
LRN$85.59▲ 5.2%Fivespan held 1.3% of Stride in June. Into 2027, Stride can't end its committee without it
Stride settled with investor Fivespan Partners on Oct. 8, it said, naming Fivespan's founder co-chair of a new committee on how Stride uses its money. The filings show how much money, and what Fivespan gave up.
KeyVex News··6 min readFact-checked against 13 public records
KeyVex News··6 min readFact-checked against 13 public records
LRN$85.59▲ 5.2%Close, Oct. 9. Prices from Tiingo.The short versionTap to readTap to close
- On Sept. 1, Fivespan Partners, an investment firm, told Stride it would nominate directors of its own, setting up a possible contested vote at the 2026 annual meeting.
- Instead, the two sides settled on Oct. 8. Fivespan's founder, Dylan Haggart, joins the board on Oct. 30 and will co-chair a new committee on how Stride uses its money.
- That money is about $1 billion in cash and investments at June 30, about 29% of what all of Stride's shares were worth on Oct. 9, by KeyVex's math.
- In August, Stride's finance chief put growth first, then acquisitions, then returning excess capital when Stride believes it creates long-term value. Stride's filings don't say what Fivespan proposed.
- Stride expects the committee's first review within three months. It says it will then publish its "target capital structure" and a framework for using future cash.
The settlement: Stride, the online-schooling company once called K12, agreed on Oct. 8 to put Dylan Haggart on its board, it said in a filing before the market opened on Oct. 9.8-K Haggart founded the investment firm Fivespan Partners in 2023 after a decade as a partner at ValueAct Capital.Release In return, Fivespan withdrew its director nominations, a shareholder proposal and a demand to inspect Stride's books.Agreement The filings don't say what the proposal was.8-K
The money: Haggart will co-chair a new Capital Allocation Committee, which recommends to the board how Stride should be financed and what it does with its cash.8-K While the agreement lasts, into 2027, the committee can't be disbanded or have its powers cut without the written consent of both sides.Agreement At June 30, Stride had $1.03 billion in cash and investments.Results It also owes $420 million on convertible notes due in September 2027. Holders can convert them under certain conditions, but Stride says it will pay cash up to that $420 million.10-K
Why it matters: Fivespan held about 1.3% of Stride's stock in June, its latest public holdings report shows.13F From Oct. 30, its founder co-chairs the committee that will recommend what Stride does with cash worth about 29% of its stock market value at the Oct. 9 close, by KeyVex's math. Net of the $420 million in notes, it is about 17%.Chart data
Stride's stock since October 2025Daily close, Oct. 1, 2025 to Oct. 9, 2026 ▼ 40.8%Show chartHide chart
How much money, and where it went last year
Stride earned $338.2 million in the year to June 30, yet its cash and investments ended the year about where they began.Results Its operations brought in $433.8 million of cash. It spent $78.8 million on equipment, software and curriculum, leaving what the company calls free cash flow of about $355 million.10-KCall The largest single use of the rest was its own stock: $188.7 million for 2.3 million shares.10-K
Stride bought $88.6 million of stock in the last three months of 2025, none from January through March, and $100.0 million in May and June.10-Q10-Q10-K At June 30, $311.3 million of the authorization was left. In August, Stride extended it to Oct. 31, 2027.8-K
View the data
| Amount, millions of dollars | Note | |
|---|---|---|
| Stride's stock market value (41,559,845 shares at the Oct. 9 close of $85.59) | $3,557.1M | $3,557,107,134 by KeyVex's math; share count as of July 31, 2026 (10-K cover) |
| Cash, cash equivalents and marketable securities (June 30, 2026) | $1,034.1M | $1,034.1 million (fiscal 2026 results release) |
| Convertible notes due Sept. 1, 2027 (Principal outstanding) | $420.0M | $420.0 million, 1.125% Convertible Senior Notes due 2027 (10-K, Note 7) |
| Buyback authority left (June 30, 2026; runs through Oct. 31, 2027) | $311.3M | $311.3 million (Aug. 4, 2026 Form 8-K, Item 8.01) |
| Stock bought back in fiscal 2026 (2,314,944 shares, July 2025 to June 2026) | $188.7M | $188.7 million at an average $81.50 a share (10-K, Note 10) |
Cash, cash equivalents and marketable securities, as Stride reports them. Sources: Stride Form 10-K and fiscal 2026 results release; Form 8-K of Aug. 4, 2026; Tiingo close via KeyVex.
Stride's stock buybacks by quarter, fiscal 2026Show chartHide chart
View the data
| Quarter | Stock repurchased, millions of dollars | Note |
|---|---|---|
| Oct.-Dec. 2025 | $88.6M | 1,272,790 shares at an average $69.65 (10-Q for Dec. 31, 2025); $500 million authorized less $411.4 million left |
| Jan.-Mar. 2026 | $0.0M | No shares repurchased (10-Q for March 31, 2026) |
| Apr.-June 2026 | $100.0M | 1,042,154 shares: 331,205 in May at $91.87 and 710,949 in June at $97.88 (10-K, Item 5); $411.4 million left fell to $311.3 million |
Stride has not yet reported any buybacks after June 30, 2026. Sources: Stride Forms 10-Q for Dec. 31, 2025 and March 31, 2026; Form 10-K for June 30, 2026.
