3x founder

Ross Cranwell

Demand Generation I YC Alum I | Former CEO of Milk Video (Acquired)

Co-founder

Milk Video· Winter 2021 🇺🇸 Larchmont, New York, United States

in LinkedIn 𝕏 @rosscranwell

2026Head of Demand Generation· TrueNAS

Founder · since 2010

Company

TrueNAS

Role

Head of Demand Generation

current

Stage

—

no public source

Raised

—

no public source

Based

New York, United States

current

Founder / co-founder — the company's markEmployee / research role

Source: LinkedIn work history

Profile coverage5 of 7 · missing posts, contact

Milk Video

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Winter 2021

Experience

Career

TrueNAS
Head of Demand Generation · New York, United States · 2026 – Present
2026
Self-Employed
GTM Consultant · New York City Metropolitan Area · 2025 – 2026
2025
Milk Video
Co-founder
CMO & Co-Founder [Acquired by Oktopost] · New York, United States · 2020 – 2025
2020
Medallia
Head of Demand Generation [Acquired by Medallia] · New York City Metropolitan Area · 2017 – 2020
2017
New York Film Academy
Head of Marketing · New York City Metropolitan Area · 2016
2016
Chegg Inc.
Head of Marketing [Acquired by Chegg] · Greater New York City Area · 2014 – 2016
2014
italki
Global Marketing Director · Shanghai · 2012 – 2014
2012
LingoBite
Founder
Founder & Head of Marketing · Shanghai · 2011 – 2013
2011
People Squared
Co-founder
Co-Founder and Head of Marketing · Shanghai · 2010 – 2013
2010
Self-Employed
Fractional Chief Marketing Officer to Startups · Shanghai, Beijing, Los Angeles · 2010 – 2012
2010
ChinesePod
Marketing Manager [Acquired by Bigfoot Ventures] · Shanghai, China · 2007 – 2010
2007
The American Chamber of Commerce in Shanghai (AmCham Shanghai)
Marketing Executive · Shanghai City, China · 2005 – 2007
2005

Bio

20+ years leading marketing and product innovation across multi-national companies in New York and Shanghai. I specialize in building and scaling from zero to one and beyond - crafting positioning, launching products, and driving GTM alignment. I recently sold Milk Video (YC 21) and am looking for new GTM contract and full-time roles.