Head of Product
United States · Remote
Senior +1 · Full time
Posted a year ago
Why is this role awesome?
This role will have a front row seat to creating the product, vision, and roadmap of Fiveable. As part of the leadership team, this role will also play a large part in the hiring and creating of product teams as we scale.

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.


Fiveable in the news:

Fiveable lands $10M Series A to become ‘the hallways of the educational internet’ (Tech Crunch)

How one founder identified a gap in education working as a teacher and built a startup to fix it (Tech Crunch Podcast)

Fiveable Offers Free AP Test Prep and Tips For Optimizing Remote Learning (Forbes)

A Former Oakland Unified Teacher Now Helps Even More Students Pass AP Tests (Edsurge)


The Fiveable Team

We're a creative group of former teachers, community builders, game designers, and generally curious people who are driven by social impact. We're focused on building a diverse team and are inclusive of all backgrounds. And we're big on growth mindsets - we're all learning!


Who we're looking for

Listen to our founder discussing our vision & product challenges:

As the Head of Product, 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 and Hours.

You’ll join the leadership team and will own the product vision, strategy, roadmap, and team. You are excellent at execution and are not afraid to get your hands dirty and jump into the action when needed — we are an early stage startup after all. 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 will report directly to the CEO.

You are:

  • Creative - You always find a way to get something done.
  • 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 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 product teams, as well as working alongside design and engineering teams
  • Demonstrated success in web product management and deep understanding of best practices for browser-based experiences
  • Exceptional written and verbal communication skills along with an ability to consider multiple perspectives and how to best include that in collaborative processes
  • Advanced with product workflows, scoping features, analyzing data in Amplitude and Google Analytics, and communicating progress with all stakeholders
  • Experience in people management to build and support teams



Lead product strategy and a cross-functional product team to grow and into essential platforms for high school students.


  • Collaborate with design, engineering, content, and community teams to ship a world-class product that helps students study together
  • Work with leadership to maintain a deep understanding of business objectives to ensure outcomes effectively meet strategic and tactical goals
  • Build and develop a company-wide process for evaluating new product ideas based on A/B tests, user needs, and analytics.
  • Incorporate data analytics, user feedback, usage data, and research to ensure consistency and quality in product decisions.


  • Collaborate with design and engineering leadership to scope the vision for integrating and
  • Scale and lead a team of product managers with a student-centered vision aligned to business needs
  • Establish, maintain, and review quarterly OKRs alongside the leadership team
  • Work cross-functionally to improve efficiencies of product and data workflows with an emphasis on async, clear communication, and exceptional documentation
  • Maintain a a high level of quality and standards across all products and deliverables that drive signups and retention
  • Own the internal and external company changelog



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
Fiveable is a social network for education where students learn together through content, community, and courses.
Size:  11-50 employees
Year Founded:  2018
Right Side Capital Management
BBG Ventures
Matchstick Ventures
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