How to build a community of MSP automation pioneers

Discover how automation pioneers, settlers, and town planners can help MSPs build a scalable culture of automation with practical tips and best practices.

Every MSP dreams of fewer tedious tasks, more efficiency, and the satisfaction of a job well done—minus the late-night ticket marathons. Achieving this automation isn’t magic; it’s a process that starts with a vision and a framework. Simon Wardley originally created the Pioneers, Settlers, and Town Planners (PST) model for software development. The model also applies to automation building because both rely on transforming rough ideas into streamlined operations through innovation, refinement, and scalability.

In short, pioneers innovate, settlers refine, and town planners scale. Each group plays a unique role, transforming chaos into efficiency. Much like building a city: pioneers scout new workflows, settlers establish infrastructure, and town planners create a system for everyone to thrive.

So, what does this have to do with your MSP? Everything. Whether you’re a small MSP with one ambitious automation pioneer or a larger team scaling automations across the board, this model can help you build a culture of automation that sticks. And the best part? It’s about working smarter, not harder—because no one has time to reinvent the wheel.

In this blog, we will explore how the PST model can guide your journey. We break down each role and offer best practices for leveraging automation to drive success.

Understanding the pioneers, settlers, and town planners model

The Pioneers, Settlers, and Town Planners (PST) model is more than an organizational theory. It serves as a practical guide for innovation, improvement, and growth. Think of it as making sure everyone on your team understands how their role helps turn automation ideas into impactful, everyday practices.

At its core, the PST model describes how innovation evolves:

• Pioneers are dreamers and tinkerers. They’re your automation pioneers, constantly exploring what’s possible and testing new workflows. Pioneers thrive on discovery, but their prototypes aren’t always polished. Their job is to lay the foundation for what’s next.
• Settlers are builders. Once the pioneers have cleared the path, settlers refine and stabilize those wild ideas. They create workflows you can trust, ensuring automations are reliable and ready for prime time.
• Town Planners are efficiency engineers. These folks take what the settlers have refined and scale it for maximum impact. They industrialize workflows, integrate them into your operations, and keep things running smoothly.

The genius of this model lies in how these roles complement each other. Pioneers push boundaries, settlers turn potential into reality, and town planners create the infrastructure that makes it all sustainable. Without pioneers, innovation cannot occur. Without settlers, it remains chaotic and impractical. Without town planners, it becomes impossible to scale or sustain progress.

For MSPs, this framework feels surprisingly familiar. Whether you’re a scrappy one-person automation team or a larger MSP with resources to assign distinct roles, the PST model aligns with how automation evolves. Small MSPs often juggle these roles within a single person or a small group. Larger MSPs can build specialized teams to handle each process phase.

By understanding your place in this cycle and which roles to focus on, you can better align your efforts. This will help you create a strong culture of automation. In the next sections, we will explain each role. We will also show how to use its principles for your MSP’s unique challenges and opportunities.

The automation pioneers: experimentation and ideation

Every incredible automation journey starts with someone asking, “What if?” That’s the pioneer’s domain. These automation pioneers lead your MSP. They always look for ways to make things better, faster, and more efficient. They thrive on curiosity and experimentation, willing to test new ideas even when there’s a high chance of failure.

In an MSP setting, pioneers find manual, repetitive tasks. They ask how automation can help remove these tasks from the to-do list. They tinker with tools like Rewst’s low-code workflow canvas to create prototypes that solve real-world problems. But pioneers aren’t necessarily focused on delivering polished workflows. Their job is to explore possibilities, test boundaries, and pave the way for what’s next.

The pioneer’s role in small MSPs

For smaller MSPs, the role of the pioneer often falls to a single automation engineer. This person wears many hats but spends part of their time experimenting with potential solutions to common pain points. Other team members can support this process by acting as “idea scouts,” identifying areas ripe for automation.

Dustin Riley, an Automation Engineer, demonstrates how pioneers can effectively gather ideas by using Microsoft Forms. This method allows him to collect input from both technicians and leadership, ensuring a steady flow of actionable automation opportunities. You can see his approach in action in this Workflow Wednesday.

For example, a technician may notice that closing tickets for password resets eats up a chunk of their day. They flag it as an opportunity for automation, and the automation engineer prototypes a workflow to streamline the process. The initial results might be rough around the edges, but that’s okay—the pioneer’s role is to explore, not perfect.

To learn more about how you can find the right pioneer for your MSP, download our Automation Engineer Job Description Template.

The pioneer’s role in larger MSPs

In larger MSPs, pioneers may be part of a dedicated innovation team tasked with researching and developing new automations. This team often includes Director- or Manager-level individuals who provide strategic oversight, ensuring automation initiatives align with business goals. They collaborate across departments, gathering input from technicians, service desk managers, and even leadership to identify the most pressing inefficiencies. This approach creates a broader pool of ideas, ensuring innovation touches every corner of the organization.

Challenges for automation pioneers

Being a pioneer comes with its own set of hurdles. For one, resources are often limited—especially in small MSPs where a single person may juggle multiple responsibilities. There is also the risk of resistance from team members who may not immediately see the value of automation experiments. After all, rough prototypes can feel more like magic tricks than practical solutions.

