CEO Watcher Q2'26 Insider Trading Report

What’s in the report

• Massive insider buying in software

• Q1 CEO Watcher performance recap

• Software stocks with insider buying that haven’t run yet

• What we are watching in Q3

You can join the free, daily email list at ceowatcher.com. Upgrade to CEO Watcher Premium for access to the Premium daily email (which highlights the highest signal insider purchases), full access to the website (including custom alerts), the CEO Watcher Portfolio, the CEO Watcher High Signal List, the CEO Watcher Discord (with real-time insider trade alerts), and more.

Massive insider buying in software

Q2 was marked by a handful of big winners for CEO Watcher from the software industry (TENB +80%, OKTA +60%, SMWB +60%, ACVA +30%, NSP +70%).

We exited Q1 with the software industry at the top of the list of industries with the most above-average insider buying (compared to the industry’s 10y average).

In March, the industry had nearly double the amount of net insider buying versus its average and was just slightly below the peak of 2022 (software was up 60% in 2023).

Insiders tend to be a little early with their buying (it peaked in July 2022, but software didn’t bottom until September), and there are still plenty of software companies with very compelling insider buying that haven’t yet re-rated.

We’ll take a look at these in a later section.

Q1 CEO Watcher Review

In Q1, there were 77 stocks added to the CEO Watcher High Signal List. Those picks are now at least 3 months old and are outperforming the S&P by over 6 points (15.81% v 9.42%).

Some of the best performers from Q1 are:

• Intel (INTC) +172%

• Ceva Inc (CEVA) +130%

• Travelzoo (TZOO) +100%

• Insperity Inc (NSP) +100%

• First Guaranty Bancshares (FGBI) +80%

• Ralliant (RAL) +70%

• Varonis Systems (VRNS) +60%

• Intellia Therapeutics Inc (NTLA) +60%

• Zenas Biopharma (ZBIO) +60%

• AirJoule Technologies (AIRJ) +50%

• Grocery Outlet (GO) +50%

A nice mix of industries (biotech, software, semis, banking, consumer staples).

We tightened up the criteria for the High Signal List in Q2 and added fewer than half as many names. So far, the performance has been better, outperforming the S&P by over 10 points on average, with over 60% of the picks beating the S&P.

Some of the winners have been:

• Okta (OKTA) +80%

• Tenable (TENB) +70%

• Victoria’s Secret (VSXY) +55%

• SimilarWeb (SMWB) +55%

• Greene County Bancorp (GCBC) +40%

• Eastern Company (EML) +30%

Another interesting stat is that short-term insider dip buys have continued to outperform the S&P (particularly when paired with cluster buys).

This is particularly notable because the S&P momentum ETF has nearly doubled the S&P’s performance over the last year, yet these “value” insider buys still outperformed.

Software Stock Pitches

Let’s start with the “quality” software names, which have yet to recover.

S&P Global (SPGI)

A financial intelligence and data company. They sell data such as credit ratings, benchmark indexes, market/company analytics, and commodities data.

$120B mkt cap, $138B EV, rev +10% YoY, adjusted EPS +14% YoY, repurchased $1B in Q1, returning 100% of FCF as dividends/repurchases, adjusted operating profit margin +100 bps.

The CEO, CEO of Dow Jones, and two directors bought a combined $3.5M.

Not a pure software name, and not nearly as exposed to AI as many software names (Capital IQ makes up a tiny portion of revenue), yet still down 25%. Trading at the same P/E it was during its COVID sell-off (and 30% below its median). Nearly 60% of revenue is from ratings, Dow Jones indices, and Systems of Records, all of which are not at risk of AI competition. Market Intelligence is the other 40%, but CapIQ workstation is only 6% of enterprise rev and “undifferentiated data” makes up less than 5% of overall rev. Much of their Market Intelligence data is proprietary (private market/fundraising/M&A data, Platt’s price assessments, and data back to the 1950s). Mgmt believes AI will be a tailwind for Market Intelligence as customers are increasing renewal premiums for AI-ready data, API call volume was up 5x QoQ, and ACV growth among customers using AI data is higher than those not using AI data. Mgmt is buying stock and increased buybacks to 100% of FCF.

Autodesk (ADSK)

Design/make/operate software for AECO, manufacturing, media/entertainment, and design workflows. Q1 FY27 mix: AECO $970m, AutoCAD/LT $474m, MFG $367m, M&E $86m; product-type mix was Design $1.612b, Make $224m, Other $98m.

