AI Earnings Predictions for Upland Software Inc. (UPLD)

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EXHIBIT 99.1

Upland Software Reports Third Quarter 2026 Financial Results

Q3 revenue reported above midpoint of guidance; company outlines three-phase plan targeting approximately 35% Adjusted EBITDA margin in the first half of 2028

AUSTIN, Texas--(BUSINESS WIRE)-- Upland Software, Inc. (Nasdaq: UPLD), a leader in AI-powered knowledge and content management software, today announced its financial and operating results for the third quarter 2026, outlined its multi-year strategic plan, and issued guidance for its fourth quarter and full year of 2026.

“Three months after laying out our plan in my shareholder letter, I’m pleased to report that we are executing on it,” said Sean Nathaniel, Upland’s President and Chief Executive Officer. “Our roadmap for this next chapter has three phases: Simplify and Delever, through early 2027; Stabilize and Expand, in 2027; and Grow, in 2028 and beyond, driven by new AI use cases. We have four operational pillars underpinning that plan, including protecting and deepening our customer relationships, winning new logos with emerging AI use cases, scaling our reach through channel partnerships, and expanding margins by reimagining how we operate with AI. As we work through the plan, we are targeting an adjusted EBITDA margin of approximately 35% in the first half of 2028.”

Third Quarter 2026 Financial Highlights

•Total revenue was $47.5 million, a decrease of 6% from $50.5 million in the third quarter of 2025.

•Subscription and support revenue was $45.3 million, a decrease of 5% from $47.7 million in the third quarter of 2025.

•GAAP net loss was $0.5 million compared to a GAAP net loss of $1.1 million in the third quarter of 2025. Non-GAAP net income was $6.4 million, a decrease of 41% from $10.8 million in the third quarter of 2025.

•Adjusted EBITDA was $12.6 million, or 27% of total revenue, compared to $16.0 million, or 32% of total revenue, in the third quarter of 2025.

•GAAP operating cash flow was $2.8 million, compared to GAAP operating cash flow of $6.9 million in the third quarter of 2025. Free cash flow was $2.7 million, compared to free cash flow of $6.7 million in the third quarter of 2025.

•Cash on hand as of the end of the third quarter of 2026 was $28.9 million, and the company’s $30.0 million revolving credit facility remained undrawn.

•Upland repaid $4.2 million of term loan principal in the third quarter of 2026, including $1.5 million of scheduled amortization and $2.7 million of additional payments, bringing year-to-date repayments to $13.1 million. The term loan balance was $225.4 million as of September 30, 2026, down from $238.5 million as of December 31, 2025.

Nathaniel added, “We have already made meaningful progress. We reorganized around three product groupings aligned to our customers, brought in Jennifer Simon as CFO, and added Carahsoft as a channel partner to bring our knowledge management solutions to the public sector. In the third quarter, we delivered revenue above the midpoint of our guidance, improved our adjusted EBITDA margin

sequentially and continued to pay down debt. With HGGC as a long-term sponsor and a healthy balance sheet, we have the foundation to see this plan through and turn our AI advantage into margin expansion and, ultimately, revenue growth.”

Third Quarter Business Highlights and Updates

•We welcomed 77 new customers to Upland in the third quarter, including 10 new major customers. We also expanded relationships with 185 existing customers, 14 of which were major expansions.

•We announced a strategic partnership with Carahsoft Technology Corp., The Trusted Government IT Solutions Provider®. Under the agreement, Carahsoft serves as Upland’s Master Government Aggregator®, making the company’s knowledge management and contact center solutions available to the Public Sector. These products will be available through Carahsoft’s reseller partners and NASA Solutions for Enterprise-Wide Procurement (SEWP) V, The Interlocal Purchasing System (TIPS), National Association of State Procurement Officials (NASPO) ValuePoint, OMNIA Partners, E&I Cooperative Services Contract, and The Quilt contracts. This partnership marks a strategic expansion of Upland's partner network, providing Government organizations with new capabilities to accelerate digital transformation and deliver better service, faster.

•We were recognized in the Gartner® Magic Quadrant™ for Customer Service Knowledge Management Systems, published on July 16, 2026(1). “This research helps customer service and support technology leaders identify KM innovations that enable the transformation of service operations and customer experience.” According to the report, "the CS-KMS market is undergoing a structural shift from passive content repositories to active, AI-driven reasoning layers powered by machine-readable knowledge."

