Top insider trades (Wed, Jul 1)

Author

Connor Van Ooyen
July 01, 2026

Connor’s Commentary

Tenable (TENB) is closing in on 70% returns in less than two months since we added it to the CEO Watcher Portfolio.

As I’ve mentioned numerous times, software insiders were buying a ton of software stock a couple of months ago, and we found a handful of very compelling insider purchases.

Two of those were in cybersecurity stocks (OKTA and TENB), both of which quickly returned more than +60%.

OKTA quickly returned to its median EV/Sales multiple, so it was cut for a 60% gain in just a couple of weeks. Tenable (TENB) is still trading a full standard deviation below its median EV/Sales multiple (3.8x v 5.4x).

Here was the note I shared with CEO Watcher Premium subs in the May 7th email, when Tenable was $21.77 (v $37 now).

Tenable Holdings, Inc. (TENB)

  • Insider info

    • Chief Financial  Officer purchased $258.48K

    • Purchase Price: $21.54 | Last Close: $21.02 (-2.41%)

    • First-ever purchase

    • Increased listed holdings by 64.72%

    • Dip Buy: no

    • Reversal: sold the stock 2 times over 6 days before this purchase

    • Cluster Buy: yes, two directors bought in February at around the same price

    • Insider signal: 4.5/5

  • Stock info

    • Returns: 2% 1w / 23% 1m / -5% 3m / -28% 6m / -35% 1y

    • Price v SMA: 7% v 20d / 7% v 50d / -19% v 200d

    • Price v 52wk high: -40%

    • Price v 52wk low: 31%

  • Company info

    • Market cap: $2.41B

    • Enterprise value: $2.47B

    • Dividend yield: N/A

    • Tenable Holdings, Inc. provides cyber exposure management solutions in the Americas, Europe, the Middle East, Africa, the Asia Pacific, and Japan. 

    • Sector/industry: Information Technology / Software and Services / Software

    • Industry net buying (last 90d): 54.32% vs 28.25% median

    • Buyback yield (LTM): 12.59% v -0.29% 5y median

    • Shareholder yield (LTM): 12.59% v -0.29% 5y median

    • Net Debt Paydown yield (LTM): 0.16% v 0.09% 5y median

    • Total Capital Return yield (LTM): 12.74% v -0.17% 5y median

    • Shares Outstanding growth: -4.68% (1y) / -3.51% (2y)

    • Interest coverage: 1.11x (EBIT) / 1.83x (EBITDA)

    • Net Debt/EBITDA: 1.21x

    • Unlevered FCF yield (LTM): 11.00% v 4.24% 5y median

    • FCF yield (LTM): 10.62% v 3.75% 5y median

    • EBIT yield (LTM): 1.26%

    • EBIT margin (LTM): 3.03%

    • ROIC (LTM): -0.80%

    • Gross margin (LTM): 78.17% v 77.96% 5y median

    • Dividend growth (LTM): N/A

    • Valuation multiple (EV/S NTM): 2.3x v 5.5x 5Y median

  • Conclusion

    • Add to CEO Watcher Portfolio (filled at $21.44)

    • Insider signal is strong: CFO purchase + reversal + stock trading at all-time low valuation + buying back shares + software stocks are seeing significantly above average insider buying in the industry. Two directors also bought in early 2026 at around the same price.

    • Management clearly believes the stock is too cheap as they bought back 13% of the company over the last year and increased the buyback authorization

    • TENB is a vulnerability management (VM) platform, which means it identifies potential security vulnerabilities before they get attacked. This differs from all of the big security guys which do “detect-and-respond”, which watch for attacks happening and then try to stop them in real-time.

    • TENB has been a melting ice cube for a few years because VM is commoditized and their growth has been slowing (from mid-20% rev growth in 2022 to just 10% now). Really, if you divide their EV/S by rev growth, they actually are valued similarly today as to their median (~60% lower valuation and 60% lower growth). 

    • However, there are two major changes. Back in 2022/2023, they weren’t buying back any shares (13% buybacks now) and AI has potentially massively increased the need for vulnerability detection + fixing those vulnerabilities (automatically with AI agents).