$40.1b mkt cap / $39.5b EV at June 26 close. Q1 FY27 rev $1.934b, +18% YoY / +16% constant currency; billings $1.688b, +18%; GAAP op margin 28%, +14 ppt; non-GAAP op margin 39%, +2 ppt; FCF $876m, +58%. FY27 guide midpoint: rev $8.185b, +13.6% vs FY26 actual $7.206b; FCF $2.763b, +14.7% vs FY26 $2.409b; GAAP op margin midpoint 27% vs FY26 22%; non-GAAP op margin ~39% vs FY26 38%. Margins expanding.

CEO, CFO, and Director have bought over $2M of the stock on the drawdown.

Down 35% YTD on AI fears. Mgmt’s rebuttal is that ADSK owns the data/context/physics-based 3D layer, APIs, MCP infrastructure, and workflows that make AI useful in real-world design. Customers are locked into workflows through file formats, training, regulatory/compliance requirements, and ecosystem lock-in. Double-digit rev growth and margins expanding. They also own the project data needed to train a useful AI model. AI seems unlikely to disrupt.

The chart is starting to flatten out.

Intuit (INTU)

Financial software/platform name across QuickBooks, Intuit Enterprise Suite, Mailchimp, TurboTax, Credit Karma, and ProTax. Core buyer pools are SMBs, mid-market businesses, accountants, consumers, and professional tax preparers. FY25 mix was GBS 59%, Consumer 26%, Credit Karma 12%, ProTax 3%; FY26 segment reporting now rolls Consumer/Credit Karma/ProTax into one Consumer segment.

Mkt cap $69.8B, EV $69.9B. Rev $8.6B vs $7.8B (+10%), total op income $4.0B vs $3.7B (+8%). GBS rev $3.3B vs $2.8B (+18%), Consumer $5.3B vs $4.9B (+8%). Underneath: QBO Accounting +22%, Online Services +15%, TurboTax +7%, Credit Karma +15%.

Only 1 insider purchase so far ($541k from a director - the former CFO at Visa), but mgmt doubled the repurchase plan as well.

The stock is down an insane 60% YTD due to AI fears (now at 10x P/E v 31x median). To be fair, TurboTax DIY growth decelerated from +12% to +7%, though mgmt says the low-end issue is about sub-$50K customer pricing (not AI). However, all of their other businesses (except for Mailchimp) are performing incredibly well (and Mailchimp has been underperforming for years). The non-tax business is growing 15%, and QuickBooks is growing even faster at 22%. TurboTax Live is also growing quickly (expected to grow 36% this year and become more than 50% of total TurboTax revenue), so it is only TurboTax DIY that is potentially being affected by AI (and TurboTax Live TAM is 7x larger than DIY, according to mgmt). Mgmt increased buyback to 12% of float. FY guidance was raised.

HubSpot, Inc. (HUBS)

HubSpot sells a cloud CRM/customer platform for mid-market B2B companies: Marketing, Sales, Service, Content, Operations, Commerce, Smart CRM, and Breeze AI/agents. Subscription-led model, with products aimed at customer-facing GTM teams and a partner ecosystem that sourced or co-sold a large share of revenue in 2025.

$8.7b mkt cap, $7.3b EV. Stock is still -67% below its 52w high and -53% over 6m from AI fears. Q1’26 fundamentals still fine: rev $881m, +23% as reported/+18% cc; sub rev $862m, +23%; non-GAAP op margin expanded to 17.8% from 14.0%; non-GAAP FCF $154m vs $122m. Q2 guide: $897-898m rev, +18%; FY26 guide: $3.700-3.708b rev, +18%.

CEO, CTO (and founder), and a director bought a combined $2.6M.

This company is probably the toughest near-term story because not only is AI a risk, but they are overhauling the entire company to better fit into an AI world. They are focusing on their AI agent products, changing their pricing model to outcome-based pricing, introducing free trials, and spending a week retraining their entire salesforce. This led to net new ARR being below revenue for the first time ever, but could prove to be the optimal move if AI transforms enterprise SaaS as much as many believe.

