In the early weeks of the world's breakneck pivot to remote work, companies scrambled to shore up IT systems, dole out Zoom subscriptions and clarify what to actually do with all those Slack channels.

Now, as it becomes clear that COVID-19 is anything but a fleeting emergency, the demands on remote employees working and living in confined environments are shifting dramatically. With Silicon Valley's famous in-office perks in limbo, companies are being inundated with pitches for tech add-ons that cater to distributed teams, like employer-paid child care apps, calendars that use AI to avoid meeting overload, and encrypted online systems for whistleblowers to report concerns from anywhere.

For Cara Brennan Allamano, who heads up HR for online learning company Udemy, the shift to "remote-first work" necessarily means wading deeper into employees' personal lives. The company has invested in training managers to talk with employees not only about project deadlines and work goals, but also whether they're eating, sleeping and staying active.

"What used to be that divide between personal and professional has now coalesced," said Brennan Allamano. "We're now responsible for the whole employee in a different kind of way."

If the barrage of pandemic-derived enterprise tech can be overwhelming for executives already navigating an economic upheaval, it also points to bigger questions about what kinds of changes employers might need to make for their workforces to stay productive at home for the long haul.

Companies like Shopify, Twitter and Square have all announced that they'll allow employees to permanently work remotely. On Friday, Facebook CEO Mark Zuckerberg said he is considering making 50% of employees remote in the next five to 10 years, which could involve technical adaptations like "employees teleporting to work with VR" in place of time-sucking, carbon-emitting commutes.

Tech critics have been quick to point out that the erosion of boundaries between the personal and professional will also mean navigating thorny issues around mental health and in-home electronic privacy. Workers may demand to be compensated for home office space as companies consider offloading real estate. The fundamental shape of the work day may never be the same.

Though the future of work is far from certain, we spoke with the CEOs of three companies on the front lines of the fast-evolving remote workforce for their perspectives on what's next.

The child care conundrum: Can an app fix a 'sick joke'?

Sarahjane Sacchetti tried virtual babysitting, and it didn't go well. The CEO of Silicon Valley employer benefits startup Cleo — used by companies such as Salesforce, Uber and Pinterest — experimented with online child care for her own family as a test case in handling extreme strain from closed schools and the specter of no summer camp while parents work from home.

"There's no virtual product that's going to fix this, as much as I would love to say there is," Sacchetti said. "I tried virtual babysitting, and my 3-year-old literally dumped paint on himself and made a huge mess. It made my day worse, not better."

Amid that misadventure, Saccheti and her team were ramping up work on a new "Cleo Care" app that will include online matchmaking with other working families looking to form local child care co-ops and vetting of in-person babysitters available to work as shelter-in-place orders ease. The subscription app, which Saccheti is pitching employers to subsidize for workers, will also include educational content developed by licensed teachers.

The overall goal: to ease the burden on working parents who may otherwise be forced to choose between work and family life. This spring, the company found in a survey of clients that 1 in 5 working parents were considering leaving the workforce due to the "current demands of child care and work."

"I'm really terrified that after all of the diversity gains for highly skilled women, the bottom's going to drop out," said Sacchetti, who took over as CEO in December. "Employers can do something."

Cleo itself struggled under past leadership with employee backlash to long hours and a lack of remote-work flexibility. Though Sacchetti is new to the company, and said she was once an offices-and-white-boards die-hard, she's seen "incredible progress" with remote work in recent weeks. She has yet to set a return date for offices, and her own employees will be the early testers for new products like Cleo Care.

"Five of our seven leadership team members have kids under 7, which is almost like a sick joke," Sacchetti said. "We're the ones that have to work on this, but really we need someone to fix it for us, too."

Fighting meeting fatigue and the 'tragedy of the commons'

How do you take time off work when there's nowhere to go? It's another permutation of coronavirus whiplash that has Matt Martin and his team at calendar automation company Clockwise warning employers to be more mindful of daily schedules.

"Companies are going to have to watch out for their employees getting burned out," said Martin, who co-founded the company and is now CEO. "That might mean taking stay-at-home vacations. I hear of people taking mental health days."

Employees of companies including Lyft, Asana and Slack used Clockwise before the pandemic to carve out uninterrupted chunks of time to get work done. The app — free for individual users but requiring fees for company-wide versions — uses algorithms to group meetings together and automatically reschedule conflicting events.

Since the start of COVID-19 office closures, Martin has tracked an average 30% increase in team meetings and a 25% jump in one-on-one meetings across calendars managed by Clockwise.

"The natural tendency is to reach out more, to connect more," Martin said. "Over time, you have to find better patterns to do that without swamping people's days with Zoom calls."

He's been reaching out to companies founded with remote teams to understand how they manage workers' schedules, and he encouraged Clockwise's own employees to "push back" on meetings that seem unnecessary. Longer term, the company is working toward alternatives to "networked calendars" visible across organizations, which can feed a temptation to add meetings to any unfilled time slots.

"Time inside an organization kind of becomes a tragedy of the commons," Martin said. The dynamic, he said, only stands to worsen in a remote context where days blend together.

Misbehavior can go remote, so whistleblowing must follow

For years, Neta Meidav brushed off the harassing text messages she'd gotten from a hiring manager early in her career. She left the student job, moved from her native Israel to study in the U.K., and eventually worked her way up to the British Civil Service.

By 2017, at the height of the #MeToo movement, she finally saw an opening to channel her lingering unease about the harassment into an anonymous channel for workers to report other forms of misconduct. Her company, Vault, is an online version of old-school anonymous HR hotlines. Clients include several large Silicon Valley tech companies, along with employers in HR, entertainment, media and advertising.

"I never saw myself as a victim. I was young, and I thought, 'as long as it wasn't physical,'" said Meidav, who is based in London and runs Vault with her husband, CTO Rotem Hayoun-Meidav. "Looking back as an adult, I can tell that it changed the course of my life."

The recent flight from offices unfolded in Silicon Valley amid ongoing backlash to corporate labor practices seen as unfriendly to workers, including lax handling of sexual harassment and forced arbitration. Meidav pivoted to pitching the platform as a tool to ensure that whistleblowing didn't fall through the cracks of the shift to remote work.

Vault frames itself as a neutral third party that allows employees to securely store evidence of misconduct, then send that information to HR directly, anonymously or in a group with other employees.

One early concern with the virus outbreak was an uptick in anti-Asian harassment, bullying and discrimination. Now, as companies consider going back to offices, Vault has reconfigured its app for employees to securely report COVID-19 symptoms or diagnoses.

"Everyone is under immense amounts of stress and going through difficult times no matter where in the world you are," Meidav said, noting that anxiety can be magnified by all-online communication. "People might write things that they wouldn't consider saying face-to-face."