On the 20th episode of Enterprise Software Innovators, hosts Evan Reiser (Abnormal Security) and Saam Motamedi (Greylock Partners) talk with David Smoley. David has had a storied career, leading technology teams at several large and defining companies including General Electric, Flex, and AstraZeneca. He most recently led an engineering team as a VP at Apple. Today, David shares anecdotes about being an early advocate for innovation, best practices for collaborating with startups, and his experiences with hands-on digital transformation.

Throughout his career, David has remained at the frontier of innovation, and at several different companies has been an impactful change agent for helping companies holistically digitally transform. Though the term has become somewhat of a buzzword, it’s a process that every company now must grapple with. As David shares, the term means different things to different companies: “...transformation depends on your starting point. What would be a radical digital transformation for one company might be meaningless to another. I think of digital transformation as being very contextual around a particular problem that you're trying to solve.”

When he was leading the IT team at Flextronics, a multinational manufacturing company, getting HR solutions to work effectively for 350,000 employees across 70 different countries was a monumental challenge. At the time he joined, there were multiple HR solutions sprawled across the globe, attempting to serve an increasingly diverse and scattered workforce. Many were homegrown and on-prem, and over time became unwieldy and difficult to optimize. Seeing the writing on the wall, David was told about a company called Workday, which at the time was a small SaaS company hoping to revolutionize the world of HR. It was unheard of at the time for an enterprise company to partner with a small startup for something as fundamental as HR, but David saw something special: “…the first time I got onto Workday, I could tell this was going to be a game changer. It was so much more user friendly; and when you looked at the model and thought about the fact that you didn't have to run the infrastructure, you could scale up and there was mobile access plus all these different features, it became incredibly interesting. I had to convince the head of HR and the CEO that this might be worth taking a risk and fortunately Flextronics is a company that was built in the tech industry. So even though it was supply chain-oriented, manufacturing-oriented, the idea of taking risks, of trying new technology of change was very comfortable.”  

As this partnership was an example of a larger enterprise (Flextronics) collaborating with a startup (Workday), David saw first-hand how these connections could lead to meaningful working relationships. David describes that when Flex brought Workday into the fold, it was less of a ‘buy-sell’ relationship and more of a holistic approach that benefited both companies: “When you're doing a deal with an early stage company like [Workday], it's not a procurement, buy, sell deal.  It's like, here's my wish list and here's my product feature roadmap and let's align and negotiate and then enter into kind of a co-engineering, almost a co-development, multi-year project where we knew they couldn't do what we needed at that time, but we knew where they were headed was the right direction. We agreed jointly to create this reciprocated relationship where we evolved together.” It’s an excellent example of the symbiosis that can be found with enterprise/startup partnerships, and one David helped facilitate with Workday during his tenure at Flextronics. 

When it comes to driving innovation, David’s myriad experience has seen him at technology-first companies like Apple, where innovation is woven into the framework of the company, and companies like AstraZeneca, where the pharmaceutical industry lends itself to a slower and more methodical innovation horizon. While it’s hard to compare industries, David’s experience proves that innovation is never a one-size-fits-all approach. At Apple, David describes a ‘messy’ approach to experimentation and harnessing technology for exciting new product features: “…when you're looking at new, innovative ways of ordering or doing health on your watch and linking it to your phone, it's messy and it's pure innovation. But just because it's messy, they know that, they live with that. They've got the processes and the people and the approach to make that work.” 

He contrasts that with his time at AstraZeneca, where the process for discovering new medicine and getting it to market requires a much cleaner and more predictable approach. For his org, it meant a certain level of skepticism from executive stakeholders: “...when you come in and say, ‘now we're going to look at how we could possibly digitize our clinical trials or automate part of the drug discovery process,’ that stuff that hasn't been done before, right? So now you're talking about applying technology in a way that has a significant rate of failure.” With potential failure comes unpredictability, and as David describes it, “...anytime you got the money for technology, if it didn't go perfectly and exactly execute what they thought, [senior leadership] viewed it as a failure and they were ready to throw the whole thing out.” It’s an important illustration of a lesson David learned throughout his career, and one technology executives in all industries should heed: “The reality is that transformation depends on your starting point. And so what would be a radical digital transformation for one company might be meaningless to another company, or not important at all. I think of digital transformation as being very contextual around a particular problem you're trying to solve.”

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Listen to David's episode here and read the transcript here.