Sergey Karayev
About Sergey Karayev
Sergey Karayev is a software entrepreneur based in the Bay Area. He studied at the University of Washington and earned a PhD at UC Berkeley, where he worked on computer vision with Trevor Darrell. He co-developed the open-source Caffe deep learning framework.
He co-founded Gradescope, an AI-assisted tool for grading exams and assignments. Turnitin acquired it, and he worked there as Head of AI. He then co-founded Volition, a product studio with the other Gradescope co-founders, which builds software with AI agents. Its product is Superconductor, a platform for building software with agents. He also co-organizes Full Stack Deep Learning, a set of courses on building AI-powered software, and has been a lecturer at UC Berkeley.
Karayev's public investing record is thin. Crunchbase lists him as a board member at GSV Ventures since June 2019. He is named as an individual participant, alongside Gradescope co-founder Arjun Singh, in the seed round of Pensieve. He has not published a full list of angel investments, so only deals confirmed in public sources are described here.
The AI round on the Lounge deals desk is Pensieve's $6.9M seed (February 2026). Pensieve builds AI-assisted grading for instructors. Its announcement said the round was led by Mayfield. Other participants included Reach Capital, Anti Fund, BASS Ventures, Vela Partners, and the Sequoia Capital and a16z scout funds. Karayev and Singh were named as founders of Gradescope. Reported round sizes differ by source: the founder's LinkedIn post says $6.8M, and a Dealroom report says about 10 billion won, or $7.3M.
Karayev has not published a thesis, a target stage or a check size. The one confirmed deal is a seed round in AI education technology, which is the field of his own first company. His operating work is in AI agents, developer tools and AI-assisted education. Founders in those areas will find the most overlap with his experience. His site and Crunchbase profile list no check size, so ask him directly.
- Pensieve: AI-assisted grading for instructors, used by US universities. Seed round of about $6.9M led by Mayfield, with Karayev participating (2026-02).
Investing activity
Sergey Karayev appears in 1 AI deal tracked by the Lounge deals desk. The rounds are mostly Seed, with a median round size of $7M. The most recent is Pensieve (Seed, $6.9M, Feb 2026).
Sergey Karayev most often invests alongside Mayfield, Karim Atiyeh, Sequoia Scout and Bass Investment, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Sergey Karayev
Who is Sergey Karayev?
He is a software entrepreneur and co-founder of Gradescope, Volition and Superconductor. He holds a UC Berkeley PhD in computer vision and co-organizes Full Stack Deep Learning.
What AI startups has Sergey Karayev invested in?
The confirmed AI investment is Pensieve, an AI grading startup, in its seed round announced in 2026-02. No other portfolio list is public.
What is Sergey Karayev's angel check size?
It is not public. He has not stated a check size or fund size in any source we found.
What stage does Sergey Karayev invest in?
His one confirmed deal is a seed round, and he has not published a stage preference.
Does Sergey Karayev invest in AI education startups?
His one confirmed investment, Pensieve, builds AI grading tools. He previously co-founded Gradescope and led AI at Turnitin, so he has direct experience in that field.
How can founders contact Sergey Karayev?
His public channels are his personal site, LinkedIn and X (@sergeykarayev). Founders can reach him through any of them or through a warm introduction.
Is Sergey Karayev an angel investor?
Yes. Sergey Karayev invests personally as an angel.
What AI companies has Sergey Karayev invested in?
Sergey Karayev's AI investments include Pensieve. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
What stage does Sergey Karayev invest at?
In the rounds tracked on Lounge, Sergey Karayev has invested at Seed, with a median round of $7M.
Who does Sergey Karayev co-invest with?
Sergey Karayev's most frequent co-investors on Lounge are Mayfield (1 deal), Karim Atiyeh (1 deal), Sequoia Scout (1 deal), Bass Investment (1 deal) and Reach Capital (1 deal).