Chief of Staff

At Unicycle, we welcome you for who you are, regardless of where you’re from, what you look like, or who you love. Our mission to make learning more empowering, more equitable, and more human begins with a diverse and inclusive ecosystem within.


We’re not chasing a small problem, and we’re not addressing a small market. By 2025, global digital expenditure in education will top $340 billion. But to combat the inertia of decades-old frameworks and emerge with truly impactful tools requires highly-skilled, creative problem-solvers with simultaneously uncapped and laser-focused vision. 

We’re looking for a Swiss Army knife generalist who once had an existential crisis about not being able to “pick a lane” and now finds him / her / themself thriving at the center of it all. Most companies make their ‘Chief of Staff’ hire two years later; in our opinion, that’s two years too late. And while this role can sometimes feel amorphous, the value and impact delivered when it succeeds are crystal clear.

You’ll be the pulse of this company—the knowledge-keeper, dot-connector, efficiency-creator, program-manager, and most of all, problem-solver. You’ll touch and inform every aspect of our business, across operations, people, finance, product, growth, and brand. From All Hands to board meetings to critical launch-dependencies, you’ll lead, manage, prioritize, inspire, and execute from the stratospheric to the minute. You’ve run the marathon of a high-growth startup and are passionate about engineering and tracking the early sprints into scalable, sustainable processes.

Far more than the CEO’s right hand, you’ll be her 10x multiplier. And together, you’ll unlock the team’s potential to move with urgency, discipline, rhythm, and focus, while cultivating a culture of thoughtfulness and human care.

There's work, and then there's the work of your life. Should this inspire the mission-driven voice in the back of your head, please be in touch.

Who you are:

  • You are intellectually curious
  • You have high emotional intelligence and the ability to establish meaningful relationships, both internal and external
  • You are a self-starter and problem-solver who loathes stagnancy, and can identify and seize opportunities for impact without needing an abundance of direction or oversight
  • You thrive in uncertainty and find meaning in leading organizational transformation around new goals, priorities, teams, or projects
  • You are a strategic systems-thinker, and can break a complex problem down into actionable component parts
  • You possess persuasive, thoughtful, tactful, and precise communication skills
  • You are a talented multi-tasker, unafraid to juggle multiple responsibilities and priorities
  • You have the organizational prowess, meticulous attention to detail, strong sense of responsibility and ownership, and generalist skill set to take on a wide range of department-agnostic challenges and opportunities
  • You pride yourself on your reliability and high standard for great work
  • You are passionate about education and the future of learning
  • Above all, you are a collaborative teammate who practices inclusivity, empathy, and human kindness

What you’ll do:

  • Be a thought-partner to the CEO and COO, helping shape and inform business strategy, prioritization, and execution
  • Collaborate with the CEO to identify, evaluate, and execute opportunities for business development
  • Build strong collaborative relationships across the company as we grow and scale
  • Spearhead special projects across marketing, creative, operations, people, finance, and growth, and manage their timelines, progress, reporting, and success
  • Bring key project stakeholders together to ensure team-wide clarity of vision and progress, as well as elimination of roadblocks
  • Support planning, creation, and distribution of materials for investors, board members, and external partners, and lead ongoing engagement
  • Support user and market research and ad-hoc initiatives as needed
  • What you won’t do (unless it’s for yourself): get coffee, pick up dry cleaning, other EA duties etc :)
Interested in this role? Apply below, we look forward to getting to know you.
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