•We earned 43 badges in G2's Fall 2026 market reports, driven by customer reviews

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EXHIBIT 99.1

Upland Software Reports Second Quarter 2026 Financial Results

AUSTIN, Texas--(BUSINESS WIRE)-- Upland Software, Inc. (Nasdaq: UPLD), a leader in AI-powered knowledge and content management software, today announced its financial and operating results for the second quarter 2026 and issued guidance for its third quarter and full year of 2026.

Second Quarter 2026 Financial Highlights

•Total revenue was $49.1 million, a decrease of 8% from $53.4 million in the second quarter of 2025, primarily due to divestitures completed in 2025.

•Subscription and support revenue was $46.2 million, a decrease of 9% from $50.5 million in the second quarter of 2025, primarily due to divestitures completed in 2025.

•GAAP net loss was $35.3 million compared to a GAAP net loss of $13.0 million in the second quarter of 2025, primarily due to a non-cash goodwill impairment recorded in June 2026. Non-GAAP net income was $6.6 million, an increase of 18% from $5.6 million in the second quarter of 2025.

•Adjusted EBITDA was $12.8 million, or 26% of total revenue, compared to $13.6 million, or 25% of total revenue, in the second quarter of 2025.

•GAAP operating cash flow was $5.4 million, compared to GAAP operating cash flow of $3.3 million in the second quarter of 2025. Free cash flow was $5.3 million, compared to free cash flow of $2.7 million in the second quarter of 2025.

•Cash on hand as of the end of the second quarter of 2026 was $31.0 million.

"We are still in the early innings of building the company I described in my shareholder letter issued on July 28, 2026 - one that concentrates capital where we believe we can actually win and turns our AI advantage into both revenue growth and operating margin expansion," said Sean Nathaniel, Upland's President and Chief Executive Officer. "Q2 gave us real proof points along that path. We exceeded the midpoints on both revenue and Adjusted EBITDA, added 81 new customers, and earned notable industry recognitions. While there is more work ahead, like sharpening our operating groups around the areas with the clearest AI land-grab opportunity and deleveraging the balance sheet, the groundwork being laid today is what the next chapter of Upland will be built on."

Second Quarter Business Highlights

•We welcomed 81 new customers to Upland in the second quarter, including 7 new major customers. We also expanded relationships with 200 existing customers, 19 of which were major expansions.

•Upland was recognized in Forrester's "The Knowledge Management Solutions Landscape, Q2 2026," published June 22, 2026. We believe our inclusion in this report showcases the strength of our knowledge management offering, Upland RightAnswers, in a market being reshaped by the shift from human-only to agent-automated knowledge management. The report notes that of the extended use cases Forrester identified, Upland reported a focus on agentic curation automation, knowledge as AI infrastructure, and secure knowledge sharing, reflecting its investment in helping knowledge serve both human users and AI agents alike.

•We earned 43 badges in G2's Summer 2026 market reports, reflecting the real AI impact our solutions deliver for customers. Upland Panviva and Upland RightAnswers, our leading AI-powered knowledge management solutions, earned numerous badges, with Panviva earning 12 across contact center knowledge base, customer self-service, and knowledge management categories. Upland BA Insight, our AI enablement solution, continued to secure recognition from customers, and Upland InterFAX, our AI-enabled cloud fax service, also received several badges, proving ongoing value to customers on their AI journeys.

Business Outlook

For the quarter ending September 30, 2026, Upland expects reported total revenue to be between $45.7 and $48.7 million, including subscription and support revenue between $43.7 and $46.2 million, for a decline in total revenue of 7% at the midpoint from the quarter ended September 30, 2025. This year-over-year revenue decline is primarily due to divestitures completed in 2025. Third quarter 2026 Adjusted EBITDA is expected to be between $11.9 and $13.4 million, which at the midpoint is a decline of 21% from the quarter ended September 30, 2025. Third quarter 2026 Adjusted EBITDA margin is expected to be 27% at the midpoint as compared to the 32% Adjusted EBITDA margin for the quarter ended September 30, 2025.

For the full year ending December 31, 2026, Upland expects reported total revenue to be between $190.1 and $196.1 million, including subscription and support revenue between $180.0 and $185.0 million, for a decline in total revenue of 11% at the midpoint from the year ended December 31, 2025. This year-over-year revenue decline is primarily due to divestitures completed in 2025. Full year 2026 Adjusted EBITDA is expected to be between $49.8 and $52.8 million, which at the midpoint is a decline of 12% from the

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EXHIBIT 99.1

Upland Software Reports First Quarter 2026 Financial Results

AUSTIN, Texas--(BUSINESS WIRE)-- Upland Software, Inc. (Nasdaq: UPLD), a leader in AI-powered knowledge and content management software, today announced its financial and operating results for the first quarter 2026 and issued guidance for its second quarter and full year of 2026.

First Quarter 2026 Financial Highlights

•Total revenue was $48.7 million, a decrease of 24% from $63.7 million in the first quarter of 2025, primarily due to divestitures completed in 2025.

•Subscription and support revenue was $46.1 million, a decrease of 23% from $60.2 million in the first quarter of 2025, primarily due to divestitures completed in 2025.

•GAAP net loss was $1.2 million compared to a GAAP net loss of $25.8 million in the first quarter of 2025. GAAP net loss attributable to common stockholders was $2.7 million compared to GAAP net loss attributable to common stockholders of $27.3 million in the first quarter of 2025. GAAP net loss per share attributable to common stockholders was $0.09 per share, compared to a GAAP net loss per share attributable to common stockholders of $0.97 per share in the first quarter of 2025.

•Adjusted EBITDA was $12.7 million, or 26% of total revenue, compared to $13.1 million, or 21% of total revenue, in the first quarter of 2025.

•GAAP operating cash flow was $5.6 million, compared to GAAP operating cash flow of $8.3 million in the first quarter of 2025. Free cash flow was $5.5 million, compared to free cash flow of $7.9 million in the first quarter of 2025.

•Cash on hand as of the end of the first quarter of 2026 was $29.8 million.

"I am excited to be joining Upland as CEO, and we delivered a solid Q1 — beating our guidance midpoints for total revenue, recurring revenue, and Adjusted EBITDA, while also generating strong free cash flow," said Sean Nathaniel, Upland's Chief Executive Officer. "Our AI-powered knowledge and content management solutions serve as a core intelligence layer for the agentic enterprise, enabling customers to unlock the full value of their knowledge, content, and data as they scale AI and agent-driven operating models."

First Quarter Business Highlights

•We welcomed 107 new customers to Upland in the first quarter, including 7 new major customers. We also expanded relationships with 189 existing customers, 16 of which were major expansions.

•We earned 42 badges in G2’s Spring 2026 market reports, showcasing impactful results and customer value delivered through its products. Upland Panviva and Upland RightAnswers, our leading AI-powered knowledge management solutions, secured many recognitions this season. Upland BA Insight, an AI enablement solution, continued to earn noteworthy badges, while AI-enabled cloud fax service, Upland InterFAX, also received many accolades.

•We announced the new Upland BA Insight Platform – incorporating the product's SmartHub, ConnectivityHub, AutoClassifier, Smart Preview, and Connectors – delivering search experiences that are more connected, more contextual, and more actionable. This launch reinforces our goal of empowering complex organizations with smarter, more integrated search capabilities for both traditional enterprise and next-generation AI environments.

•We launched AI Conversational Search for Upland Panviva Sidekick, a browser-based assistant that transforms how enterprises retrieve knowledge. By combining natural language processing with trusted organizational data, this release solves the critical challenge of balancing AI efficiency with strict regulatory compliance. The tool builds upon an organization's existing, human-approved, compliance-driven knowledge base by leveraging a hybrid model of Retrieval Augmented Generation and Large Language Models.

•We also launched Upland Second Street’s Text‑to‑Vote, a powerful new audience engagement and revenue‑driving feature. Designed for publishers, media companies, and news organizations, the Text‑to‑Vote capability enables users to boost audience participation, streamline mobile‑first voting experiences, and unlock new advertiser revenue opportunities through a frictionless SMS workflow.

Business Outlook

For the quarter ending June 30, 2026, Upland expects reported total revenue to be between $47.1 and $50.1 million, including subscription and support revenue between $45.1 and $47.7 million, for a decline in total revenue of 9% at the midpoint from the quarter ended June 30, 2025. This year-over-year revenue decline is primarily due to divestitures completed in 2025. Second quarter 2026 Adjusted EBITDA is expected to be between $12.0 and $13.6 million, which at the midpoint is a decline of 6% from the quarter ended June 30, 2025. Second quarter 2026 Adjusted EBITDA margin is expected to be 26% at the midpoint as compared to the 25% Adjusted EBITDA margin for the quarter ended June 30, 2025.

For the full year ending December