Freelance Marketing Designer, Web

📍 Job Overview

Job Title: Freelance Marketing Designer, Web

Company: PolicyMe

Location: Remote in Toronto, Ontario, Canada

Job Type: Contract

Category: Marketing Operations / Design

Date Posted: 2026-09-09

Experience Level: Mid-Level (2-4 years)

Remote Status: Fully Remote

🚀 Role Summary

• Design and implement high-quality marketing web pages and components within a Webflow CMS environment to enhance customer trust and conversion rates.

• Collaborate closely with Growth and Content teams to translate briefs into visually compelling, responsive, and accessible digital experiences.

• Own the end-to-end quality assurance and publishing process for marketing site updates, ensuring brand consistency and technical accuracy.

• Contribute to the evolution of PolicyMe's web and marketing design identity, leveraging AI design tools to boost efficiency and explore creative variations.

📝 Enhancement Note: This role is specifically for a visual designer focused on the marketing website, distinct from product or UX design. The emphasis is on design craft, visual polish, and CMS execution rather than deep technical development. The "Remote in Toronto" designation suggests a preference for candidates within the Toronto region for potential in-person events or collaboration, though the role is primarily remote.

📈 Primary Responsibilities

• Translate Growth and Content team briefs into polished Figma designs for various marketing assets including landing pages, product pages, editorial hubs, and campaign-specific pages.

• Develop clear, conversion-aware, accessible, and responsive layouts by leveraging the existing design system and reusable components.

• Design and integrate new components into the design system, ensuring cohesion and reusability across the marketing site.

• Continuously improve the marketing site's user interface, including navigation, templates, content modules, and both English and French language experiences.

• Actively participate in shaping PolicyMe's visual identity for web and marketing assets, collaborating with Growth and Design leadership.

• Utilize Webflow and other CMS/no-code tools to build, update, and publish marketing web pages.

• Conduct comprehensive pre- and post-launch quality assurance, including responsive checks, visual QA, content validation, and localization review.

• Maintain and enhance reusable Figma components, CMS templates, and design guardrails to streamline future development and maintain quality.

• Prepare detailed handoffs for Webflow/development partners, including interaction states, edge cases, annotations, and walkthroughs.

• Manage design feedback throughout the implementation phase, ensuring launched work aligns with design intent.

• Coordinate with cross-functional teams (Growth, Content, Design, Engineering) to clarify project scope, identify dependencies, and ensure timely project completion.

• Support selected creative needs for broader marketing initiatives, such as campaign creative, digital ads, slide templates, email UI, and illustrations.

• Employ AI design tools, such as Claude Design, for rapid exploration, wireframing, and variation generation, ensuring human judgment guides final output.

📝 Enhancement Note: The responsibilities highlight a blend of core design execution and CMS management, emphasizing the importance of understanding how design translates into a live, functional web experience. The expectation to "extend an existing component system" indicates a need for designers who think systematically rather than creating one-off solutions.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles is expected, often gained through formal education in Graphic Design, Visual Communications, Digital Design, or a related field, or through equivalent professional experience.

Experience: 2–4 years of professional experience in marketing design, web design, brand design, or a related digital design capacity. Exceptional portfolios demonstrating relevant work are valued more highly than a strict adherence to years of experience.

Required Skills:

• Proven ability to design highly polished marketing websites and landing pages, showcased in a comprehensive portfolio.

• Demonstrated breadth of design capabilities across various formats, including campaign work, motion graphics, illustration, presentations, digital ads, or email design.

• Advanced proficiency in Figma, with a keen eye for typography, spacing, composition, visual hierarchy, image selection, and responsive design principles.

• Experience working within a Content Management System (CMS) or a no-code/low-code website builder platform.

• Ability to work within and thoughtfully extend an existing component system and design system, promoting reusability and consistency.

• Meticulous attention to detail and a reliable approach to quality assurance for both high-visibility launches and routine maintenance tasks.

• Strong written and verbal communication skills, capable of writing clear specifications, providing actionable feedback to developers, and collaborating effectively with non-design stakeholders.

• Demonstrated ability to manage concurrent requests, make practical trade-offs, and leverage AI tools to enhance production speed without compromising design quality. Preferred Skills:

• Direct experience with Webflow, including familiarity with CMS collections, global components, slots and variables, responsive page building features, or publishing workflows.

• Basic understanding of HTML and CSS principles.

• Experience in briefing, reviewing, or quality assurance of work produced by external agencies or freelance developers.

• Experience within a high-trust, regulated industry, or a consumer-facing business with a significant content presence.

• Familiarity with web accessibility standards (WCAG), localization best practices, SEO-aware content templating, or conversion-oriented web design principles.

