# Casandra Stewart

> Casandra Espinoza Stewart is the CEO and co-founder of Homeroom, a San Francisco software platform that brings the messy, paper-bound world of after-school enrichment, summer camps and extended care online. A Stanford public-policy grad and former Greylock Partners analyst, she traded venture capital for venture building, teaming up with former teacher Christina Walker to give PTAs, parents and class vendors one place to schedule, book and get paid. Homeroom hit a $1M GMV run rate in month one and raised $3.5M in seed funding led by Forerunner Ventures in 2019.

- **Role:** CEO & Co-Founder at Homeroom
- **Organizations:** Homeroom, Greylock Partners, Delphix, Kauffman Fellows, Stanford Student Enterprises, QuestBridge, The Young Vets
- **Nationality:** American
- **Education:** B.A. in Public Policy, Stanford University, Fellow, Class 16, Kauffman Fellows
- **Known for:** Co-founded and leads Homeroom as CEO, Raised $3.5M seed funding led by Forerunner Ventures (2019), Surpassed a $1M annual GMV run rate in Homeroom's first month

## Career timeline

- **Stanford** — Studied public policy; served as COO of Stanford Student Enterprises, a student-run company with $14M in assets
- **Post-grad** — Spent two years at Greylock Partners on the operations team, working on due diligence, deal flow, marketing and network development
- **Pre-Homeroom** — Led marketing efforts focused on healthcare at enterprise software company Delphix
- **Kauffman Fellows** — Named a Kauffman Fellow (Class 16); mentored under Reid Hoffman and received a peer-selected leadership award
- **~2017** — Co-founded Homeroom with Stanford classmate Christina Walker
- **2019-06** — Raised $3.5M seed round led by Forerunner Ventures to scale the after-school enrichment platform

## Achievements

- Co-founded and leads Homeroom as CEO
- Raised $3.5M seed funding led by Forerunner Ventures (2019)
- Surpassed a $1M annual GMV run rate in Homeroom's first month
- Grew 400% within ten months and scaled to 17 districts across five states without a dedicated sales team
- Kauffman Fellow (Class 16), mentored under Reid Hoffman, peer-selected leadership award
- COO of Stanford Student Enterprises ($14M in assets) as a senior

## Latest updates

- **2019-06** — Homeroom announced $3.5M in seed funding led by Forerunner Ventures, with Felicis, Precursor and Kapor Capital participating, to expand its after-school enrichment platform.

## Links

- Website: https://homeroom.com
- LinkedIn: https://www.linkedin.com/in/casandrastewart/
- Twitter/X: https://twitter.com/joinhomeroom
- Facebook: https://www.facebook.com/joinhomeroom

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Profile page: https://yespress.io/casandra-stewart
Published by YesPress — https://yespress.io
Last updated: 2026-06-25