Chief of Staff

United States (US)


Full Time


Full-time, remote only, USA. $100-140K salary. Equity with 4-year vesting.

Do you enjoy creating processes that enable others to flourish? Does it excite you to experience first-hand what it‘s like to run an early-stage, high-growth tech startup?

Boost My School is looking for a Chief of Staff to join our team passionate about helping schools set all their students up for success.

Why work at Boost My School?

1. Be proud of your impact helping schools and students

  • Boost is trusted by 100+ K-12 and higher ed customers to bring in $50M a year from 60,000 families and donors
  • Every Boost team member has clear accountability over results that directly impact the success of our company and customers
  • Our business model is designed so that we succeed only when our customers succeed
  • You’re given a monthly budget to donate to schools of your choice on Boost

2. Work with thoughtful teammates building a champion company together

  • Openly view all company communication outside of personal matters – we mostly communicate over Slack public channels and Notion public wikis
  • Openly view company, team, and individual performance metrics
  • Use our weekly No Meetings Day to get uninterrupted work done (or to do your laundry while you work)
  • Take on tasks in which you have the final say over your manager or the CEO
  • Receive regular professional development through weekly 1-on-1s and quarterly career check-ins
  • Get to know your remote teammates at our annual week-long in-person retreats and our optional coworking weeks

3. Join a culture that wants you to be your best self at work and outside of work

  • Internal meetings are scheduled during our core working hours (12pm to 4pm ET) so you have more flexibility over your time
  • Take care of errands or pick up your kids as long as you communicate accountability over the things you’re responsible for
  • Our company calendar is aligned with the school year – we have 15 company days off across major holidays and Summer Fridays
  • Outside of the 15 company days off, we suggest taking an additional 10 to 15 days off, and require taking 1 week of continuous time off per calendar year
  • Company covers medical, dental, and vision insurance premiums and out-of-pocket expenses through QSEHRA ($512/mo for individuals, up to $1,037/mo for those with families)
  • Use your remote working stipend ($200/mo) for your internet bill, to buy lunch, or for professional development
  • Take on any type of internal, non-technical responsibilities to allow our CEO & Founder to be more strategic
  • Run weekly all-hands meetings, monthly team check-ins, quarterly coworking weeks, and our annual retreat
  • Create processes to manage OKRs, 1:1s, hiring, and performance reviews
  • Lead remote culture efforts like social events and virtual celebrations
  • Manage our internal wiki (Notion) and docs (Google Drive)
  • Support HR, finance, and legal responsibilities (Gusto, Quickbooks, Clerky)
  • Step in to support go-to-market operations (e.g. set up Hubspot CRM & automations)
  • Assist with financial models and monthly investor updates
About you
  • You build champion habits: You set yourself up to be a champion by continuously improving what you do day-to-day
  • You overcommunicate: You go above and beyond to ensure you’re on the same page with your teammates
  • You embrace ownership: You demonstrate to the team that you’re fully accountable for the results of your actions
  • You use radical candor: You proactively use radical candor so that your teammates trust you to deliver critical feedback
  • You move fast with intention: You make decisions and execute quickly so that you both succeed and learn faster
  • 5+ years of experience in a strategic, operations, or finance role, with a preference for experience with B2B SaaS financials and operations
  • Comfort and confidence to be an operations jack-of-all-trades – your responsibilities will range from creating processes to analyzing financials to building culture
  • Strong preference for candidates willing to grow quickly with the company into our head of operations, if you consistently exhibit the habits needed to succeed in the added responsibilities
  • Able to co-work in person with our CEO for a few days a month for at least your first year on the team. Slight preference for being based in NYC area, where our CEO is based
  • Bonus: You’re a past or future startup founder
  • Bonus: You’re familiar with the school fundraising industry – e.g. you helped raise money for your school or you know what “advancement” means
If you want to apply for this position

Please email with:

  • your LinkedIn or resume
  • why you would excel in this position at Boost My School
  • explanation of a process that you created for others that you’re proud of

Boost My School