📝 Enhancement Note: The "Need to have's" emphasize practical application and a portfolio-driven assessment, suggesting that candidates should curate their portfolios to specifically highlight their web design and CMS capabilities. The preference for experience within specific business types (regulated, consumer-facing) indicates a potential alignment with PolicyMe's industry.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated collection of your best marketing website and landing page designs, demonstrating a strong grasp of visual hierarchy, typography, layout, and responsive behavior.

• Case studies or examples showcasing your ability to design new components that extend an existing design system or component library cohesively.

• Evidence of your quality assurance process, such as examples of detailed visual QA checks, responsive testing documentation, or content validation procedures.

• Demonstrations of your ability to work within or extend a CMS or no-code/low-code platform, ideally including examples of Webflow projects or similar.

• Examples of how you've collaborated with developers or agencies, including the type of handoff documentation you provide (e.g., annotations, interaction states). Process Documentation:

• Showcase your approach to translating Growth or Content briefs into design deliverables, including any wireframing or iterative design processes.

• Provide examples of how you ensure accessibility and responsiveness in your web designs, perhaps through annotated mockups or style guides.

• Include examples of how you maintain and improve reusable design components and templates for efficiency and consistency.

• Demonstrate your experience with quality control and publishing workflows for web content.

📝 Enhancement Note: The portfolio requirements are heavily geared towards demonstrating practical design execution and system thinking within a web context. Candidates should be prepared to articulate their process for design creation, QA, and developer handoff, highlighting efficiency and quality.

💵 Compensation & Benefits

Salary Range: As a freelance contract role, compensation will be determined based on experience and expertise. For a mid-level Marketing Designer with 2-4 years of experience in Toronto, Canada, freelance rates typically range from $40 - $70 CAD per hour. This estimate is based on industry benchmarks for contract design roles in major Canadian cities, considering the required skills in Figma, Webflow, and CMS management.

Benefits:

• Generous Paid Time Off (PTO) - 20 vacation days.

• Comprehensive benefits plan with premiums paid in full by PolicyMe.

• Investment in professional development, including an L&D budget and an AI tooling budget.

• Access to stock options based on performance.

• Opportunity to work remotely.

• Twice-yearly in-person social events, with travel costs covered by PolicyMe.

Working Hours: The role is based on a standard 40-hour work week, typical for contract positions. Flexibility may be available, but core hours for collaboration with the team and adherence to project deadlines are expected.

📝 Enhancement Note: The salary range provided is an estimate for a contract role in Toronto. The benefits are quite generous for a contract position, suggesting PolicyMe values its contractors highly and may offer a path to full-time employment for strong performers, as hinted in the role overview.

🎯 Team & Company Context

🏢 Company Culture

Industry: InsurTech (Insurance Technology), focused on Life Insurance, Critical Illness Insurance, and Health & Dental Insurance in Canada. PolicyMe aims to simplify and make insurance more affordable through digital solutions.

Company Size: PolicyMe is a growing startup, having sold over $10 billion in insurance coverage since its launch in 2018. The team is described as "extremely high performing, low-ego."

Founded: 2018, by insurance experts and technology entrepreneurs.

Team Structure:

• The design function appears to be integrated within or closely aligned with the Growth and Content teams, indicating a strong focus on data-driven marketing and user acquisition.

• The role involves collaboration with Growth, Content, Design leadership, and Engineering, suggesting a cross-functional operational structure.

• As a remote-first company, team interactions are likely facilitated through digital collaboration tools. Methodology:

• Data-driven decision-making is implied through the involvement of the "Growth" team and the focus on conversion-aware design.

• Emphasis on efficiency and speed, particularly with the integration of AI design tools.

• A culture of continuous improvement, evident in the ongoing refinement of the marketing site and design system.

Company Website: www.policyme.com

📝 Enhancement Note: PolicyMe's culture is characterized by a blend of startup agility and a focus on professional growth and high performance. The remote-first approach suggests a need for strong self-management and digital communication skills. The company's mission to simplify insurance resonates throughout its operational and design philosophy.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a mid-level designer capacity, focused on executing and improving marketing web experiences. It offers significant autonomy in design quality and CMS ownership.

Reporting Structure: The designer will likely report to a Design Lead or Head of Design, working in close partnership with Growth and Content leads.

Operations Impact: The role directly impacts PolicyMe's customer acquisition and brand perception by enhancing the visual appeal, usability, and conversion effectiveness of its marketing website. This is crucial for a digital-first company where the website is a primary touchpoint.

Growth Opportunities:

• Skill Specialization: Deepen expertise in Webflow, CMS management, conversion-focused web design, and AI-assisted design workflows.

