Senior Product Designer (Remote)

📍 Job Overview

Job Title: Senior Product Designer

Company: Jack Westin

Location: Remote

Job Type: CONTRACTOR

Category: Product Design / Marketing Operations

Date Posted: 2026-08-21

Experience Level: 5+ Years

Remote Status: Fully Remote

🚀 Role Summary

• Owns the end-to-end design of marketing-facing student experiences, from initial ad click through to purchase or booked calls, ensuring a cohesive and premium user journey.

• Drives data-informed design decisions by researching market trends, analyzing customer data (GA4, heatmaps, session recordings), and collaborating with performance marketers on A/B testing.

• Establishes and maintains a consistent, premium visual language across all marketing touchpoints, including course pages, subscription experiences, and editorial content.

• Develops and documents a comprehensive marketing design system to ensure scalability and ease of use for the development and graphic design teams.

📝 Enhancement Note: While the primary role is Product Design, the emphasis on marketing funnels, conversion optimization, A/B testing, and collaboration with performance marketing indicates a strong intersection with Marketing Operations and Revenue Operations principles. This role will leverage design to directly impact conversion metrics and revenue generation.

📈 Primary Responsibilities

• Design and iterate on user interfaces and user experiences for marketing websites, landing pages, subscription models (JW+), and e-commerce checkout flows.

• Conduct thorough user research, analyze student interviews, support tickets, and competitive landscapes to inform design strategies and product development.

• Define and implement a premium, consistent visual identity and design system for the marketing site, addressing existing inconsistencies.

• Collaborate closely with copywriters to co-create compelling headlines, microcopy, and form elements that resonate with a US-based pre-med audience.

• Identify and resolve known conversion rate bottlenecks, such as inconsistent CTAs, lengthy booking forms, and underperforming high-traffic pages.

• Partner with performance marketers to propose, design, and analyze A/B tests, iterating on designs based on data-driven insights.

• Create detailed design specifications and handoffs for WordPress developers, ensuring accurate implementation of states, breakpoints, and edge cases.

• Design scalable and engaging blog and editorial templates that support SEO strategies and enhance reader experience.

• Develop and maintain a marketing design system, ensuring clear documentation for developer and graphic designer utilization.

• Continuously research and understand the competitive landscape and the specific needs of the US-based pre-med student demographic.

📝 Enhancement Note: The responsibilities highlight a deep dive into conversion rate optimization (CRO) and a data-driven approach, which are core tenets of Revenue and Sales Operations. The emphasis on measurable outcomes and A/B testing indicates that success will be tied to tangible business impact.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent experience and expertise in product design, particularly for marketing and conversion-focused platforms, is essential.

Experience: Minimum of five years of experience designing marketing sites, landing pages, subscription funnels, or e-commerce funnels. The depth and quality of the work will be prioritized over the exact number of years.

Required Skills:

• Product Design: Proven ability to design end-to-end user experiences for digital products.

• Marketing & Conversion Design: Expertise in designing for marketing sites, landing pages, funnels, and e-commerce platforms with a focus on conversion rate optimization (CRO).

• User Research & Analysis: Proficiency in conducting qualitative and quantitative user research, analyzing GA4 data, heatmaps, and session recordings to inform design decisions.

• Design Systems: Experience in creating, documenting, and maintaining design systems for consistency and scalability.

• Visual Design: Strong aesthetic sense with the ability to establish and elevate a premium visual language.

• Collaboration: Excellent ability to partner with copywriters, developers, and performance marketers, influencing outcomes through effective communication.

• Written & Spoken English: Exceptional command of English for clear communication with a distributed team and crafting customer-facing copy.

• US Audience Understanding: Strong instincts and ability to design for a US-based audience, particularly students.

• Problem-Solving: Aptitude for identifying and resolving complex design and conversion challenges.

• Adaptability: Ability to quickly learn new industries and translate understanding into effective design solutions.

Preferred Skills:

• WordPress/Page Builder Experience: Familiarity with designing within WordPress or similar page builder environments.

• Prototyping: Experience in advanced prototyping, including code-based or AI-assisted build tools.

• Industry Background: Experience in education, test prep, or other high-consideration purchase categories.

• Editorial Design: Background in editorial or publication design.

• AI Workflow Integration: Demonstrated use of AI tools in the design workflow, with an understanding of their benefits and limitations.

📝 Enhancement Note: The emphasis on "outcomes" and "moving a number" suggests that candidates with a strong understanding of marketing analytics and conversion metrics will be highly valued. Experience in roles that directly impacted sales funnels or revenue targets will be a significant advantage.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of one project demonstrating end-to-end design of a marketing site, landing page, or e-commerce/subscription funnel.

