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.
Vincent Jiang · 3 min read
On October 23, Raymond B 1. Bentley, a director and 10% owner of Bentley Systems+3.14% — Bentley Systems, up 3.14 percent today (Nasdaq: BSY), filed a Form 144 with the SEC 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, 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 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 Keith A., Barry J. and 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, 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 13.
Buybacks ran at two and a half times the year-earlier pace as free cash flow fell
- Share repurchases
- Free cash flow
Data
| Share repurchases | Free cash flow | |
|---|---|---|
| H1 2025 | $50M | $273.4M |
| H1 2026 | $125.1M | $251.7M |
Growth holds, margins slip, and the AI line still has no number
Second-quarter revenue was $410.7 million, 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.
Revenue growth holds near 12% while operating margin slips year on year
- Revenue growth, year on year
- Operating margin
Data
| Revenue growth, year on year | Operating margin | |
|---|---|---|
| Q3 '24 | 9.3% | 20.5% |
| Q4 '24 | 12.6% | 17.6% |
| Q1 '25 | 9.7% | 31.1% |
| Q2 '25 | 10.2% | 23.2% |
| Q3 '25 | 12% | 22.5% |
| Q4 '25 | 11.9% | 20% |
| Q1 '26 | 14.5% | 29.8% |
| Q2 '26 | 12.8% | 21.6% |
Chief executive 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 in October, claims manual drafting in legacy tools from Autodesk+3.26% — Autodesk, up 3.26 percent today 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 12. 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 12.
What November 5 decides
Consensus expects $419.8 million of revenue, up 11.8%, and EPS of $0.34, up 25.9%, 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 12. The founder keeps ten shares for every one he is selling 12, and his own filings set the price to beat: $40.
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