Rajiv Gupta
About Rajiv Gupta
Rajiv Gupta is the founder and CEO of Axiamatic, a role Crunchbase dates from April 2021. He is based in the San Francisco Bay Area. Sycamore's announcement describes him as co-founder of Axiamatic. A third-party profile says Axiamatic uses AI to improve ERP implementation success.
Earlier in his career he was SVP, Cloud at McAfee, according to Crunchbase. Aggregated profile data also lists him as founder and CEO of Skyhigh Networks, Securent and Confluent Software. The same profile lists a Ph.D. and Master's in computer science from Caltech and a bachelor's from IIT Kharagpur. Crunchbase also lists Caltech.
Crunchbase lists three board and advisor roles: Board Director at Abnormal AI, Member of the Board of Directors at Change.org, and Member of the Advisory Board at pumpkynHead.
Crunchbase records one personal investment for Rajiv Gupta, a seed round in Sycamore. Investment date, amount and check size are not shown publicly. No fund, syndicate or stated investing thesis was found. Founders should treat him as an operator-turned-angel with a small public record.
In March 2026, Sycamore announced a $65 million seed round to build an operating system for autonomous enterprise AI agents. Coatue and Lightspeed Venture Partners led it. Abstract Ventures, Dell Technologies Capital, 8VC, Fellows Fund and E14 Fund also took part.
Sycamore's press release lists Rajiv Gupta, co-founder of Axiamatic, among its notable angel investors. Sycamore is led by CEO Sri Viswanath, formerly Chief Technology Officer at Atlassian.
Gupta has not published a thesis, preferred stage or check size that we could find. His one confirmed investment is a seed-stage enterprise AI infrastructure company in Palo Alto. His operating background is in cloud and security software (McAfee, Skyhigh Networks) and enterprise AI (Axiamatic). Public sources do not confirm which sectors he will back next.
- Sycamore: builds an operating system for enterprise AI agents covering discovery, build, deployment and governance. He joined its $65M seed round, announced March 2026.
- crunchbase.com/person/rajiv-gupta
- sycamore.so/press-releases/sycamore-raises-65m-seed
- businesswire.com/news/home/20260330376116/en/Sycamore-Raises-$65M-to-B
- siliconangle.com/2026/03/30/sycamore-raises-65m-silicon-valley-heavywe
- linkedin.com/in/rajivgupta4
- me.sh/profile/rajiv-gupta-e24a0df7
- theorg.com/org/axiamatic/org-chart/rajiv-gupta
Investing activity
Rajiv Gupta appears in 1 AI deal tracked by the Lounge deals desk, rounds totalling $65M. The rounds are mostly Seed, with a median round size of $65M. The most recent is Sycamore (Seed, $65M, Mar 2026).
Rajiv Gupta most often invests alongside Lightspeed Venture Partners, Coatue, Soham Mazumdar and Dell Technologies Capital, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Rajiv Gupta
Who is Rajiv Gupta, the AI angel investor?
He is the founder and CEO of Axiamatic and previously held the SVP, Cloud role at McAfee. He is listed as an angel investor in Sycamore's 2026 seed round.
What AI startups has Rajiv Gupta invested in?
The only confirmed AI investment is Sycamore, an enterprise AI agent platform that raised a $65M seed round in March 2026. No other portfolio companies were found in public sources.
What check size does Rajiv Gupta write?
His check size is not public. Crunchbase hides the amount and date of his Sycamore investment, and he has not stated a range.
What stage does Rajiv Gupta invest in?
His only confirmed investment is a seed round. He has not published a stage preference.
How can founders contact Rajiv Gupta?
He has a public LinkedIn profile and an X account (@trustedmind), both listed by Crunchbase. A warm introduction through a mutual contact is likely the better route, given his small public record as an angel.
Is Rajiv Gupta an angel investor?
Yes. Rajiv Gupta invests personally as an angel.
What AI companies has Rajiv Gupta invested in?
Rajiv Gupta's AI investments include Sycamore. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
What stage does Rajiv Gupta invest at?
In the rounds tracked on Lounge, Rajiv Gupta has invested at Seed, with a median round of $65M.
Who does Rajiv Gupta co-invest with?
Rajiv Gupta's most frequent co-investors on Lounge are Lightspeed Venture Partners (1 deal), Coatue (1 deal), Soham Mazumdar (1 deal), Dell Technologies Capital (1 deal) and Bob McGrew (1 deal).
How can founders reach Rajiv Gupta?
Founders on Lounge can see Rajiv Gupta's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with them under Warm Paths, and add Rajiv Gupta to their Investor Pipeline to track the conversation.