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Michael MassadSenior Associate

Pradeep Ittycheria of Kasasa on Remote Work & the Unique Challenges of 2021

In 2020, practically everyone in a knowledge-based industry was working remotely—and remote work has largely been successful. The incredible drop in productivity everyone predicted didn't happen, according to most enterprise surveys.

We spoke with Pradeep Ittycheria, CTO of Austin-based CTO of Austin-based banking technology and services provider Kasasa, about his predictions for the continuation of remote work in 2021.

"While many industries started down the digitization path, it was a poor attempt to minimize change, to safeguard entrenched business processes and business relationships," Pradeep said. "The pandemic will truly lead to digital transformation as consumers' expectations and habits change."

Here's how Pradeep responded to our questions about the remote workplace this year and beyond.

On adjusting to remote work dynamics

Michael Massad, Elsewhere Partners: As a CTO, how did you navigate the sudden shift into remote work for Kasasa last year? What challenges took you by surprise and what went better than expected? What was it like at Kasasa and how does this reflect the larger context?

Pradeep Ittycheria, Kasasa: The things the company did helped me succeed. For example, our amazing COO, Vennesa Van Ameyde, created and led a COVID response team. This team focused on communicating clearly what the company was doing, changes to policies, and support available to our employees. This well-coordinated effort took away the stress as it related to work changes and helped calm nerves.

In my teams, we doubled down on specific daily meetings such as stand-ups. We made it a point to turn video on so people could see each other. We over-communicated in the beginning. I spent a good portion of the early pandemic trying to focus on inter-team disconnects and coordination.

Massad: What were the biggest challenges for your team during the transition?

Ittycheria: The shared teams, a shared resource such as IT and Infrastructure, had to deal with some of the most significant disruptions. While individual teams over-emphasized communication, they forgot to coordinate with external teams at the same level. Plans that had dependencies of these shared teams saw misses.

Similarly, teams that need to access physical infrastructure ran into challenges. We had to allow our IT teams into the office on a strict COVID protocol. It also exposed functions that needed to be streamlined or automated, such as workstation provisioning, inventory systems that were not current, and new employee support.

Massad: What went better than expected?

Ittycheria: What surprised me was how well new employee hiring and onboarding worked. Credit goes to our HR team and all support teams, including IT. The fact that we have many new employees who have never been into our office and still embrace our mission speaks volumes of the strong culture we have built at Kasasa. A culture based on our patch values does not require a physical identified workspace to preserve it.

Every meeting, every conversation was over video and messaging applications, optimized for remote collaboration. Everyone was in the same boat and dealing with similar challenges. There was shared pain and a desire to embrace change collectively.

On how 2021 will be different

Massad: How do you think these dynamics will change in 2021? How can teams proactively plan for this?

Ittycheria: With COVID-19 vaccines on the way, 2021 is going to look different.

If given the option, many employees will prefer to work remotely permanently or to have the flexibility to work from a remote location and the office. As more people return the office in 2021, the behaviors and expectations of having remote access to conversations and meetings will come under strain. When three out of the five people in a meeting are available in-person, will they remember to turn on video conferencing and digital whiteboards?

Companies will need to lay down new meeting etiquette and invest in improving meeting room technology. Companies do not need to spend a quarter of a million dollars on a Cisco TelePresence system, but using a laptop as your primary audio video device will not cut it.

In 2021 we can expect to see more always-on conference rooms that have 24/7 live feeds. Digital whiteboards and improved screen sharing capabilities will be standard.

We will see consolidation across communication platforms with enterprise messaging products, such as Slack, expanding their video capabilities and video conferencing providers like Zoom developing more messaging capabilities. IT teams will try and consolidate vendors to improve management as these capabilities will become even more critical for business continuity.

Massad: Last spring, there was an understandable rush to invest in new technology and communication platforms to support our remote work reality. As we ease into a hybrid of remote and in-person work this year, what should CIOs and/or CTOs keep in mind when evaluating their selection of existing vendors or considering new tools?

Ittycheria: CIOs will need to consider tools that support the increasingly asynchronous nature of work with both remote and hybrid work models. So while enterprise messaging was text-only in the past, now video capabilities and intelligent reminders are required.