Best practices for pioneering success

To make the most of your pioneers:

• Encourage collaboration: Use tools like feedback forms or suggestion boxes to gather ideas from the whole team. A simple “This would be cool to automate!” form can spark meaningful innovation.
• Start small: Focus on quick wins that demonstrate value without requiring extensive development time.
• Celebrate experiments: Even if a prototype doesn’t work perfectly, acknowledge the effort and lessons learned. This builds momentum and reduces fear of failure.

Automation pioneers are the spark that ignites the automation journey. Empowering them to experiment and innovate sets the stage for the next step: turning ideas into reliable, usable workflows. That’s where the settlers come in.

The Settlers: Refinement and Adoption

Once the pioneers have laid the groundwork, it’s time for the settlers to step in. Think of settlers as the MSP’s builders—they take the pioneers’ rough, experimental workflows and turn them into polished, reliable tools that the entire team can use. Settlers bridge the gap between “cool idea” and “daily essential,” ensuring automation becomes an integral part of your operations.

If pioneers ask, “What if?” settlers are all about answering, “How do we make this work for everyone?” They refine workflows, document processes, and build trust in automation. In this phase, automation moves from innovation to implementation.

The settler’s role in small MSPs

In a smaller MSP, the automation engineer often doubles as the settler. As a pioneer, after experimenting with workflows, they can pivot to refining these prototypes based on feedback from the team. Settlers focus on making workflows user-friendly, reliable, and scalable.

For example, let’s say your pioneer tested a password reset workflow that worked in 70% of cases but fell short in others. The settler goes over the process again. They fix problems, automate special cases, and write down the steps. This way, any technician can use it with confidence.

Team members in small MSPs also play a crucial role in this phase as testers and validators. Their real-world feedback helps settlers identify and resolve issues, ensuring workflows are practical and effective.

The settler’s role in larger MSPs

Larger MSPs often have teams of pioneers who execute automation concepts, while settlers oversee strategy, ROI, and operational alignment. At Air-IT, Automation Engineer Charlie Carter develops workflows, and Chief Automation and AI Officer Peter Pendlebury ensures they align with business goals.

This collaboration saves 400 hours monthly, as Peter highlights in this customer testimonial video. Settlers also standardize pioneer-created workflows, turning multiple approaches—like automating user onboarding—into unified, adaptable solutions.

Challenges for settlers

Settlers face a delicate balancing act. They need to refine workflows without overcomplicating them. This can happen when addressing edge cases or incorporating too much feedback. They must actively manage expectations, especially in smaller MSPs where they stretch resources thin.

Best practices for settlers

To make the most of your settlers:

• Start small: Begin by identifying an achievable end goal that addresses the most critical use cases, then work backward to layer in additional components. For example, automating a simple yet essential task like password resets is a foundational step before tackling broader workflows like streamlining the entire onboarding process.
• Test thoroughly: Engage team members to test workflows in real-world scenarios, providing valuable feedback for improvement.
• Focus on reusability: Create sub-workflows or modular components you can reuse in other automations. For instance, a password reset sub-workflow can seamlessly integrate into broader automations like user onboarding, offboarding, incident response, and auditing.
• Document everything: Good documentation makes workflows easy to understand. This helps everyone on the team, even those new to automation tools.
• Start simple: Start with smaller automations that address immediate pain points. As you build confidence, you can tackle more complex workflows.

Settlers are the steady hands that bring automation from concept to reality. The pioneers ensure they can implement their ideas effectively and ensure their reliable use. With workflows refined and trust established, it’s time for the town planners to scale things up. That’s where the real magic of automation takes off.

The Town planners: scaling and industrialization

When the settlers finish refining workflows, the town planners take the baton. These efficiency experts industrialize automation and scale it to maximize impact. If settlers build the house, town planners design the neighborhood, ensuring everything runs smoothly and is easy to maintain.

For MSPs, town planners integrate refined workflows into everyday operations, making automation a seamless part of your business. They focus on creating repeatable, reliable, and scalable systems across teams or clients. Their work transforms automation from a handy tool to a critical driver of efficiency and growth.

The town planner’s role in small MSPs

In smaller MSPs, leadership often steps into this role. They actively adopt refined workflows, continuously optimize them, and measure their ROI. For example, password reset automation might start as a workflow for a single client. However, under the town planner’s direction, it expands to all clients with centralized reporting to track its effectiveness.

The town planner’s role in larger MSPs

In larger MSPs, dedicated teams or leaders focus on scaling automation. They implement dashboards to monitor usage, identify new opportunities, and communicate results to stakeholders. This ensures automation aligns with business goals and evolves alongside the organization’s needs.

Best practices for town planners

• Focus on adoption: Train your team to integrate automation into their routines, ensuring consistent usage.
• Leverage tools: Use platforms like Rewst to simplify scaling with prebuilt Crates and reusable components.
• Communicate ROI: Regularly share metrics like time saved and productivity gains to align leadership and teams.

By scaling automation thoughtfully, town planners ensure workflows deliver consistent value and support long-term success, completing the journey started by pioneers and settlers.

Tying it all together

Pioneers, settlers, and town planners form a collaborative cycle transforming automation from idea to impact. Whether you’re a small MSP with one multitasking automation engineer or a larger organization with specialized teams, this model ensures innovation, refinement, and scalability work hand in hand.

By promoting experimentation and improving workflows, you build a culture of automation. This culture helps increase efficiency and growth. With the right tools and a clear understanding of these roles, your MSP can turn automation into a cornerstone of success. Remember, it’s not about perfection; it’s about progress, one workflow at a time.