    • Tenable has a platform called Tenable One that ingests data from its own products and other security products (like CrowdStrike, SentinelOne, Palo Alto, Wiz, etc). It then prioritizes them and surfaces the highest priority vulnerability. This platform has been growing (from 25% of their new customer rev to over 40% in two years). In H2, they are launching Hexa AI, which will then use AI agents to go fix those high-priority vulnerabilities.

    • If companies adopt Hexa AI, this increases revenue per customer AND increases the retention of the customer because they will be unlikely to switch when they have Hexa AI integrated into all of their infra.

    • Mgmt believes they are not at risk from Anthropic/OpenAI because those products will do a better job writing code that prevents vulnerabilities, but they will not go into running AWS environments to fix misconfigured S3 buckets. Mgmt’s bet is that the LLMs remain at the source code layer, while Hexa AI is actually integrating with running infrastructure. Also, they believe the number of vulnerabilities will 10-20x as AI is able to find more vulnerabilities (which will need patched).

    • There appears to be progress already happening. In Q4, they signed their first 7-figure AI-exposure deal and then added 43 net-new 6-figure contracts in Q1 (v just 5 in Q4). That 7-figure exposure deal was from a major telecom that just needed more insights into how agents were being used, how data was being shared, how their attack surfaces were expanding, etc. That shows that AI is creating an urgency around security. Hexa AI is then the next layer to actually solve any issues being found.

    • Tenable One was also already growing well before AI. It made up 33% of revenue in 2025 and 41% of new business. It’s probably safe to assume that legacy VM growth was very low growth at best, and possibly negative (based on overall declining revenue growth and mgmt stating that they expect overall growth rate to inflect higher because Tenable One is growing faster than legacy VM). So there is upside from a mix-shift to the Tenable One platform + more upside from Hexa AI adoption

    • As with any internal mix shift like this, there is risk that the growth of Tenable One is mostly coming from legacy users switching to Tenable One and the growth will stall once most users have switched. They don’t cleanly break this out, which is a concern that maybe it’s not as bullish as we hope

    • There is also risk from larger competitors entering their space (AI does enable incumbents to build products faster) and potentially LLMs continuing to build further security integrations with customers

    • Two data points that are at odds with management optimism: NDR ticked down from 106% to 105% (increased churn) and their midpoint growth guide for 2026 is lower than Q1’s growth which means they are guiding for growth to be lower in second half of the year. This is either them sandbagging guidance or proving that maybe the optimism management expresses is premature

    • However, I think the near-term is weighted to the upside. They have an Investor Day on May 21st in which they are supposed to announce mid-term (2027/2028) growth targets. The CFO also just bought the stock for the first time and obviously knows what they will say at the Investor Day. If they present increased growth guidance, that would back-up their stated optimism around the growth potential from AI. We’ve also seen some massive 20%+ jumps in software stocks with strong earnings and a positive AI story (like Atlassian and DataDog - DDOG is especially relevant)

    • Even at flat rev growth + no multiple expansion/contraction + buybacks, you get to 20% CAGR (at least while buybacks continue). Any growth inflection and/or renewed software optimism will lead to a re-rating and materially increase upside.

Today’s Largest Unscheduled Trades

There were 136 new insider trades filed.

1 insider trade was flagged as High Signal because the CEO made a large $2M purchase after only selling the stock for 11 years + the stock is trading below its median EV/EBITDA multiple + they are in the middle of an antitrust case right now, which will provide upside if it goes their way (and it appears the CEO believes it will). 

Our system gave high scores to 2 insider purchases (I shared our system’s notes on those in the High Scoring Purchases - Quick Notes).

We also found 1 insider purchase from an insider who averages 20%+ 1y returns.

CEO Watcher Premium subs can see those notes in later sections of this email.