• Design System Contribution: Play a key role in evolving and expanding PolicyMe's design system, influencing future design consistency and efficiency.

• Full-Time Transition: The job posting explicitly mentions a full-time opening is also available, suggesting a potential pathway for a high-performing freelancer to transition into a permanent role.

• Broader Creative Exposure: Gain experience across a wider range of marketing collateral beyond web design.

📝 Enhancement Note: The "Growth Opportunities" section is critical here, particularly the mention of a potential full-time opening. This implies that successful freelancers can be evaluated for more permanent positions, offering a clear career progression path within PolicyMe's design team.

🌐 Work Environment

Office Type: PolicyMe operates on a remote-first model. While they have a Toronto-based office, the primary work environment is virtual. They do host in-person events twice a year.

Office Location(s): Toronto, Ontario, Canada. The remote designation "Remote in Toronto" suggests a preference for candidates in or willing to relocate to the Toronto area for these events.

Workspace Context:

• A fully remote setup requiring self-discipline and effective digital communication tools.

• Access to modern design and collaboration software, including Figma and AI design tools.

• Opportunities for periodic in-person collaboration and team-building during company-wide social events.

• A culture that values high performance and low ego, fostering a collaborative yet autonomous work environment.

Work Schedule: A standard 40-hour work week is expected for this contract role. While remote, maintaining consistent availability for team collaboration and meeting project deadlines is essential.

📝 Enhancement Note: The remote-first nature of PolicyMe necessitates strong asynchronous communication skills. The biannual in-person events are a unique perk designed to foster team cohesion despite the remote setup.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess alignment with the required skills and experience.

• Design Challenge/Portfolio Review: A deeper dive into your portfolio, focusing on specific examples of marketing web design, CMS work, and your design process. This may involve a practical design exercise or a detailed walkthrough of past projects.

• Hiring Manager/Team Interview: Discussion about your experience, approach to collaboration, problem-solving skills, and cultural fit with the PolicyMe team. Expect questions about how you handle feedback, manage deadlines, and utilize AI tools.

• Final Interview: Potentially with senior leadership to discuss strategic alignment and long-term potential.

Portfolio Review Tips:

• Highlight Web & CMS: Prioritize showcasing your strongest marketing website and landing page designs. Include specific examples of work done within a CMS or no-code platform like Webflow.

• Demonstrate System Thinking: Clearly illustrate how you've worked with or extended component systems and design systems, showing examples of reusable elements.

• Showcase Process & QA: Include case studies that detail your design process from brief to launch, emphasizing your approach to quality assurance, responsive design, and developer handoffs.

• Quantify Impact: If possible, include metrics or qualitative feedback that demonstrate the impact of your designs on conversion rates, user engagement, or brand perception.

• Visual Polish: Ensure your portfolio itself is well-designed, visually appealing, and easy to navigate, reflecting your own design craft.

Challenge Preparation:

• Figma Proficiency: Be ready to demonstrate your Figma skills, particularly in creating responsive layouts and components.

• Webflow/CMS Understanding: Familiarize yourself with common Webflow concepts or the general principles of CMS-based website building if you lack direct Webflow experience.

• Problem-Solving Scenarios: Prepare to discuss how you would approach common design challenges, such as improving an existing page's conversion rate or designing for specific user segments.

• AI Tool Integration: Be prepared to discuss how you've used or would use AI design tools to enhance your workflow, with a focus on maintaining design quality and human oversight.

📝 Enhancement Note: The emphasis on a "portfolio made up of highly polished marketing websites" and "evidence of breadth across formats" means candidates should carefully curate their submissions to align with these priorities.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core design tool for creating mockups, prototypes, and design systems. Proficiency is essential.

• Webflow: The primary CMS and no-code website builder used for marketing site development. Experience is preferred, but learnability is key.

• AI Design Tools (e.g., Claude Design): Used for rapid exploration, wireframing, and generating design variations.

Analytics & Reporting:

• While not a direct responsibility, understanding how web designs impact analytics (e.g., conversion rates, bounce rates) is beneficial. Familiarity with tools like Google Analytics or similar web analytics platforms would be advantageous. CRM & Automation:

• Not directly specified for this role, but understanding how marketing website interactions feed into CRM systems or marketing automation platforms is a plus.

📝 Enhancement Note: The explicit mention of AI design tools like Claude Design indicates a forward-thinking approach to design workflows and an expectation for candidates to be comfortable with integrating new technologies.

👥 Team Culture & Values

Operations Values:

• Craftsmanship & Quality: A strong emphasis on visual polish, attention to detail, and delivering high-quality design outputs for marketing and web experiences.

