The Outsider — An Analog Guy in a Tech World
Jim Mathewson

I am a simple, lifelong sales and operations guy who has spent the majority of his career focusing on human behavior. Despite this, I currently find myself building an amazing software platform alongside an incredible team of Software Engineers in the PropTech space. What does this mean? It means I had a lot to learn in order to be an effective teammate and leader in a customer first technology business. Here’s some important concepts I’ve picked up along the way:

Product vs Project: Key Operational Differences Between the Two


  • Defined idea, moves from A to B
  • Key players direct the specified outcome
  • There is a decision to execute an idea
  • Project team makes it happen on time
  • Engineers build it
  • Getting to the finish line is the focus


  • Customer first perspective
  • Holistic goal is discovered with a team
  • Problems are presented
  • Integrated team works to solve the problem through creativity
  • Design is an artifact of this plan
  • We work together to get to a solution
  • Idea of learning from launch, iterate from the learning

As a company, SIBI needed to determine what is more important, delivering a product that is “done” (Project) or one that is sustainable (Product). We had to decide if we were going to be a business supported by tech, or a business led by tech. The first looks at the engineering team as a resource, while a tech-led business integrates all stakeholders into one consolidated team with a customer first perspective (Engineering, Product and Business combined into one team). Both approaches work depending on what kind of business you want to build…but we landed on Product as our driver. Technology first, customer first.

Importance of Planning

Less is more: Keep it simple. Human behavior typically leans towards wanting more. When it comes to having a customer first approach and building a sustainable tech platform, simpler is better. Effective planning of goals, with a focus on building simple and elegant solutions to complex problems will win every single day. We don’t focus on how many lines of code can be written in one day, we focus on creating the best user experience possible, with the least complexity. The more time we spend on planning how to do that, the more boundless our platform becomes in its ability to make quick and subtle changes at low cost of impact.

Keeping the Cost of Change Low

Some basic concepts I have learned so far:

  1. Engineering time is very valuable
  2. Aim for small releases
  3. Shorten the feedback loop
  4. Mistakes are ok
  5. Make sure to course correct quickly

Software/Human Relationship

Before I had a chance to look “under the hood,” the only interaction I had with software was as a user. Now that I have had the chance to watch a platform come to life, I recognize that software is more than just an interface between humans and a machine. Software itself becomes a living, breathing entity that intuitively engages itself with the user’s behavior, allowing both the user and the software to improve and become more efficient. It’s a symbiotic relationship, not a stand-alone “thing.” This is one of the primary reasons SIBI landed on a customer first, technology first approach. We are not just a product for people to use, we are a product for people to become a part of.

Communication Amongst Teams

I often use the analogy of connecting the pipes to convey this idea. If you are trying to get water from one place to another, the pipes need to be connected, and the same holds true with software. If one team is not connected to another through great communication, then we will have leaks. Our domain focused teams are each building their own piping system that connects different aspects of our platform to each other. Since we need to ensure successful end to end builds, communication across teams is of utmost importance. The foresight of our team leaders to communicate dependencies on one another has allowed us to make sure that our pipes connect.

Humanistic Implications of Tech

Humans select the easiest route from A to B — this is an historic fact. As a result, human behavior leans towards less change. Because it requires learning and inertia, change can be difficult to conjure. However, as we all know, nothing good was ever easy. While anything new will require change, SIBI’s goal has always been to take the heavy lift of change and make it an easy transition for the user, again, emphasizing our customer first approach. I have learned that this is not always an easy task, especially when it comes to the intersection of people and technology, but we are working towards supporting this outcome, as a team. There is never a single solution that will be the best solution for all, but the more we focus on who our customer is, the better we can nail a large breadth of our customer needs.

What’s Next?

We have a great tailwind of things to come. PropTech and SIBI as a business are ever evolving, and it excites me! When I look at when we started SIBI in 2016, we were a very different company. We thought our goal was the outcome of our product and used technology as a resource to get us where we wanted to go. We have grown significantly both in our understanding of who we are, what we are building, and who we want surrounding us in pursuit of our reality. We are a technology first, customer first company. And while our focus is to be the best version of us, we also want to enjoy the ride.

Some characteristics of SIBI are:

  • Culture.
  • Fun.
  • Experience.
  • Development.
  • Leadership.

I am incredibly grateful to be part of SIBI, but I want others to experience this as well. Stop by, see who we are and what we are all about here. Maybe you too can find a great fit, and become part of something great!

James Mathewson


P.S. feel free to connect with me on Linkedin