Mgmt says HubSpot is more valuable in AI because agents need customer data, context, workflow logic, permissions, and APIs. Early proof points: credits +67% q/q; Customer Agent 53% of credits, Prospecting Agent 17%, Data Agent 16%; core seats +90% YoY. But usage-based credits/outcome pricing/free trials create ARR timing and unit-economic questions.

Growth engine is also changing. Q1 net adds were 10.8k and mgmt still expects 9-10k quarterly adds, but search/organic discovery is under pressure. Mgmt says customer organic traffic is down 27%; Q4 says YouTube leads +68%, newsletter leads +53%, and AEO/LLM visibility are offsets.

Adobe (ADBE)

Adobe sells subscription software and cloud services for creative/professional content creation, PDF/document productivity, and enterprise marketing/customer-experience workflows. FY2026 reporting moved to one operating/reportable segment, so formal segment revenue is no longer split.

Director (current CEO at Eli Lilly) bought $1.95M (largest purchase ever). He also bought last January and is down 50%. Prior to that, he bought the 2022 dip (+70% in 1y) and in 2018 (+50% in 1y).

The stock is down 50% on AI fears, but Adobe raised earnings and revenue guidance. EPS/EBITDA estimates are higher than they were in 2023-2025, yet the stock is trading 70% below the high and 30% below the low of that period. Trading at an 8x P/E v 25x median (and 20% below the multiple they traded at during the GFC).

Rev +12%, op income +6%, GAAP op margin down to 33.8% from 35.9%, non-GAAP op margin down to 44.5% from 45.5%. Operating leverage and ARR guidance (cut by $500M) are down a bit as management focuses on user acquisition / freemium traffic instead of the planned optimizations for Creative Cloud. Those have been postponed until 2027, which should help juice rev and margins.

Market obviously believes that AI is going to have long-term negative impacts on Adobe, but management disagrees. They also authorized a $25B repurchase program (30% of market cap).

The chart has started to move in the right direction over the last couple of weeks.

-

Now for the “lower quality” software names.

Tenable (TENB)

* Stock is up ~70% since we added it to the CEO Watcher Portfolio and High Signal List, but still 30% below its median EV/Sales multiple

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, who do “detect-and-respond”, which watch for attacks happening and then try to stop them in real-time.

Tenable was a melting ice cube for the last few years as VM was commoditized, but they may have received a second wind from AI.

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.

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 (for example). 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.

Similarweb Ltd. (SMWB)

* Stock is up ~60% since we added it to the CEO Watcher Portfolio and High Signal List, but still only at 1.6x EV/Sales

Sells a proprietary estimate of digital traffic/behavior across websites and apps (and LLMs soon) and is now licensing data to LLMs.

$451m mkt cap, $425m EV. FY25 rev $282.6m, +13% YoY. Q1’26 rev $73.9m, +10%; non-GAAP op profit $2.4m / 3% margin; normalized FCF $6.6m; cash $65.3m. FY26 guide: $307-315m rev, +10% at midpoint; non-GAAP op profit $17-19m.

4 insiders bought a combined $1M (first-ever purchases).

Revenue up 10%, RPO up 18%, and multi-year contracts growing from 49% of ARR to 64%. They are going all-in on AI offerings. They recently closed a $10M+ ARR deal with an LLM, switched to consumption-based pricing, built MCPs for Claude and ChatGPT, and are gathering ad data from ChatGPT. AI revenue grew from 8% of rev to 11% and tripled YoY.

Sprout Social, Inc. (SPT)

* Stock is up ~30% since we added it to the CEO Watcher Portfolio, but still only at 0.8x EV/Sales and still below the price the CEO paid

Sprout sells social media management SaaS: publishing, engagement/care, analytics, listening, influencer, employee advocacy, and NewsWhip predictive media intelligence. Mostly subscription, one operating segment, >100 countries, with the product aimed increasingly at mid-market/enterprise social teams rather than pure SMB.

$394m mkt cap, ~$329m EV. Q1’26 rev $121.5m, +11% YoY; subscription was 99% of revenue. GAAP gross margin 77%, GAAP net loss $6.3m, OCF $25.2m. Mgmt called out 11.6% non-GAAP op margin and $24.7m non-GAAP FCF. RPO $395m, with ~71% expected inside 12 months. SBC is way too large (mgmt will need to do something about it).

The CEO and a director bought the stock in December/January. No other insider purchases since 2021.

