A Record Quarter, A Founder's Own Check, And Cash Flow Catching Up

August 16, 2026

This week's movers span three corners of tech: a hardware maker that just printed a record quarter and raised its outlook, a real estate platform where the founder is putting personal cash to work, and a messaging company finally converting growth into real free cash flow. Each setup carries a different flavor of risk, and you should size them accordingly.

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SaaS

monday.com's AI Pivot Is Finally Showing Up in the Numbers

monday.com (NASDAQ: MNDY) leaned into its AI Work Platform this month, and the Q2 print gave the pitch some teeth. Look at the numbers: Q2 revenue hit $364.6 million, up 22% year-over-year, with ARR from AI products doubling from Q1 and representing 17% of net new ARR, per the company's Q2 2026 release.

The pitch is simple: AI agents bolted onto the work-management boards your team already lives in every day. Picture your own project board answering a question and drafting the next task instead of just holding it. That is the upsell, and it lands on seats you are already paying for.

Here is the tension you are buying into. Shares change hands near $94, roughly 57% below the $220.80 52-week high, with a market cap around $4.0 billion. Growth at 22% was never the problem; the multiple was. If AI ARR keeps compounding at this pace, you are looking at a re-rating candidate. If net new ARR stalls, you get more of the same drawdown.

Cloud Infrastructure

Institutions Keep Adding Cloudflare Ahead of Its AI Story

Cloudflare (NYSE: NET) is pulling serious institutional flow into earnings. Per Quiver Quantitative, 613 institutions added shares last quarter versus 462 that cut positions. One fund alone added over 1.5 million shares, a 124% bump to its book.

That's not a rounding-error rotation. That's positioning.

The thesis is straightforward. Cloudflare sits at the intersection of two spends that aren't slowing: edge security and AI inference. Every AI application you build needs low-latency compute close to the user, and Cloudflare's global network is built for exactly that. Workers AI, its inference platform, is the wedge.

The risk: NET already trades at a rich multiple, so any earnings miss or guide-down gets punished hard. If you own it, that is the tradeoff you accept for a growth name with genuine AI exposure.

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Industrial Software

Trimble's Recurring Revenue Just Hit a Record While the Stock Sits Near Multi-Year Lows

Trimble (NASDAQ: TRMB) reported second quarter revenue of $972.0 million on August 12, up 11% year over year and 10% organic, and annualized recurring revenue of $2.51 billion, up 14%. That ARR figure is a company record; non-GAAP operating margin came in at 26.8%, and management raised full-year guidance to $3.90 billion to $3.95 billion of revenue with non-GAAP earnings of $3.60 to $3.70 per share. The board also authorized a fresh $1.0 billion buyback.

Here is why you probably missed it. The same quarter carried a $562.0 million goodwill impairment on the Transportation and Logistics business, which turned the headline into a GAAP net loss of $471.7 million, or $2.02 per share. Non-GAAP earnings were $0.86. Screens that read the GAAP line first flagged a blowup; the recurring revenue base underneath it grew 14%.

The setup you are looking at is a subscription software business selling to construction, agriculture, and geospatial customers, trading near $58 with a market cap around $13.4 billion, roughly a third below where it traded a year ago and closer to its 52-week low of $47.92 than its $84.42 high. If the impairment was the last of the T&L cleanup, you are paying a depressed multiple for a growing recurring base. If more write-downs follow, the discount is telling you something real, so watch the next quarter's ARR growth rate as you tell.

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Recent Tech Movers

Zebra Technologies (NASDAQ: ZBRA): Record quarter, raised outlook

Zebra reported second quarter net sales of $1.56 billion on August 4, up 20.4% year over year, with non-GAAP diluted earnings of $6.35 per share and adjusted EBITDA of $431 million, and it raised its full year outlook. The company returned more than $560 million to shareholders in the first half, including $268 million of buybacks in the quarter. The number to watch is how much of that growth is pulled forward ahead of tariffs, since the quarter also included $73 million in tariff recoveries.

CoStar Group (CSGP): Founder writes his own check

CoStar (NASDAQ: CSGP) CEO Andy Florance bought shares in the open market this month, per Insider Weekends' August 9 report. Founder buys after a rough stretch tend to matter more than routine director grants, so weight this signal accordingly. Check the next filing window for follow-through purchases before you decide.

Twilio (NYSE: TWLO): Cash generation catches up to the growth story

Twilio reported second-quarter revenue of $1.50 billion on August 6, up 22% year over year with organic growth of 17%, and converted that into $352.6 million in free cash flow, a 24% margin. Management raised its full-year operating income and free cash flow ranges on the same print. The catch is that you are buying third-quarter guidance of 11% to 12% organic growth, a step down from the quarter just delivered, so the question is whether cash conversion holds while growth decelerates.

Speculative Play

Joby Aviation (NYSE: JOBY)

First passenger flights on the clock

The setup:

Joby (NYSE: JOBY) told you on August 5 that its first flights under the White House-backed eIPP program are expected in September in Texas, targeting first passengers this year. The stock trades near $8.26 with a market cap around $8.2 billion, down 54% over the past year and much closer to its $6.63 low than its $19.98 high. A hard-dated catalyst against a beaten-down price is the setup you hunt in this section.

Your bull case:

The Blade acquisition is already producing revenue, $36.2 million in the second quarter, and management raised the full-year outlook to $115 million to $125 million. Five aircraft are flying, with 12 more in production; the company says it made its strongest progress yet in the fifth and final stage of FAA type certification, and the Toyota joint venture is the manufacturing partner that most of this sector lacks. On August 11, Joby also agreed to buy Resonant Sciences to push into defense. There is $2.3 billion of cash and short-term investments behind all of it.

The risk:

This is pre-revenue economics dressed up by a charter business. Joby guided to $385 million to $415 million of cash use in the second half, so the burn is real, and certification timelines in this industry slip more often than they hold. If September flights push to 2027, the story resets. Treat it as a starter position sized for a total loss, add only on certification milestones actually cleared, and let the September flight window be your first checkpoint.

That's our coverage for today; thanks for reading! Reply to this email with feedback or any tech stocks you want me to check out.

Best Regards,
—Noah Zelvis
Tech Stock Insider