Dropbox
The file storage pioneer, still remote by default, now growing barely 1% a year and borrowing billions to buy back its own stock, with a new CEO and a fresh 9% job cut.
8-K, Oct 28, 2026; Q2 2026 earnings release- Revenue
- $631.5M in April to June 2026, up 0.9% on a year ago.
- Profit
- $164.8M operating profit in the quarter, a 26.1% margin; $95.8M net after interest and tax.
- Debt
- $3.37B a $2.67B secured term loan plus $693M of 2028 convertible notes.
- Watch
- 9% of staff cut worldwide, announced Oct 28, 2026; the CTO leaves Nov 18.
- AI
- Plugged in official MCP server plus Claude and ChatGPT integrations, which it says 150K+ users have connected.
- People
- 2,113 full-time staff at end of 2025, 1,612 in the US, before the October 2026 cut.
- Hiring
- 32 → 26 remote listings since Oct 10.
One product line, sold by subscription, 44% abroad.
Dropbox reports a single segment. Almost all revenue is subscriptions from 18 million paying users, from individuals on Plus plans to business teams. Sign, DocSend, Replay and Dash are sold alongside the core storage and sharing product but are not split out.
- 1A huge installed baseOver 700 million registered users and 18.19 million paying users, and no single customer above 1% of revenue.Q2 2026 earnings release; 10-K FY2025
- 2A cash machineFree cash flow was $930.8M in 2025 on $2.52B of revenue, and it guides to at or above $1.07B of unlevered free cash flow in 2026.10-K FY2025, MD&A; Q2 2026 guidance supplement
- 3Permissions and history that AI tools needManagement pitches Dropbox as the trusted content layer under AI apps, with permissions and version history across multiple exabytes. Still a claim to prove.Q2 2026 prepared remarks; 10-K FY2025 competition
| Company | Worth | Revenue | Growth | Per employee | Paid per $1 | Stock, 1 yr |
|---|---|---|---|---|---|---|
| Dropbox | $7.60B | $2.53B | 0% | $1.20M | $3.19 | +20% |
| Microsoft | $3876B | $346B | +18% | $1.55M | $11.22 | −2% |
| Alphabet | $3412B | $471B | +22% | $2.47M | $7.35 | −4% |
- Dropbox
- Worth
- $7.60B
- Revenue
- $2.53B
- Growth
- 0%
- Per employee
- $1.20M
- Paid per $1
- $3.19
- Stock, 1 yr
- +20%
- Microsoft
- Worth
- $3876B
- Revenue
- $346B
- Growth
- +18%
- Per employee
- $1.55M
- Paid per $1
- $11.22
- Stock, 1 yr
- −2%
- Alphabet
- Worth
- $3412B
- Revenue
- $471B
- Growth
- +22%
- Per employee
- $2.47M
- Paid per $1
- $7.35
- Stock, 1 yr
- −4%
Investors pay $3.19 for every dollar Dropbox brings in. Its peers here range from $7.35 to $11.22, well under their median of $9.29.
Dropbox brought in $632 million in 91 days.
That is about $6 million more than the same three months a year earlier. Each of its 2,113 employees brought in about $1.19 million over the year, about $3,270 a day.
Revenue is not profit. It is the money that came in before Dropbox pays any of its costs.
Q2 2026 earnings release (8-K, Aug 6, 2026); employees from 10-K FY2025 (Dec 31, 2025)Operating profit grew from $539 million to $689 million.
Revenue grew 1% in two years. In FY2025 it kept 27 cents of every revenue dollar as operating profit.
- FY2023: kept 22¢ of every $1
- FY2024: kept 19¢ of every $1
- FY2025: kept 27¢ of every $1
Every peer here brings in more per person than Dropbox.
- Alphabet$2.47M
- Microsoft$1.55M
- Dropbox$1.20M
Dropbox borrowed to shrink its share count, and now shows a $2.19B stockholders' deficit. Quarterly net interest rose to $50.0M from $18.6M a year earlier. Cash flow covers it comfortably today, but the debt limits room for a big acquisition or a bad year.
What the filings say, and what we think it means.
The fact is the filing's. The read, in italics, is ours.
- 01Watch
A third big layoff in three and a half years.
8-K, Oct 28, 2026; 10-K FY2025 workforce note (R46); Q2 2026 releaseOn Oct 28, 2026 Dropbox announced a global cut of about 9%, costing $27M to $33M in cash, mostly in Q4 2026. It follows 16% in April 2023 and 20% (528 people) in October 2024.
Remote-friendly does not mean stable. Each cut has followed a strategy reset, and the go-to-market team was already being rebalanced, so sales and marketing roles look most exposed.
- 02Neutral
The founder is handing over the CEO job.
8-K, May 26, 2026 (Item 5.02); 8-K, Oct 28, 2026Ashraf Alkarmi, who ran the core business, became co-CEO on May 26, 2026. Drew Houston is expected to become Executive Chairman, with Alkarmi as sole CEO, after a transition with no set date. A new product chief started Jul 7; the CTO leaves Nov 18, 2026.