Super cheap: 0.8x NTM sales (v 7x median). Pivoting to enterprise. Mgmt says $30k+ ARR customers are now >60% of subscription revenue and grew 21% YoY; $50k+ customers grew 18%. Sold off on AI fears (-30% YTD). Mgmt’s answer is that Sprout is not just a workflow wrapper; it owns hard-to-access, real-time, cross-network social data and governed enterprise workflows, and Trellis turns that data into AI-native insights inside the platform. They have partnerships with the data providers that are expensive and/or not available to others.

Via Transportation (VIA)

Public-transit software / tech-enabled services platform. Sells planning, scheduling, operating software, passenger tools, data/insights, and services like driver/fleet management to cities, transit agencies, school districts, universities, healthcare providers, and corporations.

$1.25B mkt cap, $0.92B EV. Q1 rev +29% YoY, platform ARR +29%, customers +23%, adj GM 40% vs 41%, adj EBITDA improved to -$5.8M from -$8.3M. FY26 platform rev guide +26.0% to +26.6%, Q4 2026 adj EBITDA > $0 target.

CEO, CFO, and a director bought a combined ~$487K in June.

Not clean SaaS. ~40% adj GM, services/ops-heavy COGS, Germany drag, and Q1 OCF worsened on AR timing. But still growing quickly: Q1 rev +29%, ARR +29%, customers +23%, FY26 platform rev guide +26%, Q4 adj EBITDA > $0 target. However, mgmt is being cagey about a recent acquisition they made, which contributed over 60% of the customer growth (they won’t delineate organic v M&A growth).

Stock at ~2.2x EV/Sales / ~5.5x EV/GP. Market underwriting lower margins and inorganic growth. If EBITDA actually turns positive in Q4 (as guided), it should start screening more favorably and possibly re-rate. Mgmt is also targeting GM to move from ~40% toward 50% LT target. Mgmt says near-term GM flat, but levers are mix, higher-margin software, AI/AV, lower cost-to-serve, and M&A. Germany is the main offset: 16% of rev, only +3% growth. Need U.S./U.K. + network wins to keep overwhelming that with strong organic growth. Weak organic growth offset by M&A will likely keep multiple compressed.

Probably my least favorite of the software names.

Sagtec Global (SAGT)

Malaysia/BVI microcap software operator. Sells Speed+ digital ordering/POS software, QR/table ordering, self-service kiosk systems, software customization, data/analytics, social media management, and power-bank / kiosk hardware mostly into F&B and adjacent SMEs. Revenue model is mixed: subscription services plus custom projects plus tangible product sales; 2025 top categories were subscription services, food-ordering kiosks, and data management.

Mkt cap $28.3m, EV $27.8m at the 6/26/26 close of $1.05; stock is 60.8% below its 52w high and down 55.3% over 3m. FY25 rev $19.1m, +49% YoY; gross profit $4.3m, +45%; EBITDA $3.4m, 17.8% margin; net profit $1.8m, basically flat YoY. FY26 guide is rev $25.8m, +35%, EBITDA $4.6m, +38%, net profit $2.2m, +22%; gross margin guide expands to ~26.1% from ~22.7%, while EBITDA margin is roughly steady/slightly up.

CEO bought $1.56M (first-ever insider purchase). This is sizable given the company's $20M market cap. The stock jumped like 50% on the news, but gave most of it back.

Tiny company that has likely sold off for a variety of factors: software + financial services industry weakness, foreign company, tiny/illiquid micro cap. Other financial services stocks sold off heavily around the same time (April), so that may be the main factor. Not much info on the company, but the numbers look quite good. The main issue is that capex is growing incredibly fast ($7M, up 500% YoY).

This is a microcap, so it has all the volatility (and lack of info) as any other microcap.

What we’re looking at in Q3

We are always looking for dip buys, cluster buys, reversals (insiders flipping from selling to buying), and insider purchases in industries with significantly above-average net insider buying. Even better if the insider purchase meets multiple of those criteria.

This quarter, the industries with the most above-average insider buying are Automobiles/Components, Consumer Staples, Commercial/Professional Services, and Telecom Services.

The Commercial/Professional Services industry is particularly interesting because it sold off on AI fears (similar to software), but has not recovered as much as software has.

Insperity (NSP)

Insperity was our favorite name in the space, as there was a bunch of insider buying between March and June.

