Welcoming Leo Spiegel as Crane’s Newest Venture Partner to Help our Portfolio Accelerate Go-To-Market and Launch in the U.S.

Scott Sage
Oct 23 · 4 min read
Leo Speaking at Crane FLIGHT 2020

We recently sat down in London with Leo to talk about founding, running, investing and even acquiring software businesses — which he has done for his entire career! From several CEO roles to VC and then back into the operating saddle as a Founding Exec in the formation of Pivotal, Leo has seen it all.

We were first introduced to Leo in 2017 by Gary Butler, the co-founder and CEO of Harbr (a Crane portfolio company). Gary was an early employee at Greenplum where Leo was an investor/board member. Leo had been advising Gary and Anthony Cosgrove at Harbr before officially becoming their Chairman earlier this year (thank you Team Harbr!).

Leo has already had a meaningful impact on the trajectory of some of the Crane portfolio companies he is working with and will continue to help our founders get in front of F500 companies, soft land in the US and think strategically about the right path forward.

Leo, tell us about your startup journey and what first led you to start a technology company in the 80’s?

I wish I could say that I had a plan but the honest answer is that I fell into it. I was doing a research project at university trying to disprove the ‘Random Walk Theory’ of the stock market (which I could not disprove :-) ) and as part of the project, my advisor required me to work in a stock brokerage firm to actually witness the realities of the stock market. While I was working in the brokerage firm I observed that all the brokers were buying computers to impress their clients but did not have any actual application software. I was a starving college student so I began to program their computers building portfolio management and customer relationship management solutions. I never wrote a business plan and was just present and let everything happen in the natural order.

After starting a few companies and other CEO gigs, you were then a Managing Partner at Mission Ventures for over a decade in Southern California. What prompted you to move from the operating side to the investing side?

I always wanted to have two careers — when I was younger I thought I would design furniture as my second career but was really fortunate to have the opportunity for my second career to be venture capital. Mission Ventures hired me to be the CEO of Sandpiper Networks. After that, my partners at Mission were eager to add operating experience to the partnership since they had mostly grown up as investors. I was honored to be asked to join. We would joke that the requirement to become a partner is that you need to return an entire Fund — luckily Sandpiper was able to do that!

After a successful investing career, what excited you about joining Pivotal’s exec leadership team to formalize their strategy and GTM model?

My most successful investment at Mission Ventures was Greenplum which we successfully sold to EMC. While at EMC, the leadership of the now Greenplum Division wanted to acquire Pivotal Labs. They needed help getting the acquisition approved, executed and integrated and asked if I would consult for them and help make that happen. I got the OK from my partners and LPs to do the project and in a way the rest is history. Soon after closing the transaction we began to work on the early ideas and plans for Pivotal. What excited me most was the opportunity to do something that could change the landscape of the technology industry, really move our customer’s businesses forward in a transformational way and lastly and most importantly I loved the people. Working with Paul Maritz (the CEO) was also a major bonus.

You’ve led and invested in a number of successful startups. What do you think made them successful?

The most important thing is the people and the culture. Startups are SUPER hard and you need to have the right people and the right culture to execute. In addition, you need a great idea/product with the right timing relative to the market. You also need to be lucky — though luck and hard work seem to be synonymous! Relative to culture, I think authenticity, open and honest communication and relentless execution (drive and passion) are key components of a winning formula.

What are some important lessons you’ve learned that you would share with founders?

1. Every day matters! — Drive your company around 4–5 key objectives.

2. Market fit is critical to get right early! Make sure what you’re selling is a “must-have” with a proven ROI vs a “nice to have”.

3. Successful companies are bought not sold! Build out your ecosystem early so your potential buyers are close to you.

Why did you choose to work with Crane specifically?

Simple — the team! I am really blown away by every member of the team. I also felt I could really contribute and bring a unique skill set to enhance the team. I also really love the data/enterprise strategy and in particular the seed and Pre-Series A phase at which Crane invests. I feel like my skills are best leveraged in the earlier phases of a company’s life. Lastly, there are many folks like me in the US but I feel like my skills are most leveraged in Europe as the startup scene evolves and matures here.

Crane — Taking Flight

Building European Software Champions

Scott Sage

Written by

Co-founder & Partner @crane_vc — @tessian @onfido @OpenSensors @thoughtriver @avora @senseontech. Texan in London. Drummer.

Crane — Taking Flight

Building European Software Champions

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