What management has said comes first
Stride's stock lost 54% on Oct. 29, 2025, the day after its quarterly report.Chart data On Nov. 3, its board authorized a $500 million buyback.8-K On July 29, 2026, chief executive James Rhyu left, and director Robert Knowling took his place.8-K
On the August earnings call, finance chief Donna Blackman said Stride's priorities "remain unchanged." She said Stride would invest first in growing its existing business, then "evaluate strategic acquisitions," then return excess capital when it believes that creates long-term value. That is according to a transcript published by The Motley Fool.Call Knowling said that once Stride's trading window, the period when insiders may trade, opens at the end of October, he intends "to actively consider opportunistic stock repurchases," the transcript shows.Call
How Fivespan pressed Stride
The settlement lists what Fivespan had sent. On Sept. 1 it gave notice that it would nominate directors and put a proposal to shareholders at the 2026 meeting. It also said it would seek proxies, the right to vote other shareholders' shares.Agreement It added to that notice three times in September. On Sept. 28, its lawyers at White & Case demanded Stride's books and records under Section 220 of Delaware's corporate law, a step shareholders use to look inside a company.Agreement
The filings don't say whom it planned to nominate. Fivespan has not said publicly why it invested in Stride beyond the release, Boardroom Alpha reported.Boardroom Alpha In the release, Haggart said: "We believe in Stride's significant long-term growth potential."Release
What it got
Haggart joins the board at the close of business on Oct. 30, and Stride will nominate him on its own slate at the Dec. 10 annual meeting. Steven Guttentag, a former head of EPS Learning and co-founder of Connections Education, becomes a director after that meeting and attends meetings as a non-voting observer until then.8-KRelease Haggart takes the seat of director Allison Lawrence, who becomes a non-voting observer and rejoins the board after the meeting. The board then grows from eight seats to ten.8-K
The new committee has three voting members: Haggart, director Brian Shepherd, who joined the board in July, and director Aida Alvarez. Knowling sits on it without a vote.8-K Stride says it will ask shareholders for their views on how to use its capital.Release Stride also agreed to repay Fivespan's costs, including preparing for a possible proxy fight, up to a cap the filing does not disclose.Agreement The clause on the committee reads in full:Agreement
The Capital Allocation Committee shall not be disbanded or have its responsibilities or authorities curtailed during the term of this Agreement without the mutual written consent of the Investor Group and the Company.
What Fivespan gave up
Until 30 days before the deadline for nominating directors for the 2027 meeting, Fivespan may not beneficially own more than 7.5% of Stride's stock. It must vote its shares for the board's director picks and most other board recommendations, and the two sides may not publicly criticize each other.Agreement
Fivespan gets the right to name a replacement if Haggart or Guttentag leaves, but only if it has held at least 1,038,995 shares the whole time. That is about 2.5% of Stride's shares, by KeyVex's math.Agreement10-K Fivespan's latest public holdings report, for June 30, listed 553,151 Stride shares, its first Stride position. The floor is almost twice that.13F The copy of the agreement Stride filed leaves out how many shares Fivespan owns now.Agreement
Haggart takes his seat at the close of business on Oct. 30.8-K Stride expects the committee's first review within three months. It says it will then publish "a clear framework for allocating future cash flows."Release
What to watch
Haggart joins Stride's board, and the Capital Allocation Committee takes effect, at the close of business.
Stride's trading window opens, when Knowling said in August he would consider buybacks.
Stride's 2026 annual meeting. Fivespan must vote with the board on directors.
The committee's first review, "expected to occur within the next three months," Stride said Oct. 9.
Stride's $420 million convertible notes mature.
The buyback authorization expires.
The paper trail
Selected Stride filings, Oct. 28, 2025 through Oct. 9, 2026, and Fivespan's June 30 holdings report, with the time EDGAR accepted each one (Eastern).