• Include at least one case study detailing measurable outcomes, specifically showing "before and after" numbers that illustrate the impact of your design work on conversion rates or key business metrics.

• Present a premium visual quality that could confidently be presented to clients paying top-market rates.

• Demonstrate a clear understanding of how design decisions align with business objectives and user needs. Process Documentation:

• Be prepared to discuss your design process, from initial research and hypothesis generation to iteration based on A/B test results.

• Explain how you would approach building and documenting a marketing design system for a distributed team.

• Detail your experience collaborating with copywriters and developers to ensure cohesive product delivery.

• Articulate how you leverage data analytics tools (GA4, heatmaps) to inform your design process and validate solutions.

📝 Enhancement Note: The portfolio requirements are heavily geared towards demonstrating ROI and process efficiency. Candidates should prepare to articulate how their design work directly contributed to business goals, a key expectation for roles within Revenue and Sales Operations.

💵 Compensation & Benefits

Salary Range: $1,800 – $2,500 per month (as a contractor).

Benefits:

• Fully remote position with flexible working arrangements.

• Full-time engagement with a stable, US-based company.

• Opportunity to work on meaningful projects with a professional, collaborative team.

Working Hours: While not explicitly stated, the role is described as a "Full-time engagement" and implies a standard 40-hour work week, with flexibility inherent in a remote, contractor position.

📝 Enhancement Note: The monthly salary for a contractor position indicates a specific compensation structure. For candidates accustomed to annual salaries, it's important to annualize this range ($21,600 - $30,000 USD per year) and compare it against market rates for senior product designers with a strong CRO focus in remote roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Education Technology (EdTech), specifically focused on test preparation for high-stakes exams like the MCAT.

Company Size: Jack Westin appears to be a growing company, likely in the small to medium-sized business (SMB) range, indicated by the small, focused marketing team structure.

Founded: The founding date is not specified, but the company's mission suggests it has been operating long enough to establish a significant student base and online presence.

Team Structure:

• The Marketing team is lean and highly cross-functional, comprising a copywriter, a WordPress developer, a graphic designer, a performance marketer, and this Senior Product Designer.

• The Senior Product Designer will be a key design voice, expected to lead and influence design quality and strategy within this small team.

• Collaboration is essential, with a focus on integrated design, copy, development, and performance marketing efforts. Methodology:

• Data-Driven Decision Making: Strong emphasis on using analytics (GA4, heatmaps) and A/B testing to inform design choices and measure impact.

• Customer-Centric Design: Starting from the customer's needs and journey, rather than just a brief.

• Iterative Improvement: Continuous refinement of designs based on performance data and user feedback.

• Integrated Workflow: Close collaboration between design, copy, and development to ensure cohesive product delivery.

Company Website: https://www.jackwestin.com/

📝 Enhancement Note: The company's focus on high-stakes exams like the MCAT implies a culture that values academic rigor, student success, and professional development. The marketing team's structure suggests a fast-paced, collaborative environment where each member's contribution is critical.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor. This role is positioned as a lead design voice within the marketing team, responsible for elevating design quality and strategy across a critical user journey. It requires significant autonomy and strategic input.

Reporting Structure: While not explicitly stated, the Senior Product Designer would likely report to a Head of Marketing, Marketing Director, or a similar leadership role within the marketing department. The close-knit team structure suggests direct collaboration with peers and potentially significant interaction with other department heads.

Operations Impact: This role has a direct and measurable impact on revenue and business growth. By optimizing marketing pages, funnels, and conversion flows, the designer will directly influence lead generation, customer acquisition, and ultimately, revenue. Success will be measured by improvements in key performance indicators (KPIs) such as conversion rates, user engagement, and sales volume.

Growth Opportunities:

• Specialization: Deepen expertise in conversion rate optimization (CRO), marketing analytics, and user experience design for high-consideration purchases.

• Leadership: Potential to grow into a Design Lead role as the company scales, potentially managing a small design function or mentoring junior designers.

• Cross-Functional Expertise: Develop a strong understanding of marketing strategy, performance marketing, and content strategy through close collaboration.

• Impactful Projects: Contribute to shaping the user experience for hundreds of thousands of students annually, impacting their educational journeys.

📝 Enhancement Note: The "contractor" employment type might limit traditional growth paths within the company, but the seniority of the role and the direct impact on business metrics offer significant professional development and portfolio-building opportunities.

🌐 Work Environment

Office Type: Fully Remote. This implies a distributed team environment where asynchronous communication and self-discipline are key.

