Head of Product Design

  • Full Time
  • Remote

Website thinkfiveable Fiveable

Making learning social

Who we are

Fiveable is a social learning platform that engages students through community-powered content, interactive study rooms. Think of us as “the hallways of the educational internet”, where we connect students to each other and to new resources.

The Fiveable platform has two core experiences — content & community. Within our content library, student writers have published thousands of posts explaining concepts, detailing processes, and sharing advice. This is peer-to-peer knowledge sharing that opens up opportunities for students across academics, future-planning, and all kinds of topics beyond the classroom.

The community spaces connect students by subject, affinity, and interest to create uniquely segmented support groups. This happens within virtual spaces on Hours, our newly acquired platform, and on our Discord server.

During the 2020-2021 school year, we had 5.5 million unique visitors on our platform. And we are just getting started.

We’ve raised $14.2M backed by world class investors including Union Square Ventures, Owl Ventures, BBG Ventures, Metrodora Ventures (Chelsea Clinton), Serena Ventures, and many more. Check out a list of our other investors here.


Who we’re looking for

As the Head of Product Design, you’ll lead and manage a growing creative team to help tackle our biggest challenge right now: unifying and building a cohesive social learning experience across Fiveable.me and Hours. You’ll work alongside Product leadership to help identify areas of improvement in the scoping, planning, and wire-framing process while optimizing for speed and efficiency. You’re not afraid to get your hands dirty and jump into the action when needed — we are an early stage startup after all. You feel genuinely excited about establishing a design-first culture focused on solving student problems and unlocking innovation across the company. You believe in the power of advocating for the needs of our students and working cross-functionally to create a holistic user experience between different products. The Head of Product Design will report directly to the Chief Operating Officer.

You thrive in fast-paced environments and feel comfortable making decisions that benefit and center the needs of our students as well as the company. Building new systems, optimizing existing infrastructure, and creating cross-functional feedback loops genuinely excite you. Most importantly, you aren’t afraid to experiment, fail, learn from your efforts, and try again.

You are:

  • Passionate – You care deeply and pour yourself into what you do
  • Efficient – You work smarter, not harder
  • Candid – You communicate consistently and authentically
  • Flexible – You go with the flow and find new paths to your goals
  • Empathetic – You understand how others feel and know why they act the way they do
  • A Thought Leader – You’re up-to-date on industry trends and are eager to be a part of a culture of continuous learning
  • A Problem-Solver – You take initiative to present solutions to problems that you encounter or notice

You have:

  • 6-10+ years of experience building and managing agile design teams, as well as working alongside Product and Engineering teams in the execution phase
  • Exceptional written and verbal communication skills along with an ability to consider multiple perspectives and how to best include that in collaborative processes
  • Demonstrated success in building platforms, especially those with multiple product lines
  • Expert-level proficiency with Figma, design systems, and project management capabilities from ideation to execution and retrospectives
  • A sincere interest in visual storytelling and empowering our users through a strong brand presence and customer journey

Own large-scale design initiatives end-to-end and grow an empathetic, design-first mentality across Fiveable and Hours through exceptional visual storytelling.


  • Collaborate with product and engineering leadership to bring a cohesive experience to life that incorporates the Fiveable content and Hours study rooms.
  • Oversee the reorganization and optimization of our Figma Organization setup, team structures, and corresponding asset libraries
  • Integrate design team processes into Hours’ development workflows for visual consistency and improved collaboration across brands


  • Scale and lead a team of designers and advocate for their growth & development at the organization, stepping in when needed on the most strategic and complex projects
  • Work cross-functionally to establish a process for better incorporating student feedback and voices into the product design workflow
  • Establish, maintain, and review quarterly OKRs alongside Product leadership
  • Evangelize critical design frameworks and tools and identify how to best operationalize them, along with a strong emphasis on data gathering and user research
  • Work alongside Product and Engineering to develop efficient project workflows with an emphasis on async processes, clear communication, and exceptional documentation
  • Maintain an exceptional level of design quality and standards across all products and deliverables that drive signups and retention


Fiveable is a small, but growing edtech startup that is fiercely committed to its employees. Here is what you can expect from your Fiveable experience:

  • A front row seat to education innovation at an early stage startup
  • A company that prioritizes inclusion and diversity
  • The ability to work remotely from anywhere in the world
  • Competitive compensation with stock options
  • Comprehensive benefits (Health, Dental, and Vision) 100% covered by Fiveable for individuals and families
  • Access to a 401k and life insurance policy
  • Unlimited paid days off and mental health support through Talkspace

To apply for this job please visit apply.workable.com.