guidelines, and governance model.

• Highlight how design decisions were tied to business objectives and user needs, ideally with quantifiable results or key performance indicators (KPIs) where available.

📝 Enhancement Note: For a Principal level role, especially one focused on establishing foundations, the portfolio should not just show finished products but also the process of how those products were conceived, designed, and scaled. Evidence of system-building and standard-setting is crucial.

💵 Compensation & Benefits

Salary Range: $220,000 - $260,000 USD per year

• This salary range is competitive for a Principal Designer role in New York City, reflecting the high cost of living and the seniority and specialized skills required for this position. The range accommodates significant experience and the expectation of strategic leadership within an individual contributor capacity. Benefits:

• Competitive Equity Package: Significant stock options or equity grants, aligning the Principal Designer's success with the company's growth and long-term value.

• Comprehensive Health Insurance: Medical, dental, and vision insurance plans to support employee well-being.

• 401(k) Plan: Retirement savings plan to help employees plan for their future.

• Paid Time Off (PTO): Generous vacation, sick leave, and holiday policies.

• Professional Development: Opportunities for continued learning, attending industry conferences, and skill enhancement.

• Hybrid Work Environment: A structured hybrid model offering a balance between in-office collaboration and remote flexibility.

Working Hours:

• Standard full-time hours, approximately 40 hours per week, with flexibility expected due to the dynamic nature of a high-growth startup environment. The hybrid model requires 4 days per week in the New York City office.

📝 Enhancement Note: The salary range is explicitly provided, which is excellent. The "Competitive equity package" is a significant component for a Principal role in a VC-backed startup, indicating a strong incentive for long-term commitment and company success.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Services (Life Insurance Brokerage) / Technology

Company Size: High-growth startup, likely between 50-200 employees based on funding and stage.

Founded: Modern Life was founded to modernize the complex and consequential life insurance purchase process through technology and expert advice.

Team Structure:

• The design function is currently a solo role, with the Principal Designer acting as the de facto leader and sole in-house designer.

• This role will be responsible for directing a "bench of specialty contractors" (brand, illustration, graphic, UI/UX), requiring strong vendor management and delegation skills.

• Close collaboration is expected with Product Management and Engineering teams, forming a core product development triad.

• The company is backed by top-tier investors, suggesting a culture focused on rapid growth, innovation, and data-driven decision-making. Methodology:

• The company utilizes an AI-driven approach, indicating a commitment to leveraging cutting-edge technology.

• Emphasis on user-centered design principles to simplify complex insurance workflows.

• A hybrid work model is in place, balancing in-office collaboration with remote flexibility.

• The company culture is described as "passionate," with a "product-minded" team focused on making a tangible difference.

Company Website: https://www.modernlife.com/ (Assumed based on company name and industry)

📝 Enhancement Note: The company operates at the intersection of a traditional industry (insurance) and modern technology (AI, digital platforms). This duality will likely shape the design challenges and opportunities, requiring a balance between user trust and intuitive digital experiences. The "AI-driven brokerage" aspect is a key differentiator.

📈 Career & Growth Analysis

Operations Career Level: Principal Individual Contributor (IC)

• This role is at a senior individual contributor level, signifying deep expertise and the ability to operate autonomously. The "Principal" title suggests a level of influence and strategic impact comparable to a Director or VP in a larger organization, but without direct people management responsibilities initially. The focus is on hands-on execution and foundational building. Reporting Structure:

• The Principal Designer will likely report to a senior leader within Product, Technology, or potentially the CEO, given the early stage and the foundational nature of the role. The exact reporting line is not specified but implies close proximity to executive decision-making. Operations Impact:

• The Principal Designer will have a significant impact by making complex insurance workflows more accessible and usable, directly influencing advisor efficiency and client satisfaction.

• Design decisions will directly tie into business priorities, impacting user acquisition, conversion rates, client retention, and overall revenue growth by improving the digital experience.

• The role is instrumental in shaping the company's brand perception and market positioning through consistent and compelling design across all channels. Growth Opportunities:

• Team Building & Leadership: As the company scales, there will be a clear opportunity to build and lead a design team, transitioning from an IC to a management track.

• Strategic Influence: Direct involvement in shaping product strategy and company direction, leveraging design expertise to drive business outcomes.

• Skill Specialization & Expansion: Opportunity to deepen expertise in specific areas like AI-driven design, complex B2B workflows, or advanced design system architecture.

• Industry Impact: Contribute to the transformation of the life insurance industry through innovative technology and design.

📝 Enhancement Note: The growth path from a senior IC to a potential Design Lead/Manager is a significant aspect of this role, appealing to candidates who want to build and scale a function. The "doing the work" phase is critical for understanding the company's needs before scaling.

🌐 Work Environment

Office Type: Hybrid model, requiring 4 days per week in a physical office.

Office Location(s): SoHo, New York City. This location is known for its vibrant tech and creative scene, offering a dynamic work environment.

