---
title: "Bentley Systems director Raymond Bentley filed to sell $67.5 million of stock before the November 5 print"
description: "Raymond B. Bentley, a director and 10% owner and one of the founding brothers, filed to sell 1.5 million Class B shares on October 23 and had already sold $6.2 million of them at about $40. Bentley Systems reports third-quarter results on November 5 with slipping margins and $1.2 billion of debt."
publisher: "The Inference"
section: "Applications"
published: 2026-11-01T15:11:02.032Z
modified: 2026-11-01T15:11:02.032Z
canonical: https://theinference.org/article/bentley-systems-director-raymond-bentley-filed-to-sell-67-5-million-of-stock-before-the-november-5-print
language: en
keywords: "Insider Trades, Earnings, Software, Infrastructure Software, SEC Filings"
---

# Bentley Systems director Raymond Bentley filed to sell $67.5 million of stock before the November 5 print

> Raymond B. Bentley, a director and 10% owner and one of the founding brothers, filed to sell 1.5 million Class B shares on October 23 and had already sold $6.2 million of them at about $40. Bentley Systems reports third-quarter results on November 5 with slipping margins and $1.2 billion of debt.

On October 23, Raymond B [1]. Bentley, a director and 10% owner of [Bentley Systems](https://theinference.org/markets/companies/bentley-systems) (Nasdaq: BSY), [filed a Form 144 with the SEC](https://www.stocktitan.net/sec-filings/BSY/144-bentley-systems-inc-sec-filing-628534f405c3.html) proposing to sell 1,500,000 Class B shares for an aggregate $67.5 million, $45.00 a share on the filing's own arithmetic, through Charles Schwab [1]. [His Form 4, filed three days later](https://www.sec.gov/Archives/edgar/data/1031308/000110465926119159/0001104659-26-119159-index.htm), showed the program already running: 16,662 shares sold at $40.0009 on October 23 and 139,135 at $40.0544 on October 26, roughly $6.2 million in total, leaving him 14,660,607 shares [2]. [The stock traded near $39.43](https://kalkine.com.au/news/technology/when-bentley-systems-nasdaqbsy-reports-on-5-november-which-infrastructure-software-metrics-will-matter) on October 28 [3].

The seller sits on the founder side. The Form 144 lists the shares as compensation shares acquired from the issuer on May 1, 2018 [1]. [Wikipedia's infobox names](https://en.wikipedia.org/wiki/Bentley_Systems) Keith A., Barry J. and [Raymond B. Bentley](https://theinference.org/markets/people/raymond-b-bentley) as the company's founders, though its history section says Keith and Barry founded it in 1984 and that brothers Greg, Scott and Ray joined later [4].

Forbes data as of October 19, 2026, [values Keith at $2.0 billion](https://vista.today/2026/11/chester-county-billionaires-2026/), Barry at $1.7 billion and Gregory at $1.5 billion; Raymond does not appear on Chester County's four-name billionaire list [5].

## The company is buying back shares faster than it frees up cash

In the first half of 2026, Bentley Systems repurchased $125.1 million of its own Class B stock, two and a half times the $50.0 million of a year earlier, while free cash flow fell to $251.7 million from $273.4 million [3]. Cash stood at $147.0 million against $1,210.3 million of long-term debt, 1.9 times net leverage, and convertible notes mature in mid-2027 [3]. One founder-side holder is selling $67.5 million of the same Class B shares the company spent the first half bidding for [1][3].

*Chart: **Buybacks ran at two and a half times the year-earlier pace as free cash flow fell** Column chart comparing Bentley Systems' Class B stock buybacks and free cash flow in the first half of 2025 and the first half of 2026.*

*Bentley Systems share repurchases and free cash flow in the first half of 2025 and the first half of 2026, in millions of dollars. Compiled from Bentley Systems' SEC filings. [3]*

## Growth holds, margins slip, and the AI line still has no number

[Second-quarter revenue was $410.7 million](https://www.sec.gov/cgi-bin/browse-edgar?action=getcompany&CIK=0001031308), up 12.8%, with annual recurring revenue at $1,536.0 million against $1,379.2 million a year earlier and dollar-based net retention flat at 109% [3]. Operating margin slipped to 21.6% from 23.2% [7]. Eight quarters of filings show the shape: double-digit revenue growth, margins peaking in the first quarter and settling lower through the year [7].

