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The Workplace of the Future is Digital

digital workplace


At our 2021 SaaSMe event, entirely focused on SaaS Management in the new era of the digital workplace, we sat down with several CIOs and product strategy leaders to dig into your most pressing questions.

Moderated by Harry Moseley, CIO at Zoom, the session covered new research, new tools and new ways of thinking.

“When we all got thrown into this pandemic, everything changed for every industry,” Harry said at the start of the session. But we adapted quickly, Harry noted. “This work model that we’ve adopted over the last 21 months has become like a muscle memory. This is the way we lead, this is the way we manage, this is the way we work.”

The Zoom leader was joined by four panelists:

  • Ken Cushman, CIO, Yahoo
  • Helen Kupp, Head of Product Strategy & Partnerships, Future Forum (Slack)
  • Deepika Rayala, CIO, Yext the CIO and CIO
  • Mark Settle, seven-time CIO

Keep reading for a shortened version of the session, with the best answers to Harry’s questions. Or, watch the full session below. If you love this conversation, there’s more good stuff coming at the next SaaSMe Virtual! See what’s in store and register here.

What has your research uncovered that can help today’s CIO understand the dynamics impacting the new digital workplace?

Helen Kupp: 

“We found that flexibility is key, and that the desire for flexibility has stayed consistent quarter over quarter. When we look at the data, employees continue to have a strong preference for this flexibility. We saw 76% of global knowledge workers want flexibility in where they work. More importantly, we’re finding that employees are going to vote with their feet—in terms of what they want from their employers. The same study showed that flexibility ranks second only to compensation when it comes to job satisfaction. 57% of knowledge workers are open to looking for a new job in the next year. I think those two things are an important context for us to set our discussion today.”

Ken Cushman:

“If you’re not a leader that’s being super empathetic and reaching out to your people to understand how they’re doing, you won’t be in a place to encourage that flexibility. For when and where they do their best work—you have to leave it up to the teams to decide.”

Deepika Rayala:

Executives are three times more inclined to come into the office versus employees. I think it’s about: what happens to that creative process? Do we have the tools and the process to make sure we maintain it? We’ve embraced a lot of different SaaS tools, but now we are on the verge of having SaaS burnout, trying to go digital. I think we need to figure out how to get to that right balance.”

Flexible work options seem to be here to stay. So what’s changed? How are you using SaaS now to empower workers? 

Ken Cushman:

“At Yahoo, we’re lucky in the context that we had really been driving on a modernization journey for quite a while before the pandemic. We’re really largely a SaaS-first company from a tooling and productivity perspective. As the shift happened, it became more about how I can really drive the employee experience even more. What can we do to accelerate and ensure that we’re continuing to deliver as good or better services than we were in an in-person environment? Things like virtualizing our walk up windows, ensuring that we have the same kind of phone chat, and really amplifying a lot of the collaboration tools that we had in house.”

Mark Settle:

I think there was a big push early on during the pandemic to consider SaaS alternatives to a lot of legacy business applications. We kind of forget that there’s a whole bunch of Fortune 2000 companies who still have a big mixed portfolio of on-prem applications that they’re supporting, and some SaaS tools. And plenty of companies had ‘Blue Bird’ opportunities early during the pandemic—customers showed up that they hadn’t even talked to, saying that they were ready to seriously consider an alternative to their on-prem systems.” 

Deepika Rayala:

We’re still trying to figure out the optimal balance. And how do these SaaS platforms even talk to each other, so they all don’t feel very disjointed? So that’s really what we’re working on. We don’t want our Zendesk and our Slack and our Help Desk to all be different—we want to give a streamlined experience for users.”

digital workplace saasme

When we think about all these new tools your organizations have implemented over the past year—who is bringing them? Employees? Lines of business? IT itself?

Deepika Rayala:

“Here at Yext, we put software into three buckets. 

The first one is IT managed and administered. Platforms like Salesforce and NetSuite and Workday and Tableau. The second bucket is business managed and IT administered. It’s very integrated to how the business unit operates. The third bucket is business managed and business administered. These are platforms like sales, marketing, HR and engineering tools for individual teams.

But, overall, we have a new software request process so that we always know what new software is being purchased. It goes into our software catalog and gets weighed against what we already have in place.”  

Ken Cushman:

It’s really about ensuring that people buy things the right way so we can catalog and manage them. Shadow IT is not a bad thing. I think it all needs to be relabeled as ‘business lead IT’. We really push teams and work with our business groups to say, ‘Let us help you. We will help you get through the purchasing process faster, we will get all these tools rubber stamped faster with security, we will ensure it will work in the environment, and we can get you up and running that much faster.’ So we’re here to help. It’s not that they want to manage and drive IT decisions—they just need to be able to drive their business with velocity.”

Helen Kupp: 

“Before, when we had offices as the single default headquarters, we were thinking with more of a hybrid approach: on-prem and SaaS together. Now, in the digital-first space, there’s an opportunity for us to think about how we create a seamless experience with a kind of digital workplace, or digital headquarters. We’re looking for a connected approach that doesn’t create the kind of burnout Deepika mentioned. We’re looking at things like overall satisfaction, work/life balance, and even sense of belonging. I think there’s an opportunity to uplevel the CIO role to start thinking about these things.” 

Mark Settle:

“I would encourage people to think about establishing some rules of engagement with your business partner. It’s about who’s going to manage what and who’s going to administer what. I think a lot of people make the mistake of thinking through it on a case-by-case basis. But if you’re in the earliest stages of adopting SaaS, you’ll be better off having at least some kind of agreement about who’s handling what. If you don’t write down some rules of the road, then everything becomes contentious—every new tool you bring in or they bring in can create a very painful set of conversations.”

What’s one prediction you have for SaaS and the new digital workplace in 2021?

Helen Kupp:

“It’s not quite a prediction, but I do believe that flexibility is here to stay. And we’re all going to need to figure out new ways of supporting that both from the digital infrastructure perspective and the process perspective. But I think what’s going to be unlocked, beyond productivity, are things like creativity and innovation. What about sense of belonging? Can technology do that for us as well? In the data, we’re starting to see that, yes, it’s possible. And we need to be more intentional about it.”

Mark Settle: 

“I think we’re at the very early innings of developing effective collaboration tools—having a suite of effective collaboration tools for this hybrid work environment and digital workplace. We’ve picked up most of the standard tools that we had before (email and texting and file sharing and video conferencing) and we enabled them from home environments, and a lot of non-office environments. But now we’re facing a fairly high level of mental fatigue and kind of burnout because of the way employees are using the tools. They’re working longer hours, there’s more asynchronous communication that’s happening. I can’t help but believe that somebody will crack the code and start thinking of ways to integrate communication channels and prioritize the way you can use your time. I think there’s a challenge out there for the VC community to start making those kinds of investments.”

Ken Cushman:

“For many companies, I think flexibility is going to be a huge competitive advantage in the context of how we compete for talent. I think there will be an emergence of a whole new way of tooling. Jumping in with Zylo several years ago has taken us from being very operationally focused to a place where we can be more proactive and add a lot of value. Now it’s time to get out of the silo and drive kind of to that next level of maturity and governance.”

Deepika Rayala:

“Hybrid is here to stay. So the focus will be on employee wellbeing, not just productivity. We need a sort of digital office and map of integrated tools. We know there are already startups working frantically on these things—I think something like that is required for us to be really effective in this long term, hybrid world.” 

Hear more about what this star-studded panel of CIOs had to say about the future of the digital workplace and watch the other SaaSMe sessions at