Do you trust the data & reports from the big analysts?

Top Answer: You have to be careful in the context the data and reports are being presented. The data and reports often tell a story, but be cautious from the viewpoint of how it is being presented.

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How should startups look to sell to CIOs?

Top Answer: First and foremost, really work on your messaging and positioning. It’s easy to get enamored with the technology how instead of the strategic why - why is this important to them and why should they listen to you. If you can’t articulate that in a couple of minutes, you don’t want to go talk to a CIO.

Once you have that, it’s about finding the right warm introductions, or reaching out to meet if you’ll be at the same conference/event and just having a conversation. Hard selling doesn’t work. Find out what they are working on, what their priorities are, and then if applicable work it in. Take a trusted advisor approach instead of a cold email or call, which may work sometimes but certainly doesn’t scale.

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Are you happy in your current role?

Top Answer: May I ask, why one would stay in their role if they were unhappy? How does one decide when it’s time to move on?

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What are real ways enterprises will consume AI in %YEAR%?

Top Answer: Many AI-based applications are finally making the jump across the hype cycle from ‘promising’ to ‘delivering’ real value. Chatbots are one that have made a dent in 2017 and will continue to do so in 2018. Messaging has proved to be a simple, and extremely effective way to communicate and interface with information. Message based apps leverage a commonly used medium to provide a conversational interface to complex workflows. This has already dramatically simplified how enterprise users interact with applications and collaborate at work, especially as more and more millennials enter the workforce with drastically different expectations for software than their prior generation.

But adding AI to chat takes us beyond just simple question and answer commands. Instead of typing “File HR Ticket” to a SupportBot, an employee can simply describe their actual challenge, e.g. “what is our maternity leave policy?” Bots can handle complex NLP, decompose the question, search for potential answers across multiple applications/ backends, and instantly provide the user with the right answer. This greatly simplifies workflow and massively boosts productivity and customer/ employee satisfaction.

Zooming out a bit, the bigger picture going into 2019 is very clear. AI will be built in as a layer across every application going forward — just as “mobile” used to be a standalone category, it is now seen as a necessary component of any software product.

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What are the top KPIs for IT for the next 3 years?

Top Answer: I think it should be a lot more elastic. Businesses are changing rapidly and what’s important to measure and improve today is likely not important or measurable next year. Long-term KPIs have the danger of being rear-facing rather than forward-facing or predicting. CIOs need to collaborate with their C-Suite peers to drive business KPIs and metrics that matter to them to move the business forward and increase revenue.

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What is the best alternative to S3?

Top Answer: Wasabi

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As a large enterprise, why do you engage with startups and how do you choose the right ones?

Top Answer: It's not a secret that engaging with startups and emerging technologies is crucial for every business. It's no longer about being good enough, it's about being the best and taking advantage of new products and innovations comes with the territory. My primary motivation to engage with startups is to deliver business value at Flex. My secondary motivation is to learn from people smarter than me (the entrepreneurs I meet) about the latest technologies, products, and solutions being created to shape the future of enterprises.

Our business priorities are very clear and we work as a team to figure out which technologies (and then companies) will help us drive our goals. This top-down approach is methodical - we have a budget and a structured approach on how to work with vendors (big or small) to select the right one. The bottom-up approach is equally important, and requires a team that is passionate about technology to make it work. One example for us is that, as a team, we spend a few hours every Friday morning learning about new technologies, products, and innovations that may be helpful for us. We then come together as a team and share our learnings. If one or more products stand out, we dig deeper and explore how we can leverage it at Flex.

Regardless of top-down or bottom-up, seeing a meaningful ROI is generally important to us. That doesn't always hold true, but these are rare exceptions, not the rule.
Startups we engage with have a few things in common:
  • We get to know the team before we get to know the product because we're betting on the people and the vision as much as the product. How strong is their technology, sales, and executive team?
  • Is the product easy to use and does it have an adoption strategy in place?
  • And finally, in return for us coming in as an early customer, are they willing to have us shape their product and roadmap to fit our needs?
With thousands of startups, it can be daunting to figure out the right ones to engage with, but a few channels have been helpful to curate the best — my peer network (we exchange emails on a weekly basis), curated online IT communities that go beyond what traditional analysts provide, and working with select VCs like a16z, Lightspeed, and others.

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Which of the following best describes your biggest challenge with object storage?

Top Answer: For those that chose: Price. There are more cost effective alternatives to mainstream object storage (aws s3 and azure blob) like wasabi

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How do we completely rebrand what IT is going to do as we grow? Specifically how do we stop talking about IT as IT and transform into a product organization?

Top Answer: For younger companies, this has happened organically. When a company starts, people who come in are increasingly expected to bring their technology solutions along to help grow the business. As the company scales, the need for an organized approach arises and IT comes into play. At Twitter the internal technology team grew out of this necessity and this has helped us in two ways:
  1. Stay lean
  2. Focus on the customer demand
We're no different than a consumer-focused product team in that we build what the customers need, in this case the customers are Twitter employees and partners. There are 3 things that help position Twitter’s IT team as a product org, not just a cost center.

