Pioneers, Settlers, and Town Planners: The Unspoken Framework Behind Every Tech Org That Works (or Implodes)

Have you ever walked into a meeting where everyone’s solving different problems, from different timelines, in different universes...where the meeting is almost off the rails before it begins? You've got someone talking about scaling a prototype. Someone else is pushing for security sign-off. And someone is already rewriting everything in Rust “just because.”

Sound familiar?

I don't personally think it's dysfunction. Well, okay, maybe it’s a little dysfunction (who's not at least a little dysfunctional these days?). But more often than not, I feel we're witnessing the reality of most tech orgs that's not discussed out loud, nor formalized. Tech orgs are built on three very different mindsets.

Pioneers. Settlers. Town Planners.

Researcher Simon Wardley borrowed the idea of Pioneers, Settlers, and Town Planners from Accidental Empires by Robert Cringely (dating back to 1992) and turned it into a practical framework for building orgs that can actually innovate without imploding. Instead of rigid org charts, it shifts teams into a more fluid structure where different mindsets drive different phases of work: from exploring new ideas to scaling them reliably over time.

This framework breaks down innovation and execution within organizations into three types of work and corresponding mindsets:

• Pioneers explore new, uncharted ideas and build prototypes characterized by high uncertainty and risk.

• Settlers take those prototypes and turn them into stable, customer-ready products.

• Town Planners industrialize and scale the products, ensuring they are robust, compliant, and efficient.

  
  

The key insight is recognizing that each stage requires different skills and attitudes. The other part? Forcing one group to do another’s job leads to friction, inefficiency, and burnout. Ultimately, innovation should flow from exploration (Pioneers), through stabilization (Settlers), to industrialization (Town Planners).

This model isn’t just a metaphor. It’s a map. One that explains the lifecycle of innovation in a tech organization (I'd even argue you could apply this to MORE than tech), and why things break when you don’t align people to where you actually are in that lifecycle. After spending this past Thursday at PlatformCon 2025's live day in NYC where it was referenced, I thought it might make for an interesting blog post to put into the universe.

Act 1: Pioneers - The Agents of Mayhem and Progress

Pioneers are the ones blazing trails through uncharted territory with caffeinated fever dreams in one hand and an untested prototype in the other. These are the creative misfits who see something that doesn’t exist yet and can’t stop until they build it. They're often the first to ask, “What if we did this totally insane thing...and it worked?” They thrive on ambiguity, velocity, and doing things that have never been done before. They don't want approval. They want space. They don't want Jira tickets (although most of us don't want Jira tickets). They want napkin sketches and hackathons. They are idea-forward, risk-embracing, and detail-avoidant.

You need Pioneers to survive in tech. Without them, your org becomes stagnant. These are the "big thinkers" that a lot of folks work with and can identify. But you also need to protect your platform and production environments from them at all costs. They will absolutely YOLO your infrastructure into oblivion “just to see what happens.”

They’re not here to scale. They’re here to challenge what’s possible. And when you try to force them into a sprint cadence or wrap them in governance, they either quit, break the process, or start a skunkworks project.

Let them dream. Just make sure someone else is building the foundations.

Act 2: Settlers - The Bridge Between Chaos and Order

The Settlers are the unsung heroes of every functioning tech org. They are the ones who walk into the Pioneer’s sandbox and say, “Cool idea…but how does this thing not explode under real load?”

Settlers are realists, builders, and translators of brilliance into usable, stable systems. They understand enough of the Pioneer mindset to respect innovation, and enough of the Town Planner mindset to know this can’t go to production like this. They don’t just ship code. They ship value, with process, documentation, monitoring, and at least some concern for cost.

In my opinion, this is where Platform Engineering lives. This is where SREs, DevEx, and early-stage product teams operate. They take bold ideas and ask the hard, unsexy questions.

"Is this repeatable?" "Will it scale?"

"Can other teams use this?"

"What happens if this breaks on a Friday at 5pm?"

Settlers sit in the tension between speed and safety. Too often, they sit alone, overworked, underappreciated, and downstream from chaos. When you forget about the Settlers, your org becomes a graveyard of half-built innovation. When you empower them, you get real platforms, real velocity, real progress.

They are the fulcrum of your delivery.

Act 3: Town Planners - The Architects of Scale and Sanity

Now we arrive at the Town Planners. The grown-ups. The infrastructure introverts. The people who lose sleep over misconfigured IAM roles and unexplained cost spikes. Town Planners are not the fun part of your org. They’re the necessary part. They take what the Settlers have stabilized and make it scalable, secure, compliant, and economically sound. They create paved roads, guardrails, and shared services. They build the internal tooling and automation that lets ten times the number of developers ship with a fraction of the risk.

