The Good, The Interesting, and the Surprising: Key Learnings from the 2014 iNovia Capital CTO Summit

by on July 31, 2014

iNovia invests in technology and startups offering technology enabled services. We believe that the Chief Technical Officer is the cornerstone of such companies — and thus a great place to invest in creating value. My partners and I are afflicted with insatiable curiosity, and tend to invest in like teams. We’ve found that life-long peer-learning is the most satisfying antidote to chronic curiosity.

It should seem natural then that we would organize a day for our CTOs to share the experiences (good and bad) that they’re having along their company building journeys. Pre-work was assigned to pairs of participants across six topics selected in advance.


We convened in AppDirect’s spectacularly inspirational boardroom overlooking San Francisco bay from 250’ above the financial district late Thursday morning and continued into dinner with an unprecedented level of engagement.

What did we learn? Apart from the fact that 0% of high growth startup CTOs use Windows (1 Linux, 1 iOS and 11 MacOS) — the topics they are most curious about are:


Cloud Security: How little can I afford?

Every CTO has sleepless nights as the balancing act of security vs. speed to market constantly evolves. But I was surprised how much the bar has risen — even our seed stage investments almost universally employ external security audits now. Ryan Marples (of Allocadia) and Kevin Falk (of LightSpeed) walked through a comprehensive set of topics here and I think this is one area where virtually every person in the room went away planning changes in their organization. An A-Ha moment for several of our early stage entrepreneurial CTOs came from the suggestion that, for SaaS companies, your life is a lot easier if consider “lower security expectations” as a filter in selecting initial beachhead customers!


Lean and Agile. Contrary to my expectations, this was everything but the usual love-in for Eric Ries. Our CTOs are pragmatists, focusing on real results and there emerged a theme that it is actually quite difficult to get agile “right”. The room dug into Wayne Malkin’s (CTO of Drivewyze) incredibly deep experience on how to constructively build an agile culture, concluding that when agile is NOT implemented correctly, it can be like a disease that spreads quickly. A framework of strong vision and ensuring alignment of each team on What, Why and How is essential. The conversation evolved into estimating practices and that universal pain point of how to set expectations with non-technical business stakeholders in your organization. Some clever approaches were exposed here. I enjoyed Mike Deering’s comment that “hourly estimates should be rounded off to powers of two”.


Culture, Teambuilding and Hiring. One of the trends we see across our portfolio is an increased focus at the top on hiring for cultural fit. AppDirect and Solium provided particularly poignant examples of this at scale and it was fascinating to see the variety of strategies employed. Healthy debate erupted on the merits of coding challenges, remote workers, using contractors, incentivizing quality, retention, reinforcing values, hiring process and more. One of the lessons that struck home for me is how easy it is to make candidates feel uncomfortable in an interview setting, effectively hiding ‘the real person’ and distorting useful assessment. From the CTO that has made over 50 hires already this year, to the one still planning his first hire, this topic is of universal value and I’m sure it will be on the agenda of future events.


I’ve only scratched the surface of conveying the depth and breadth of learnings but hopefully given you an idea of the formula applied, and inspired you to either participate in such events as they’re made available to you, or organize your own. What made the day work for us was the a priori investment made by each participant, and the intimacy of limiting it to twelve “related” portfolio CTOs (which makes for thirteen opinions on what the best language is incidentally 🙂

In the end, our post-event survey tells us that the most valuable takeaway is the set of ongoing relationships between our CTOs. I wish that — as CTO of Rainbow Technologies — I would have had such a learning forum available to me!