1 - Team Titles and Team Structure
From a team PoV, it’s important to use terms that others in the organization are familiar with and respect. The team at Twitter consists of Product Managers and Engineering Managers. Product Managers are by function (e.g. finance, marketing) whereas Engineering Managers are by technology (e.g. Oracle, Salesforce etc.). The PMs don’t think about finance as Oracle, but rather as a collection of applications, systems, and processes that drive finance. This in turn helps them influence and direct some of the strategic vision as opposed to just being request-driven. The PMs stay close to the operations teams within the business units (e.g. sales ops, marketing ops) and work with them in creating roadmaps organized by sprints that align with the goals of the finance team. It’s not unlike how consulting organizations would operate, except business units have a long-term partner who they can trust and who knows the workings of Twitter.

2 - Capacity-driven and Agile
While this isn’t a differentiator anymore, agile is key to our success. We are capacity-driven and have a deep understanding of our historical velocity and trends which helps us accurately forecast timelines for projects when creating roadmaps. We also have weekly syncs with the business teams on sprints, and deliverables, which brings transparency to our work. We have bi-weekly meetings to prune the backlog and stay current, and we also have quarterly business planning meetings to set and understand the overall vision and direction of the business units. All our meetings have the business counterparts (typically the ops teams) present and actively participating.

3 - Focus on Relationships
Getting started, a large portion of my time was spent on Public Relations, especially in the first year - probably close to 60% of time. We began by establishing relationships with the business executives (our customers), understanding their priorities, explaining our team setup and goals as well as establishing the right terminology, culture, language etc. And while this gets easier over time, it continues to drive our success and is critical at every level of the organization. As with all PR, it takes a bit to get going but once it kicks in, the benefits are tremendous and really help position IT as no different than a product organization.

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What sets apart outstanding CIOs from good ones?

Top Answer: For some time, IT has been seen and thought of itself as a service provider. But it’s now at the forefront of most businesses because of digitalization. When I look at my peer network, I see that outstanding CIOs have quickly embraced this role change by doing two things:
  1. They are close to the customer and don’t rely on others to bring back customer insights and requirements. They are on-site with their business counterparts to help close deals, support existing customers, understand requirements, and also ensure that that customer-centricity is reflected in their overall goals as an IT organization.
  2. This second one I have seen for years — great IT leaders are always eager to take on new technologies. They are able to influence IT and in most cases the broader organization as well to be bold and always set aside some budget to experiment with innovations.
You need to have the basics in place as well which includes building the right team, culture, hierarchy, relationship with the business. But these two points in particular seem to set great CIOs apart.

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Which of these digital skills are most in demand in your organization? (select all that apply)

Top Answer: What, no security on this list?

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In setting up a security team, how should CIOs think about the right org structure, roles, budget and goals?

Top Answer: There is no right answer here, it really depends on the size of the company, the industry they’re in, the assets they have. What is important and consistent across the board however is to recognize two things:
  • Don’t look for an ROI here. You can measure things like number of breaches, time to respond to threats, threats detected and patched, percent of systems fully patched etc.
  • There is a big investment to be made on the cultural side of things too - awareness and training for the organization. Use internal webinars where the CEO sends a message about mandatory attendance to show how important this is. This also needs to be a recurring thing, which is easier said than done.

How will the CIO's role transform over the next 5 years?

Top Answer: I see IT taking on a more strategic role for nearly every business going forward. The expectation is and will continue to be for CIOs to help modernize the business. Some companies create a CDO role for this transformation (especially if the CIO is culturally seen as a back office function). As a result, CIOs will no longer have their traditional KPIs. Instead new KPIs will be tied to revenue, profitability, customer acquisition, and others that haven’t traditionally been within the IT org.

Because technology now touches every part of the business, another change is that the CIO will likely take on more responsibility in connecting the business end-to-end. One example of this is with IoT. Some of the mining companies in Australia have recently invested in autonomous mining trucks, which work 24*7 and can be manned remotely. While this was under the purview of the Operations group in the field, it is now rolling into IT, which makes sense. IT now collects this data and optimizes scheduling, maintenance, routing and at some point will also be able to bring in ML, AI, and robotics to automate the entire process.

Lastly, due to rapid progress in the commoditization of standard offerings, a number of things will transform within the domain of the CIO. One example of this is that at SAP, we have an IT strategic direction of cloud first, which implicitly means IT will own less infrastructure in the future, but become the broker of services sourced from many places. We want to get everything as a service and while we continue to provide value-added services on top, directionally, it’s unlikely IT would focus on bare metal infrastructure. Unless it’s part of the core business, I also see this happening across the board for CIOs.

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