PRGS Stock: Insider Activity, Filings & Research

Progress Software Corporation (PRGS) — Drillr’s hub for PRGS insider activity, SEC filings, earnings signals and AI research. Over the trailing 3 months, PRGS insiders filed 0 open-market buys and 7 sales (SEC Form 4).

Sentiment

0/100

Buys (3m)

Sells (3m)

Net (3m)

-$1.1M

Insider trades by month Buys Sells

Aug

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May

Context3-month price -17.4%Institutions mixed (13F)

Date	Insider	Type	Shares	Price
May 20, 2026	WANG YUFAN STEPHANIEofficer: Chief Legal Officer	Sell	3,519	$29.04
May 20, 2026	FOLGER ANTHONYofficer: Chief Financial Officer	Sell	4,074	$29.05
May 20, 2026	FOLGER ANTHONYofficer: Chief Financial Officer	Sell	400	$29.96
May 20, 2026	WANG YUFAN STEPHANIEofficer: Chief Legal Officer	Sell	1,500	$28.44
Apr 3, 2026	Ainsworth Johnofficer: EVP/GM App & Data Platform	Tax	518	$24.96
Apr 3, 2026	Ainsworth Johnofficer: EVP/GM App & Data Platform	Tax	519	$24.96
Apr 3, 2026	WANG YUFAN STEPHANIEofficer: Chief Legal Officer	Tax	545	$24.96
Apr 3, 2026	FOLGER ANTHONYofficer: Chief Financial Officer	Tax	1,122	$24.96
Apr 3, 2026	WANG YUFAN STEPHANIEofficer: Chief Legal Officer	Option	1,070	—
Apr 3, 2026	Subramanian Sundarofficer: EVP/GM Infrastructure Mgmt	Tax	519	$24.96
Apr 3, 2026	Jarrett Lorenofficer: EVP/GM Digital Experience	Tax	495	$24.96
Apr 3, 2026	FOLGER ANTHONYofficer: Chief Financial Officer	Tax	1,353	$24.96
Apr 3, 2026	Ainsworth Johnofficer: EVP/GM App & Data Platform	Option	1,709	—
Apr 3, 2026	Ainsworth Johnofficer: EVP/GM App & Data Platform	Option	1,167	—
Apr 3, 2026	Subramanian Sundarofficer: EVP/GM Infrastructure Mgmt	Option	1,709	—

Source: PRGS SEC Form 4 filings, latest May 20, 2026. For informational purposes only — not investment advice.

Overview

Progress Software Corporation (NASDAQ:PRGS) is a Massachusetts-based enterprise software company founded in 1981 and publicly traded since 1991. The company has evolved from its origins as a database and development tools provider into a diversified software company serving businesses worldwide. Through strategic acquisitions and organic growth, Progress has built a portfolio of infrastructure software, development tools, and business applications that help organizations build, deploy, and manage critical business applications across cloud, hybrid, and on-premises environments.

Business

Progress Software operates in the enterprise software industry, providing infrastructure software, development tools, and business applications to organizations globally. The company's business is built around several core product categories that serve different aspects of enterprise software needs. OpenEdge represents the company's largest revenue segment, accounting for approximately 40% of total business. This is a comprehensive application development platform that enables businesses to build, deploy, and manage multi-language applications across various platforms including cloud, mobile, desktop, and on-premises environments. OpenEdge includes database management capabilities and development tools that allow organizations to create secure, scalable business applications. Infrastructure and DevOps Tools form another significant portion of the business, including products like Chef (infrastructure automation platform), MOVEit (secure file transfer solutions), WhatsUp Gold (network monitoring), and the recently acquired Kemp LoadMaster and Flowmon solutions for load balancing and network performance monitoring. These tools help IT departments automate deployment, manage infrastructure, and ensure secure data transfer across enterprise environments. Development Tools and Digital Experience products include DataDirect Connect for data connectivity, Sitefinity for web content management, DevTools for user interface development, and Corticon for business rules management. These products enable developers to build modern applications with features like AI capabilities, mobile interfaces, and automated testing. The company's most significant recent addition is ShareFile, acquired in late 2024 for $875 million. ShareFile is a cloud-based secure file sharing and collaboration platform that serves over 100,000 customers, primarily in small and medium-sized businesses. This acquisition dramatically increased Progress's Software-as-a-Service (SaaS) revenue component from 3% to nearly 30% of total revenues, adding approximately $250 million in annual recurring revenue.

