The Future of Work is Personal: Why I Invested in Fleetsmith

I’m thrilled to announce that Upfront is leading Fleetsmith’s $7.7 million Series A round.

Fleetsmith has the “unfair advantage” we look for at Upfront Ventures. The world-class founding team — Zack Blum, Jesse Endahl, Ken Kouot, and Stevie Hyrciw — has built IT teams and custom device-management platforms from scratch at Dropbox and Fandom. They’re insanely innovative and obsessively focused on execution.

And in classic founder fashion, they built a product that solves their own problem: automating the burden IT organizations shoulder to keep Macs (and later, everything else) up-to-date, patched, and secure.

Many call Fleetsmith a security company. Some call it an IT device management, or DevOps company with killer Bay Area talent. None of them are wrong. Fleetsmith’s roster of customers includes Monzo Bank, Robinhood, Fandom, HackerOne, and Sentry, and they’re in a space that’s blowing up — the cyber and IT security market is in the many billions of dollars today and a high growth category projected to grow 25 percent+ a year for the foreseeable future.

This is all great, phenomenal, impressive. But Fleetsmith is doing more than making device management effortless — it’s making the human future of work possible.

Future of Work = Identity + Convenience + Control + Personal Growth

We’re going through a huge shift in how workers work and how they’re managed. Personal and professional identities are merging in every arena. The future of scale isn’t uniformity everywhere, but rather customization is happening everywhere, even at large uniform employers or consumer mass market. It’s not Starbucks on every corner; it’s Squarespace, Eventbrite, and Docusign powering groups within each mass market corner. In practical application to the workplace: When an employee moves from job to job — 93 percent of people who took new roles took them at different companies — she wants to live in devices and apps that make her feel at home.

What’s the first thing we do when we get our “work” computers? Download our apps that make us feel most comfortable, most at home, most productive: Chrome, Slack, Adobe, Zoom, Evernote, Spotify. We login from home, from WeWork, from Costa Rica. (The teams at Github and Trello are already more remote than not.) At night, we watch Netflix. Our devices aren’t “work” computers. They’re our homes. They represent how we work and how we view the world. Setting them up to fit our needs and preferences shouldn’t be a violation of company policy or the nascency of a security vulnerability.

Fleetsmith recognized the need for employers to shift how they manage IT to support how employees live and work today — and set out to make it easier for companies to do just that.

Remember how everyone used to wear a suit to work — even in tech — until companies like Google started allowing people to wear hoodies and sneakers and “dress their identity?” These days, the devices and apps we use at work aren’t too far off from our wardrobes. We expect to be able to express our identities through them — so we can work the way we work, rather than conform to the way our current employer works. It’s the reason you’re as likely to see me in the office in a pair of Nike Cortez and a puffy coat as silver slingbacks and a moto jacket.

We need to embrace this conflation of the personal and the professional, and the declining cost of distance. We need to automate the administrative burden currently on our IT departments, and free our security teams from being the “just say no” men and women and the (anti)heroes who have to swoop in to save our melting devices from big attacks.

The Future Organization = Security becomes the YES Team

A modern security team culture seeks creative engineering solutions to allow the security team to say “yes” instead of “no.” This type of environment enables the worker to BYOI (“Bring Your Own Identity”), while keeping the organization secure.

The team at Fleetsmith is one of the first generations to grow up in this type of security culture at leading edge companies like Dropbox. Fleetsmith is now positioned to be a key part of the tech stack to empower and secure modern work environments.

A culture that enables employees to accomplish their goals without compromising on security is both critical and difficult to roll out in practice. By 2021, cyber attacks will cause $6 trillion in annual worldwide damages. But even the most technologically advanced organizations are underperforming in this area. Most companies have between 30 and 50 different security applications in use, each requiring central IT to deploy them, according to data from Cisco and IBM. Often, IT teams build custom internal tools based on open-source libraries such as Munki and Puppet to manage their Mac fleets. Of course, Macs aren’t just for creatives anymore: 91 percent of enterprise workplaces have Macs; 99 percent have iPhones or iPads. Google itself is a 50-percent Mac shop.

No IT department will say they’re satisfied with their current solution — even though it’s the one thing that enables employees to work how they want, and do so securely. They’re all too eager to abandon these time-consuming, imperfect solutions. The Fleetsmith team knows this firsthand — Jesse designed and built such a platform at Dropbox using open-source tools.

Fleetsmith provides a very different kind of approach to onboarding, security, and support. It once took IT an afternoon to order, build, and set up a machine for a new employee. Fleetsmith’s zero-touch deployment from (and to) anywhere in the world takes just a minute. When it’s time to off-board, wipe, and reassign, Fleetsmith does that too, no manual IT administration needed.

It isn’t just a security + IT platform. It’s the future of work. And Fleetsmith built the (very complicated) tech platforms that make that future possible. Just as we’ve all moved from on-premise Exchange servers with dedicated teams to simple solutions like G Suite and Office 365, Fleetsmith brings the device management space into the cloud-native world. G Suite is a no-brainer, and so is Fleetsmith.

We couldn’t be more excited to welcome Zack, Jesse, Ken, Stevie and the team at Fleetsmith to the Upfront family, and to work with them on empowering the workers and workplaces of the future.