Design Lead Web Operations

🇨🇦 Canada - Remote
🎨 Design🟣 Senior

Job description

About Winona:

Winona is one of the leading telemedicine companies providing HRT for women in menopause. We’ve built all of our technology in house including an EHR, patient care admin system, patient portal, website, marketing technology etc. Winona has two compounding pharmacies and a team of in house physicians providing world-class care via a fully vertically integrated business model.

About the Role:

We are looking for a Design Lead, Web Operations to own the operational side of our web design projects — spanning marketing sites, CRO initiatives, and product design. You’ll ensure tickets are actionable, processes run smoothly, Figma stays organized, and designs are always dev-ready. This role is critical to upholding design quality, enforcing system standards, and keeping projects on track.

Seniority Level: Senior Level

Key Responsibilities:

Ticketing & Documentation

  • Translate high-level project briefs into detailed, actionable project tickets that holistically account for development, SEO, copy, and design requirements

  • Ensure all project tickets and documentation are continuously up-to-date and complete throughout the entire project lifecycle.

  • Proactively identify potential roadblocks, missing specifications, or project risks before design or development work begins.

Design QA & Standards Enforcement

  • Conduct thorough review and Quality Assurance (QA) of all design deliverables before they are submitted for final approval or developer handoff.

  • Ensure strict adherence to:

    • Ticket requirements and specifications.

    • Design system and component usage, ensuring consistency and efficiency.

    • Typography, spacing, and accessibility standards, and overall visual hierarchy.

    • Creative consistency and cohesion across all breakpoints and devices.

  • Provide clear, constructive, and direct feedback to designers to elevate the quality of their work and ensure rapid iteration.

Project Management for Web Design

  • Own and manage all web design timelines, priorities, and due dates for the design team.

  • Balance quality vs. speed and business impact in tradeoff decisions.

  • Conduct daily check-ins with designers to identify and remove blockers and ensure continuous progress.

  • Maintain and update the Marketing Web Design (MWD) and Product Web Design (PWD) project boards in our project management system.

  • Report on project status, risks, and capacity in weekly website leadership meetings, and provide early alerts if deadlines are at risk or new work needs to be queued.

Design Operations & Process Optimization

  • Maintain and continuously optimize Figma organization (file hierarchy, CRO test structures, etc.).

  • Identify, document, and implement better workflows, plugins, and tools to streamline the design process.

  • Document and enforce design standards, file organization, and best practices across the creative team.

  • Evaluate and explore new software or systems to improve operational efficiency (e.g., onboarding flows, file management, advanced QA tools).

Miscellaneous Web Support

  • Assist in managing and updating no-code landing page platforms (e.g., Swipe Pages)

  • Contribute to creative and technical problem-solving discussions within the broader design ecosystem.

Qualifications:

  • 5+ years of professional experience in Web Design, Product Design, or Design Operations.

  • Possess a basic working knowledge of Figma and familiarity with design systems, including their structure, maintenance, and governance

  • Proven ability to lead projects from brief to launch, specifically handling detailed ticket creation, timeline ownership, and final QA.

  • Experienced in balancing design quality vs. business priorities.

  • Systems- and process-minded; enjoys auditing, documenting, and optimizing workflows for maximum team efficiency.

  • Excellent organizational skills, with the ability to manage multiple projects simultaneously.

  • Confident decision-maker, willing to enforce standards and provide direct feedback.

  • Willingness and ability to work collaboratively with teams during US business hours.

What’s in it for you?

As a full-time member of our team, you’ll enjoy:

  • Flexible hours, work wherever you choose.

  • Unlimited Paid Time off

  • Paid non-working holidays per country of residence.

  • Medical/ Dental/ Vision insurance (US-W2).

  • Pro-rated 13th-month bonus in select regions.

  • Referral bonuses.

  • Financial support for online courses.

  • Fun and casual work environment.

  • Employee engagement activities and virtual gatherings.

  • We are a diverse, global team! 🌍

Equal Employment Opportunity

Winona provides equal employment opportunities to all qualified individuals without regard to race, color, religion, sex, gender identity, sexual orientation, pregnancy, age, national origin, physical or mental disability, military or veteran status, genetic information, or any other protected classification. Equal employment opportunity extends to all aspects of employment including, but not limited to, recruitment, hiring, training, promotion, demotion, transfer, leaves of absence, and termination. Winona takes allegations of discrimination, harassment, and retaliation seriously and will promptly investigate such behaviors.

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