For more than a decade, Aaron Wilkins helped scale Human-I-T — a nonprofit that refurbishes donated technology and provides it to organizations and people in need — from a $4,000 startup into a $30 million social enterprise.
He worked as CFO and SVP of people, finance and compliance, and like many CFOs who spend their time untangling complex workflows, and like many homebuyers chugging through a fragmented process, he saw firsthand at work and during his own home buying process how needlessly complicated a major financial transaction can be.
That realization sparked the idea to apply his operating and finance background to the problem of an arguably antiquated homebuying process. Wilkins recently started MoveWize, an AI-powered platform that guides home buyers and sellers through the entire process. The product is aimed to reduce friction for both parties caused by organizing timelines, documents, inspections, vendor handoffs and more.
In a recent interview, he discusses the CFO skills that translate to entrepreneurship, the process of bringing a business idea to fruition, what he’d want in a CFO and technology success stories from his previous work.
Aaron Wilkins
Co-Founder and CEO, MoveWize
First CFO position: 2013
Notable previous employers:
- Human-I-T
- J&S Management
- Morgan Drexen
This interview has been edited for brevity and clarity.
ADAM ZAKI: What CFO skills carried over right away into the launch process at MoveWize?
AARON WILKINS: The biggest one for me is problem-solving. It cannot purely be a finance skill. It is the habit of staying curious and keeping a beginner’s mindset. When you spend years in the finance seat, you learn to ask the right questions and you learn where to start. That translates well when you become a CEO.
On the finance side, understanding what good looks like numerically is extremely helpful. You know how to evaluate decisions logically. You know how to pressure test assumptions. You know when the numbers tell you something you might not want to hear.
The other skill that carried over is prioritization. In finance, you learn that time is the most valuable resource. Where you put yourself is your best use of talent. That is true as a CEO. You have to know when to pivot, when to pause and when to move fast. Scaling Human-I-T in a volatile market built that muscle for me. Those habits of prioritization, time management and grounding your decisions in logic are what carried over the most.
Did the decision to break ground with MoveWize have a catalyst moment, or was it more of a gradual mind change?
It was gradual. I reached a point at Human-I-T where I had done what I needed to do, and I wanted a new challenge. I grew up around residential and commercial real estate. My grandfather built a business in that space, and I was around it my whole life, but I did not want to go back into it in a traditional way. I wanted to solve a real problem with technology.
The buying and selling process is an old system. The roles are the same. The workflow is the same. New tools have been added, but they are plugged into old processes. Very few people step back and look at the process itself. That is what pushed me to start MoveWize. I wanted to reduce friction and bring clarity to something incredibly stressful for most people.
When I realized the process had not improved at all since my wife and I bought our home in 2019, that is when it felt like the right time to take the leap.
What specifically convinced you that the homebuying workflow was broken enough to build a business around?
There were three stages. The first was my own home purchase in 2019. It was harder than it needed to be. That stuck with me.
The second stage was going through a 1031 exchange recently. You are forced to sell a property and buy another quickly. It is the same pain as in 2019. You deal with seven to nine vendors, handoffs are poor and communication is fragmented. There is no single platform that guides the process end-to-end. Most buyers and sellers are not experts. If we remove even 30% or 40% of that stress, that is meaningful.
The third stage came from working with my co-founder, who comes from legal tech and [contract lifecycle management]. I spent my career driving digital transformation. We were both dealing with our own homebuying and selling frustrations at the same time. Inspections were a big one. When you get a report that reveals something unexpected, you have to track down quotes in a fragmented market with no guidance. It is stressful and inefficient.
We asked questions like what would happen if inspection reports could be licensed instead of being pulled multiple times. What if quotes could be sourced inside the same platform? What if listings, inspections, quotes, title and escrow could live in one guided workflow?
What stage is MoveWize in now, and what is the long-term vision?
We are in alpha. We are starting with process simplification. The first goal is to remove friction for buyers and sellers. From there, we will expand outward into partnerships with inspection companies, service providers, real estate agents, brokerages, title companies and escrow groups.
The long-term vision is a global marketplace that supports buyers and sellers with a full ecosystem of vendors. It is not about cutting people out. It is about giving them a better process. When you do that, everyone wins. Vendors get better information and smoother workflows. Buyers and sellers get clarity and transparency. Trust is the core. If users feel guided instead of overwhelmed, we have done our job.
You may eventually need a CFO. What traits will you look for, and how do you think about timing?
Timing depends on asset levels and scale. There is a point where it becomes clear that you need a full-time finance leader. If we ever pursue going public, that may require someone with IPO experience. The person who excels in early-stage build and scale is not always the same person who excels in a public-company environment.
There are really four core traits I will always look for in any hire, but they would be critical in a potential CFO.
Curiosity. A former IT leader at Human-I-T used to say, ‘Be curious, not furious.’ That mindset matters. When you are frustrated or think you are ten steps ahead, curiosity brings you back to the right questions. If you do not ask questions, you miss perspective.
Empathy. A CFO must be empathetic to everyone at the organization, from front-line workers to executives. If you cannot do that, you are not ready to lead here.
Ability to empower leadership. People doing the work usually have the best ideas. Leaders should not micromanage. I believe in circular leadership where insights come from the bottom, middle and top.
Strong decision-making. I want someone with a track record of decisions that moved an organization forward. Good judgment and context are as important as technical skill.
Those traits matter more to me than any specific credential.
You have led several digital transformations as a nonprofit CFO. In your experience, what tools delivered the clearest ROI?
Brex delivered a strong ROI. I like the spend management space. We looked at Rippling and Ramp. They are all strong tools, but what stands out about Brex is the people running it and their vision. We rolled it out in stages. Accounting got it first. Then we rolled it to power users. Then we added reimbursements before travel, so the experience felt consistent. The travel module cut booking time by about 50% and removed a major bottleneck.
Docusign’s CLM was another major win. After implementing it, our contract volume increased about 38% in six months without adding staff, and external legal expenses dropped about 46%. A lot of legal cost is hidden in email chains, redlines and back and forth. CLM removed that waste.
The lesson always starts with the process. Ask why you are struggling, what you are spending money on, and what the user experience looks like. When you understand that, the technology choice becomes clear. And once you know the process you are solving for, you can pick tools that integrate well with your broader stack.
