What is your business applications strategy when you think about purchasing platforms like Salesforce, Workday, SAP, Oracle, etc?

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Director of IT in Software, 1,001 - 5,000 employees
The first thing is to just evaluate the landscape, figure out where the company is at, and understand where they're trying to go in the next 12 to 24 months. I don't like to go beyond that, especially in early stage, because there's so much change and shift going on that trying to plan beyond that will always turn around and bite you. And, implementations always take a certain amount of time, so by the time you're finished, you're having to reevaluate and restart, which you want to avoid.  Right now it's a very interesting landscape. Thinking about it from a CRM, ERP, and HCM perspective, there's definitely some players in the forefront that people always gravitate towards (e.g., Salesforce, Workday, Oracle) but there are some disruptors in that space and that's getting very interesting. Snowflake just went public.  So, as I'm looking at this, coming in with fresh eyes on any organization, I'm trying to understand what are the goals and objectives of the organization and make sure that we're aligning processes to the technology, not the other way around. We never want to start with the technology forward approach. We always want to start with:  what are the goals of this organization,  what do we need technology to enable in that 12 to 24 month timeframe, is it scalable.
Sr Director Bus Ops & SW Transformation in Software, 5,001 - 10,000 employees
I look at it in terms of scale, simplicity, and operational efficiency. I think those are my 3 big tenets. I completely subscribe to the philosophy that tools can only do so much.  One has to take a step back and look at the business process and model, and ask, who are your users and what are you trying to accomplish? All of that really plays into that decision with respect to the technology stack that one is going to enable for that specific environment. I've been part of companies that have been hardware centric and are now trying to move into the software space. That in itself is a very disruptive motion. There are a few industry trends that are definitely taking place: one is the entire move towards software, two is customer experience. More than anything else - more than product or price - customer experience is the biggest brand differentiator today, so how do you enable applications that give you that 360 view of the customer? When we're thinking about the technology stack, it's super important to me to actually provide that 360 view of the customer; to provide that customer and partner experience; to provide that intimacy with the sales organization. I think a huge part of this is business process. A huge part of this is taking it beyond sales/partner/finance and actually putting a customer lens on it.  We're now looking to manage the entire customer lifecycle, and that's how I look at: both from a process perspective as well as from a technology perspective.
Head of Business Technology in Software, 201 - 500 employees
I like to look at this problem from two different angles. When you get into an organization like in an SMB or enterprise, it has certain technologies already available on top of which you’re now trying to build.  They’ve probably already purchased whatever they think is the best, so now you are walking in after the investment has already been made.  But they are not being put to the best use. In my last two roles, I spent a lot of my time in situations where the investment was already made, and a multiyear engagement was already there, and I would ask, “What is needed for the company to grow?”  Yes, certainly the people, process, technology are important, and I throw a policy also on top of it to make sure they adhere to that.  But the one thing I always say is, “The technology limitations must be solved through the process and the process limitations must be solved by the people.”  Streamline your process, streamline your technology. Once my foundation is solid, then I can spend time on innovation. But if you are trying to bring that as a core competency, and if the product is not solid, then you are at risk in the overall organization.

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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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