Why We Invested in Pairwise

Opinion Pieces
November 9, 2026

Why We Invested in Pairwise

When we look at AI companies selling to finance teams, we ask three questions. Pairwise had strong answers to all of them.

1. Does it solve a problem finance leaders actually feel?

Yes. Board and investor reporting is one of the highest-stakes things a finance team produces, and it's still surprisingly manual. Numbers get copied out of accounting systems, explanations get written in slide decks, and months later it's hard to say exactly where a figure came from or who signed off on it.

Pairwise reads the exports a company already produces, from QuickBooks and NetSuite to profit and loss, general ledger and bank files, so numbers aren't retyped by hand. AI drafts the explanation behind each figure, and a person approves it before it goes anywhere.

2. Would a CFO trust it?

This is where most AI tools for finance fall short, and where Pairwise is strongest. Every number traces back to its source. Nothing enters the board narrative until it's approved, and each approval is recorded with the owner's role and the date. The AI suggests; the finance team decides, and there's a record of both.

For a CFO, that's the difference between a tool that saves time and one that creates risk.

3. Does it get more valuable over time?

We think so. Founder Krystal Briggs puts it simply: anyone can copy the language model, but no one can copy a company's decision history. Every approved number and explanation becomes part of an institutional memory of how and why the business made its calls. The longer a team uses Pairwise, the harder it is to replace.

What comes next

Pairwise is early. The next steps are winning its first finance teams, adding direct connections to the tools on its roadmap, including HubSpot, Ramp, Stripe, Snowflake and Salesforce, and proving that auditable AI can become the standard for board reporting.

Welcome to the portfolio, Pairwise.

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