Vice President of Product Design

The RoleTimelyCare is seeking a Vice President of Product Design to lead and evolve our design organization. This leader will define how design shapes AI-driven experiences that anticipate user needs, amplify clinical impact, and scale empathy through technology. As both a visionary and hands-on practitioner, the VP will guide the team in integrating AI, data insights, and human-centered research into every stage of the product lifecycle—across student, clinician, and campus experiences. They will build and nurture a high-performing design culture that thrives on collaboration, experimentation, and measurable impact.As TimelyCare has transitioned fully to AI-enabled development using tools like Claude Code and Cursor, this role will be pivotal in defining how design and AI work together to deliver seamless, meaningful user experiences. Partnering closely with product, engineering, and other teams, this leader will ensure design solutions align with business goals and truly meet user needs in a fast-paced, AI-first environment. They will evolve design processes to better integrate continuous feedback, user insights, and rapid validation—ensuring that every TimelyCare product remains intuitive, inclusive, and deeply impactful.What You'll DoDefine and execute a design strategy that leverages AI technologies to enhance access, engagement, and health outcomes across TimelyCare’s digital ecosystem.Develop systems and processes that integrate user feedback, behavioral data, and research into every design decision—ensuring deep understanding of user needs, motivations, and experiences.Recruit, develop, and inspire a high-performing team of designers and researchers, fostering a culture of curiosity, experimentation, and evidence-based design.Collaborate cross-functionally with Product, Engineering, and Care teams to ensure design principles and user insights inform AI model training, product requirements, and feature prioritization.Advance TimelyCare’s design systems to support adaptive, data-informed experiences and streamline iteration cycles—balancing innovation with quality and accessibility.Champion human-centered AI practices that ensure trust, inclusivity, and ethical design in all AI-driven experiences.Define and measure success metrics linking design outcomes to user satisfaction, engagement, adoption, and overall well-being impact.Communicate design impact and insights to executive stakeholders, using data and storytelling to guide company strategy and product direction.Serve as a key voice in leadership discussions, representing the product design function and advocating for user experience as a driver of innovation, differentiation, and growth in digital healthcare.Adapt and evolve with the organization’s needs, taking on strategic projects that advance TimelyCare’s mission and design maturity.Champion ongoing learning and development by equipping the design team with skills in emerging AI tools, accessibility standards, and behavioral health UX—ensuring continuous growth and future-ready expertise.What You Bring10+ years of design leadership experience in product led, innovative organizations with 5+ years managing design teams.Strong experience in AI informed product design and the ability to leverage data and AI tools.Motivation to embrace emerging AI practices and proactively experiment with new tools, workflows, and design methods as the field evolves — fostering a team culture of exploration and innovation.Commitment to continuous learning and professional development, modeling curiosity and growth to help the team stay ahead of AI-driven changes in product design and user experience.Proven ability to translate voice of customer insights into scalable design strategies and differentiated user experiences.Strong understanding of design systems, user research, analytics, and design operations in complex product environments. Passion for building customer first solutions and human centered innovation, advancing access to quality care through technology. Exceptional storytelling skills with the ability to connect design impact to business strategy.Demonstrated adaptability in a fast paced, agile environment with a growth mindset and readiness to scale.Experience in healthcare, edtech and/or telehealth is a plus.Benefits + PerksPaid Company Holidays + No work on your birthday!Flexible PTO + Volunteer Time Off (VTO) as an organization to give back to the communityVariable bonus eligibility on a quarterly basisCompany-sponsored Health Insurance (Medical, Dental, Vision) + Pet Insurance Company-paid group Life Insurance + Company-paid Short Term DisabilityConcierge benefit support services401(k) with employer match Free access to TimelyCare virtual medical and mental health support Mission-Driven Purpose with a Supportive Team CultureThe salary range for this opportunity is $225,000 – $250,000 per year, depending on education and experience. This is the base pay. You will be eligible for a discretionary bonus in addition to the base pay, to be discussed during the interview process.