Workspace Context:

• The SoHo office environment likely offers a collaborative and inspiring workspace conducive to creative work and team interaction.

• As the sole designer initially, the workspace will need to support focused individual work as well as collaboration with remote and in-office colleagues.

• Access to modern design tools and technologies is implied, given the company's AI-driven focus and investment.

• Opportunities for direct interaction with founders, product managers, engineers, and potentially key stakeholders from investor firms. Work Schedule:

• Full-time employment with a hybrid schedule requiring 4 days per week in the SoHo office. This implies a need for strong time management and organizational skills to balance in-office collaboration with focused remote work or design system development.

📝 Enhancement Note: The emphasis on being "based in NYC and open to working from our SoHo office, in person hybrid 4 days a week" is a critical requirement, indicating a company that values in-person collaboration for design and product development.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A call with a recruiter or hiring manager to assess overall fit, experience, and alignment with role requirements.

• Portfolio Review & Deep Dive: A session dedicated to walking through your portfolio. Expect detailed questions about your process, decision-making, challenges faced, and outcomes achieved for each case study. This is where your "product depth and visual and brand range" will be scrutinized.

• Design Challenge/Exercise: A practical exercise, potentially involving a design problem related to insurance workflows, AI tools, or design system development. This might be a take-home assignment or an in-person/virtual workshop.

• Cross-functional Interviews: Meetings with Product and Engineering leads to assess collaboration style, technical understanding, and ability to integrate design into the development lifecycle.

• Executive/Founder Interview: A final discussion with senior leadership to evaluate strategic thinking, cultural fit, and long-term vision for design at Modern Life.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest projects that clearly demonstrate both product depth (UX/UI, user research, problem-solving) and brand/visual range. Prioritize projects that align with B2B, fintech, or complex workflows if possible.

• Tell a Story: For each project, clearly outline the problem, your role, the process you followed, key decisions made, trade-offs considered, and the measurable impact or outcome. Use visuals effectively.

• Highlight System Thinking: If you have experience building or contributing significantly to design systems, make this a prominent part of your portfolio or presentation.

• Showcase Contractor Management: If possible, include examples or describe your process for briefing, managing, and reviewing work from external designers.

• Emphasize AI Exploration: If you have experience with AI tools in design, be prepared to discuss it and showcase any relevant outcomes.

• Be Ready for "Solo Designer" Questions: Prepare to discuss how you prioritize, manage your time, and influence stakeholders when you are the sole design voice.

Challenge Preparation:

• Anticipate challenges related to simplifying complex financial/insurance processes. Focus on user empathy, clear information architecture, and trust-building elements.

• Be prepared to discuss how you would leverage AI tools to enhance efficiency or creativity in a design context.

• Practice articulating your design rationale clearly and concisely, linking it back to user needs and business goals.

• Consider how you would approach building a design system from scratch or scaling an existing one.

📝 Enhancement Note: The emphasis on "doing the work" and "setting the standards" means the interview process will heavily scrutinize the candidate's ability to execute at a high level and to think strategically about process and system design. A strong portfolio demonstrating both execution and strategic thinking is paramount.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI/UX design, prototyping, and design system development. Mastery is essential.

• Prototyping Tools: While Figma has strong prototyping capabilities, familiarity with other advanced tools (e.g., ProtoPie,

Framer) might be beneficial.

• AI-Native Design Tools: This is a key area of interest. Expect tools for:

  • Generative Design: AI assisting in idea generation, mood boards, or initial concepts.
  • Content Generation: AI helping with copy variations or placeholder text.
  • Workflow Automation: AI assisting in repetitive design tasks.
  • Research Analysis: AI tools for synthesizing user feedback.

• User Research Platforms: Tools for conducting user interviews, surveys, and usability testing (e.g., UserTesting.com, Typeform, SurveyMonkey).

Analytics & Reporting:

• Familiarity with product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) is crucial for understanding user behavior and measuring design impact.

• Experience with data visualization tools or methods to communicate insights effectively. CRM & Automation:

• While not a direct CRM role, understanding how design integrates with CRM systems (e.g., Salesforce) and marketing automation platforms (e.g., HubSpot) for B2B workflows is advantageous.

• Familiarity with project management tools (e.g., Jira, Asana, Trello) for collaborating with engineering and product teams.

📝 Enhancement Note: The specific mention of "AI-native tools" indicates a forward-looking company keen on adopting new technologies. Candidates should be prepared to discuss their experience or willingness to explore and integrate such tools into their design workflow.

👥 Team Culture & Values

Operations Values:

• Innovation & AI Adoption: A drive to leverage cutting-edge technology, particularly AI, to disrupt a traditional industry.

• User-Centricity: A commitment to simplifying complex financial processes and delivering exceptional experiences for advisors and clients.

• Ownership & Autonomy: Expectation that individuals will take initiative, drive projects forward, and operate with a high degree of independence.

• Impact-Driven: Focus on delivering tangible business results and making a meaningful difference in people's lives through financial protection.

• Collaboration: A "product-minded" team that values strong partnerships between design, product, and engineering.