Revenue model

Progress Software generates revenue primarily through software licensing, subscription services, and maintenance contracts. The company has successfully transitioned to a recurring revenue model, with approximately 87% of total revenue now coming from recurring sources, including software subscriptions, maintenance contracts, and SaaS offerings. The company's revenue model varies by product category. Traditional products like OpenEdge generate revenue through perpetual licenses combined with annual maintenance contracts, while newer acquisitions like ShareFile operate on pure SaaS subscription models with primarily annual contracts and auto-renewal mechanisms. Development tools and infrastructure products typically combine licensing fees with ongoing support and maintenance revenue. Progress's customers span multiple industries and organization sizes, from small businesses using ShareFile for secure file sharing to large enterprises running mission-critical applications on OpenEdge. The company serves end-users directly, independent software vendors who embed Progress technologies, original equipment manufacturers, and system integrators who build solutions for their clients. Several factors influence the company's profitability margins. Positive margin drivers include the high-margin nature of software businesses (gross margins typically exceed 80%), the recurring revenue model that provides predictable cash flows, and operational leverage from SaaS businesses where incremental customers don't proportionally increase costs. The company's focus on mission-critical applications also provides pricing power and reduces customer churn. Margin pressures come from the need for continuous research and development investment to stay competitive, integration costs from frequent acquisitions, and the challenge of maintaining growth in mature product categories. Additionally, the shift toward SaaS models, while beneficial long-term, can initially pressure margins as the company invests in cloud infrastructure and transitions from upfront license revenue to subscription-based recognition.

Competitive moat

Progress Software's competitive moat is moderate and varies significantly across its product portfolio. The company's strongest moat exists in its OpenEdge platform, where high switching costs create significant customer stickiness. Organizations that have built critical business applications on OpenEdge face substantial technical and financial barriers to migration, as replacing these systems would require extensive redevelopment, testing, and potential business disruption. This creates a reliable revenue base with high customer retention rates. The company also benefits from domain expertise and integration capabilities across its infrastructure software portfolio. Products like MOVEit, Chef, and the Kemp solutions serve specialized technical needs where reliability and security are paramount. The complexity of enterprise IT environments creates opportunities for cross-selling and bundling, though Progress has been conservative in pursuing these synergies. However, the company's moat faces several challenges. In the development tools space, Progress competes against well-funded technology giants like Microsoft, Amazon, and Google, which can offer integrated development environments as part of broader cloud platforms. The rapid pace of technological change, particularly around cloud-native development and artificial intelligence, requires continuous innovation investment to maintain relevance. The ShareFile acquisition, while strategically important, operates in the highly competitive file sharing and collaboration market where companies like Dropbox, Box, Microsoft, and Google compete aggressively. ShareFile's moat primarily relies on its focus on compliance-heavy industries like legal, healthcare, and accounting, where security and regulatory features provide differentiation. Overall, Progress Software's moat is best characterized as a collection of niche positions rather than a single dominant competitive advantage, with sustainability dependent on continued innovation and strategic acquisitions.

Risks & safety

Progress Software presents a mixed margin of safety profile with both strengths and concerns in its financial position. Liquidity and Debt Concerns: • Current ratio of 0.79 indicates potential short-term liquidity pressure • High debt-to-equity ratio of 3.54 following ShareFile acquisition financing • Cash position of $124 million against $429 million current liabilities • Management plans aggressive debt repayment of $150 million in fiscal 2025 Valuation Metrics: • Price-to-earnings ratio of 54.0 appears elevated for a mature software company • EV/EBITDA of 13.5 is reasonable for recurring revenue software business • Price-to-book ratio of 5.47 reflects significant intangible asset base from acquisitions Cash Generation: • Strong free cash flow of $68 million in recent quarter • Annual free cash flow guidance of $225-237 million provides debt service capability • Operating cash flow demonstrates consistent generation ability Other Considerations: • High goodwill and intangible assets create potential impairment risk • Net retention rate over 100% indicates healthy customer expansion • Recurring revenue model (87% of total) provides predictable cash flows • Management's acquisition strategy creates execution risk but also growth potential

Recent development

Over the past few years, Progress Software has executed a transformation strategy focused on three key areas: sustained product innovation, customer success, and disciplined mergers and acquisitions. The company's most significant strategic move was the $875 million acquisition of ShareFile in late 2024, which dramatically shifted the company's profile toward Software-as-a-Service offerings and nearly doubled its total addressable market. The company has made artificial intelligence integration a central theme across its product portfolio. Progress appointed Ed Keisling as Chief AI Officer and is pursuing AI capabilities in three directions: helping customers build AI-powered applications, integrating AI features into existing products, and using AI internally for operational efficiency. Products like MarkLogic now support generative AI with retrieval augmented generation, while Sitefinity offers AI-powered content creation and Flowmon provides AI-driven anomaly detection. Progress has maintained an active acquisition strategy, completing several strategic purchases including MarkLogic (data platform), Kemp (load balancing solutions), and Flowmon (network monitoring). The company has demonstrated ability to integrate acquisitions effectively while maintaining operational margins, and management continues to signal appetite for additional acquisitions in the $50-150 million revenue range. The company successfully navigated the MOVEit security incident in 2023, where a vulnerability in their file transfer software was exploited by cybercriminals. Progress worked with customers and regulators to address the issue, and investigations by the SEC and international data protection agencies concluded without enforcement actions. The incident demonstrated the company's crisis management capabilities and didn't significantly impact long-term customer relationships. Financial strategy evolution has included suspending dividend payments to focus capital on acquisitions and debt reduction, while maintaining share buyback programs. The company has also filed a universal shelf registration to provide flexibility for future acquisitions, indicating continued strategic ambitions.

PRGS company profile · for informational purposes only — not investment advice.

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