Boost My School careers: remote jobs, culture and where they hire

Boost My School announced a $10M round led by High Alpha on August 26, 2025, which the company said brings total funding to $10 million. High Alpha co-founder Mike Fitzgerald sits on the board, and Scot Chisholm, founder of the fundraising platform Classy, is an advisor.

Boost My School is an advancement platform built specifically for K-12 schools: annual funds, giving days, galas and auctions, alumni events, ticketing, school stores and a CRM that integrates with Raiser's Edge NXT. The company says it is the only advancement platform built for K-12 teams, and as of October 2026 it is trusted by 350+ schools that bring in $200M a year from 100,000 families and donors, with 97% school retention and an 85 NPS. Schools that switch to Boost report raising 20% more dollars from 25% more donors.

Founder and CEO Holman Gao, a former Silicon Valley software engineer, built the first version after being asked to write a paper check to keep his high school's math team alive; the tool helped his alma mater double its annual donors, and he cold-called nearby schools to test broader demand. The platform launched commercially in 2019 and now runs as a fully remote, roughly 30-person team spread across US cities, with Gao in New York and product leadership in San Francisco. The business model note on the careers page is explicit: Boost succeeds only when its schools succeed, and every team member gets a monthly budget to donate to schools of their choice on the platform.

Holman Gao, Founder and CEO. Software engineer turned entrepreneur. Started as a senior software engineer at venture-backed Silicon Valley startups, one of which was acquired by Google. Holds a B.S. in computer engineering and mathematics from the University of Maryland and competed in the ACM-ICPC World Programming Finals. Built the first version of Boost to help his high school math team fundraise, then launched the company in 2019. Based in New York.

The impact loop is unusually direct for B2B SaaS: engineers deploy to production multiple times in their first week, own initiatives end to end, and can see schools raise real money through what they ship. The stack is an isomorphic React/Relay web app talking to a Rails GraphQL API, with continuous deployment, incremental pull requests, strict linting, type checking and strong test coverage. As of October 2026 the public team page lists nine engineers plus a two-person product group led by VP of Product Nathaniel Okun, previously a product manager at Apple and senior product engineer at Flexport.

Pay and benefits are published on every posting. The Senior or Lead Software Engineer role lists $157K to $181K base and $174K to $201K all-in cash, with equity on 4-year vesting; sales roles publish base and OTE the same way (the Associate/Junior Account Executive lists $73K base, $128K OTE). Benefits include medical, dental and vision premiums plus out-of-pocket expenses covered through QSEHRA ($537/month for individuals, up to $1,091/month for families), a $200/month remote working stipend, an annual company bonus tied to top company goals, and a company laptop shipped before day one.

The careers page describes a work culture inspired by championship sports teams, with radical transparency as the operating default: company communication happens in public Slack channels and Notion wikis, and company, team and individual performance metrics are openly viewable. Team members take on tasks where they have the final say over their manager or the CEO, and the stated hiring goal is for each person to stay 5+ years.

Time is structured around flexibility: internal meetings sit inside core hours of 12pm to 4pm ET, there is a weekly No Meetings Day, and the company calendar follows the school year, with 15 company days off across major holidays and July Fridays Off, a suggested additional 10 to 15 days, and a required 1 week of continuous time off per calendar year. The remote team meets at an all-company in-person retreat in July and departmental coworking onsites in fall and winter.

Roles are listed at https://www.boostmyschool.com/careers with full descriptions and pay. As of October 2026 there are five openings: Senior or Lead Software Engineer (full-time, remote, USA only), iOS Engineer on contract (remote from the USA, Canada, South America or Europe with some US-hours overlap), Business Development Representative, Senior School Support Specialist (school advancement experience required) and Associate/Junior Account Executive, with the non-engineering full-time roles also remote USA only.

There is no ATS: applications go by email to careers@boostmyschool.com. The engineering posting asks for a LinkedIn or resume, a short cover letter on why you would excel at Boost, and a short explanation of code you are proud of; it targets 6+ years of software engineering experience, ideally at a B2B SaaS company, with bonus points for familiarity with school fundraising. Expect to deploy to production in week one and to travel about twice a year for retreats.