Where Are The Software Insiders?

Every week for nearly 16 years, we have put together a series called Insider Weekends that includes a list of top five insider purchases and insider sales. A few years ago we also started doing a deeper dive into one of these insider purchases or sales for InsideArbitrage each Sunday.

For example, in late December we talked about an unusual insider purchase by the VC firm Andreessen Horowitz of their portfolio company Navan (NAVN) that had seen its stock drop sharply following an IPO.

Four weeks ago, we covered the former CEO of TSMC (TSM) buying shares of Micron (MU) despite a massive jump in the stock price of the high bandwidth memory manufacturer. We wrote the following about the purchase in that article: 

“The insider purchase last week that prompted us to pick Micron for this week’s Insider Weekends article was the largest purchase Micron has ever seen over the last fifteen years. Director Teyin Liu had 2,710 shares before he decided to pick up 23,200 shares at an average price of $337.14 for $7.82 million.

This is his first insider purchase of Micron since he joined the board in March 2025 and is also the first insider purchase of any kind at Micron in over eight years. The only other insider who purchased shares during the last fifteen years was Micron’s former CFO Ernest Maddock who picked up shares between 2015 and 2017 in a series of small transactions and then retired from the company in 2018.

On a related note, Ernest Maddock scores a perfect 100 in our system that ranks insiders and has generated an IRR of nearly 165% on his infrequent insider purchases of Micron (MU), Ouster (OUST), Teradyne (TER) and Ultra Clean Holdings (UCTT).”

Investors have been wondering when software company insiders will step in to buy stock in an industry that has seen most stocks decimated on concerns of disruption from AI.

Why is this important?

When an industry has seen a big decline due to external shocks, insiders have often stepped up to buy hand over fist and while they tend to be early, the subsequent outcomes have been very favorable.

Three examples from the last six years include:

1. Insiders of oil and gas companies stepping up to buy after WTI crude futures dipped into negative territory in May 2020. Harold Hamm of Continental Resources went so far as to issue a press release about his buying (normally a negative signal). He eventually bought out the whole company and provided a second opportunity to arbitrageurs through a revised higher bid.

2. Insiders of regional banks were buying like it was a carnival sale after Silicon Valley Bank failed in March 2023. We could barely keep up with the filings every night as we tend to look at each filing that meets our filters and even read the footnotes of the filings.

3. Insiders of biotech companies buying aggressively in late 2024 and early 2025. It helped us pick up companies like Avadel $AVDL, which incidentally was acquired a few months later (with bidding war drama included) and the deal closed yesterday.

I figured I would use this article and subsequent replies/edits in the coming weeks to keep track of insiders of software companies who are buying stock on the open market.

This list will include buying by management and directors but not 10% owners who have no board representation. Most of the buying thus far has been by directors and we expect to see management buying once the quiet period related to earnings ends. Some of these companies have a shifted fiscal year that ends in January instead of December and hence their insiders are still unable to buy.

List of Insider Buys in the Software Industry

Here is the list of insider buys in the software and software adjacent companies I have seen since the start of 2026 (dates are filing dates and not purchase dates):

1. GTLB: Jan 5, 2026, William Staples, the Chief Executive Officer of DevOps company Gitlab (GTLB), purchased 3,276 shares at an average price of $38.08 totaling $124,750.

2. NAVN: Jan 6, 2026, Ben Horowitz, a Director of travel and expense management software company Navan (NAVN) purchased 976,975 shares at an average price of $16.31 totaling $15.94 million. Shares were acquired indirectly through Andreessen Horowitz. They bought again on Jan 9.

3. SPT: Jan 13, 2026, Ryan Paul Barretto, the CEO of social media management company Sprout Social (SPT), purchased 93,984 shares at an average price of $10.67 totaling $1 million.

4. ACVA: Jan 13, 2026, George Chamoun, the Chief Executive Officer of online auto auction platform ACV Auctions (ACVA), purchased 14,286 shares at an average price of $8.81 totaling $125,860. He bought again on Feb 10.

5. IBM: Jan 30, 2026, David Farr, a Director of IBM (IBM), purchased 1,000 shares at an average price of $304.00 totaling $304,000.

6. AGYS: Feb 3, 2026, Melvin Keating, a Director of hospitality software company Agilysys (AGYS), purchased 600 shares at an average price of $83.96 totaling $50,379.

7. PAYX: Feb 5, 2026, Joseph Doody, a Director of human capital management company Paychex (PAYX), purchased 1,000 shares at an average price of $98.76 totaling $98,760. Director Tom Bonadio also purchased 1,000 shares at an average price of $98.50 totaling $98,498.

8. ROP: Feb 6, 2026, Thomas Patrick Joyce Jr, a Director of software company Roper Technologies (ROP), purchased 1,400 shares at an average price of $358.46 totaling $501,844.

9. TENB: Feb 9, 2026, Arthur Coviello Jr, a Director of cybersecurity company Tenable Holdings (TENB), purchased 12,000 shares at an average price of $21.50 totaling $258,000.

10. VRNS: Feb 10, 2026, Yakov Faitelson, the CEO and Chairman of data security company Varonis Systems (VRNS), purchased 26,725 shares at an average price of $22.41 totaling $598,907. Three other insiders also purchased shares, with the next largest purchase coming from Director Avrohom Kess, who purchased 17,800 shares at an average price of $22.29 totaling $396,762.

11. RDDT: Sarah E. Farrell, a Director of Reddit (RDDT), purchased 50,500 shares at an average price of $148.16 totaling $7.48 million.

Did I miss anything?

Voluntary Disclosure: I hold long positions in Micron (MU) and Navan (NAVN).

Disclaimer: Please do your own due diligence before buying or selling any securities mentioned in this article. We do not warrant the completeness or accuracy of the content or data provided in this article.