In the past, CIOs would think about premium features like unlimited video as only required by teams that were client-facing or on the road. My prediction is now, everyone will need those capabilities.

CIOs will rethink bandwidth considerations around access to their corporate systems. There will be a renewed focus on improved VPN security with possible upgrades to infrastructure. Companies are still figuring out what their long-term work plans will be. Some, like Salesforce, have already decided that a majority of their company will be remote permanently.

With this uncertainty, CIOs should consider building in flexibility around their 2021 technology evaluations. Flexibility in terms of licensing and contract lock-ins will be prudent. Today, you may think that 50% of your company will go fully remote, but three months from now, you may find out that only 30% are planning to.

In general, I predict that IT teams will favor the ecosystem providers such as Microsoft and Google, because there is a good chance their companies use Microsoft 365 or Google Enterprise products, and using single-source providers will make provisioning and management more effortless. Advanced users, such as product development teams, will prefer the best-in-class solutions, even if it means combining many vendors' solutions. The age-old friction between ease of maintenance and the best feature set will be magnified.

Massad: What are your predictions for how this will affect culture?

Ittycheria: Many companies will try to reduce office space. Savings on physical infrastructure can be used for upgrading telecommunication capabilities. IT teams will invest in remote user provisioning and troubleshooting solutions. Companies will try and pull manual order to cash business processes that require people interactions into their CRM solutions.

Measuring employee and team productivity will also take on a new focus. Managers will second-guess productivity in this distributed world because of the lack of direct, in-person feedback. They will lean on systems that can link work activity to outcomes. Companies will look at solutions that measure employee engagement and effectiveness. Performance management systems will evolve to capture employee sentiment more effectively. Companies will track employee morale more closely.

A successful organization's key is to have a culture based on a firmly held and widely shared set of beliefs supported by strategy and structure. Communicating these beliefs and ensuring that these structures work well in a mostly remote, distributed company will add a new set of challenges for companies.

On redefining "good service"

Massad: Most people are now not only remote employees; they’re remote consumers, too. We’re experiencing a lot of our daily lives through a digital lens, from grocery shopping to banking to socializing. How has this impacted digital adoption across industries?

Ittycheria: According to the Commerce Department, from July to September, consumers spent $199.44 billion online with U.S. retailers, up 37.1% from $145.47 billion for the same quarter the prior year. That means nearly $1 in every $5 spent came from orders placed online during Q3.

We see a lot more banking being done digitally. Digital transformation of banking has been going on for some time; 2020 just put things in high gear. Much of traditional banking has been a person to person relationship business.

In 2020 with bank branch closures, more people used their digital banking tools. In a survey earlier in the year, just after the pandemic started, Fidelity National Information Services (FIS), one of the largest bank software providers globally, saw a 200% jump in new mobile banking registrations in early April, while mobile banking traffic rose 85%.

Masad: At Kasasa, you’re empowering community banks and credit unions with best-in-class digital tools for a better customer experience—demonstrating the necessity of these tools for them to stay competitive with big banks, even more so during the pandemic. How could democratizing data and digital tools in a similar way support other types of local businesses?

Ittycheria: This shift is here to stay. Knowing your banker's name may still be relevant in commercial banking; consumer banking is all about the best and most convenient digital experiences for consumers.

Similar disruptions have been seen in other industries such as car buying. Unshackled by franchise regulations, used-car dealers have innovated quicker than new-car dealers. Used-car chains such as Carvana and CarMax have innovated with technology adoption, changing how consumers buy a car.

We can expect new car dealers also to adopt technology in evolving the car-buying experience. Upstarts like Tesla have been fighting the dealers' networks; however, the pandemic and the changing consumer behavior will force new thinking in this industry steeped in decades of traditions, regulations, and hard-sell tactics.

There's no industry that won't be touched by change this year.


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About the Author

Michael Massad

Michael is a software investor at Elsewhere Partners where he co-leads all sourcing efforts and conducts operational / financial due diligence. Michael strives to connect capital and operational expertise with growing software companies across industries – most recently in infrastructure and cybersecurity – that are located outside of traditional VC hubs