Head of Creative and Content Design

Homeward • San Mateo, CA

12d • $155,000 - $183,000

About The Position

Homeward Health is seeking a senior, hands-on creative leader to serve as the Head of Creative & Content Design for our Care Experience organization. This role is the single accountable owner for member-facing creative and content design—setting strategy, leading execution, and modernizing how creative and content are produced across the organization.
This is intentionally not a traditional Creative Director role. Instead, it is a hands-on creative leadership position designed for a builder who operates comfortably at both the strategic and executional levels. You will define creative and content direction, work with junior creative team members, implement scalable systems and AI-enabled workflows, and personally deliver high-impact assets across channels.
Design and content play a critical role in how members understand their benefits, trust Homeward’s care model, and take action. This role ensures our creative output is clear, compliant, empathetic, and operationally scalable—especially for our highest-volume channel: contact center and member outreach.

Requirements

• Demonstrated, hands-on experience using AI-assisted tools in professional creative or content workflows
• Ownership of selection, implementation, and expansion of AI-enabled tools supporting design, content creation, and creative operations
• Ability to design and operationalize AI-supported workflows that improve creative speed, consistency, personalization, and scalability
• Experience ensuring AI outputs meet brand standards, accessibility requirements, and healthcare compliance expectations
• Ability to clearly demonstrate how AI tools have elevated creative quality, efficiency, or scale in prior roles (portfolio or case examples required)
• 7–10 years of progressive experience in creative design, content design, or senior-level roles with ownership of both strategy and execution
• Strong portfolio demonstrating senior-level, consumer-facing creative work with clear ownership of creative direction, systems, and end-to-end execution (portfolio required)
• Expert proficiency in Adobe Creative Suite (Illustrator, InDesign, Photoshop), including advanced or emerging AI features
• Strong experience with Figma and/or Canva in collaborative, system-based design environments
• Experience designing for email marketing and automation platforms (Customer.io or similar)
• Experience designing and structuring content for web platforms such as Webflow or comparable CMS tools
• Deep understanding of typography, layout, color systems, accessibility standards, and visual hierarchy
• Comfort operating as a senior creative leader who is equally comfortable setting direction and executing hands-on work

Nice To Haves

• Experience working in healthcare, insurance, or other regulated environments strongly preferred

Responsibilities

• Own creative and content design strategy for the Care Experience organization, ensuring all member-facing communications are clear, consistent, accessible, and effective
• Serve as the senior creative authority across Care Experience, Marketing, and Engagement—setting standards for visual quality, tone, and execution
• Personally design and deliver high-impact creative assets across email, SMS, print, web, digital campaigns, and supporting materials for contact center and care teams
• Translate complex healthcare, benefits, and care program information into approachable visual and content-driven experiences that build trust and drive action
• Establish and evolve creative systems, templates, design standards, and asset libraries to support scale and consistency
• Evaluate, implement, and optimize AI-enabled content workflows using tools such as Jasper, Sanity, Redpoint, GMC, and other content management platforms to increase throughput, personalization, and channel deployment efficiency
• Partner closely with Engagement Strategy, Marketing Operations, Product, Clinical, and Data teams to ensure creative intent is preserved through execution
• Support campaign and initiative planning by shaping creative and content approaches early—balancing strategy, feasibility, and execution speed
• Provide hands-on mentorship, creative direction, and quality oversight to the creative group and provide additional support as design or content roles are added over time
• Manage multiple concurrent initiatives with strong prioritization and accountability in a regulated healthcare environment

Benefits

• Competitive salary, equity grant, generous paid time off
• Comprehensive benefits package including medical, dental & vision insurance with 100% of monthly premium covered for employees
• Company-sponsored 401k plan
• Flexible working arrangement

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed