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Upland Software, Inc. Stock: price and insider trades · United States
No insider purchase over the last 90 days. The latest, by MCDONALD JOHN T, was filed 12 Aug 2024.
Upland Software, Inc.: what insiders have been doing
This page follows insider dealings at Upland Software, Inc. as filed with SEC (Form 4), a company from the Technology sector. 11 insiders have disclosed 31 filings since 18 October 2025.
No insider bought on the market over the period, while 1 insider filed 6 sales totalling €22k. The largest single trade was a sale of €3,928 by Mattox Timothy, published on 6 August 2026, equal to 0.043% of the market capitalisation.
For context, the typical company on the same exchange (median of 5,811 companies) published 19 filings over the same period, against 31 filings here. Since 2016, the database holds 20 purchases and 22 sales by insiders of the company. The 10-K for the year ended 31 December 2025 shows 216.9 m USD of revenue and -38.9 m USD of net income.
Between a trade and the moment it shows up on SEC (Form 4), the median delay is 2 days. The legal deadline for a Form 4 is two business days after the transaction. Sales are harder to read than purchases, since they often meet personal needs such as tax or diversification.
For comparison within the same sector, see the insider buying recorded at Core Scientific, Inc./tx and Gitlab Inc. Every figure here comes from the filings published by SEC (Form 4) and describes the past, not future prices; it is not investment advice.
Insider Decl.
205
Thresholds
n/a
Buy Volume
€763,376
20 ops. · all time
Sell Volume
€2M
22 ops. · all time
Who traded when
BuySaleTimothy Mattox9 sales
John T. Mcdonald1 sale
Since the insiders bought
- -7.8%Entry US$20.50 · Close at T+365 US$18.90
- +72.0%Entry US$69.70 · Close at T+365 US$119.90
Entry is the close on the day after publication, the first price a reader could act on. Prices in the listing currency. Past moves are not a forecast.
This score ranks the purchase within its own market. A position size is suggested only on the venues of the backtested strategy universe; elsewhere, signals stay on watch. Not investment advice.
Fundamental score
Ranked 20,605 of 23,476 companies
24.4
score / 100
Value14
Quality35
FCF yld·
Earn yld·
EV/EBITDA26.5x
ROE-58%
Gross mgn75%
Net mgn-21%
Debt/EBITDA·
Pillars2/3
Transparent value + quality ranking, distinct from the insider signal.
Financial data
as of FY 2025FY ended December 2025 · cache
US$3.12
Analyst consensus
2 analysts1.50/5
US$10.00Target US$12.50(+301%)US$15.00
Income statement
RevenueUS$216.9M
Gross profitUS$162.1M75% margin
EBITDAUS$9.3M4% margin
Net income-US$44.8M-18.5% margin
Valuation
PER (forward)0.5x
Beta1.43
Balance sheet & cash
Market capUS$9.2M
Total debtUS$235.2M
Free Cash FlowUS$24.4M
Debt / Equity534%
Profitability & ownership
ROE-58.0%
ROA3.8%
% insiders30.0%
% institutions33.4%
Last declaration on 21 September 2026
Declarations205 total
1,117 shares@ US$3.9450.042% mcap100.0% of flowCommon StockSEC:0002147950-26-000008:0
1,640 shares@ US$3.9450.061% mcap100.0% of flowCommon StockSEC:0001870221-26-000013:0
30,000 shares0Common StockSEC:0002147950-26-000005:0
847.4 shares@ US$4.28010.034% mcap3.2% of flowCommon StockSEC:0001624067-26-000008:0
1,000 shares@ US$4.270.040% mcap3.8% of flowCommon StockSEC:0001624067-26-000006:0
848 shares@ US$4.28010.034% mcap14.1% of flowCommonSEC144:0001950047-26-007778
1,000 shares@ US$4.270.040% mcap16.6% of flowCommonSEC144:0001950047-26-007723
1,000 shares@ US$4.330.041% mcap3.8% of flowCommon StockSEC:0001624067-26-000004:0
1,000 shares@ US$4.530.043% mcap4.0% of flowCommon StockSEC:0001624067-26-000004:1
1,000 shares@ US$4.530.043% mcap17.6% of flowCommonSEC144:0001950047-26-007677
1,000 shares@ US$4.330.041% mcap16.9% of flowCommonSEC144:0001950047-26-007617
1,000 shares@ US$4.480.042% mcap4.0% of flowCommon StockSEC:0001624067-26-000002:0
1,000 shares@ US$4.450.042% mcap3.9% of flowCommon StockSEC:0001624067-26-000002:1
1,000 shares@ US$4.450.042% mcap17.3% of flowCommonSEC144:0001950047-26-007495
1,000 shares@ US$4.480.042% mcap17.5% of flowCommonSEC144:0001950047-26-007456
8,931 shares@ US$0.540.4% of flowCommon StockSEC:0001289889-26-000004:0
18,605 shares@ US$0.540.3% of flowCommon StockSEC:0001094792-26-000002:0
70,000 shares0Common StockSEC:0001289889-26-000002:0
8,856 shares@ US$1.4851.0% of flowCommon StockSEC:0001289889-25-000005:0
25 of 205 declarations
About Upland Software, Inc.