If a Pioneer’s job is to invent, and a Settler’s job is to productize, the Town Planner’s job is to institutionalize. They create infrastructure that survives reorgs, CTO swaps, and even public cloud region outages.

And yes, they also create friction. Sometimes friction is the point it slows you down just enough to keep you from deploying storage accounts full of sensitive data to the public internet. Again.

In my opinion, Town Planners are the backbone of any mature tech org. They’re also the ones left holding the bag when your startup decides to move fast again.

Where Things Fall Apart

Here’s the punchline:

Most orgs don’t recognize this model and that means they don’t resource it correctly. They don’t respect the different needs, tempos, and values of each group.

So they ask Pioneers to document and secure their half-working experiments. They expect Settlers to clean up everything and hit unrealistic deadlines. They treat Town Planners like blockers instead of builders of scale. ...or worse, they pretend everyone is the same cross-functional, full-stack, full-cycle, DevSecDataOps unicorns who can ideate, build, test, secure, and scale without breaking a sweat...

That’s not real, y'all.

Innovation should flow from Pioneer to Settler to Town Planner. When you get that flow right, magic happens (I've seen it + witnessed it at a few jobs).

Platform Engineering — The Settler’s Stronghold

Platform Engineers are your Settlers with a toolbelt and a vendetta. They build the frameworks that other teams rely on. They productize infrastructure. They balance speed, safety, and developer joy.

But here’s the thing. Platform Engineering only works when it’s not treated as a dumping ground for every unfinished idea.

It’s not a fixer team. It’s a force multiplier.

If your platform team is buried under tech debt from three previous Pioneer-led MVPs that nobody ever finished, you don’t have a platform problem, you have a lifecycle problem. You've got the wrong people doing the wrong jobs at the wrong time.

As hard as it might seem, you need to fix that first.

So...Where Are You?

Take a breath. Zoom out. Think about your team, your work, your leadership. Are you a Pioneer frustrated because you keep getting asked for cost estimates before you even have a prototype? A Settler drowning in half-baked ideas you’re expected to make reliable yesterday? A Town Planner wondering why nobody follows your standards until they break something again?

None of these roles are better than the others, but they ARE fundamentally different with different personality types at the helm. The key to scaling sustainably isn’t to move faster, it's to move with clarity.

Why you Gravitate Toward Certain Role (Spoiler: It's Personality, Not Just Skill)

If you’re wondering why you might lean toward Pioneer, Settler, or Town Planner, it might have less to do with your job title and more to do with how your brain is wired. I kind of equate this all to The Myers-Briggs Type Indicator (MBTI) or The Big Five (OCEAN) model. MBTI is technically considered outdated, pseudoscientific, and not very reliable by modern psychologists and behavioral scientists (despite it being easy to understand, non-threatening, and it lends itself well to team-building exercises..."Hey, I'm ALSO an ENFJ!"). The Big Five is a model that's validated by psychological research. So let's talk a bit about the Big Five Personality Traits (OCEAN), since MBTI is not something we should use (even though I personally like it), to describe how people show up in work and life. Here’s a (very oversimplified) cheat sheet:

Trait	Pioneer	Settler	Town Planner
Openness (creativity, curiosity)	High	Moderate	Lower (pragmatic)
Conscientiousness (organization, dependability)	Low to Moderate	High	Extremely High
Extraversion (sociability, energy)	High	Moderate	Variable
Agreeableness (cooperativeness, compassion)	Moderate	High	High
Neuroticism (emotional stability)	High risk if unsupported	Moderate	Low (by design)

This doesn’t mean you’re stuck in a box, but it does explain why that one teammate is obsessed with building governance frameworks while another is rewriting the same CLI tool for the fifth time because it “just didn’t feel right.”

The Big Five gives language to the tension:

• Pioneers crave novelty. They score high on Openness, low on Conscientiousness, and don’t mind breaking things to see what happens.

• Settlers are the Goldilocks zone. They blend structure and adaptability, sitting in the middle of most traits.

• Town Planners feel comfortable with predictability. High Conscientiousness, lower Openness, and a deep love for things like “stability” and “compliance checklists.”

  
  

Understanding these differences doesn’t just help you empathize with your team...it helps you build roles, handoffs, and workflows that fit people’s strengths. Because a Pioneer forced to follow a six-step change control process? That’s not innovation. That’s burnout with better documentation (ok hopefully that got you to laugh by now).

Final Thought: Build the Flow

The future of any org isn’t in a single role. It’s in how you build a flow between them.

You need Pioneers to challenge the status quo. You need Settlers to stabilize the chaos. You need Town Planners to make it all scale. Respect the phases. Fund the handoffs. Name the tension. If you're skipping stages or smashing them together, you're not accelerating. You're compounding risk. And that’s a velocity nobody wants.