# Twilio Inc. (TWLO)

> Source: Nexqual · https://nexqual.com/TWLO · data as of 2026-10-22 20:00 UTC · cite as "Nexqual, Twilio Inc. (TWLO), nexqual.com/TWLO" · informational, not investment advice.

**Price:** USD 253.63 (-4.89% on the day) · last close of Oct 22, 2026; US market pre market, not a live price. Prev close 266.68 · day 251–268.21 · 52w 105–308.4 · market cap $39.0B · NYQ

## Key facts
- Last four reported quarters (through Jun 30, 2026): revenue $5.57B, net income $1.15B (20.6% margin) (SEC filings).
- Valuation: P/E 33.9x (avg 671.8x at the last 1 fiscal year-ends), EV/EBITDA 90.8x, net cash $1.66B.
- Earnings quality: non-operating income -$117M vs operating income $290M over the last four quarters; P/E excluding non-operating income ≈30.8x (estimate: non-operating income taxed at the company's 0% effective rate).
- 2 of 80 tracked superinvestors hold TWLO (13F, Q2 2026): 1 new, 1 added, 0 reduced, 0 unchanged.
- Insider open-market sales, last ~7 months: 21 Form 4 filings, $481M; 9 not under a Rule 10b5-1 plan ($450M); 0 by opportunistic insiders, 14 by routine insiders (three-year test, Cohen, Malloy & Pomorski 2012).
- Analysts: Buy (mean 2.10 on a 1–5 scale) (31 analysts), mean target USD 272.37 (range 165–335).
- Total return with dividends: 1Y +128.9% vs S&P 500 +14.9%; 5Y -29.2% vs S&P 500 +80.3%.
- Next earnings: 2026-10-29, EPS estimate USD 1.47, revenue estimate $1.51B.

## Financials (SEC 10-K; TTM = last four 10-Q/10-K quarters)
| USD | FY2021 | FY2022 | FY2023 | FY2024 | FY2025 | TTM |
|---|---|---|---|---|---|---|
| Revenue | $2.84B | $3.83B | $4.15B | $4.46B | $5.07B | $5.57B |
| Gross profit | $1.39B | $1.81B | $2.04B | $2.28B | $2.48B | — |
| Operating income | -$916M | -$1.21B | -$877M | -$53.7M | $158M | $290M |
| Net income | -$950M | -$1.26B | -$1.02B | -$109M | $33.8M | $1.15B |
| EPS (diluted) | -$5.45 | -$6.86 | -$5.54 | -$0.66 | $0.21 | — |
| Free cash flow | -$104M | — | — | — | — | — |
| Gross margin | 48.9% | 47.4% | 49.2% | 51.1% | 48.9% | — |
| Operating margin | -32.2% | -31.5% | -21.1% | -1.2% | 3.1% | 5.2% |
| Net margin | -33.4% | -32.8% | -24.4% | -2.5% | 0.7% | 20.6% |
| Revenue growth | +61.3% | +34.6% | +8.6% | +7.3% | +13.7% | — |
| Cash + short-term investments | $5.36B | $4.16B | $4.01B | $2.38B | $2.47B | — |
| Total debt | $986M | $987M | $989M | $991M | $992M | — |
Fiscal years end Dec. EPS is split-adjusted.

## Valuation (price ÷ last four quarters, through Jun 30, 2026)
P/E 33.9x · P/E ex non-operating (est.) ≈30.8x · P/S 7.0x · EV/EBITDA 90.8x · EV/Sales 6.7x · P/B 4.3x · Earnings yield 2.95% · Buyback yield (TTM) 2.23% · Net cash $1.66B · EV $37.3B
P/E at fiscal year-ends: Dec 2025 671.8x.

## Superinvestors (SEC 13F-HR, Q2 2026)
2 of 80 tracked investors hold TWLO. Each row is the investor's latest 13F; change is vs their prior-quarter share count.
| Investor | Firm | % of portfolio | Value | Change |
|---|---|---|---|---|
| Henry Ellenbogen | Durable Capital Partners | 3.70% | $381M | New position |
| Polen Capital | Polen Capital Management | 0.01% | $1.1M | Added +105.8% |

