
Tim Guleri
MANAGING PARTNER
Tim Guleri is a former serial entrepreneur, having built two successful software infrastructure companies: Scopus Technology (IPO in 1995) and Octane Software (M&A – Epiphany $3.2 billion). He joined Sierra Ventures as Managing Director in 2001, focusing on Big Data and Artificial Intelligence. Since joining, he has taken two companies public (Sourcefire – $FIRE, and MakeMyTrip – $MMYT) and has been responsible for several M&As.
Tim holds a BA in Electrical Engineering from PEC University of Technology (India) and an MS in IEOR/Robotics from Virginia Tech. His passion (outside of his family and companies) is soccer.
Focus
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Artificial Intelligence / Machine Learning
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Enterprise Software
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Infrastructure / DevOps
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Vertical SaaS
Insights from Tim
Tell us how you’d like to be approached by a founder with their initial pitch.
I think it is important for founders to be resourceful when trying to connect with a VC. Cold outbound is always going to be challenging because, these days, most VCs openly share their email. That typically translates to a flood of inbound pitches.
As a founder navigating and extending the network, you is key. Go to meetups, reconnect with past colleagues, and find inroads to get warm introductions. This also shows hustle, which is a key attribute to be a successful entrepreneur.
I like a “prepared” mindset entrepreneur who has done their work on their target customer, the market dynamics, their competition, and me. Ie its important to have done your work on if the VC you’re pitching is the right fit from a sector and temperament standpoint.
What’s one mistake founders make when pitching AI companies today?
A lot of founders pitch AI like it’s magic. But CIOs—and by extension, we as investors—care about results in the context of enterprise complexity. AI that doesn't align with existing enterprise workflows or deliver measurable ROI won’t get adopted. Don’t just say ‘agent’ or ‘copilot’—show how it works in the wild.
As a former founder, how do you decide who to invest in?
I call it ‘Founder Love.’ I was in the trenches myself—twice—so I look for the founder I can go to war with. Grit, clarity of thought, and obsession with customer pain are non-negotiables. The best founders are magnets for talent and won’t quit when the market turns.
What book do you recommend to founders?
One of the best and most practical books I have read and gift to all my founders is "The Great CEO Within: The Tactical Guide to Company Building" by my good friend Matt Mochary.