How CIOs Are Evolving for Remote Work


An Interview with Softchoice’s SVP of IT, Jeff Reis

When Canada’s most valuable public company Shopify announced it was going “digital by default,” it was a clear sign that the brick-and-mortar office era was forever changed.

“We cannot go back to the way things were. This isn’t a choice. This is the future,” tweeted chief executive Tobi Lutke.

Not to say the move was surprising, especially not for IT professionals. At Softchoice, our team has been active in adjusting our remote work policies and hiring practices with the same set of assumptions. We, too, have made digital the default, at least until October 2020. After that, we will be making remote work a bigger part of the Softchoice employee experience for the long run.

We are far from alone. In one survey conducted by Gartner, 3 in 4 senior business leaders say they are shifting budgets and resourcing to support permanent remote work. In another report from The Global Workplace Survey, 75% of respondents said flexible work from home is the “new normal.”

So, what does this mean for IT?

We met up with Softchoice’s Senior Vice President of Information Technology, Jeff Reis, to learn more about how our own IT team has been handling the sudden disruption to the workplace.

What we uncovered was a clear signal that the role of IT leadership has evolved once again. The COVID-19 event has forced IT to pivot, to re-prioritize and change the way they look at leadership and resourcing. What follows is an edited interview, highlighting the key insights from our conversation.

Insight #1: Always be prepared – even if your plan isn’t perfect

When asked about how Softchoice overcame the sudden, cross-company requirement to go remote, Jeff said most of the hard work was already done, thanks to existing business continuity plans.

 “The experience was relatively seamless. … This isn’t to say we anticipated a pandemic. I’m not saying this is something we saw coming.”

“I would say overall the experience was relatively seamless from an IT perspective,” he said. “When we thought of business continuity planning (BCP), we always had a view on remote work. This isn’t to say we anticipated a pandemic. I’m not saying this is something we saw coming. But the approach we took for each of our branch locations, from a BCP perspective, assumed the scenario where for example, the Chicago office could all work remotely for an indefinite period of time. That really drove our decisions around how we provision, whether that’s hardware, software, and the key decisions around networking, infrastructure and our own cloud strategy.”

He added that Softchoice’s flexible culture was also an asset in the early days of the lock down.

“More importantly, our remote working strategy was already part of our culture, of how Softchoice operates. Softchoice has always had flexibility around remote work. We have always believed everyone should be able to work remotely if they need to, when they need to.”

Insight #2: Time to get resilient with work-from-home  

While Softchoice’s IT leader said the transition was “relatively seamless,” he pointed out a few areas that needed urgent attention. Because existing remote working strategies had been created for temporary or isolated situations, Softchoice needed more resilient and robust networking, application and provisioning capabilities.

“As an example, we had VPN provisioning for the entire organization, but we didn’t have a redundant VPN solution. That meant we had a single point of failure with VPN.  We had plans around what a redundant VPN solution would look like, we just hadn’t executed on them. Fortunately, the team was able to execute on the plan quickly. Within a month of everyone moving to remote, we were able to deploy it,” he said.

“Today it’s: Ship a box. Open it up. Turn on your laptop. And it will self-configure, ready to go. You are off to the races with little intervention or support from the help desk.”

“Another one was how do we deploy new machines, like laptops, to new hires, or when refreshing aging hardware?  We had kicked off a strategy to be able to activate and provision a machine anywhere, anytime, last year. We accelerated that work this year, allowing that to happen with little to minimal support from help desk. Today it’s: Ship a box. Open it up. Turn on your laptop. And it will self-configure, ready to go. You are off to the races with little intervention or support from the help desk.”

INSIGHT #3: It’s never been more important to align to the business  

Before COVID-19, e-commerce and telesales played a key role in how we served the needs of our clients. After COVID-19, virtual services became downright essential. Reis uses this point to illustrate the growing business value of IT in the post-pandemic economy.

 Well, e-commerce has always been a big driver for a lot of organizations like ours. But it’s become even more important given COVID-19. We are working with key stakeholders who want to enhance functionality, to drive that stronger digital experience, which is gaining a lot of momentum,” he said.

“It really underlines how IT should be partnering with the business as a strategic enabler, as a part of the business, as a part of the organization that really helps drive business outcomes.”

