Back To Where It Started…RRE

This post is slightly overdue, and I can promise my return to blogging as a VC will involve much more interesting subjects than myself, but nonetheless I can’t be more excited to announce that I’ve rejoined RRE as a Senior Associate.

I originally joined RRE as an Analyst back in the Spring of 2010 and have been fortunate enough to work alongside and learn from some of the smartest, most thoughtful and down-to-earth folks in the VC business. RRE is a unique place; a firm that has no ego, truly puts the interest of the entrepreneur first and places an inordinate amount of trust in its junior people to develop their own perspective and learn by doing. As an Analyst, I was incredibly lucky to have had the chance to source and help lead investments in companies such as WhipTail Technologies and Datadog and be afforded the type of responsibility that far outstripped my experience, let alone title. So when Jim and Stu extended the offer to come back – after a two year stint getting my MBA – to the firm, the decision was a no-brainer.

I’ll be spending my time developing and shaping RRE’s thinking around enterprise technologies. I’ve said this before, but is has never been a more exciting yet daunting time to be an early stage enterprise investor. The tech stack is being wholly re-written and infrastructure re-designed to support the massive scale of what soon will be hundreds of billions of connected devices. Mobile and cloud have fundamentally changed the game, crushing barriers to entry, innovation and adoption. The rate of technological change never been faster – today’s winners can become tomorrow’s losers in the blink of an eye – making venture investing incredibly fun but also incredibly challenging. Personally, I couldn’t be more excited to take on this challenge.

With that said, some themes I’ll be digging in on in the next 12 months (and I’ll follow up with a blog post on each in the coming weeks) include:

  • Intelligent SaaS – As predicative analytics, machine learning and AI become more pervasive, software will move from enabling smarter decisioning by humans to making the decisions on its own
  • DevOps 2.0 – If DevOps 1.0 was characterized by convergence of software development and IT operations, DevOps 2.0 will be about making ops virtually invisible thanks to higher levels of automation and abstraction
  • The Post-Hypervisor Datacenter – Software-defined everything + containers + cluster/resource managers (Mesos, CoreOS, etc.)
  • Security – This one is self-explanatory, but in particular looking for deterministic approaches to malware detection, cryptography and mobile and API security solutions

So if you’re a passionate entrepreneur trying to solve a deeply technical facing today’s enterprise or if you’re just someone who likes to geek out about subjects like Docker or machine learning, get in touch! You can find me at, on twitter @lennypruss and my blog