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How AI-ready is your portfolio?
Every founder now has an AI story. Here is how investors can test which stories hold up, and where portfolio support will make the biggest difference.
By Kesho Partners
9 minute read
An AI-ready portfolio company can show three things: AI makes its product meaningfully better, AI makes the business cheaper or faster to run, and it owns something, usually data or workflow position, that competitors cannot easily copy. Investors should also check a fourth point: that what the company says about AI is true. US regulators have already fined firms for overstating AI capabilities. Assess every company on the same four questions, then direct support to the companies with the most value at stake and the biggest gaps.
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Why portfolio AI readiness matters now
Almost every company now uses AI somewhere. In McKinsey's 2026 survey, nearly nine in ten respondents said their organization uses AI regularly, but only 37% reported any effect on operating profit. Using AI and benefiting from it are different things.
For investors, that gap cuts both ways. Companies that turn AI into better products or leaner operations can pull ahead quickly. Companies whose product can now be rebuilt cheaply with AI may find their position weaker than their last valuation suggests. Our article "Is software IP dead in the age of AI?" looks at that second risk in detail.
A consistent, company-by-company view lets a fund or accelerator see both at once, and decide where time and capital will do the most good.
Survey figures are self-reported by respondents and describe their organizations' experience, not audited financial results.
Sources: [1]
Four questions for every portfolio company
These questions are deliberately simple. A founder should be able to answer each one in a few minutes, with evidence. If they cannot, that is itself a finding.
- Product advantage
- Does AI make the product meaningfully better for customers, in a way they would notice if it were removed? Ask for usage and retention evidence, not demos.
- Operational leverage
- Does AI let the company serve more customers, ship faster, or run with a leaner team? Ask which costs or timelines have actually changed.
- Data defensibility
- Does the company own data, customer relationships, or a position in the workflow that a competitor with the same AI tools could not easily copy?
- Claim integrity
- Is everything the company says about AI, in pitch decks, sales material, and its website, accurate and supported by evidence?
Product advantage and operational leverage
The strongest companies use AI on both sides: to improve what customers buy and to change how the business runs. BCG found the companies getting real value from AI focus on fewer opportunities, scale more of them, and get most of their value from core business functions rather than side projects.
McKinsey's 2026 data shows the same pattern. AI high performers are about three times as likely to have fundamentally redesigned workflows, and about twice as likely to have leaders who visibly support the work and a defined way to measure impact.
For a portfolio company, a simple test is whether AI shows up in the metrics the board already reviews, such as gross margin, sales cycle, support cost per customer, or release frequency. If AI is only visible in the product roadmap, it is still a plan.
Data defensibility: what cannot be copied
When anyone can access powerful AI models, the model is rarely the advantage. What matters is what the company feeds it and where it sits in the customer's work. Proprietary data, feedback that improves the product with use, and deep integration into customer workflows are all harder to replicate than features.
Investors should test data claims rather than accept them. Where did the data come from? Does the company have the right to use it this way? Does more customer usage actually make the product better? Our article "AI due diligence starts with the data" sets out how to trace those claims back to evidence.
| Claim | Ask for | Warning sign |
|---|---|---|
| Our data is proprietary | Where it came from and the contracts that allow its use | The same data is publicly available or rights are unclear |
| The product improves with use | Evidence that feedback is captured and measurably improves results | Usage data is collected but never used |
| Customers depend on us | Integration depth, switching costs, and retention | Customers could replace the product with a general AI tool |
The risk of overstating AI
Pressure to look like an AI company is real, and some companies give in to it. Regulators have noticed. In March 2024 the US Securities and Exchange Commission settled charges against two investment advisers, Delphia and Global Predictions, for making false and misleading statements about their use of AI. They paid $400,000 in total. The SEC called this "AI washing" and said it hurts investors.
In September 2024 the US Federal Trade Commission announced five actions against companies using AI claims to mislead customers. One, DoNotPay, marketed itself as the "world's first robot lawyer" but had not tested whether its output matched the quality of a human lawyer. It agreed to pay $193,000. The FTC's chair said there is no AI exemption from the laws on the books.
For a fund, overstated AI claims are a valuation risk, a legal risk, and a reputational risk. Checking that a company's AI story matches what it has actually built protects both the company and its investors.
- Compare the pitch with the product
- Ask the team to show where AI runs in the product and what it does, using real customer data.
- Check the language
- Words like "first", "fully automated", or "replaces" need evidence behind them.
- Ask how it was tested
- Strong AI claims should be backed by testing against a clear standard, not a handful of examples.
Triage: which companies need support first
Once each company is assessed on the same four questions, sort them by two things: how much value AI could create or destroy for that business, and how ready the company is to act. This turns a long list of companies into a short, prioritised support plan.
| Segment | Profile | Recommended support |
|---|---|---|
| Accelerate | High AI opportunity and strong readiness | Help scale what works and protect the advantage, including data rights and governance |
| Fix first | High AI opportunity but weak data, skills, or delivery | Priority hands-on support to close the specific gap blocking progress |
| Defend | Product could be copied cheaply with AI | Rethink positioning around data, workflow, and customer relationships |
| Verify | Strong AI claims with limited evidence | Independent technical review before the next raise or major customer deal |
| Monitor | Low AI exposure either way | Light-touch check at each board cycle |
How to run a portfolio review
Keep it light and consistent. A short questionnaire for founders, followed by a one-hour conversation with the technical lead, is usually enough to place a company in a segment. Deeper technical review can then be focused on the companies where it matters.
Use a shared vocabulary for risk so findings can be compared across companies. The NIST AI Risk Management Framework is a useful, widely recognised reference. For companies preparing to raise or sell, our AI technical due diligence scorecard sets out what a serious buyer or investor will test.
To check readiness inside each company in more depth, use our AI readiness assessment framework. It scores six areas, from strategy to the capacity to deliver change, and works for start-ups as well as larger businesses.
Sources: [5]
What good looks like
At the end of a review, a fund or accelerator should have a readiness baseline for every company, a clear view of which companies are exposed and which are positioned to win, and a prioritised plan for founder support. Repeat it each year, and before major fundraising rounds.
The goal is not to make every company an AI company. It is to make sure every company has an honest answer to how AI changes its market, and that the portfolio's support goes where it will make the biggest difference.
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