---
title: "Bentley Systems co-founder sold $13.9 million of stock at $40.24, five days before the market paid $47.71"
description: "Bentley Systems beat the quarter, raised its ARR outlook and rallied 9.33 percent in a falling Nasdaq. The filings underneath show September-quarter cash flow down year over year and a founder's sale executed at $40.24 before the pop."
publisher: "The Inference"
section: "Platforms"
published: 2026-11-06T15:30:31.423Z
modified: 2026-11-06T15:30:31.423Z
canonical: https://theinference.org/article/bentley-systems-co-founder-sold-13-9-million-of-stock-at-40-24-five-days-before-the-market-paid-47-71
language: en
keywords: "Bentley Systems, Insider Trades, Earnings, Infrastructure Software, Stock Moves"
---

# Bentley Systems co-founder sold $13.9 million of stock at $40.24, five days before the market paid $47.71

> Bentley Systems beat the quarter, raised its ARR outlook and rallied 9.33 percent in a falling Nasdaq. The filings underneath show September-quarter cash flow down year over year and a founder's sale executed at $40.24 before the pop.

## A founder sold at $40.24 on October 30. Five days later the market paid $47.71.

[Raymond B. Bentley](https://theinference.org/markets/people/raymond-b-bentley), one of the founding Bentley brothers of the Exton, Pennsylvania infrastructure software company, [sold 344,203 Class B shares on October 30 at a weighted average of $40.24](https://www.sec.gov/Archives/edgar/data/1031308/000110465926122004/tm2628336-3_4seq1.xml), leaving 14,316,404 shares in his name, about 4.6 percent of the company's 310.5 million weighted basic shares outstanding [1][2]. The trades ran under a Rule 10b5-1 plan adopted on March 12, 2026, the first slice of [a notice to sell 1.5 million shares](https://www.sec.gov/Archives/edgar/data/1031308/000194984626000619/primary_doc.xml), roughly $67.5 million, filed with the SEC on October 23 [3]. An Inference report on November 1 covered the notice [3]. The quarter arrived five days after the trades cleared.

## The beat that earned the premium

[Bentley Systems](https://theinference.org/markets/companies/bentley-systems) [reported third-quarter revenue of $421.5 million](https://www.stocktitan.net/sec-filings/BSY/8-k-bentley-systems-inc-reports-material-event-dbdb88482f52.html), up 12.2 percent, adjusted EPS of $0.36 against a $0.33 consensus, and constant-currency ARR growth of 13 percent, above its own annual outlook, on a record 110 percent net revenue retention [4][5][6]. Revenue was only in line: one tracker pegged the estimate at $420.6 million, another at $424.8 million [6][7].

Management raised the full-year ARR growth outlook to 12.5-13.5 percent from 10.5-12.5 percent, excluding the Cohesive divestiture [4][5]. The market paid against the tape: with [the Nasdaq down 5.52 percent in its worst session in 18 months](https://www.fool.com/coverage/stock-market-today/2026/11/05/stock-market-today-nov-5-nasdaq-suffers-worst-day-in-18-months-as-ai-trade-comes-under-fire/), [BSY rose 9.33 percent to $47.71](https://weissratings.com/en/instant-news-alerts/bentley-systems-incorporated-bsy-up-9-3-do-i-ride-the-momentum), 6.1 percent under its 52-week high of $50.80, at a forward P/E of 46.43 [6][8].

*Chart: **The co-founder sold at $40.24 on October 30; the close on November 5 was $47.71** Bar chart comparing the $40.24 weighted-average price of co-founder Raymond Bentley's October 30 share sales with the $47.71 close on November 5 and the $50.80 52-week high.*

*US dollars per Class B share. Sale price is the weighted average of multiple trades on October 30 reported on SEC Form 4, filed November 3, 2026. Close and 52-week high from Weiss Ratings market data, November 6, 2026. [1][6]*

## The filing underneath: cash down, AI money narrow

[Cash from operations was $109.4 million against $116.4 million a year ago](https://www.tradingkey.com/news/transcripts/262283452-), free cash flow was $101.4 million against $110.7 million, and year-to-date free cash flow of $353.1 million is down 8 percent [4][5]. On the earnings call, management located the AI money precisely: Asset Analytics, AI that inspects infrastructure assets and is priced per asset per year rather than per user per day, drove about half the sequential ARR improvement [5].

