Good day, CIOs. Trucking, logistics and supply-chain operators are taking the digital tools used to automate repetitive tasks around the office and using them in the cabs of long-haul trucks.

Hub Group Inc., which operates a fleet of more than 4,000 trucks, last month unveiled a set of artificial-intelligence-driven capabilities, leveraging more than 10 million data points, promising to offer more accurate delivery times.

CIO Vava Dimond tells CIO Journal's Angus Loten that the goal is to make deliveries more efficient and boost productivity. But first, to get buy-in from truckers, Hub Group added functionality to its data initiative that made it easier to handle paperwork, including logs along their routes and other forms. “In the past their reaction has been ‘more big brother watching us,’” she said. “So we wanted to make sure that when we handed them their new tools, it would be something they would use right away.”

Almost five months into her job, Zendesk Inc. Chief Information Officer Colleen Berube is shaping internal IT systems for the Silicon Valley big leagues.

The San Francisco-based maker of customer service software aims to reach $1 billion in revenue by 2020, up from $598.7 million in fiscal 2018.

"I've got to think about, How do I help the company scale?" said Ms. Berube, who came to Zendesk from Fisher Investments, where she was chief technology officer.

One goal is to wrangle 200 disparate apps and services accumulated over the years into an integrated system. That move could cut down on the pain points associated with onboarding employees, often a time-consuming process.

For CIOs at midsize firms, approaching the $1 billion in annual revenue mark represents an inflection point, said Joe Pucciarelli, group vice president and IT executive adviser at International Data Corp. It is a time when CIOs need to start thinking bigger, he said, shifting the mindset from solving IT problems to helping deliver smoother business outcomes.

Compared to CIOs at companies in the early stages of digital transformation, CIOs at digital-native companies, such as Zendesk, may have the advantage in some technology-specific areas, most notably in not having to handle legacy systems, said Dora Vell, CEO at Vell Executive Search, which conducts CIO searches for companies.

"As a head of technology they have a responsibility to tell the business side, 'Hey, this is what we can enable, and this is how much bang-for-the-buck or value it'll drive,’” Ms. Vell said.

Ms. Berube has been in CIO-type roles for more than a decade. She picked up the mechanics of digital transformation during her years at Adobe Systems Inc. from 2007 to 2015, where she was part of the leadership team that led the company's transition from boxed software to cloud services.

She has spent the past few months getting a better understanding of Zendesk's processes, technology, architecture, business capabilities and redundancies, as well as what needs to be scaled.

She has also started cross-training the IT team in emerging skills.

“She has to reassure the people that their performance is no longer the delivery of one particular service to the organization,” Mr. Pucciarelli said.

— Agam Shah

The race to save encryption. The WSJ's Christopher Mims reports on the race between engineers trying to secure internet communications and those who are creating the quantum computers that can break today's encryption.

Today. Information is encrypted by your PC or smartphone, then passed through the internet as a string of indecipherable 1s and 0s. On the other end, the recipient uses a secret key to validate your password.

10 years from now. A quantum computer eavesdropping on information communicated with today's encryption standards could decrypt that data in hours or even minutes.

An alternate future. Computers using so-called lattice encryption, where data is encoded in a multidimensional “lattice” of data, could make information "quantum safe."

Automation is expected to affect men and women nearly evenly, according to a new McKinsey Global Institute study. The WSJ has more.

The lawmakers to watch as Congress confronts big tech. From the WSJ comes a list of the key lawmakers in the Senate and House who will be playing an outsize role in the debate over competition in digital markets.

Elizabeth Warren takes the message to the Valley. A New York Times reporter asked passersby their thoughts on the billboard, above, located near the main Caltrain station servicing Silicon Valley. Everyone, it appears, had an opinion.

Salesforce raises earnings outlook. The business-software firm said it delivered record revenue in the latest quarter, reporting a profit of $392 million, up from $344 million a year earlier, the WSJ reports.

Developers sue Apple over App Store monopoly. The lawsuit takes aim at the years-old policy requiring that iOS apps be sold through the App Store, the WSJ reports. 

Baltimore logs on after ransomware attack. City officials tell the Baltimore Sun that a May 7 ransomware event has cost taxpayers $18 million in recovery expenditures and lost or deferred revenue. Officials expect 90% of workers to be back online this week.

NYC still calls to Amazon founder. Amazon.com Inc. may have abandoned plans for a second headquarters in Long Island City, but CEO Jeff Bezos is nevertheless investing in the city. The WSJ reports that Mr. Bezos is close to finalizing a Fifth Avenue real-estate deal valued at about $80 million.

Millions of farm acres are set to go unplanted with corn this spring as persistent wet weather leaves U.S. farmers facing an agonizing choice: whether or not to risk trying to raise a crop. (WSJ)

The House passed a bill that would provide permanent legal status and a path to citizenship for hundreds of thousands of young immigrants who came to the country illegally as children—but the legislation is unlikely to be brought up for a vote in the Senate. (WSJ)

Senate Republicans were weighing possible ways to block President Trump’s planned tariffs on Mexico, amid fears of U.S. economic disruptions and 2020 election fallout. (WSJ)

Va. Gov. Ralph Northam said he would call a special legislative session to address gun control after a gunman killed 12 at a Virginia Beach government building. (WSJ)

Write to Steve Rosenbush at steven.rosenbush@wsj.com.

Follow the WSJ CIO Journal Team on Twitter: @steve_rosenbush, @scastellWSJ, @angusloten, @agamsh, @tomloftus.

The editor, Tom Loftus, can be reached at thomas.loftus@wsj.com.