Today’s largest unscheduled insider trades:

  • Chief Executive Officer at 51Talk Online Education Group $COE purchased $16.52M (largest purchase ever, out of 5). Dip Buy: the stock was down -41% in the previous month. This insider has purchased the stock 5 times in the last 30 days. Part of a 10b5-1 plan.

  • 10% Owner (DART KENNETH BRYAN) at Flutter Entertainment plc $FLUT purchased $3.51M. Dip Buy: the stock was down -53% in the previous 6 months. This insider has purchased the stock 8 times in the last 30 days.

  • Senior Portfolio Manager (GEORGE W WHITNEY) at SPROTT FOCUS TRUST INC. $FUND purchased $848.00K.

  • Director (Pack Jay A) at Mission Produce, Inc. $AVO purchased $484.00K (2nd largest purchase, out of 3). 1 other insider also purchased the stock in the last 30 days.

  • CEO at Navios Maritime Partners L.P. $NMM purchased $249.26K (23rd largest purchase, out of 29). This insider has purchased the stock 7 times in the last 30 days. Part of a 10b5-1 plan.

  • Director (Hudson Daniel Timothy) at HALLADOR ENERGY CO $HNRG purchased $169.40K (largest purchase ever, out of 2). This increased their listed holdings by 200%. 1 other insider also purchased the stock in the last 30 days.

  • SVP, CLO AND SECRETARY at Liberty Latin America Ltd. $LILA purchased $99.74K (first-ever purchase). Rip Buy: the stock was up 30% in the previous week. Reversal: they made 3 straight sales before this purchase. 4 other insiders also purchased the stock in the last 30 days.

  • CEO, SMD at MSC INCOME FUND, INC. $MSIF purchased $69.72K (largest purchase ever, out of 7). 3 other insiders also purchased the stock in the last 30 days.

  • Director (MANCHESTER KEITH S) at Roivant Sciences Ltd. $ROIV sold $56.44M (2nd largest sale, out of 8). Rip Sell: the stock was up 34% in the previous 3 months. 3 other insiders also sold the stock in the last 30 days.

  • Director (Silver Lake Group, L.L.C.) at Dell Technologies Inc. $DELL sold $6.61M (12th largest sale, out of 19). Rip Sell: the stock was up 152% in the previous 3 months. 9 other insiders also sold the stock in the last 30 days.

  • SVP at VALERO ENERGY CORP/TX $VLO sold $2.01M (largest sale ever, out of 4). This decreased their listed holdings by -27%. Rip Sell: the stock was up 63% in the previous 6 months. This insider has sold the stock 2 times in the last 30 days.

  • Chief Legal Officer at CASEYS GENERAL STORES INC $CASY sold $1.60M (largest sale ever, out of 5). This decreased their listed holdings by -20%.

  • Chief Financial Officer at IDT CORP $IDT sold $1.33M (largest sale ever, out of 13). This decreased their listed holdings by -39%. 2 other insiders also sold the stock in the last 30 days.

  • Executive Officer at TARGET CORP $TGT sold $966.49K. This decreased their listed holdings by -16%. 1 other insider also sold the stock in the last 30 days.

  • Vice President at Afya Ltd $AFYA sold $623.12K (largest sale ever, out of 3). This decreased their listed holdings by -53%. 1 other insider also sold the stock in the last 30 days.

  • Director (Hunt Jolie A.) at KILROY REALTY CORP $NYSE: KRC sold $597.10K (largest sale ever, out of 2). This decreased their listed holdings by -53%. Rip Sell: the stock was up 38% in the previous 3 months. Their last sale was 2581 days ago. 2 other insiders also sold the stock in the last 30 days.

  • Chief People Officer at J M SMUCKER Co $SJM sold $583.48K (5th largest sale, out of 12). This decreased their listed holdings by -21%. Their last sale was 455 days ago. 3 other insiders also sold the stock in the last 30 days.

  • Chief Financial Officer at WIDEPOINT CORP $WYY sold $561.12K (largest sale ever, out of 7). This decreased their listed holdings by -52%. Rip Sell: the stock was up 48% in the previous month. 3 other insiders also sold the stock in the last 30 days.

  • and more…

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