Office Location(s): Remote, with a specific mention of targeting a "US audience" and requiring strong English skills, suggesting a preference for candidates who understand or can quickly adapt to US market nuances.

Workspace Context:

• Collaborative & Independent: While the team is small and collaborative, the remote nature requires significant individual initiative and self-management.

• Technology-Enabled: The team relies on digital tools for design, communication, project management, and analytics. Proficiency with these tools is essential.

• Impact-Focused: The environment is geared towards achieving measurable business results, with design playing a crucial role in driving conversions.

Work Schedule: Flexible, within the context of a full-time engagement. The emphasis on asynchronous communication and remote work suggests that while core hours might exist for collaboration, there's likely flexibility in daily scheduling.

📝 Enhancement Note: Remote work environments demand strong communication skills, particularly written communication, and the ability to manage one's own time and workload effectively. Candidates should highlight their experience with remote collaboration tools and strategies.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely involves a review of your resume and portfolio to assess experience, skills, and alignment with requirements.

• Portfolio Presentation: Expect to present a curated selection of your work, focusing on projects that demonstrate your ability to design for marketing funnels, drive conversions, and achieve measurable outcomes. Be prepared to walk through your process, rationale, and the results.

• Skills Assessment: This may involve technical questions about design tools, user research methodologies, A/B testing, and data analysis. You might also be asked to discuss your experience with design systems and collaboration.

• Case Study/Design Challenge: A potential exercise to assess your problem-solving skills, design thinking, and ability to work within constraints relevant to Jack Westin's marketing challenges.

• Cultural Fit & Team Interview: Discussions to gauge your ability to work within a small, distributed, and collaborative team, and your understanding of the company's mission and student audience.

Portfolio Review Tips:

• Highlight Outcomes: Ensure your portfolio prominently features case studies with quantifiable results (e.g., increased conversion rates, improved engagement metrics). Clearly articulate the "before" and "after" states.

• Showcase Process: Detail your design process, from research and ideation to iteration and final implementation. Explain your rationale for key design decisions.

• Demonstrate Range: Include examples of marketing sites, landing pages, funnels, and potentially subscription or e-commerce experiences.

• Visual Quality: Ensure all presented work is polished, visually appealing, and reflects a premium aesthetic.

• Tailor to the Role: Emphasize projects that align with Jack Westin's needs: conversion optimization, US audience design, and experience with data-driven design.

Challenge Preparation:

• Understand the Context: Research Jack Westin, their mission, the MCAT exam, and their key competitors.

• Analyze the Funnel: Think about the typical student journey from discovering Jack Westin to purchasing a course or service. Identify potential design friction points.

• Data & Analytics: Be ready to discuss how you use data (GA4, heatmaps) to inform design and how you would approach A/B testing for conversion improvement.

• Design System Thinking: Prepare to discuss how you would approach building or evolving a marketing design system for a small, distributed team.

📝 Enhancement Note: Given the emphasis on measurable outcomes and data, candidates should be prepared to discuss not just what they designed, but why they designed it that way, and what impact it had.

🛠 Tools & Technology Stack

Primary Tools:

• Design Software: Proficiency in industry-standard design and prototyping tools such as Figma, Sketch, Adobe Creative Suite (Photoshop, Illustrator), or similar.

• Prototyping Tools: Tools for creating interactive prototypes, potentially including advanced or code-based options.

• AI Design Tools: Experience and willingness to leverage AI in the design workflow for acceleration and ideation.

Analytics & Reporting:

• Google Analytics (GA4): Comfortable navigating and extracting insights from GA4 to inform design hypotheses.

• Heatmapping & Session Recording Tools: Familiarity with tools like Hotjar, Crazy Egg, or similar for understanding user behavior on the website.

CRM & Automation:

• WordPress: Experience designing for or within WordPress environments is a significant plus.

• Page Builders: Familiarity with common WordPress page builders may also be beneficial.

Collaboration & Project Management:

• Tools for asynchronous communication (Slack, email) and project management (e.g., Asana, Trello, Jira) will likely be used.

📝 Enhancement Note: While specific CRM or automation tools are not listed, the role's focus on marketing funnels and conversion implies an indirect interaction with marketing automation platforms and CRMs through the data they generate and the journeys they facilitate.

👥 Team Culture & Values

Operations Values:

• Data-Driven: Decisions are informed by data and performance metrics, not just intuition.

• Customer-Centric: A deep understanding and focus on the needs of the pre-med student.

• Efficiency & Optimization: Constantly seeking ways to improve processes and outcomes, particularly conversion rates.

