Experimenting with Remote First: Humans Shouldn't Be Your Only Strategic Hires

What if your next strategic hire wasn't a person at all?

Nearly every human candidate we talk to these days at Prefect has a similar question:

• How does Prefect think about remote work?
• How are you thinking about return to office mandates?
• Where will your team members be able to live and work in the next few years?

It's become a defining conversation of 2024, especially as more companies push for returns to office…and talented people push back.

The more I talk about this topic, the more annoyed I’ve become at the notion that teams can only be successful by being pushed into an office. For example, only if your team shows up every Tuesday and Thursday to a hyper specific location, month after month, great work will suddenly (and magically) start to happen. When companies push folks to gather in that way, that lack of freedom usually means they don't trust their people very much. We have a high degree of human trust at Prefect. We strategically hire each person because we seek to trust them. We lay the foundation for that trust in hiring frameworks and rigor tailored to each role. And that’s exactly why our next strategic hire isn't going to be a human at all.

The Remote First Spectrum

When I look at how companies approach remote work, I see a spectrum that reveals something deeper than just location preferences. It exposes how much organizations can attract talent, deeply collaborate, and ultimately trust their people to make good decisions:

• Remote Only…
  • team members choose where they work, fully virtual and no physical location
  • high individual freedom, but no opportunities for in-person collaboration and few opportunities for organic interactions
• Remote First…
  • team members choose where they work, and given opportunities for both purposeful in-person gatherings and virtual interactions
  • high individual freedom with mix of opportunities for collaboration in person and virtually
• Hybrid…
  • companies mostly, and team members sometimes, choose where team members work
  • limited individual freedom with mix of opportunities for collaboration
• Fully In-Person...
  • only the company chooses where team members work
  • minimum individual freedom with abundant IRL opportunities to collaborate

What's interesting is how this plays out in practice. Remote first is about folks being drawn into collaboration, while hybrid and fully in-person approaches push people together whether it makes sense or not. And this is where most companies miss something crucial - they're so focused on when and where people should work, they seem to forget to ask why they’re bringing people together in the first place.

Why Companies Miss the Mark

As our CEO Jeremiah Lowin pointed out in a recent conversation, hybrid probably comes from good intentions – trying to take the best parts of being together in a space and remote work…and then pushing them together. Instead you end up with the worst of both worlds - with people commuting into an office just to sit on their laptop in exactly the same way they could have done more comfortably at home on their couch.

We're seeing this play out across the tech landscape right now. Major companies are mandating three, four, or five days in the office, and then watching some of their most talented people not walk through those office doors ever again. Others go fully remote, don’t have to think about space at all, hope their teams will keep running smoothly on a virtual treadmill forever. Both approaches miss something fundamental: space isn't just a place to work—space when combined with freedom is a strategic asset that can multiply your team's impact.

At Prefect, we've been intentional about building our culture. We became a remote first company in 2018, and continue to back it with concrete support like a $800/month remote work stipend. But we’ve always tended to lean on the remote, in our remote first culture. When we recently got together for our once yearly all-hands gathering in Chicago, something clicked. The energy was amazing, and it got us thinking: how could we recreate that on a more constant basis than once a year without losing what makes remote work so valuable for our team?

The answer came from an unexpected place: our hiring playbook.

A New Approach: Thinking About Spaces as Strategic Hires

I’m willing to bet there is at least one common thread between your best hires. They don't just execute their role—they transform what's possible. They make everyone around them better. They spark new initiatives. They create opportunities that didn't exist before. They build flywheels that accelerate the whole company forward.

Now imagine if you thought about spaces the same way.

At Prefect, we would never hire someone without clear objectives and a 90-day plan, and then let them work indefinitely without measuring their impact. So why do companies do exactly that with their spaces? They sign 10 year leases, fill them with individual desks separated by walls, and hope something magical happens.

Here’s the thing…we decided to try something new–treat our spaces with the same framework and rigor we apply to hiring exceptional talent. Just like a human strategic hire, each strategic space must have:

• A clear purpose and mission
• A human to lead it (we're calling them "ambassadors")
• Measurable outcomes
• Compounding value (beyond just being a place to work)
• The flexibility to experiment and evolve

This framework pushed us to think differently about what spaces could be. Instead of asking "Where should people work?" we started asking "What kinds of spaces would act as multipliers for our team, community, and product evolution?"

Three Experiments

This framework has led us to launch three distinct experiments, each operating at a different scale with its own strategic purpose:

1. The Embassy (Washington, DC)

This space isn't about having desks – it's about engaging with our broader community. The KPI I'm really excited about? How many people without Prefect email addresses we can bring into the space. Whether they're customers, investors, or members of the DC data community, it's about creating a home for meaningful external interactions. That led us to find a place with a 100+ person collaboration room and an inspiring social rooftop rather than searching for the biggest private office possible for the least cost per square foot. Our CEO Jeremiah will be the ambassador here, creating a consistent presence that makes it easier for others to engage.

2. The Bridge (New York City)

This experiment, championed by our VP of Product Adam, is focused on bringing customers together for product councils and direct engagement. NYC happens to be a natural customer epicenter for Prefect. This location correspondingly provides the best opportunity to foster rich and convenient customer interactions with each other and our team. With a goal a shaping our product direction with more velocity. We're starting with a managed co-working space, which gives us the most flexibility to learn and scale as we go.

3. The Lab (Half Moon Bay, CA)

This might be our most unique experiment. Led by our CTO Chris, it's not actually a permanent office but a destination, both physically and metaphorically. Think of it as a creative retreat where teams can come together for short stints to tackle specific projects or dive deep into technical challenges. They have access to a beautiful farm overlooking the California coast, with catered meals and space to think deeply about what they're architecting and building.

We've already seen the power of this approach: during a similar pilot program at Lake Tahoe, a handful of engineers built our managed execution feature in just three focused days. That kind of breakthrough happens more easily when you give talented people the right environment and purpose for gathering. The Lab takes this concept and makes it regularly repeatable for us.

What Makes This Different

When you think about these experiments as three different strategic hires, unlike three similar offices, each can operate at a different scale and timeline. For example:

• The Embassy aims for our broadest engagement with the entire Prefect community – investors, developers, government, and companies we may never sell to but want to interact with.
• The Bridge expands outward, focusing on creating more direct connections between our customers and product.
• The Lab is inward facing, focused on our internal team's creativity and productivity.

This also means that rather than investing in three more people right now, we are choosing to invest in these three physical spaces as “hires". I'd rather have our current team of extremely talented Prefectionists be more effective and have more opportunities to increase their impact and velocity.

The Future is Both Unknown and Remote First

Look, we don't have this all figured out. That's exactly why these are experiments backed by hypotheses and measurable outcomes. We’re going to learn and each space is going to evolve. Some aspects might work better than we imagined. Others we might sunset entirely.

One thing I do know: these experiments only have the potential to work when team members who don't visit these spaces are held in the same regard as those who do show up IRL. Period.

As more companies struggle with a false choice between fully remote and in-person work, we're betting on a different future. A Remote First Future. One where you don't just hire strategic humans—you hire strategic spaces that can pull your people together and multiply their impact in ways we haven't imagined yet.

That's a future worth experimenting for.