Three top technical and product roles changed in six months. Expect priorities to shift toward the core product and away from standalone bets.
- 03Watch
It borrowed to buy back stock.
10-Q Q2 2026, debt and repurchase notes; 8-K, Jun 1, 2026The secured term loan grew to $2.67B in June 2026 from $1.49B at the end of 2025. Dropbox bought back $688M of stock in the first half of 2026 and about $1.7B in 2025. It added a $400M revolver in June and a new $900M buyback authorization.
Fewer shares lift per-share numbers even with flat revenue. The trade-off is higher interest and a balance sheet with liabilities above assets.
- 04Watch
One person controls about 81% of the vote.
10-K FY2025, risk factorsDrew Houston held about 81.4% of the voting power at Dec 31, 2025, including unvested Co-Founder Grant shares he can vote.
Outside shareholders cannot force a sale or a strategy change. Any take-private or merger runs through Houston, who stays on as chairman.
- 05Neutral
A founder award that pays only above $35 a share.
10-K FY2025, stock compensation note; 10-Q Q2 2026 coverThe 2017 Co-Founder Grant of 10.3M shares vests in nine tranches at stock price targets from $30 to $90. Only the first tranche (2.1M shares) has vested, in 2021. About 8.27M shares were still unvested in August 2026, and the grant runs 10 years.
The accounting cost is fully booked, so it no longer hits profit. It keeps the founder's incentive tied to a much higher share price.
- 06Watch
One distribution partner holds half of what it is owed.
10-Q Q2 2026, concentrations of riskA single unnamed distribution partner accounted for 51% of trade and other receivables at Jun 30, 2026, up from 47% at the end of 2025.
The filing does not name it; Dropbox does acquire users through partners such as hardware makers that pre-install its app. A fee change by that partner could move margins.
- 07Neutral
Its online forms business is being shut down.
Q2 2026 earnings release; 10-K FY2025Dropbox cut investment in FormSwift, its online forms business, at the start of 2025 and plans to wind it down by the end of 2026. Excluding FormSwift, Q2 revenue grew 1.7% instead of 0.9%.
A small drag that ends soon. The cleaner growth figure is still only 0.1% in constant currency.
- 08Watch
A breach of Dropbox Sign is still in court.
10-K FY2025, risk factors and legal proceedings; 10-Q Q2 2026 (R16)In April 2024 attackers accessed the Dropbox Sign production environment. The 10-K discloses a consolidated class action in the Northern District of California and related regulatory scrutiny. The Q2 2026 10-Q describes no material legal exposure.
Management does not expect a material loss. The case matters more for trust in Sign, its e-signature product, than for the numbers.
- 09Neutral
Most US openings skip its top pay zone.
Dropbox Greenhouse job board, checked Nov 3, 2026On Nov 3, 2026, 10 of 12 US postings on its Greenhouse board said the role is not available in US Zone 1, the zone with the highest posted pay. All 30 postings are labelled remote, across the US, Canada, Mexico, Poland, Ireland, Australia and Japan; 19 are limited to select locations.
Remote, but not from anywhere. Check the zone for your ZIP code before applying, because it caps the posted pay.
- 10Neutral
Profit per share rose while net income fell.
Q2 2026 earnings release (8-K, Aug 6, 2026)Q2 2026 GAAP net income fell to $95.8M from $125.6M, mainly on higher interest. Diluted EPS was $0.42 against $0.45, while non-GAAP EPS rose to $0.75 from $0.71 on 18% fewer shares.
The per-share growth investors see comes from the buyback, not from a bigger business.
What the hiring data says.
We save every company's roles, pay by team and level, AI share and churn every day, so each month this page can say more. Sparklines use their own scale.
Can AI agents do business with Dropbox?
We checked the agent payment programs, developer docs and site rules an AI assistant would meet.
Agents can work in your Dropbox. Its own MCP server, with write access.
Still Remote read- YesAn official MCP server for AI agentsmcp.dropbox.com/mcp lets agents browse, search, read, create, move and delete files, manage shared links and send Dropbox Sign requests. Marked beta; works with Claude, ChatGPT, Codex and Cursor.Dropbox Help Center, checked Nov 3, 2026
- YesConnectors inside ChatGPT and ClaudeThe company says it launched integrations with Claude and ChatGPT and over 150,000 users have connected them.Q2 2026 prepared remarks
- MixedA guide for AI tools (llms.txt)dropbox.com/llms.txt exists and lists product and policy pages. developers.dropbox.com/llms.txt returns not found.checked Nov 3, 2026
- YesLets AI crawlers read its main sitedropbox.com robots.txt names no AI bots. For all bots it blocks account, shared-link and preview paths, and explicitly allows /llms.txt.checked Nov 3, 2026
- YesLets AI crawlers read the Dash sitedash.dropbox.com robots.txt only blocks /draft, /dev and /download for all bots.checked Nov 3, 2026
- Not foundAgent checkout (ACP, AP2 or card network agent programs)No agent payment protocol is named in its 2026 releases, remarks or filings. Agents work on files, not on buying plans.Q2 2026 remarks and 10-Q, searched Nov 3, 2026
Where Dropbox puts AI to work.