• Efficiency & Speed: Utilizing tools and processes, including AI, to increase production speed without sacrificing the quality bar.

• Collaboration & Low Ego: Working effectively with cross-functional teams, valuing open communication, and contributing to a supportive team environment.

• Data-Informed Design: Understanding how design choices impact business metrics like conversion rates and applying insights to improve web experiences.

• Customer Focus: Designing with the customer's journey and trust-building in mind, particularly within the insurance context.

Collaboration Style:

• Cross-Functional Integration: Close partnership with Growth, Content, Design Leadership, and Engineering to ensure cohesive project execution.

• Feedback-Driven: An environment where feedback is regularly exchanged to refine designs and processes.

• Remote-First Communication: Reliance on digital tools and clear, concise communication for effective collaboration across distributed teams.

📝 Enhancement Note: The "low-ego" culture suggests that candidates should be humble, open to feedback, and collaborative, rather than territorial about their design ideas.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Speed and Quality: Effectively using AI tools and efficient processes to deliver high-quality designs rapidly within a startup environment.

• Extending Component Systems: Thoughtfully growing a design system and component library to meet evolving marketing needs without introducing inconsistencies.

• Cross-Functional Alignment: Managing design expectations and feedback from various stakeholders (Growth, Content, Engineering) to ensure project success.

• CMS/Webflow Learning Curve: Adapting to and mastering PolicyMe's specific CMS environment (Webflow) if not already an expert.

Learning & Development Opportunities:

• Webflow Expertise: Gaining in-depth knowledge and practical experience with Webflow, a widely used platform for marketing sites.

• AI Design Tool Mastery: Developing advanced skills in leveraging AI for design ideation and production.

• Growth Marketing Design: Deepening understanding of conversion-oriented design principles and their application in a high-growth startup.

• Design System Development: Contributing to and influencing the growth of a foundational design system.

• Potential Full-Time Conversion: Opportunity to transition into a permanent role with expanded responsibilities and benefits.

📝 Enhancement Note: The challenges are framed as opportunities for growth, particularly in adapting to new technologies and collaborative workflows, which is characteristic of a dynamic startup environment.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you turned a Growth or Content brief into a complete marketing web page. What was your process, and what were the key design decisions you made?" (Focus on process, problem-solving, and design rationale).

• "How do you approach ensuring responsive design and accessibility in your web projects, especially when working within a component system?" (Highlight your technical design knowledge and systematic approach).

• "Imagine you're asked to design a new component for our marketing site. Walk me through how you'd ensure it fits seamlessly with our existing design system and is reusable." (Demonstrate your understanding of design systems and component thinking). Company & Culture Questions:

• "Why are you interested in PolicyMe and our mission to simplify insurance?" (Showcase research and alignment with company values).

• "How do you handle receiving critical feedback on your designs, especially from non-design partners?" (Assess your collaboration style and ability to work with a low-ego culture).

• "How have you used AI design tools in your workflow, and what are your thoughts on their role in the future of design?" (Gauge your comfort with new technology and your approach to maintaining craft). Portfolio Presentation Strategy:

• Storytelling: For each portfolio piece, tell a clear story: the challenge, your solution, and the outcome. Emphasize your role and decision-making.

• Process Visualization: Show, don't just tell, your process. Include sketches, wireframes, iterations, and QA documentation where relevant.

• Webflow/CMS Focus: If you have Webflow experience, highlight it. If not, clearly articulate your understanding of CMS principles and your ability to learn quickly.

• Component Examples: Dedicate specific slides or sections to illustrating how you've worked with or extended component systems.

• Conciseness: Be prepared to present your most relevant work efficiently, focusing on the aspects most aligned with this role's requirements.

📝 Enhancement Note: Candidates should be prepared to articulate not just their design output but also their process, rationale, and how they integrate with broader marketing objectives and team dynamics.

📌 Application Steps

To apply for this freelance Marketing Designer position:

• Submit your application through the provided Lever link, ensuring all required fields are completed accurately.

• Curate Your Portfolio: Select 3-5 of your strongest pieces that best showcase your marketing website design, CMS experience, and ability to work within component systems. Prioritize visual polish and demonstrate your process.

• Tailor Your Resume: Highlight experience with Figma, CMS platforms (especially Webflow if applicable), responsive design, and successful collaboration with marketing or growth teams. Quantify achievements where possible.

• Prepare for a Walkthrough: Be ready to verbally walk through your portfolio, explaining your design decisions, process, and the impact of your work during an interview. Practice articulating your experience with AI tools.

• Research PolicyMe: Understand their mission, target audience, and current marketing website. Consider how your design approach can contribute to their goals of building trust and driving conversions.

⚠️ 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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