We flagged the stock as High Signal on the very first dip buy after the massive post-earnings sell-off led to the CEO buying the stock after 16 straight years of selling. They basically run the HR department for SMBs. They weren’t a pure “AI-fear selloff,” they got smoked on healthcare claim costs, which ran at 9% per covered employee v the 5-6% average. They renegotiated contracts, which began on Jan 1, 2026, and profit per employee almost fully recovered to Q1 2025’s $338 (came in at $332). ~60% of customers still had not yet been re-priced to higher rates, which will be another tailwind. Even after the 100% run-up from the bottom, they are still trading 30% below their median EV/EBITDA multiple, but obviously less compelling here.

Aecom (AEM)

AECOM (AEM) looks interesting. The President just bought $300k (first-ever purchase, reversal after 3 straight sales over the last 7.5 years, cluster buy, dip buy). They are an infrastructure consulting company that sold off as part of the industry sell-off and working capital issues in H1. Their claims rose 70% in one quarter, which killed their FCF. However, mgmt claims this is a timing issue (Middle East payments delayed due to war and claims from two customers from 2019/2020 taking longer to collect than expected) and maintained full-year guidance. They claim the Middle East delays are already resolved, and the President is buying just 2 weeks before the quarter ends, which suggests the quarter is on track. The chart is pretty ugly, though.

Onterris (ONT)

Onterris sells consulting, engineering, permitting, emergency response, water/soil remediation, air monitoring, leak detection, and lab testing to commercial and government customers that need environmental compliance, risk mitigation, and remediation work.

CFO and a Director bought a combined $600k (first cluster buy since 2023).

~30% drawdown after poor Q1 earnings. Rev fell 5% YoY, Adj EBITDA fell 6%, margin roughly flat. Big miss was a huge cash flow break. OCF flipped from $5.5M to -$11.6M. Rev was down from lower emergency response rev (2025 was unusually large, so emergency response rev won’t recover) and weather delays. OCF was down due to $16M more in bonus payments tied to 2025 outperformance

FY26 guide remained intact. +8% organic growth, +10% adj EBITDA growth. Q2 still expected to come in below 2025 numbers (due to an unusually strong Q2 2025 in emergency response - it made as much revenue in one quarter as the typical yearly rev), with recovery in the back half of the year

Another one where the FY guide was maintained, and an insider bought the dip. The CFO purchase suggests that management believes H2 will be strong (as guided). 2025 FCF was unusually strong (93% conversion v 60% goal), so they won’t reach that FCF level, but their FY guidance is above $75M, which is significantly above 2021-2023 ($20-$56M) when the stock traded at a $1.5-$1.7B (v $1.1 today).

This is another one that has run ~20% since we found the insider buying, but is still trading almost 50% below its median EV/EBITDA multiple.

-

We have only flagged two Automobile/Components insider purchases so far, but both are up 30% so far

Strattec (STRT) designs lock components for vehicles (mostly the US big 3). The products themselves are pretty undifferentiated, but they have a cost advantage due to most of their manufacturing being in Mexico. The CFO, CEO, and a director all bought the stock after the earnings dip, but the stock has fully recovered from the dip. If/when industry production recovers, they likely have more upside.

Eastern Company (EML) is a micro-cap holding company for three industrial businesses: Eberhard (access hardware: latches, locks, hinges, handles for trucks, military, off-road/UTV), Velvac (vision systems: mirrors and mirror-cameras for trucks, RVs, buses, plus aftermarket), and Big 3 Precision (returnable transport packaging racks/dunnage and injection-mold tooling for auto and consumer-goods customers). End markets are automotive, which have been in a multi-year downturn. Based on previous cycles, the stock still probably has some upside when the cycle. But I did mention in the original notes for CEO Watcher Premium subs that when the stock turns, it tends to turn quickly. That has proved accurate as the stock is up over 30% in two weeks.

-

We haven’t highlighted any stocks in the Consumer Staples and Telecom Services industries yet, but we will continue to watch all four industries.

We are also entering earnings season and will be looking for any insiders buying earnings’ dips.

Sign up for CEO Watcher

You can join the free, daily email list at ceowatcher.com. Upgrade to CEO Watcher Premium for access to the Premium daily email (which highlights the highest signal insider purchases), full access to the website (including custom alerts), the CEO Watcher Portfolio, the CEO Watcher High Signal List, the CEO Watcher Discord (with real-time insider trade alerts), and more.