Jasjit Singh

About

Founder of Rockstar, blending human intelligence and GenAI to revolutionize hiring for SMBs. Previously held leadership roles at Chegg Inc. as Vice President & General Manager, Skills for Students, and Vice President & Head of Growth. Successfully scaled Thinkful's bootcamp revenue leading to a $100M acquisition by Chegg. Co-founded Hotspot, a social ticketing app, achieving significant user and revenue growth. Experienced in growth marketing and product strategy across tech and education sectors.

Experience

• Founder · Rockstar2023-09-01 –

  We're blending humans & GenAI to help small-to-medium sized businesses hire professionals for less than $2K per role (~2-3% of 1st year salary) -- Learn more @ www.tryrockstar.com

• Vice President & General Manager, Skills for Students · Chegg Inc.2022-10-01 – 2023-10-01
• Vice President & Head of Growth, Chegg Skills · Chegg Inc.2021-10-01 – 2022-10-01
• Vice President & COO, Thinkful · Chegg Inc.2020-09-01 – 2021-10-01
• Director & Head of Growth, Thinkful · Chegg Inc.2019-10-01 – 2020-09-01
• Vice President, Growth & Product Marketing · Thinkful2018-01-01 – 2019-10-01

  Validated and led Thinkful’s local, new program, and ISA growth strategies. Together these strategies drove online bootcamp revenue from $5M to $30M in under 3 years leading to an acquisition by Chegg (NYSE: CHGG) for $100M in Oct 2019

• General Manager · Thinkful2017-02-01 – 2018-01-01
• Co-Founder · Hotspot2013-02-01 – 2016-11-01

  Built and bootstrapped a social ticketing app for everyday events to 35K users, 140 venues and $600K in annual revenue.

• Customer Experience Manager · Redfin2012-06-01 – 2013-02-01

  - Coordinated marketing support new markets, buy-side feature launches and new homepage - Drove the effort to launch Redfin’s new title service (TitleForward) web presence - Led a full refresh of customer photography assets to help improve conversion rates

• Management Associate Intern · Bridgewater Associates2011-06-01 – 2011-08-01

Education

• Yale UniversityBA, Ethics, Politics, and Economics
• Williams College
• Marist Catholic High School

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