Ari Engelberg

Ari Engelberg serves as Head of Communications and Strategic Initiatives at Harvard-Westlake School in Los Angeles, a position he has held since 2015. In that role, he manages the school’s brand and its portfolio of print and electronic communications efforts. He also oversees a wide range of strategic projects, from new curriculum and programs to the school’s response to COVID to major capital projects such as the school’s new 17-acre River Park athletic campus.

In 1996, while attending graduate school at UCLA, Ari co-founded Stamps.com (NASDAQ IPO in 1999, taken private in 2021), which is now the Internet postage leader, commanding over 85% market share. At Stamps.com, Ari was responsible for raising venture capital, managing the company’s relationship with the United States Postal Service, and developing strategic marketing and distribution partnerships with other companies.

In 2000, after the company’s initial public offering, Ari left Stamps.com to co-found Archive, Inc., a venture-funded data storage services provider, which was sold in 2002. Ari then returned to his alma mater, Harvard-Westlake, to teach American history and coach basketball for several years.

In 2007, Ari became the Executive Director of Bright Star Schools (www.brightstarschools.org), the operator of two successful public charter schools in the mid-city area of Los Angeles. Over eight years of service to Bright Star, Ari helped to grow the organization into one of the leading Charter Management Organizations in Los Angeles. Today, Bright Star Schools operates nine schools that together serve 4000+ students from some of the city’s most underprivileged communities.

Ari’s diverse work experiences blend classic entrepreneurship with more traditional operating roles. Regardless of the job he has held, Ari’s focus has been on creative problem solving and strategic thinking to help organizations and businesses large and small to thrive.

Ari has served extensively as an executive coach to CEOs and Executive Directors and as a board member of non-profit and for-profit companies.

Ari serves on the Board of Directors of Extrico Health, a venture-backed health care analytics platform with several major health system customers. Ari regularly invests in and advises start-ups. Recent investments and engagements include FormaPath, Gipper Media, FanFix (sold to SuperOrdinary), Juno Insurance, Bravago, and Everchron.