## Insider sales (SEC Form 4, open-market, last ~7 months)
12 of 21 under a Rule 10b5-1 trading plan (scheduled in advance). Unplanned sales were timed by the insider.
| Trade date | Insider | Role | Shares | Value | % of holdings sold | 10b5-1 plan | Insider type |
|---|---|---|---|---|---|---|---|
| 2026-10-05 | Shipchandler Khozema | Chief Executive Officer | 14,442 | $4.2M | 7.5% | Yes | Routine (sold in Jan & Jun & Oct each year 2023–2025) |
| 2026-09-30 | Viggiano Aidan | Chief Financial Officer | 9,084 | $2.7M | 8.4% | No | Routine (sold in May & Jun & Jul & Aug & Oct & Nov each year 2023–2025; this trade is outside those months) |
| 2026-09-30 | Shipchandler Khozema | Chief Executive Officer | 13,898 | $4.1M | 6.7% | No | Routine (sold in Jan & Jun & Oct each year 2023–2025; this trade is outside those months) |
| 2026-08-17 | Viggiano Aidan | Chief Financial Officer | 1,394 | $327K | 1.3% | No | Routine (sold in May & Jun & Jul & Aug & Oct & Nov each year 2023–2025) |
| 2026-08-12 | Stafman Andrew | Director | 500,000 | $124M | 78.9% | No | Too little history (no open-market trades in 2023 or 2024) |
| 2026-08-10 | Rottenberg Erika | Director | 3,500 | $881K | 11.1% | Yes | Too little history (no open-market trades in 2023 or 2024) |
| 2026-07-06 | Shipchandler Khozema | Chief Executive Officer | 14,458 | $3.0M | 6.5% | Yes | Routine (sold in Jan & Jun & Oct each year 2023–2025; this trade is outside those months) |
| 2026-07-02 | Viggiano Aidan | Chief Financial Officer | 8,528 | $1.8M | 7.2% | Yes | Routine (sold in May & Jun & Jul & Aug & Oct & Nov each year 2023–2025) |
| 2026-06-30 | Viggiano Aidan | Chief Financial Officer | 9,093 | $1.8M | 7.1% | No | Routine (sold in May & Jun & Jul & Aug & Oct & Nov each year 2023–2025) |
| 2026-06-30 | Shipchandler Khozema | Chief Executive Officer | 13,881 | $2.8M | 5.9% | No | Routine (sold in Jan & Jun & Oct each year 2023–2025) |
| 2026-06-04 | Shipchandler Khozema | Chief Executive Officer | 44,158 | $10.4M | 15.8% | Yes | Routine (sold in Jan & Jun & Oct each year 2023–2025) |
| 2026-06-01 | Rottenberg Erika | Director | 2,000 | $398K | 6.1% | Yes | Too little history (no open-market trades in 2023 or 2024) |
| 2026-05-27 | Stafman Andrew | Director | 1,000,000 | $184M | 61.2% | No | Too little history (no open-market trades in 2023 or 2024) |
| 2026-05-26 | Shipchandler Khozema | Chief Executive Officer | 32,158 | $6.0M | 12% | Yes | Routine (sold in Jan & Jun & Oct each year 2023–2025; this trade is outside those months) |
| 2026-05-19 | Viggiano Aidan | Chief Financial Officer | 1,828 | $366K | 1.4% | Yes | Routine (sold in May & Jun & Jul & Aug & Oct & Nov each year 2023–2025) |
| 2026-05-15 | Viggiano Aidan | Chief Financial Officer | 1,376 | $272K | 1.1% | No | Routine (sold in May & Jun & Jul & Aug & Oct & Nov each year 2023–2025) |
| 2026-05-12 | Stafman Andrew | Director | 675,000 | $131M | 29.2% | No | Too little history (no open-market trades in 2023 or 2024) |
| 2026-05-04 | Rottenberg Erika | Director | 1,500 | $278K | 4.3% | Yes | Too little history (no open-market trades in 2023 or 2024) |
| 2026-04-21 | Rottenberg Erika | Director | 1,800 | $268K | 5% | Yes | Too little history (no open-market trades in 2023 or 2024) |
| 2026-04-06 | Shipchandler Khozema | Chief Executive Officer | 15,715 | $2.1M | 6.3% | Yes | Routine (sold in Jan & Jun & Oct each year 2023–2025; this trade is outside those months) |
% of holdings sold = shares sold ÷ (shares sold + all holdings the insider reported on that Form 4, direct and through trusts).
Insider type follows Cohen, Malloy & Pomorski (Journal of Finance, 2012). An insider who traded the stock in the same calendar month in each of the past three years is a routine trader; one who traded in each of those years without such a pattern is an opportunistic trader. In their study, trades by opportunistic insiders predicted future returns and trades by routine insiders did not. Counts open-market purchases and sales only (SEC Form 4 codes P and S) by that insider in that company. Not investment advice.

## Analysts
Consensus Buy (mean 2.10 on a 1–5 scale), 31 analysts; mean target USD 272.37 (low 165, high 335).
Rating changes, last 120 days:
| Date | Firm | Action | Rating | Price target |
|---|---|---|---|---|
| 2026-10-21 | Oppenheimer | Target raised | Outperform | $275 → $325 |
| 2026-10-16 | BTIG | Target raised | Buy | $285 → $315 |
| 2026-10-14 | B of A Securities | Target raised | Buy | $270 → $320 |
| 2026-10-08 | JP Morgan | Target raised | Overweight | $260 → $335 |
| 2026-09-25 | HSBC | Downgrade | Hold → Reduce | $211 |
| 2026-09-22 | TD Cowen | Target raised | Buy | $260 → $300 |
| 2026-09-22 | Rosenblatt | Target raised | Buy | $275 → $290 |
| 2026-09-11 | BTIG | Reiterated | Buy | $285 |
| 2026-08-27 | Citizens | Reiterated | Market Outperform | $275 |
| 2026-08-08 | UBS | Target raised | Buy | $200 → $285 |
| 2026-08-07 | TD Cowen | Target raised | Buy | $245 → $260 |
| 2026-08-07 | Piper Sandler | Target raised | Neutral | $192 → $247 |

