The information advantage of operators

The information advantage of operators

Public markets are extraordinarily good at pricing information that has been published. Earnings, filings, analyst notes and news are absorbed within minutes. What markets cannot price is information that has not been written down anywhere: which vendor a large company just standardised on, which product its engineers refuse to give up, which startup its procurement team is quietly negotiating with.

That information lives with operators. It is the most durable edge left in private investing, and it is the one CrossWork is organised around.

What operators know that investors do not

A former chief technology officer, head of revenue or chief financial officer carries a specific kind of knowledge. It is not a view on valuations. It is a working map of how technology is actually bought and used.

They know what gets renewed. Pilots are easy to sell. Renewals are the truth. An operator who has sat through budget reviews knows which tools survived and which were cut, and why.

They know what engineers adopt without being told. The strongest early signal for developer and infrastructure companies is bottom-up usage inside large organisations, long before a formal contract. Operators hear about it in their own teams and their peers' teams.

They know where the bottleneck is. Every technology wave hits a constraint: compute, data, security, compliance. People who have run systems at scale tend to see the constraint before it shows up in market commentary.

They know the people. Operators have hired, managed and worked alongside the engineers and executives who go on to found and run companies. A reference from someone who has seen a founder under pressure is worth more than any amount of desk research.

Why this gap persists

One might expect this edge to be competed away. It has not been, for structural reasons.

Private companies disclose little. Their revenue, retention and customer lists are not public, and the headline valuation of a funding round tells an outsider almost nothing about product pull. Companies are also staying private for far longer than they used to; the median age at IPO has roughly doubled since 1980 (Ritter, University of Florida, 2025). That extends the period in which the only reliable information is informal.

At the same time, the volume of capital chasing visible AI companies has grown enormously. Anthropic alone raised tens of billions of dollars across successive rounds in 2026 (Crunchbase News, 2026-02; TechCrunch, 2026-05-28). When capital crowds into what is visible, the relative value of seeing what is not visible increases.

How operator insight shows up in practice

Two examples from our own history illustrate the pattern without needing to discuss results.

With Cerebras, which we backed in 2023, the insight that mattered was an infrastructure operator's view that memory bandwidth and inference speed, not training alone, would become the binding constraint on AI deployment. That was not the consensus framing at the time. Cerebras went public in May 2026 in what CNBC called the largest US tech IPO since Uber (CNBC, 2026-05-13).

With AuditBoard, held in Midas I, the relevant knowledge came from finance and audit leaders who knew which tools their teams depended on. AuditBoard had raised relatively little venture capital and attracted little attention, yet by 2024 it served nearly half the Fortune 500 (Crunchbase News, 2024-05-23). Hg acquired it for more than $3 billion in what Crunchbase ranked as the year's largest VC-backed M&A exit (Crunchbase News, 2024-05-23).

In neither case did operators predict an outcome. They identified a product that customers valued more than the market realised.

How CrossWork sources

CrossWork's deal flow runs through an advisory board of former operators drawn from technology, finance and enterprise software. Their role is threefold.

Origination. Advisors surface companies they encounter as buyers, users, board members or former colleagues, often before a formal round is being marketed.

Diligence. When we evaluate an opportunity, we ask advisors with relevant experience the questions a buyer would ask. Would you renew? What would it take to replace this? What does the team do when something breaks?

Access. Many of the best late-stage allocations and secondary blocks are relationship-driven. Advisors' networks with founders, early employees and existing investors open doors that a cold approach does not.

Access to CrossWork is itself invitation-only, for the same reason. The model depends on trust and discretion on both sides, and it does not scale by broadcasting.

The limits of the edge

Operator insight is powerful, and it is not infallible. Operators can be anchored on how things worked in their era. Their networks are concentrated in certain sectors and geographies. And a strong product does not by itself make a good investment if the entry price already assumes success. We treat advisors as a source of evidence, not a source of conclusions, and we weigh their views against valuation, structure and downside.

Why it matters now

The companies that will define the late 2020s are private today, and most of what matters about them is not written down. Investors who rely on published information will meet those companies when they list, at prices that reflect years of private compounding. Investors with access to operator insight have a chance to meet them earlier.

CrossWork Midas II is our current vehicle for applying that edge. Holdings across our funds include Stripe, Perplexity, Neo4j, SambaNova, DataRobot and Scale AI.

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Sources

• Jay R. Ritter, "Initial Public Offerings: Median Age of IPOs Through 2025," University of Florida (2025).
• Crunchbase News, "Anthropic raises $30B at $380B valuation" (2026-02).
• TechCrunch, "Anthropic raises $65 billion, nears $1T valuation ahead of IPO" (2026-05-28).
• CNBC, "Cerebras prices IPO above expected range" (2026-05-13).
• Crunchbase News, "An auditing startup produced 2024's biggest VC-backed M&A exit" (2024-05-23).

Past performance is not indicative of future results. This is not an offer; offering documents govern. Detailed performance is available to verified investors in the CrossWork portal. This is not investment advice.