# Eric Oldfield

> Eric Oldfield is a New York technology executive and operator whose career runs through online music, digital advertising, real-estate technology, workplace software, education technology, and streaming discovery. At Brainly, where he served as Chief Business Officer, his long experience commercializing consumer internet products met an extraordinary test: the 2020 shift to learning at home, when the platform reported 200 million monthly users and a 200 percent rise in U.S. demand.

- **Role:** Chief Business Officer at Brainly
- **Organizations:** Brainly, Reelgood, Justworks, Zillow Group, Trulia, LiveIntent, Everyday Health, Mail.com, N2K Entertainment, AOL, Alloy, Publicolor
- **Known for:** Built or led sales and commercial operations leading up to or through four IPOs: Trulia, Everyday Health, Mail.com and N2K Entertainment., Co-founded advertising technology company LiveIntent., Led sales and B2B strategy at Justworks across demand generation, sales operations and business development.

## Career timeline

- **1997** — Worked in advertising and sponsorship at N2K Entertainment's Music Boulevard during the early online music era.
- **Before 2010** — Held sales, business development and general-management roles across N2K Entertainment, Mail.com, Everyday Health, AOL, Alloy and Muzac; his commercial work touched four companies that reached public markets.
- **2005-2008** — Served as a volunteer mentor with Publicolor in New York.
- **2009-2010** — Co-founded LiveIntent and served in sales and business development leadership.
- **2010-2016** — Held consumer-services leadership roles at Trulia and Zillow Group, helping build and scale the media business.
- **2016** — Joined Justworks as Senior Vice President and General Manager, leading sales and B2B strategy.
- **2016-2020** — Served as Chief Business Officer of Brainly and as general manager for the U.S. market.
- **2020** — Helped represent Brainly during the abrupt move to learning at home, when the company reported 200 million monthly users and U.S. demand growth above 200 percent.
- **2021** — Began serving as Chief Operating Officer at streaming-discovery company Reelgood, according to public executive directories and professional activity.

## Achievements

- Built or led sales and commercial operations leading up to or through four IPOs: Trulia, Everyday Health, Mail.com and N2K Entertainment.
- Co-founded advertising technology company LiveIntent.
- Led sales and B2B strategy at Justworks across demand generation, sales operations and business development.
- Helped lead Brainly's U.S. business as the platform reported 200 million monthly users in April 2020.
- Served as a Publicolor mentor from 2005 through 2008.

## Latest updates

- **2023-05** — Shared Reelgood's analysis of how the Hollywood writers' strike could affect streaming.
- **2022-10** — Publicly celebrated Reelgood CEO David Sanderson's inclusion in Media Play News' 40 Under 40 in home entertainment.
- **2021-04** — Began a Chief Operating Officer role at Reelgood, according to public executive profiles.

## Links

- Website: https://brainly.com
- LinkedIn: https://www.linkedin.com/in/eoldfield

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Profile page: https://yespress.io/eric-oldfield
Published by YesPress — https://yespress.io
Last updated: 2026-09-27