*Chart: **Revenue growth holds near 12% while operating margin slips year on year** Line chart of Bentley Systems quarterly revenue growth year on year and GAAP operating margin, Q3 2024 through Q2 2026.*

*Bentley Systems total revenue growth year on year and GAAP operating margin as a share of revenue, in percent, quarterly, Q3 2024 through Q2 2026. First quarters carry seasonal margin peaks. Compiled from SEC filings. [7]*

Chief executive [Nicholas Cumins](https://theinference.org/markets/people/nicholas-cumins) says customers already use Bentley's infrastructure AI on live projects and the company plans to monetize that value over time, with no figure attached [3]. Mach9, an AI drafting startup that [raised a $34 million Series A](https://theailandscape.com/news/mach9-raises-34m-series-a-ai-cad/) in October, claims manual drafting in legacy tools from [Autodesk](https://theinference.org/markets/companies/autodesk) and Bentley Systems takes about a week per mile [6].

## The trading plan explains the timing, not the size

Both filings point to a Rule 10b5-1 plan adopted on March 12, 2026, well before this quarter [1][2]. A scheduled program is the standard defense against trading on inside information, and the proposed 1.5 million shares are about a tenth of his stake and half a percent of the 290,577,762 shares outstanding [1]. The filings still leave a spread: $45.00 filed, $40.05 taken [1][2].

## What November 5 decides

[Consensus expects $419.8 million of revenue, up 11.8%, and EPS of $0.34, up 25.9%](https://uk.finance.yahoo.com/news/bentley-systems-incorporated-bsy-reports-130014929.html), with the surprise model leaning negative [8]. Four readings settle the November argument: recurring revenue growth against 12% in constant currency, net retention against 109%, operating margin against the slide, and whether infrastructure AI finally carries a number [3].

The convertibles due mid-2027 put a refinancing clock on any of it [3]. Results land on November 5 [1][2]. The founder keeps ten shares for every one he is selling [1][2], and his own filings set the price to beat: $40.

## Takeaway

Raymond B. Bentley, a director, 10% owner and founding brother, filed on October 23 to sell 1.5 million Class B shares, $67.5 million at $45.00, and his Form 4 shows $6.2 million already gone at about $40, a level the stock traded below into the November 5 print. The sale runs on a Rule 10b5-1 plan from March 12, so the timing says nothing about inside information, but the size is a founder cashing out while the company he helped start spent the first half buying back the same Class B shares with falling free cash flow and $1.2 billion of debt against $147 million of cash. What settles November 5 is the print: recurring growth against 12%, retention against 109%, operating margin against the slide, and whether infrastructure AI finally carries a number.

## Sources

1. [Stock Titan, Bentley Systems director proposes $67.5M share sale, SEC Form 144 accepted 23 October 2026](https://www.stocktitan.net/sec-filings/BSY/144-bentley-systems-inc-sec-filing-628534f405c3.html)
2. [SEC EDGAR, Form 4, Bentley Raymond B., Bentley Systems Inc., filed 27 October 2026](https://www.sec.gov/Archives/edgar/data/1031308/000110465926119159/0001104659-26-119159-index.htm)
3. [Kalkine, When Bentley Systems (NASDAQ:BSY) reports on 5 November, which infrastructure software metrics will matter?, 28 October 2026](https://kalkine.com.au/news/technology/when-bentley-systems-nasdaqbsy-reports-on-5-november-which-infrastructure-software-metrics-will-matter)
4. [Wikipedia, Bentley Systems, edited 6 October 2026](https://en.wikipedia.org/wiki/Bentley_Systems)
5. [VISTA Today, Who Are Chester County's Richest Residents? 4 Billionaires Make the List, 1 November 2026](https://vista.today/2026/11/chester-county-billionaires-2026/)
6. [The AI Landscape, Mach9 Raises $34M Series A for AI CAD Software for Civil Engineering, October 2026](https://theailandscape.com/news/mach9-raises-34m-series-a-ai-cad/)
7. [Bentley Systems, quarterly figures from its SEC filings, retrieved 1 November 2026](https://www.sec.gov/cgi-bin/browse-edgar?action=getcompany&CIK=0001031308)
8. [Zacks Equity Research via Yahoo Finance UK, Bentley Systems, Incorporated (BSY) Reports Next Week: Wall Street Expects Earnings Growth, 29 October 2026](https://uk.finance.yahoo.com/news/bentley-systems-incorporated-bsy-reports-130014929.html)


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Bentley Systems director Raymond Bentley filed to sell $67.5 million of stock before the November 5 print — The Inference. Canonical: https://theinference.org/article/bentley-systems-director-raymond-bentley-filed-to-sell-67-5-million-of-stock-before-the-november-5-print