## Total return (dividends reinvested)
|  | 1Y (from 2025-10-23) | 5Y (from 2021-10-18) |
|---|---|---|
| Total return | +128.9% | -29.2% |
| S&P 500 (SPY) | +14.9% | +80.3% |
| Per year | +129.5% | -6.7% |
| Volatility (annualized) | 61.8% | 62.8% |
| Max drawdown | -24.7% (Dec 2025→Feb 2026) | -88.1% (Oct 2021→Oct 2022) |

## Peers (Software - Infrastructure)
NTAP (NetApp, Inc.) USD 212.51 -2.16% · ZS (Zscaler, Inc.) USD 237.76 +2.78% · OKTA (Okta, Inc.) USD 201.33 -3.50% · XYZ (Block, Inc.) USD 79.02 +1.04% · CRWV (CoreWeave, Inc.) USD 55.6 -10.06% · MDB (MongoDB, Inc.) USD 362.24 -7.30%

## More
Full page: https://nexqual.com/TWLO · Free keyless MCP server with the same data and citations: https://mcp.nexqual.com/mcp · Guide for agents: https://nexqual.com/agents · https://nexqual.com/llms.txt

## Supply chain and relationships (SEC annual reports)

Named in TWLO's own 10-K filed 2026-02-24 (https://www.sec.gov/Archives/edgar/data/1447669/000144766926000021/twlo-20251231.htm):

| Relationship | Company | Sentence in the filing |
|---|---|---|
| Customer | Amazon (AMZN) | "or that of AWS, is compromised, if our products, platform or customer data become unavailable, or if our users are unable to use our products within a reasonable amount of time or at all, any one of which may be due to c…" |
| Customer | Zipwhip | "Our Dollar-Based Net Expansion Rate compares the total revenue from all Active Customer Accounts and customer accounts from Zipwhip in a quarter to the same quarter in the prior year." |

## Revenue by business segment (quarter ended 2025-06-30)

| Line | Revenue | Share | YoY |
|---|---|---|---|
| Communications | $1.15B | 93.9% | +14.5% |
| Twilio | $75.5M | 6.1% | +0.4% |
| Total revenue | $1.23B | 100% | — |

## Revenue by product line (fiscal year ended 2025-12-31)

| Line | Revenue | Share | YoY |
|---|---|---|---|
| Messaging | $2.88B | 56.8% | +18.2% |
| Other Communications | $746.5M | 14.7% | +7.6% |
| Programmable Voice | $615.7M | 12.1% | +13.4% |
| Email | $523.5M | 10.3% | +7.2% |
|  | $303.3M | 6.0% | +1.9% |
| Total revenue | $5.07B | 100% | — |

## Revenue by region (quarter ended 2026-06-30)

| Line | Revenue | Share | YoY |
|---|---|---|---|
| United States | $961.4M | 64.1% | +22.2% |
| International | $537.7M | 35.9% | +21.8% |
| Total revenue | $1.50B | 100% | — |

## Company outlook (8-K filed 2026-08-06)

- "Lastly, Twilio expects third quarter non-GAAP diluted earnings per share in a range of $1.42 to $1.47, based on non-GAAP weighted average diluted shares outstanding of 160 million."
- "Dollars in millions FY26 Guidance Y/Y Revenue Growth 18% - 18.5% Y/Y Organic Revenue Growth 13% - 13.5% Non-GAAP income from operations $1,135 - $1,155 Free cash flow $1,135 - $1,155 2 Conference Call Information Twilio is hosting a Q&A conference call today, August 6, 2026, to discuss its second quarter 2026 financial results."

## Analyst estimates and revisions

| Period | EPS est. | 90d ago | Change | Revenue est. | Analysts |
|---|---|---|---|---|---|
| Current quarter (ends 2026-09-30) | $1.47 | $1.40 | +4.9% | $1.51B | 26 |
| Next quarter (ends 2026-12-31) | $1.48 | $1.50 | -0.9% | $1.58B | 25 |
| Current fiscal year (ends 2026-12-31) | $5.93 | $5.71 | +3.9% | $6.00B | 29 |
| Next fiscal year (ends 2027-12-31) | $6.80 | $6.65 | +2.3% | $6.70B | 31 |

## Options: expected move (Cboe, 15-min delayed)

Expected move by 2026-10-30 (includes earnings 2026-10-29): ±15.4%; last 8 reports averaged ±17.5%.

| Expiration | Days | ATM IV | Expected move |
|---|---|---|---|
| 2026-10-30 | 7 | 130.8% | ±15.4% |
| 2026-11-06 | 14 | 105.2% | ±17.0% |
| 2026-11-13 | 21 | 92.7% | ±18.1% |
| 2026-11-20 | 28 | 84.1% | ±18.8% |
| 2026-11-27 | 35 | 78.1% | ±19.5% |
| 2026-12-04 | 42 | 75.4% | ±20.5% |
| 2026-12-18 | 56 | 72.8% | ±22.6% |
| 2027-01-15 | 84 | 67.6% | ±25.6% |