Upland Software, Inc. is a U.S.-based software company listed on the Nasdaq stock market in the United States, with headquarters in Austin, Texas. The company has been built through a long-running acquisition strategy, assembling a portfolio of cloud software assets that are designed to improve enterprise productivity, knowledge access, customer support workflows, and document-centric operations. In its recent communications, Upland describes itself as a leader in AI-powered knowledge and content management software, positioning the company around enterprise search, knowledge delivery, proposal management, and related workflow automation use cases. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/New-Upland-BA-Insight-Platform-Delivers-Integrated-AI-Search-Experiences-for-Enterprises/default.aspx?utm_source=openai))
Upland was founded in 2010 by Jack McDonald. Since then, its growth model has relied heavily on acquiring complementary software businesses and integrating them into a broader B2B platform. That strategy has shaped Upland’s market identity: it is not a single-product vendor, but rather a roll-up style software operator with multiple niche offerings that address specific operational pain points inside large organizations. In 2026, Jack McDonald stepped down from the CEO role while remaining chairman of the board, marking an important governance transition for the company. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/Upland-Announces-Commencement-of-New-CEO-Tenure-and-Inducement-Awards/default.aspx?utm_source=openai))
Read moreShow less
The company’s core product set spans knowledge management, enterprise search, proposal and RFP automation, customer service enablement, and cloud fax and related communications tools. Key brands include Upland BA Insight, Upland Panviva, Upland RightAnswers, Upland Qvidian, and Upland InterFAX. These offerings help customers organize institutional knowledge, improve access to trusted content, accelerate proposal generation, and support frontline service teams. A major strategic theme in 2025 and 2026 has been the incorporation of AI capabilities, including conversational search and broader AI-enhanced knowledge experiences. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/New-Upland-BA-Insight-Platform-Delivers-Integrated-AI-Search-Experiences-for-Enterprises/default.aspx?utm_source=openai))
From a competitive standpoint, Upland operates in a crowded and fragmented enterprise software landscape, competing with point-solution vendors as well as larger software suites. Its advantage is less about category dominance and more about specialized functionality, vertical relevance, and the ability to cross-sell across a diversified product portfolio. Recent financial disclosures also show a deliberate portfolio rationalization effort: Upland completed divestitures in 2025 to streamline the business and focus on higher-priority areas. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/Upland-Software-Reports-First-Quarter-2026-Financial-Results/default.aspx?utm_source=openai))
Geographically, Upland remains a U.S. company headquartered in Austin, Texas, with an international customer base served from that operating platform. Recent highlights include the launch of a new BA Insight platform with integrated AI search features, repeated recognition in G2 market reports, and a July 2025 debt refinancing that replaced existing borrowings with a new $240 million six-year term loan due in 2031, plus a revolving credit facility. Taken together, these developments suggest a company focused on strengthening balance-sheet flexibility while sharpening its positioning around AI-enabled enterprise knowledge management. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/New-Upland-BA-Insight-Platform-Delivers-Integrated-AI-Search-Experiences-for-Enterprises/default.aspx?utm_source=openai))
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