At a recent discussion, someone offered a wonderfully practical way to think about building software: If you want deep-dish pizza, why would you buy the restaurant?
I immediately thought about enterprise technology meetings.
Someone wants a faster way to review contracts. Someone else builds an impressive prototype. Within weeks, the company is discussing hiring engineers, connecting databases, and maintaining its own application.
Dinner now comes with payroll.
The “SaaS apocalypse” conversation gives this temptation fresh energy. If AI can help us create software, why keep paying somebody else for it? As a builder, I understand the appeal. A working prototype feels like possibility. A renewal invoice rarely produces the same emotional response.
Legal leaders should help the business think through what happens after that first burst of enthusiasm. Each technology decision creates an ongoing obligation to maintain something, depend on someone, or coordinate several moving parts.
Here is how I would approach the conversation.
Build: Who Will Own Tuesday Morning?
Building can make excellent sense when a company has distinctive expertise, data, or a workflow that creates meaningful business advantage.
The harder question concerns an ordinary Tuesday six months after launch. The system produces a questionable answer. An integration breaks. The person who wrote the prompts has moved to another team.
Who owns that Tuesday?
Before approving a build, I want to know which capability deserves the investment, who will maintain it, and how the organization will preserve the judgment embedded in it. I also want a budget that includes testing, security, documentation, support, and the inevitable changes.
The prototype proves something can work. The operating plan explains how the company intends to live with it.
Buy: What Are We Paying to Make Better?
A commercial product brings somebody else’s accumulated investment into the business. That can include specialized data, evaluation methods, integrations, support, and experience with problems the buyer has yet to encounter.
Those are worth examining closely when evaluating the price.
The discussion around value pricing raises a useful question for legal teams: What improvement will this purchase actually produce?
Consider a vendor promising to save lawyers 10 hours a week. Those hours might allow faster responses, more work handled internally, or greater attention to difficult matters. Turning them into a cash savings claim requires additional evidence.
An outcome-based fee introduces another layer. If payment depends on faster contract completion, the parties need to agree when the clock starts, how delays are treated, and whether quality remained acceptable. A system that closes matters quickly by routing every difficult issue elsewhere could look excellent on the wrong dashboard.
Legal can make the commercial promise measurable before it becomes a billing dispute.
Integrate: Follow One Decision Through The Systems
Often, the business already has much of what it needs. The opportunity lies in connecting existing tools with specialized intelligence and the company’s own knowledge.
Take a supplier review. One system holds the agreement. Another supplies benchmarks. An AI tool recommends an escalation. A procurement platform records the decision.
Walk through that sequence with the people responsible for it. Which source controls when the systems disagree? Who may act on the recommendation? Where is the correction recorded? What happens if one provider becomes unavailable?
Integration can preserve flexibility. It also creates dependencies that deserve an owner.
Legal leaders are well placed to trace those dependencies because we spend our careers asking what happens when an apparently straightforward arrangement gets complicated.
Wait: Put A Date On The Decision
Waiting deserves a place in the framework.
Perhaps the company has poorly organized data, an unresolved workflow, or too little evidence that anyone will use the proposed tool. Buying software under those conditions can add an expensive new layer to an existing problem.
A useful decision to wait includes a trigger for reconsideration. Complete the data cleanup. Test a defined workflow. Revisit the options after a limited trial.
Give someone responsibility for gathering the missing evidence and set a review date.
Bring Legal Into The Ownership Conversation
By the time a vendor agreement reaches legal, the company may already have made its most consequential choices about data, authority, cost, and dependence.
We should help shape those choices earlier. Ask what the business needs to own, what it can entrust to a provider, and what it can realistically maintain.
Before the company buys the restaurant, somebody should know who is opening it tomorrow.
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics. She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.
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