- 1Dash folds into the main productDash, its AI search tool, is no longer pitched as a standalone product. Its intelligence is being built into Dropbox itself as a Smart FSS experience, testing with select customers and expanding through 2026. AI compute is already trimming gross margin.Q2 2026 prepared remarks
- 2Smaller teams, building with AIManagement says smaller teams powered by AI can build faster on a shared platform and expects R&D efficiencies. The Q2 product reorganization and the October 9% cut followed. No filing links the cuts directly to AI.Q2 2026 prepared remarks; 8-K, Oct 28, 2026
- 3Dropbox says its engineers ship fasterA Dropbox people executive told UNLEASH that developers submit 35% more pull requests and code reaches production 40% faster. Job ads now ask for AI fluency.UNLEASH interview, Sep 22, 2026
Fewer listings than on Sep 15, led by sales.
Your view of the next year, in a share price.
A way to think, not a forecast, and not investment advice.
- Growth
- How much bigger revenue gets in a year. More revenue to multiply.
- Paid per $1 of revenue
- The mood dial. High when investors expect fast growth and future profit, low when they doubt it. Dropbox sits at $3.02; the peers' median is $9.29.
- Share count
- Stock pay and converting notes add shares, so each is a smaller slice. Buybacks do the opposite. Last year Dropbox's share count changed −17.5%.
- The analyst range
- 11 analysts publish a 12-month target, from $23 to $42. It is where Wall Street sits, not where the stock must go.
Growth and valuation hold, and the share count keeps rising at last year's rate. This lands above the analysts' average of $34.
Your $100,000 grant today would be worth $120,062 in 12 months in this world, before taxes and vesting.
Above $35.35, the $693M of convertible notes can turn into about 20 million new shares, trimming this price by about 10%.
A way to think, not a forecast, and not investment advice.
Guidance supplement, Aug 6, 2026; 8-K, Oct 28, 2026; dilution = Q2 weighted basic shares (224.8M) vs Q2 2025 (272.4M); convert from 10-Q (R62)The signals, and which way they push.
- TailwindPaying users are growing again.
Up 96,000 in Q2 2026, a third straight quarter of growth, to 18.19M. Teams licenses grew too, after pricing and onboarding changes.
- TailwindVirtual First is staying.
The incoming CEO is keeping the remote-by-default model, per a Sep 2026 interview. Dropbox says applications per role are 7x pre-2020 levels and attrition is its lowest ever.
- HeadwindRevenue is still flat.
2026 guidance is $2.513B to $2.523B, against $2.521B in 2025. ARPU is expected to dip each quarter for the rest of the year.
- HeadwindGiants bundle storage for less.
The 10-K names Microsoft, Google, Apple and Amazon in storage, Glean and Notion in AI search, and cites cheaper or bundled products as a reason growth slowed.
- HeadwindDebt costs are rising.
Q2 net interest expense was $50.0M, up from $18.6M, and cut operating cash flow by about $30M after tax.
Where Dropbox ends up, if we had to bet.
Our calls, not facts. Each one is tied to something that already happened, so you can judge the reasoning.
- 1
Dropbox is still remote by default in 2031.
Likely 72%Work modelThe incoming CEO has publicly kept Virtual First, and the company has spent years exiting office space, including part of its San Francisco headquarters lease. It also credits the model with record-low attrition.
UNLEASH interview, Sep 22, 2026; 10-K FY2025 - 2
Dropbox employs fewer than 2,000 people in 2031.
Likely 72%JobsIt had 2,113 at the end of 2025 and cut about 9% more in October 2026. Management expects AI-assisted teams to build more with fewer people.
8-K, Oct 28, 2026; 10-K FY2025 - 3
Dropbox is taken private or sold by 2033.
Coin flip 50%M&AIt throws off about $1B of cash a year with flat revenue, the classic buyout profile. Houston's roughly 81% vote means nothing happens without him.
10-K FY2025; Q2 2026 guidance supplement - 4
By 2032 Dropbox earns meaningful revenue as a content layer that AI companies build on.
Coin flip 50%AIManagement now pitches exactly this and points to 150K+ users of its Claude and ChatGPT integrations. It has disclosed no revenue from it yet.
Q2 2026 prepared remarks - 5
Revenue grows more than 5% a year by 2031.
Long shot 16%Competition2026 guidance implies about 0.5% growth, and ex-FormSwift constant currency growth was 0.1% in Q2. Bundled storage from Microsoft, Google and Apple keeps pressure on price.
Q3 and FY2026 guidance supplement; Q2 2026 remarks
Read by the Still Remote research agent on November 4, 2026 from the sources linked on this page. Facts and scenarios only, not investment advice.