Conversations with Fortune 100 Tech Leaders​

CIO Roundtable No. 2

Three leading CIOs, Alvina Antar (Zuora), Paul Chapman (Box), and Mark Settle (Okta), join Ian for a lively discussion about what it means to be a CIO today.

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Show Notes

In this special episode of IT Visionaries, some of the leading CIOs in the world of tech join Ian for a roundtable discussion.

At the table was Alvina Antar (T: Twitter, LinkedIn) of Zuora, Paul Chapman ( @Twitter, LinkedIn) of Box, and Mark Settle (LinkedIn) from Okta. Each has extensive experience in the tech world, which leads to a lively and wide-ranging discussion of everything from dealing with vendors to working in the Silicon Valley echo chamber, and how to handle the politics of being a CIO.

The conversation is loose, fun and there are even a few games and surprises sprinkled in. Enjoy the episode!

Topics discussed: Vendors, Silicon Valley, Systems Engagement, System Processes, Selling to CIOs, Optimizing Business, ROI.

Best vendor story — (2:18)

    • Alvina: Remembers listening to Eric S. Yuan, the founder of Zoom, and learning how they differentiated themselves.
    • Mark: Recalls a vendor who had a strategic, multi-quarter, multi-year perspective and who tried to optimize their abilities with his needs.
      • “I always felt they were helping me be strategic in the way I was thinking about storage.”
    • Paul: Likens relationships with vendors to relationships with friends — you can’t have too many friends because there’s not enough time to devote to them all. But the friends you do have, you want to devote a lot of time to.
      • “When you’re partnering and building relationships, there’s something mutually beneficial in the relationship. The ones that stand out are the ones that are mutually beneficial…. You want to be associated with companies that are forward-thinking and innovative.”

Being a CIO who is also selling to other CIOs — (6:50)

    • Paul: There can be situations where it can be adversarial if you are in competing companies, however, there is value in being able to relate to the situations the other person is in.
      • “The professional chemistry between CIOs is very important because you can relate. A salesperson can’t necessarily relate because they haven’t sat in your seat.”
    • Alvina: There is a greater deal of transparency.
      • “Your peers look to you to provide guidance and best practices.”  

Keeping the customer in mind — (11:15)

    • Mark: You can’t let the voice of the customer get lost.
      • “There’s a brotherhood or sisterhood of CIOs, and you’re probably going to get more direct and unvarnished feedback on why decisions are made.”
      • “The voice of the customer isn’t just some other responsibility, it’s a source of power.”
    • Paul: Just in the nature of the conversations between CIOs, there is always learning that is going on. But there is also feedback being given that can be brought back within your own organization that will help you improve.
      • “As a CIO, you are always looking to how you can bring value to your organization.”
    • Alvina: As SaaS companies, ultimately if the customer isn’t happy, they will not stick around or renew.
      • “The voice of the customer and their perspective is what should drive product strategy.”
      • It is up to the CIOs to make sure that the strategy aligns with the biggest pain points.
    • Mark: If you’ve lost a deal, call the other CIO to thank them for considering your product, and remind them you’re there if they need something in the future.
      • “Enterprise sales are long-term, relationship-building type exercises….Maybe they choose the wrong product or a competitor’s product, which might not work out. It’s important to let them know you’re there for them and it’s not that there are sour grapes.”
    • Alvina: It’s about balance and being authentic.
      • “The reality is that you can reiterate what your customer tells you all day long, but if you’re not an expert in your product, it’s just not going to hold credibility in any shape or form. Your organization needs to invest and build expertise in your own product and then reach out and get input from your customers.”
    • Paul: “You have to be an evangelist of your own capabilities.”

The nature of the echo chamber in Silicon Valley and how others can work without the same access — (19:00)

    • Alvina: We’re living in a new age of digital and business transformation. The IT industry and the people in it are driving that transformation. They need to get in front of leadership to advocate for what they believe should happen.
      • “Don’t just get in front of them, have a plan, have a vision, have a strategy on what is needed to drive the business forward and what you can do as a technology leader to support that strategy.”

Finding ways to optimize the business — (27:30)

    • Paul: The CIO has to be able to tell leadership and customers how tech will work in the real world.
    • Mark: Customers will find ways to use products that you never imagined.
      • “I find out so much about what the customers are doing with our product and I come back and either want to institute it internally or I go to the product marketing guys and tell them we need to be talking about this product use case.”
    • Alvina: You can’t provide new problems and sell new solutions. Customers have enough problems already. Solve those and understand in-depth what is needed to help them optimize their business.
      • “You can’t provide a solution unless there’s clarity around the overall directive.”

Having the conversation about where to find value and the meaning of being GBE — Good But Expensive — (31:35)

    • Paul: If we’re going to invest a dollar we want at least a dollar back. However, ROI is changing. Speed, productivity and efficiency are becoming part of the ROI equation.
    • Mark: The old CIO playbook was about standardization and cost savings. In a modern corporation, human capital has become so much more important, so today productivity trumps cost, and speed of the business trumps productivity, and security trumps everything below.

    Systems of Record vs. Systems of Engagement (38:50)

      • Systems of process that run the business — financial and HR systems — are different than engagement systems and how people engage with each other, for example, Slack, G-Chat, email, etc.
      • Paul: Systems of engagement make their way into an organization in an organic way.
      • Mark: In the same way there are business systems analysts to see how systems are working, the fantasy Mark has is to hire anthropologists and let them loose in the organization to see how collaboration actually works.
        • “The leader has a huge impact. If the leader loves voicemail, everyone does voicemail. If the leader loves Slack, everyone does Slack. And it’s not because it’s the best tool or the right tool, it’s because the leader is most comfortable with that tool.”
      • Ian: “We need to find out how humans work best together. That is a primary use case for why IT is important.”
      • Paul: You have to bring together technology, the culture of your organization, and the facilities you provide.
  • The internal politics of being a CIO — (50:10)

    • Alvina: “The world politics makes me cringe. No one has time for politics — not at our level of growth and scale. Politics just ultimately slows down the company.”
      • Both Mark and Paul disagree. They believe as soon as you get two people together, there will be politics to deal with.
    • Paul: You can’t spend too much time thinking about minority versus the majority.
      • Data has been helpful in making sure that you are focusing on what’s important.
    • Mark: “To be a successful IT executive, you have to become comfortable at being uncomfortable.”
      • There is always going to be a ton of noise coming through the system. If you can’t tune it out and focus on what you actually need to, this is not the right job for you.
  • Game time: Guess the quote — (55:35)

    • Innovation is a team sport.
    • Every CEO of a thriving company needs to have the right team and expertise in house.
    • A CIO leader needs to be a visionary.
    • It’s critical to remove friction.
  • The Lightning Round — (1:00:00)

    • Mark and Paul wish teleportation was real.
    • Paul wants a chip implanted in his brain so you can have instant access to knowledge.
    • Alvina wants a way for all the different tech to be able to talk to each other.
    • Mark: “We’re so close to The Matrix that it’s not even funny.”
    • Alvina: “You have to be able to focus on being truly present in your time with your kids.”
    • Mark: Similar to your kids, direct-reports want you to be present with them and respect their time.

Conversations with Fortune 100 Tech Leaders​

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