| Filed (ET) | Form | Filer | What it shows |
|---|---|---|---|
| Oct. 28, 2025, 4:15 p.m. | 8-K | Stride | Fiscal first-quarter results. |
| Nov. 3, 2025, 9:08 a.m. | 8-K | Stride | A $500 million buyback, through Oct. 31, 2026. |
| July 30, 2026, 8:10 a.m. | 8-K | Stride | Rhyu leaves; Knowling is CEO; Shepherd joins the board; preliminary fiscal 2026 results. |
| Aug. 4, 2026, 4:17 p.m. | 8-K | Stride | Fiscal 2026 results; the buyback is extended through Oct. 31, 2027, with $311.3 million left. |
| Aug. 4, 2026, 5:36 p.m. | 10-K | Stride | Annual report: $188.7 million of buybacks; $420 million of convertible notes due 2027. |
| Aug. 13, 2026, 11:00 a.m. | 13F-HR | Fivespan Partners | 553,151 Stride shares at June 30, 2026. |
| Oct. 9, 2026, 8:11 a.m. | 8-K | Stride | The cooperation agreement with Fivespan; Haggart and Guttentag to join the board; the Capital Allocation Committee. |
Sources
17 sources, 13 of them public records
Public records
- Stride, Inc., Form 8-K (Items 1.01, 5.02, 7.01): Cooperation Agreement with Fivespan PartnersSEC EDGAR · Oct. 9, 2026
- Exhibit 10.1: Cooperation Agreement among Stride and the Fivespan investor group, Oct. 8, 2026SEC EDGAR · Oct. 9, 2026
- Exhibit 99.1: Stride release on the board appointments and Capital Allocation CommitteeSEC EDGAR · Oct. 9, 2026
- Fivespan Partners, LP, Form 13F-HR for the quarter ended June 30, 2026SEC EDGAR · Aug. 13, 2026
- Stride, Inc., Form 10-K for the fiscal year ended June 30, 2026SEC EDGAR · Aug. 5, 2026
- Stride, Inc., Form 8-K (Items 2.02, 8.01): fiscal 2026 results and buyback extensionSEC EDGAR · Aug. 4, 2026
- Exhibit 99.1: Stride fiscal 2026 results releaseSEC EDGAR · Aug. 4, 2026
- Stride, Inc., Form 8-K (Items 2.02, 5.02, 7.01): CEO successionSEC EDGAR · July 30, 2026
- Exhibit 99.1: Stride release on its CEO succession and preliminary fiscal 2026 resultsSEC EDGAR · July 30, 2026
- Stride, Inc., Form 10-Q for the quarter ended March 31, 2026SEC EDGAR · April 29, 2026
- Stride, Inc., Form 10-Q for the quarter ended Dec. 31, 2025SEC EDGAR · Jan. 28, 2026
- Stride, Inc., Form 8-K (Items 7.01, 8.01): $500 million stock repurchase programSEC EDGAR · Nov. 3, 2025
- Stride, Inc., Form 8-K (Item 2.02): fiscal first-quarter 2026 resultsSEC EDGAR · Oct. 28, 2025
Reporting
- Stride (LRN) Q4 2026 earnings call transcriptThe Motley Fool · Aug. 11, 2026
- Stride settles with activist Fivespan, adding its founder to the boardBoardroom Alpha · Oct. 12, 2026
Data
- End-of-day prices for LRN, and for SPY and QQQ on the chart (Tiingo)KeyVex · through Oct. 9, 2026
- The chart's Filings layer: KeyVex's Congress trade, insider trade, Form 144, 8-K and lobbying records for LRNKeyVex · through Oct. 9, 2026
How we got these numbers
- Prices are end-of-day closes as traded, not adjusted for dividends (Stride pays none). Daily moves are close to close. Every Stride close in the chart's Story range is in its data table. The S&P 500 and Nasdaq 100 lines follow SPY and QQQ, also as traded, rebased to Stride's close at the start of the range shown. The Filings switch shows the filing markers from KeyVex's Stride stock page, a selection of congressional trades, insider sales, Form 144 notices, 8-Ks and lobbying filings: not every filing, and not only those tied to this story.
- KeyVex's math: Stride's stock market value at the Oct. 9 close is 41,559,845 shares (outstanding at July 31, 2026, the latest count in its filings) times $85.59, $3,557,107,134. Its $1,034.1 million in cash, cash equivalents and marketable securities at June 30 is 29.1% of that. The comparison sets a June balance beside an October price; Stride has not reported its cash since June 30.
- Fivespan's share of Stride: 553,151 shares in its 13F for June 30, 2026, divided by 41,477,230 shares outstanding at June 30 (10-K balance sheet), 1.33%. The replacement-rights floor: 1,038,995 shares divided by 41,559,845, 2.50%. The 13F is Fivespan's latest public holdings report; the agreement's schedule of its current holdings was omitted from the public filing.
- Buybacks by quarter: October to December 2025 is the $500 million authorized less the $411.4 million left at Dec. 31, 2025 (1,272,790 shares at an average $69.65). April to June 2026 is $411,354,533 left at April 30 less $311,341,375 left at June 30, $100,013,158. Free cash flow is Stride's own measure: cash from operations, $433.8 million, less capital expenditures, $78.8 million.
- Net of the notes: $1,034.1 million less the $420.0 million principal of the 2027 convertible notes is $614.1 million, 17.3% of the $3,557.1 million market value. Stride settles conversions in cash up to the principal (10-K, Note 7). "Into 2027": the agreement, and with it the committee's protection, runs until 30 days before the deadline for nominating directors for the 2027 annual meeting (Cooperation Agreement, Sections 2(c) and 18); Boardroom Alpha calculates that date as about Aug. 12, 2027.
- Cash and investments "about where they began": $1,011.4 million at June 30, 2025 and $1,034.1 million at June 30, 2026, as Stride reports them. Fiscal 2026 net income was $338.2 million.