“When you think of Inside Sales, traditionally everyone is in the same building and you have leaders and coaches walking the floor, listening and coaching. And those mechanisms go away when you work remotely. So, you want to be able to support that sales team, help in their growth and maturity, to enable new and younger sales professionals to continue to accelerate up that curve and in their craft.”

He added that IT is being driven to re-prioritize projects, to deliver the most impact to the business.

“We have had to prioritize some things and put other things on hold, to drive these larger business outcomes. We are saying, ‘If we park this, and if we re-prioritize that, there is a higher return to the business. It really underlines how IT should be partnering with the business as a strategic enabler, as a part of the business, as a part of the organization that really helps drive business outcomes. 

INSIGHT #4: A new kind of IT leadership, mentoring is in order

While IT teams might be naturally suited for remote work, that’s not to say it won’t get in the way of traditional career and management goals. Jeff said the shift has had him re-think his own leadership practices – forcing him to focus more on the “human” side of the office experience.

“I don’t see IT as being any different than leading any other team. At the end of the day, they are a group of people, trying to do best they can under a set of challenging circumstances,” he said.

“So, it comes down to more frequent touchpoints, more frequent interactions. It’s the informal virtual drop-bys, to say ‘how’s your day going?,’ the virtual socials. It’s smaller break out groups, rather than large, all in meetings, where individuals get more of a voice. We are working also to make sure we are aware of specific members in our teams, folks to be particularly sensitive with, for whatever personal circumstance they may be in, and how can we think about supporting them. So, it’s really all about staying in tune with the day to day.”

INSIGHT #5: Remind IT teams of their impact – it’s never been greater

Softchoice’s SVP of IT mentioned another leadership tactic that has helped in this crisis: Make sure everyone on the IT team sees the immense impact they are making, every day.

“Making sure they feel valued and appreciate what they bring to the table goes a long way.”

“We’re also really helping IT members understand how much of a critical enabler they are. How instrumental they have been and continue to be in supporting the rest of the organization in these challenging times.

Everyone has a role to play. And our role is certainly as important as anyone else’s. We are reminding them of that, making sure they are attached to that sense of purpose and sense of ‘how am I contributing to the rest of the organization?’ Especially at a time where they are sitting by themselves or working from home, it’s important to remind them of the criticality of their role. Making sure they feel valued and appreciate what they bring to the table goes a long way.”

INSIGHT #6: Human error remains – so amp up your security awareness

While hackers are taking advantage of a chaotic change of working habits, Jeff said his team is amping up efforts to prepare for the worst, including increasing monitoring, phishing testing and mandatory security compliance training. He’s even focused on a new set of threat vectors, as people leave the confines of compliant office spaces.

“We are publicizing best practices on how to work remotely. We are reminding people of security practices outside of IT. So, people are printing, scanning documents, what do they do with those documents, are they safely disposing of them? Are they continuing to stay compliant with any regulatory or contractual obligations? There are a number of things to remind people of, things people might have taken for granted when they were at the office.”

As the workplace changes, he says people are just as vulnerable to phishing scams as ever.

“Based on initial phishing simulations we conducted, we are probably about the same level of awareness. So, we are going to continue to iterate, to do the simulations, continue to educate. We’re sending a message to our organization that we are not going to let our guard down during this time. In fact, we are probably going to ramp it up.”

INSIGHT #7: The hottest IT skill set will be business acumen

While economic uncertainty is making new hiring plans unclear, Jeff said the future of IT skills is certainly headed in one direction. Aside from the hottest, trendy skills, such as cloud, end-user productivity, and remote working, he says young IT professionals should start getting comfortable putting on a business hat.

“IT exists because business exists.”

“Regardless of whatever circumstances we are in, the one thing I always look for in an IT professional, and the one thing I would encourage anyone who is looking to that as a career is this:  Are you able to wear a business hat? IT is what you do, but do you understand who you do it for? How do you understand what key stakeholders are looking for? How do you help shape conversations around business problems? I find a lot of IT professionals can jump to a solution, without taking the time to understand the business problem, or to understand the broader business strategy,” he said.

“IT exists because business exists. So, whatever your function happens to be, being able to wear that business hat, to have that acumen, is always a skill I look for and would encourage for anyone.”

In other words, the crisis has helped underline something we’ve known about IT for years. Your job isn’t really about technology – it’s about people. Now is not the time to shy away from focusing on how you can increase your impact with people, businesses and beyond.

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