• Quality & High Standards: A dedication to setting and maintaining a high bar for design execution and brand consistency.

Collaboration Style:

• The company fosters a collaborative environment where design is integrated early and often with product and engineering.

• Expect a "roll-up-your-sleeves" mentality, particularly in the initial phase, with a focus on shared problem-solving and execution.

• Direct communication and transparent feedback loops are likely valued, especially given the small team size and hybrid work model.

• The management of specialty contractors suggests a structured but agile approach to leveraging external expertise.

📝 Enhancement Note: The culture appears to be a blend of startup agility, a passion for technology (especially AI), and a mission-driven approach to a critical financial service. The emphasis on "doing the work" suggests a hands-on, execution-focused environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Translating intricate life insurance policies, regulations, and advisory workflows into user-friendly digital experiences is a significant challenge.

• Building from Scratch: Establishing design systems, processes, and best practices as the sole designer requires strong organizational skills and strategic foresight.

• Managing Contractors: Effectively directing and integrating the work of multiple specialty contractors without direct oversight requires excellent communication, scoping, and quality control.

• Balancing Brand and Product: Ensuring a cohesive brand identity across all product touchpoints while also optimizing for specific user workflows.

• Adoption of AI Tools: Integrating new AI design tools effectively and ethically into existing workflows and ensuring team buy-in.

Learning & Development Opportunities:

• Foundational Design Leadership: Opportunity to define and build the design function from the ground up, setting the stage for future team growth.

• Industry Expertise: Deep dive into the nuances of the life insurance industry and its digital transformation.

• AI Design Integration: Become a leader in applying AI tools to practical design challenges within a growing company.

• Strategic Business Impact: Directly influence product and company strategy through design, gaining valuable experience in a high-growth startup environment.

• Cross-functional Skill Development: Enhance collaboration and communication skills by working closely with product, engineering, and business stakeholders.

📝 Enhancement Note: The challenges are directly tied to the role's foundational nature and the complexity of the industry. The growth opportunities are substantial, particularly for someone looking to build a design practice and influence a company's trajectory.

💡 Interview Preparation

Strategy Questions:

• "Describe your process for establishing a design system from the ground up. What are the key components and governance structures you'd implement?" (Focus on scalability and maintainability).

• "How would you approach designing a complex financial workflow for advisors, considering their need for efficiency and accuracy?" (Highlight user research, information architecture, and error prevention).

• "Imagine you're given a new AI design tool. How would you evaluate its potential value for Modern Life and integrate it into our workflow?" (Showcase curiosity, critical thinking, and practical application).

• "How do you balance the needs of different stakeholders (e.g., product, engineering, marketing, leadership) when making design decisions?" (Emphasize communication, negotiation, and data-driven rationale). Company & Culture Questions:

• "What excites you most about Modern Life's mission and our approach to the insurance industry?" (Research the company's values, mission, and recent news).

• "How do you envision the role of design evolving at a high-growth startup like ours over the next 1-3 years?" (Align your vision with the company's growth trajectory and the potential for team scaling).

• "Describe your experience working autonomously or as the sole designer on a team. How do you prioritize and manage your workload?" (Demonstrate self-discipline, prioritization skills, and proactivity). Portfolio Presentation Strategy:

• Structure: Begin with an overview of your career and expertise, then dive into 2-3 key projects. For each project, use the STAR method (Situation, Task, Action, Result).

• Focus on Process: Clearly articulate your thought process, research methods, design iterations, and the rationale behind your decisions. Use diagrams, user flows, and wireframes to illustrate.

• Quantify Impact: Wherever possible, present metrics or KPIs that demonstrate the positive impact of your design work (e.g., increased conversion rates, reduced support tickets, improved task completion time).

• Address Challenges: Be open about challenges encountered and how you overcame them. This shows resilience and problem-solving skills.

• Brand & System Examples: Ensure your presentation clearly showcases your range in both product depth and visual/brand design, as well as any experience with design systems.

📝 Enhancement Note: Interviews for this role will likely focus on strategic thinking, hands-on execution capabilities, and the ability to build foundational design processes. Candidates should be prepared to discuss their experience with design systems, contractor management, and leveraging AI tools.

📌 Application Steps

To apply for this Principal Designer position:

• Submit your application through the provided link on Lever.

• Tailor Your Resume: Highlight experience relevant to digital product design, brand development, design systems, and contractor management. Use keywords from the job description.

• Curate Your Portfolio: Ensure your portfolio is easily accessible (link on resume or separate submission) and showcases projects demonstrating both product depth and visual/brand range, with a clear emphasis on your design process and outcomes. Include specific examples of establishing standards or managing contractors if possible.

• Prepare Your Narrative: Be ready to articulate your experience with AI-native tools, your approach to simplifying complex workflows, and your vision for building a design function.

• Research Modern Life: Understand their mission, target audience, investor backing, and current product offerings to demonstrate genuine interest and cultural alignment.

⚠️ 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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