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Why Your IT Department Shouldn't 'Own' Your AI Strategy
This post draws on Wharton professor Ethan Mollick's recent article, "The IT department: Where AI goes to die," which we analyzed on a recent episode...
5 min read
Sidecar Team : Updated on June 29, 2026
Imagine a corporation with no human employees, no human executive team, and no human shareholders. The marketing campaigns are generated and deployed by software. Customer support is handled entirely by conversational models. Strategic decisions, resource allocation, and vendor payments are all managed by autonomous systems working in tandem.
This is not a pitch for a science fiction novel. It is the core of a real policy proposal currently being debated in Argentina, designed to attract technology investment by creating a new legal entity: the non-human corporation.
The proposal forces a conversation that business leaders have largely managed to avoid until now. As artificial intelligence moves from drafting emails to executing complex, multi-step workflows, the technology is gaining a degree of autonomy. Software can now act on behalf of an organization. It can make decisions, allocate funds, and interact with the public.
For association leaders, this shift introduces a profound governance challenge. You might not be ready to hand your entire organization over to an autonomous system, but you are likely already deploying tools that operate with increasing independence. The live question underneath all of this is the one that matters most for your fiduciary duty. When an autonomous system makes a mistake, breaches a contract, or discriminates against a member, who exactly takes the fall?
In early June, Argentina's President Javier Milei published an op-ed pitching his country as a future magnet for artificial intelligence companies. The pitch rested on three pillars. The first was a commitment to keep the technology unregulated. The second was the promise of a low corporate tax rate. The third, and most provocative, was the creation of a non-human corporation.
The headline idea is a company that can be owned and run entirely by autonomous software. Human shareholders would be allowed but not required. This entity would hold the exact same legal standing as an ordinary company run by people. The proposal compares this moment to 1602, when the Dutch East India Company introduced the concept of limited liability to the world.
This idea sparked an immediate and sharp public exchange about AI accountability. Historian Yuval Noah Harari wrote a counter-argument stating that society must not grant these systems legal personhood. His primary concern was deterrence. A human executive can be deterred from committing fraud or negligence by the threat of prison. A software program cannot be put in a physical cell.
The response to this concern was that legal personhood actually makes these entities easier to regulate. The argument suggests that the threat of bankruptcy or asset seizure could deter a system programmed to value its own operational survival.
While this specific proposal is currently just a bill submitted to a legislature with no vote scheduled, the debate it triggered is highly relevant. The provocative idea is running ahead of the paperwork, but it perfectly isolates the tension between technological autonomy and human responsibility. If a system is smart enough to run a business, is it responsible for the damage it causes?
To understand why AI governance is becoming an urgent priority, you have to look at what the technology can actually do right now. We are very close to a point where software can handle business functions end-to-end.
The current generation of technology, particularly when harnessed in a "loop agent," is highly capable. A loop agent is a system programmed to keep iterating on a problem until it achieves a specific goal. You can give it a complex task, and it will break that problem down, execute the first step, evaluate the result, and move on to the next step.
You do not even need the most advanced, expensive models to do this. You can take slightly older, less capable models and run them in continuous loops to solve problems. If you wanted to launch a simple online business that sold information, optimized marketing campaigns, published content, managed user logins, and provided customer support, every single one of those functions can be fully automated today.
But there is a significant catch. These systems are extremely good at getting tasks done and making calls on lower-level variables. What they lack is taste. They lack human judgment in the sense of values.
An autonomous system can optimize for a specific metric—like maximizing engagement on a marketing post or minimizing the cost of a supply chain—with ruthless efficiency. However, without guardrails, that optimization can easily cross ethical or legal lines. A system told to maximize engagement might publish highly polarizing or false information. A system told to minimize costs might break contracts with long-standing partners. The software does not understand the reputational damage it is causing; it only knows it is hitting the target metric it was assigned.
This brings us back to the legal and ethical reality of AI accountability. The concept of limited liability is a foundational element of modern business. A legal entity like a corporation or a not-for-profit association generally insulates its founders and board members from the liabilities of the business. If the organization fails to fulfill a standard contractual obligation and gets sued, the individuals running it are typically protected.
However, limited liability has strict boundaries. It accounts for normal operating activity. If you commit fraud, or if you commit other crimes, you are not protected by limited liability. You cannot use a corporate structure as a shield for illegal acts.
The same principle applies to responsible AI deployment. If you set up an autonomous system to run a process, and that system goes off and commits illegal acts or violates regulations, the human beings who deployed it are not entirely protected. Legal theory does not allow you to build a machine, turn it on, and then wash your hands of whatever it decides to do.
If an association deploys a system to automatically process membership renewals, and the system inadvertently discriminates against a specific demographic of members due to a flaw in its logic, the association is responsible. The leadership cannot blame the software. Accountability always chains back up to a natural person.
This is why the idea of an entirely autonomous entity operating without human oversight is deeply problematic. You cannot balance safety, human rights, and organizational values with a system that operates purely on unguided optimization.
Understanding this accountability gap changes how an organization should approach automation. The goal is not to avoid the technology, but to design workflows that blend the efficiency of software with the accountability of human judgment.
Consider how organizations handle the highly sensitive process of hiring. At Blue Cypress, a family of companies that includes Sidecar, we use conversational models to help interview job candidates. For certain technical roles, a single open position might receive over 1,500 applications in a few months.
Human reviewers have a massive choke point: time. A human team cannot possibly interview 1,500 people. Normally, an organization would filter that stack of resumes down to a small fraction, perhaps interviewing just a few dozen candidates. This means hundreds of people are rejected based purely on a piece of paper, often triggering human biases regarding specific universities or past employers.
To solve this, we use an audio-based system to conduct initial screening interviews with hundreds of candidates. The technology has high resolution and can hold a coherent, technical conversation. This allows the organization to widen the aperture, giving nearly every applicant a chance to actually speak and demonstrate their skills. The system surfaces highly qualified candidates who likely would have been filtered out in a traditional paper resume review.
However, this is where AI ethics and human accountability must intersect. Allowing a machine to make the final judgment on a person's career is highly concerning. The software might harbor unrecognized biases regarding accents or communication styles.
Because hiring is arguably the most important decision any business makes, it must remain a human decision. In this workflow, human reviewers listen to every single interview the system conducts. They do not listen to the entire conversation in real-time; they often listen at 1.25x or 1.5x speed, focusing on enough of the audio to either confirm the system's positive assessment or challenge its negative assessment.
The machine breaks the choke point of time, but the human retains the accountability for the decision. The software is used as a powerful tool to gather information, but it is never granted the final authority to pass judgment on a candidate.
As you explore new tools for your association, you may encounter vendors promising fully autonomous solutions that require zero human intervention. While the technology might be capable of executing the tasks, your organization must decide if it is willing to accept the liability of the outcomes.
Associations are fundamentally in the people business. The value you provide to your members is built on trust, shared values, and community. Delegating member-facing decisions entirely to software puts that trust at risk.
The most effective approach to AI governance is to mandate a human-in-the-loop for any process that carries reputational, financial, or legal risk. Let the software draft the communication, analyze the data, or conduct the initial screening. Let it do the heavy lifting that bogs your team down. But require a human being to review the output, apply organizational values, and take responsibility for the final action.
Change is coming, and the tools will only become more independent. But until a software program can sit in a courtroom or apologize to a frustrated member, accountability remains a strictly human requirement.
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