Redeeming Your Time: A Conversation with Jordan Raynor on Stewardship and Custom Software

Jordan Raynor has spent his career at the intersection of faith, work, and technology. He has built and led companies, run a venture-backed tech startup as CEO, been selected as a Google Fellow twice, and served in the White House. He is also the author of several bestselling books, including Redeeming Your Time and The Sacredness of Secular Work, which have helped millions of Christians connect the gospel to their daily work.

When Jordan talks about stewarding time, talent, and capital wisely, he is not speaking from the outside. He has made the same decisions he is asking about.

RoleModel CEO Caleb Woods sat down with Jordan to talk through the discernment behind one of those decisions: custom software. When is it the right investment? When is it the wrong one? And what does it look like to approach that question as a steward rather than a consumer?

The Question Underneath the Decision

Most leaders look at custom software and see a cost. That is the wrong starting point.

Christian leaders waste God-given resources in one of two ways. They build before they have any validation that anyone will use the thing. Or they fail to automate processes that are quietly consuming their team's time and their partners' patience. Both come from the same place: treating software as an expense to justify rather than a resource to deploy.

The distinction that matters is this: investment mindset, not cost mindset. Software is not a line item. It is more like a hire. Every person you bring on carries specific goals for what they can do and how they can grow the business. Software works the same way. The question is not whether it costs money. The question is whether you are putting it to work on something that matters. That is not a question you have to answer alone.

Proverbs 21:5 draws the line clearly: "The plans of the diligent lead surely to abundance, but everyone who is hasty comes only to poverty." The goal is not to move fast. It is not to wait indefinitely. It is to move at the right time, with clear eyes about what success looks like and confidence that the business has earned the investment.

Invested, Not Buried

The instinct, when facing a significant expense, is to protect what you have. Fractional CFOs, custom software consultancies, design firms: they all read as costs, and costs feel like risks. So leaders hold back.

But stewards are not just called to protect. They are called to invest. In the Parable of the Talents, a master entrusts his servants with resources before leaving on a journey. Two put the money to work and return more than they were given. One buries his out of fear and returns exactly what he started with. The master does not commend the one who played it safe. It commends the ones who put it to work.

Investing in software is investing in people's time and expertise, directed toward a problem worth solving. The real question is not whether it is expensive. It is whether you are directing it toward something that can grow.

When Custom Software Is the Right Call

Not every problem needs custom software. That is the honest answer, and it matters.

If the problem you are trying to solve is common across your industry, a SaaS solution probably exists. Go find it. If you need an accounting system, use QuickBooks. It represents decades and millions of dollars of investment. You do not need an inferior version built from scratch. The same logic applies across most standard business functions. The market has already solved them.

Custom software earns its place when the problem is specific to your business or tied directly to your competitive advantage. When off-the-shelf tools do not talk to each other. When your operation needs a hub that connects systems and keeps data moving cleanly between them. When the expertise that lives in your best people needs to be encoded into a process that the whole team can use.

The question to ask is not "could we build something?" The question is "is this problem unique enough that no one else has solved it yet?"

Where to Start

If you have looked at the SaaS options and nothing fits, the next step is not to start building. It is to start with a conversation about what you are doing today.

Every software project begins with clarity about what success looks like. What is the process? Where does it break down? What would it look like if it worked the way it should? Those questions are worth answering before any code gets written.

All software starts as a spreadsheet. Or today, it starts as a prototype built with an AI tool. Either way, the thinking has to come before the building. That is where we come in. The goal in those early conversations is not to sell you on a solution. It is to understand your business well enough to navigate the decision together, and if custom software is not the right next step, to point you somewhere better.

Start With a Conversation

Are you spending more time working around your tools than working with them? Is there a process in your business that you know should run better, but nothing off the shelf quite fits?

That is where the conversation starts. When you schedule a conversation, you will speak with Caleb or a member of the leadership team. The goal is to listen and give honest advice about what makes sense next. Sometimes that leads to a project. Sometimes it leads somewhere else entirely.