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Panel: Two Sigma Ventures

Grant Miller is the founder @replicatedhq w/ @mccode and Creator of

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Vinay Iyengar is an investor at Two Sigma Ventures, based in San Francisco. He focuses on early-stage investments in enterprise software, machine learning, marketplaces, and infrastructure.

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Villi Iltchev joined Two Sigma Ventures in 2019 and focuses on SaaS, enterprise software, developer tools, and mobile applications. Before joining Two Sigma Ventures, Villi was a General Partner at August Capital from 2016 to 2019, where he led the investments of and served on the board of Gitlab, SendBird, Workona, HiHello, and FactoryFour. Prior to joining August, he was a member of the leadership teams at Box and Lifelock, where he held various operating roles and was primarily responsible for strategy. Previously, Villi was a Vice President at Salesforce, where he led the investments and acquisitions team, making strategic investments in over 30+ leading software companies such as Hubspot, Box, Gusto, Anaplan, Mulesoft, Adaptive Insights, Zapier, and many others. Prior to Salesforce, Villi was a member of the Corporate Development team at Hewlett-Packard and started his career as a technology investment banker at Merrill Lynch.

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This event is a OCS 2020 Fireside chat with Grant Miller, CEO of Replicated, moderated by Vinay Iyengar and Villi Iltchev of Two Sigma Ventures.

Vinay introduces himself, Villi, and Grant, as well as the presentation topic and Two Sigma Ventures - 0:00

Grant shares his background, relationship with Mark, and history of Replicated - 1:18

Villi: You didn’t start Replicated as an open-source company, but you eventually moved that way with the core product. Can you speak to your thought process on that journey and how it’s changed over time? - 3:45

Vinay: Now that you’re deep into being an open-source company yourself, what have been your key learnings around best practices for pursuing an open core strategy, and if you were to do some things over again, what would you change? - 6:25

Villi: The prevailing narrative in the open-core community tends to be that each vendor quickly needs to build a cloud, multi-tenant strategy, and if they don’t, somebody like Amazon is going to take your IP and build a service around it. Do you think that’s the case, and do you think there’s another way of building a company which is focused on modern on-prem software? - 8:09

Vinay: What has the rise of Kubernetes meant for Replicated? What has it meant for companies that are building enterprise software? - 11:32

Villi: So it seems the pieces that came together were (1) embrace Kubernetes, (2) open core and open source, and (3) the changing debate of cloud and on-prem. The question of, do you want to buy a multi-tenant service, or a single-tenant application that you can manage in your environment? Can you speak to that? Is the rise of single-tenant software something we’re going to see more of? - 15:50

Vinay: Can you give us an example or two of specific customers who are using Replicated, how they’re using it, and how they see the ROI of the product? - 23:45

Villi: Touching on the go-to-market for open core companies, obviously the bottom-up adoption of open source software is a key driver for adoption. You need to create a community and all the enablement tools in order to get the first customer phone call, after you’ve already made them successful. Can you speak to that theme when you made KOTS open core and that go-to-market motion? - 26:39

Vinay: To this point of selling to enterprise customers, you’ve become a thought leader in recent years around the keys to selling to enterprises, both with the EnterpriseReady Guide as well as the EnterpriseReady podcast. What are your top tips for selling to enterprises? - 30:43

Share your questions and comments below!

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