• Collaboration: Working effectively in a small, cross-functional team where shared goals are paramount.

• Quality & Craftsmanship: A commitment to high visual standards and well-executed design solutions.

• Adaptability & Learning: Willingness to quickly learn new industries and technologies.

Collaboration Style:

• Integrated: Design is not a silo; it's deeply intertwined with copy, development, and performance marketing.

• Asynchronous Focus: With a remote team, effective written communication and clear documentation are crucial.

• Feedback-Oriented: Openness to receiving and giving constructive feedback to improve work and team dynamics.

• Outcome-Focused: The team likely prioritizes achieving shared business objectives over individual tasks.

📝 Enhancement Note: The company's mission in test prep suggests a culture that values hard work, dedication, and achieving high standards, which should translate into the operations and design processes.

⚡ Challenges & Growth Opportunities

Challenges:

• Raising the Visual Bar: Overcoming existing visual inconsistencies and establishing a premium aesthetic across a large marketing site.

• Data Interpretation: Translating complex user behavior data (GA4, heatmaps) into actionable design improvements.

• Balancing SEO and UX: Designing blog and editorial content that serves both search engine visibility and a positive reader experience.

• Working within Constraints: Effectively designing for a WordPress environment and a lean, cross-functional team.

• Understanding a Niche Audience: Quickly grasping the unique needs and motivations of US-based pre-med students.

Learning & Development Opportunities:

• CRO Expertise: Gaining deep practical experience in conversion rate optimization through hands-on A/B testing and iterative design.

• Marketing Analytics: Enhancing skills in interpreting marketing performance data and applying insights to design.

• Design System Development: Building robust design systems and documentation practices.

• Cross-Functional Collaboration: Deepening understanding of marketing strategy, copywriting, and web development.

• Industry Knowledge: Becoming an expert in the test prep industry and the EdTech landscape.

📝 Enhancement Note: The challenges presented are typical for growth-stage companies and offer significant opportunities for a proactive designer to make a substantial impact and develop valuable skills in demand across many industries.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a marketing funnel or e-commerce flow that significantly improved conversion rates. What was your process, and what were the key metrics?" (Focus on quantifiable results and your role.)

• "How would you approach establishing a consistent visual language and design system for a marketing site that has grown organically over time?" (Discuss your methodology for audits, creating components, and documentation.)

• "Imagine you're tasked with redesigning our course booking form, which is currently too long. What steps would you take, and how would you validate your solutions?" (Focus on research, hypothesis generation, design iteration, and A/B testing.) Company & Culture Questions:

• "What do you know about the MCAT exam and the challenges faced by pre-med students?" (Demonstrate your research and empathy for the target audience.)

• "How do you typically collaborate with copywriters and developers, especially in a remote setting?" (Highlight your communication and teamwork skills.)

• "How do you use data and analytics (like GA4 or heatmaps) to inform your design decisions?" (Provide specific examples of how data led to design changes and positive outcomes.) Portfolio Presentation Strategy:

• Structure for Impact: Organize your presentation to clearly show the problem, your proposed solution, your process, and the measurable results.

• Quantify Everything: For each project, explicitly state the KPIs you influenced and the percentage of improvement or other quantifiable outcomes.

• Explain Your 'Why': Be prepared to articulate the rationale behind every major design decision, linking it back to user needs, business goals, or data insights.

• Showcase Collaboration: If possible, highlight projects where you effectively collaborated with other disciplines (copy, development, marketing).

• Address AI Use: Be ready to discuss how you use AI in your workflow, its benefits, and any limitations or areas where you still rely on manual expertise.

📝 Enhancement Note: Given the role's focus on business impact, interviewers will likely probe deeply into how your design work translates to tangible results. Prepare to discuss your understanding of marketing metrics and conversion funnels.

📌 Application Steps

To apply for this operations-adjacent design position:

• Submit your application through the provided link on rippling.com.

• Curate Your Portfolio: Select 2-3 of your strongest projects that specifically showcase your experience in designing marketing sites, landing pages, or conversion-focused funnels. Ensure each includes a detailed case study with quantifiable results.

• Tailor Your Resume: Highlight keywords and experiences relevant to product design, marketing design, conversion rate optimization, user research, A/B testing, and design systems. Emphasize achievements with measurable outcomes.

• Prepare Your Narrative: Practice presenting your portfolio projects, focusing on your problem-solving process, design rationale, and the business impact of your work. Be ready to discuss your experience with data analysis tools and remote collaboration.

• Research Jack Westin: Understand their mission, the MCAT landscape, their target audience, and their current marketing efforts. This will help you tailor your application and interview responses.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

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