What’s a CTO vs. VP Engineering?

The difference has a meaningful impact on your startup

DEV.BIZ.OPS
6 min readOct 14, 2021

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I attended my first live, in-person conference in 18 months this week, SaaStr Annual 2021. I was on the fence about attending such a large gathering. On one hand, it’s an event that brings the best and most accomplished leaders in the SaaS industry together to share actionable advice and practical tips on how they found success. On the other hand, catching COVID would suck.

For all the concerns, I have to applaud the SaaStr team for putting on a safe event. The entire conference was outside in open air tents and structures. Everyone had to show proof of vaccination, provide a negative COVID test result, and get temperature checked in the morning.

The conference itself was outstanding in terms of content and networking. I connected with people I have not seen in over two years, people that I only knew virtually, and many new folks that were eager to share and collaborate. Though I did not get to as many talks as I had wanted, those that I did attend were thought-provoking and had valuable practical insights.

David Sacks talk at SaaStr.

One of the more intriguing talks was by David Sacks on SaaS organizational structures by funding round. David was the former COO of PayPal, founded Yammer, turned around Zenefits, and has been a prolific investor. It would be fair to say he has seen quite a few startup successes and failures over the years and would have some useful perspectives to share.

When the numbers of employees were laid out next to each other by funding stage, it is a sobering realization. At Series A, a startup will have 50 employees. At Series B, it jumps to 125 employees. By the Series C stage, the typical SaaS startup will have 400 employees. Then as these companies IPO, they will have more than 1,000 employees.

As David was speaking, he touched on something that caught my attention, the idea of topping employees. This is the practice of hiring an executive over the current leader for that function. For example, a current head of marketing would be “topped” by an experienced Chief Marketing Officer who…

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DEV.BIZ.OPS

Thoughts on developers, digital transformation, startups, community building & engineering culture. Author is Mark Birch @ AWS 👉 https://twitter.com/marksbirch