About Stepful:

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—especially those from underserved communities—launch high-demand healthcare careers.

In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to build talent pipelines and address the growing shortage of allied health workers. Our graduates, including Medical Assistants, Pharmacy Technicians and more, go on to work at major employers like CVS, NY-Presbyterian, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

We’re unlocking the full potential of the global workforce—improving access to quality healthcare for everyone, everywhere.

Our values:

We credit much of our success to our exceptional team. We’re looking for mission-driven individuals who thrive in fast-paced, sometimes ambiguous environments, and embody our four core values:

Care first: We do whatever it takes for our students to succeed.

Learn quickly: We test, learn with data, and iterate.

Build together: We win when we rely on each other.

Own it: We show up, take initiative, and show pride.

The role:

As our Head of Product Design, you will be both visionary, operational, and contribute hands-on to design. You’ll define the future of design at Stepful, nurture and grow a team of senior designers and leaders, and ensure design is recognized as a key driver of company growth and innovation.

As a member of the leadership team, you’ll bring a user-centered perspective into executive decision-making, shaping company-wide product strategy and building design’s influence across all product lines. You’ll represent the values of Stepful, championing values, inclusivity, and integrity while elevating design standards to industry-leading levels.

What you’ll do:

• Define and communicate the vision for the design organization, owning the structure, health, and long-term growth of the design team

• Own and lead our most critical product vertical to improve business outcomes

• Shape decisions on org strategy, priorities, and investments alongside other leadership members by identifying cross-functional opportunities that map to business needs

• Develop and coach the design team, ensuring paths for growth and clear expectations

• Recruit, develop, and retain top design talent, building a culture of collaboration and excellence

• Establish principles, systems, and processes that ensure design excellence and culture across the organization

Deliver outcomes that expand design’s impact across all product lines

This job is for you if you have:

• 10+ years of product design experience across a variety of platforms, with at least 3-5 years in a leadership role

• Strong portfolio of work that demonstrates product work that impacts business outcomes, and leadership work shaping company-level product and design strategy

• A deep understanding of the tech that powers digital products, and how to collaborate with engineering to make the most of emerging capabilities

• Ability to move fluidly between vision, strategy, and hands-on execution, balancing innovation with operational rigor at scale

• Exceptional communicator with experience building relationships with teammates and influencing decisions at a variety of levels and across multiple teams

• Commitment to inclusivity, equity, and team well-being

Bonus points if:

• Experience leading design in startups, particularly at B2B2C or B2C EdTech/Healthcare companies

• Experience leading in experiment/data driven product development organizations

Interview Process:

In your application, please include a link to your portfolio showcasing relevant work samples. A portfolio submission is mandatory for consideration of your candidacy.

• Step 1: Screening call with Talent Acquisition

• Step 2: Intro call with Hiring Manager

• Step 3: Virtual whiteboard panel interview

• Step 4: Onsite interview at office in SoHo, NYC

Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.