AI-driven design monetization starts in 2027 and will not be a material growth driver that year [5]. Machine-speed use of engineering tools will require pricing beyond per-user models, so the 46-times multiple leans partly on pricing not yet built [5].

*Chart: **September-quarter cash generation fell year over year as revenue accelerated** Column chart of Bentley Systems operating cash flow and free cash flow for the September quarters of 2024, 2025 and 2026, both declining in 2026.*

*Cash flows from operating activities and free cash flow for the September quarters, in US$ millions, from Bentley Systems SEC filings (quarterly series retrieved November 6, 2026) and the third-quarter 2026 8-K furnished November 5, 2026. [9][4]*

## The case for the holders

The sale is not, by itself, a verdict on the business: a 10b5-1 plan adopted in March was scheduled before the run [5]. Account retention held at 99 percent, the subscription mix rises to about 95 percent of revenue after the Cohesive divestiture, and the $500 million to $570 million free cash flow outlook remains intact on management's numbers [5]. But the notice covers 1.5 million shares and 344,203 have cleared; about 1.16 million remain available under it [3][1].

## What decides it next

The fourth quarter is the year's biggest renewal quarter, and the top of the raised ARR range requires strong renewals, large Asset Analytics contracts and about 100 basis points arriving from the Eliis acquisition [5]. The Q4 print should show three reads: whether ARR lands at the top of 12.5-13.5 percent; whether year-end collections hold free cash flow inside the $500-570 million range; and whether the founder's remaining 1.16 million shares clear at prices nearer $47.71 than $40.24 [3][5][6].

A founder sold at $40.24 because a calendar told him to. The buyers at $47.71 are betting the calendar was wrong.

## Takeaway

A scheduled 10b5-1 sale put a Bentley co-founder out at $40.24; five days later the stock closed at $47.71 on a raised ARR outlook, even as September-quarter cash flow fell year over year. The Q4 print decides whether the premium holds.

## Sources

1. [SEC EDGAR, Form 4 for Raymond B. Bentley, Bentley Systems, transaction date 30 October 2026, filed 3 November 2026](https://www.sec.gov/Archives/edgar/data/1031308/000110465926122004/tm2628336-3_4seq1.xml)
2. [Wikipedia, Bentley Systems, retrieved 6 November 2026](https://en.wikipedia.org/wiki/Bentley_Systems)
3. [SEC EDGAR, Form 144 notice of proposed sale, Bentley Raymond B., filed 23 October 2026](https://www.sec.gov/Archives/edgar/data/1031308/000194984626000619/primary_doc.xml)
4. [StockTitan, Bentley Systems Q3 2026 results 8-K (Exhibit 99.1 press release), 5 November 2026](https://www.stocktitan.net/sec-filings/BSY/8-k-bentley-systems-inc-reports-material-event-dbdb88482f52.html)
5. [TradingKey, Bentley Systems (BSY) Q3 2026 earnings call transcript, 5 November 2026](https://www.tradingkey.com/news/transcripts/262283452-)
6. [Weiss Ratings Instant News Alert, Bentley Systems (BSY) up 9.3 percent, 6 November 2026](https://weissratings.com/en/instant-news-alerts/bentley-systems-incorporated-bsy-up-9-3-do-i-ride-the-momentum)
7. [ChartMill, Bentley Systems beats Q3 EPS estimates as recurring revenue momentum builds, November 2026](https://www.chartmill.com/news/BSY/Chartmill-57973-Bentley-Systems-NASDAQBSY-Beats-Q3-EPS-Estimates-as-Recurring-Revenue-Momentum-Builds)
8. [The Motley Fool, Stock Market Today Nov 5: Nasdaq suffers worst day in 18 months, 5 November 2026](https://www.fool.com/coverage/stock-market-today/2026/11/05/stock-market-today-nov-5-nasdaq-suffers-worst-day-in-18-months-as-ai-trade-comes-under-fire/)
9. [Bentley Systems quarterly figures from SEC filings, quarterly series retrieved 6 November 2026](https://www.sec.gov/cgi-bin/browse-edgar?action=getcompany&CIK=0001031308)


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Bentley Systems co-founder sold $13.9 million of stock at $40.24, five days before the market paid $47.71 — The Inference. Canonical: https://theinference.org/article/bentley-systems-co-founder-sold-13-9-million-of-stock-at-40-24-five-days-before-the-market-paid-47-71