September 9, 2021

Photo: Air Force Staff Sgt. Kaylee Dubois/U.S. Department of Defense
Welcome to Protocol | Enterprise, your comprehensive roundup of everything you need to know about the week in cloud and enterprise software. This Thursday: Nicolas Chaillan's frustration with military tech inertia, a big day for Box CEO Aaron Levie, and why Cal — not Stanford — is the new enterprise tech launching pad.
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Over the years it took for the Pentagon's much-hyped JEDI cloud contract to reach its unsatisfying conclusion, the U.S. Air Force was quietly at work on its own modernization effort, a multicloud strategy based around concepts like DevOps, containers and Kubernetes. But that project hasn't been without its own problems.
The Air Force's software officer quit out of frustration with the military's overall progress on IT modernization late last week. In a scathing post on LinkedIn, Nicolas Chaillan — who leads software for the Air Force and is one of the key architects of the broader military IT plan — chastised the military establishment's approach to critical IT projects. His departure follows an address earlier last month that took a slightly more diplomatic tack but still called out the military brass for a lack of funding and focus.
At the heart of this is a lack of understanding. Under Chaillan, the Air Force rolled out Platform One, a software-development platform that incorporated a number of open-source technologies backed by the Cloud Native Computing Foundation and support for both AWS and Microsoft Azure's cloud infrastructures. But it faced some big roadblocks.
This may be familiar to lots of companies embracing cloud computing and other modern software-development concepts: New enterprise technologies require cultural shifts in how software teams are assembled and managed to reach their full potential.
And there's a reminder for us all here. As a new round of proposals and debate begins over the military's still-pressing need to modernize its infrastructure, Chaillan's letter underscores how throwing a bunch of enterprise technology over a wall without leadership just isn't going to work.
— Tom Krazit
Over the last two years, many retailers have seen the benefit of investing in new, flexible payments. Despite the low-hanging fruit this opportunity presents, our research shows 60% of ecommerce merchants globally do not feel they receive enough payment insight to allow them to innovate their models. So how can businesses turn their ships around before it's too late?
Power up: Protocol launched the Power Index this week, introducing rankings across three different enterprise tech categories as compiled by our researchers. There will be more enterprise-oriented topics to come in future months, so please sign up to take a look at the lists and let us know what you think.
Man in the Box: Today is a big day for Box CEO and co-founder Aaron Levie, as Box shareholders are poised to vote on a slate of candidates who could take control of the company and install a new leader. Protocol's Joe Williams has a preview of the vote and some background on how Box wound up in this situation.
Larry's laughers: If you've been following enterprise tech for nearly any period of time, you've heard Oracle's Larry Ellison say something outrageous. Joe and I pored over more than a decade of public statements to find eight comments from Ellison that range from amusing to stunning in retrospect.
What was your first tech job?
I had the fortunate experience of being one of the four in the first batch of college graduates Cisco hired in the mid-'90s. It was a dream job in networking for an engineer because I had a front-row seat to the formative years of the internet.
What was the first computer that got you excited about technology?
The PC XT with Microsoft DOS in my school opened a whole new world of possibilities – from simple programs to interactive games. As a budding engineer, this PC brought endless sources of inspiration for me and eventually helped me kickstart my career.
If Protocol gave you $1 billion to start a new enterprise tech company from scratch today, what would you do?
All enterprises, traditional or tech, are reeling from the sharp increase of technologies, processes and data. What I'd want to achieve is the equivalent of what Nest did for thermostats, [but] for the IT administrator. Simplicity and experience should trump everything else. Needless to say, if I was granted this opportunity, I'd also make sure that this company would embrace both cloud and AI as these are the two basic ingredients of delivering simplicity in today's complex tech world overwhelmed by a data deluge.
Which enterprise tech legend motivates you the most?
Eric Yuan, who I was lucky to have met at Stanford, is definitely someone who I see as an inspiration. His clarity of vision, the simplicity of Zoom and his relentless mission to delight customers are all legendary. To top it all, he comes with an ocean of humility I have not seen from other tech stalwarts. Without the long-lasting impact of Zoom, the world would not have been able to manage through the pandemic. Period. It has connected many families, allowed people to work and earn money, allowed children across the world to continue to learn and has allowed for basic human connections to thrive.
What will be the greatest challenge for enterprise tech over the coming decade?
Without doubt, the biggest challenge will be navigating the precarious balance between data privacy and the comfort provided by AI and data-driven enterprise tech. On top of that, we'll have to solve who owns the last say in that balance — the private enterprise or the state or customers.
Thanks for reading — see you Monday!
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