Progress Software Corporation (NASDAQ: PRGS), headquartered in Burlington, Massachusetts, is an Application-Development-and-Data-Management-and-DevOps-Software + emerging-multi-cycle-MarkLogic-and-Telerik-and-Sitefinity-and-emerging-ShareFile-acquired leader providing distinctive multi-cycle Application-Development-Software + emerging-Data-Management + emerging-DevOps + emerging-Content-Collaboration services to substantial multi-cycle US-and-emerging-multi-cycle-international Enterprise-Software-Developer + Mid-Market-and-Large-Enterprise + Government customer base. Distinctive multi-cycle Progress-Software heritage: founded 1981 by Joseph Alsop; 1991 NASDAQ Progress-Software-IPO; 2016 Yogesh Gupta CEO; 2017 substantial Telerik-and-Kemp; 2019 Ipswitch; 2021 Chef-and-Kemp-Technologies; 2023 substantial MarkLogic-acquisition (~$355M); 2024 substantial ShareFile-acquired-from-Cloud-Software-Group (~$875M). Multi-decade strategic-evolution: 1981 Progress-Software founding; 1991 NASDAQ-IPO; 2016 Yogesh Gupta CEO + multi-cycle-disciplined-bolt-on-M&A; 2017-2024 substantial multi-cycle-disciplined-bolt-on-M&A culminating in 2024 ShareFile-acquisition; 2020-2025 substantial multi-cycle post-COVID + emerging-Application-Development-and-DevOps + emerging-MarkLogic-and-ShareFile + emerging-Government-and-Public-Sector. Under President & CEO Yogesh Gupta (since 2016, ~9+ year longtime-Progress-Software-and-Kaseya-and-Sungard entrepreneur), FY2025 (Nov-FYE) closes with selected various aggregate revenue ~$770-870M, adj. EBITDA ~$315-385M, adj. EPS ~$4.55-5.50, net debt ~$1.30-1.55B, and ~43-46M shares outstanding. The first deep-dive — Application-Development-and-Data-Management-and-DevOps-and-Content-Collaboration franchise — covers entire business + Progress positioning. Geographic + Employee composition: ~2,000+ employees + ~globally-positioned-Application-Development-Software-development-and-distribution-facilities across US (Burlington-MA-HQ + Multi-Office) + emerging multi-jurisdiction-international (EMEA + India + Asia-Pacific). Revenue mix: Application-Development-and-Data-Management-and-DevOps-and-Content-Collaboration ~95-99%; Emerging-Other ~1-5%. Customer base: Enterprise-Software-Developer + Mid-Market-and-Large-Enterprise + Government + emerging-Healthcare-and-Financial-Services-and-Manufacturing-and-Public-Sector. Distinctive multi-cycle 2023-MarkLogic + 2024-ShareFile. Competes with Microsoft (MSFT + Azure-DevOps-GitHub-Power-Platform), Oracle (ORCL), Salesforce (CRM + MuleSoft), ServiceNow (NOW), SAP (SAP), IBM (IBM + Red-Hat-OpenShift), Red Hat (IBM-subsidiary), Atlassian (TEAM + Jira-Confluence-Bitbucket-Trello), GitLab (GTLB), GitHub (Microsoft-subsidiary 2018), HashiCorp (IBM-2024-acquired ~$6.4B), Cloud Software Group (Bain-Vista-take-private 2022 + Citrix-and-TIBCO + 2024-ShareFile-divested-to-PRGS), MongoDB (MDB), Snowflake (SNOW), Databricks (private), Confluent (CFLT + Kafka), Elastic (ESTC), Splunk (Cisco-CSCO-acquired 2024 ~$28B), Cisco (CSCO), Couchbase (BASE + 2024-Haveli-take-private ~$1.5B), Dynatrace (DT), Datadog (DDOG), New Relic (Francisco-TPG-take-private 2023), AppDynamics (Cisco-subsidiary), Solace (private), DBT Labs (private), Fivetran (private), Informatica (Salesforce-CRM-acquired 2024 ~$8B), Talend (Thoma-Bravo-and-Qlik-acquired 2023), Qlik (Thoma-Bravo-private); Mid-Market Telerik (PRGS-subsidiary), Sitefinity (PRGS-subsidiary), OutSystems (private), Mendix (Siemens-SIE-DE-acquired 2018), Pegasystems (PEGA), Appian (APPN), Nintex (private), ServiceMax (PTC-acquired 2023), Boomi (Francisco-TPG-take-private 2021), Workato (private); Content-Collaboration Dropbox (DBX), Box (BOX), Microsoft (SharePoint-OneDrive-Teams), Google (Workspace-Drive), Citrix (Cloud-Software-Group-private + ShareFile-divested-to-PRGS); DevOps Red Hat (IBM-subsidiary), Puppet (Perforce-Software-private-acquired 2022), Chef (PRGS-acquired 2020-2021 ~$220M), Ansible (Red-Hat-subsidiary), SaltStack (VMware-Broadcom-subsidiary), HashiCorp (IBM-2024-acquired); Government Tyler Technologies (TYL), Verint Systems (VRNT), Booz Allen Hamilton (BAH), CACI International (CACI), Leidos (LDOS), SAIC (SAIC), General Dynamics (GD + GDIT); private-equity-Enterprise-Software Thoma Bravo (private), Vista Equity Partners (private), Bain Capital (private), Apollo (APO), Carlyle (CG), KKR (KKR), Blackstone (BX), Francisco Partners (private + 2023-New-Relic-take-private), TPG (TPG + 2024-Couchbase-emerging), Permira (private), CVC Capital Partners (CVC-AMS), Hg Capital (private), Genstar (private), Insight Partners (private), Sumeru Equity Partners (private), Mainsail Partners (private), Marlin Equity Partners (private), Haveli Investments (private + 2024-Couchbase-take-private ~$1.5B); Enterprise-Software-customer JPMorgan Chase (JPM), Bank of America (BAC), Wells Fargo (WFC), Citigroup (C), Goldman Sachs (GS), Morgan Stanley (MS), UnitedHealth (UNH), CVS Health (CVS), Walmart (WMT), Apple (AAPL), Microsoft (MSFT), Google (GOOG), Amazon (AMZN), Meta (META), Tesla (TSLA), Nvidia (NVDA); Government US-Department-of-Defense + US-Department-of-Veterans-Affairs + US-Department-of-Homeland-Security + US-state-government. The second deep-dive — Yogesh-Gupta + Multi-Cycle-Disciplined-Bolt-on-M-A + 2023-MarkLogic + 2024-ShareFile + multi-decade compounder thesis — covers Yogesh-Gupta-CEO (~9+ year longtime-Progress-Software-and-Kaseya-and-Sungard entrepreneur) expertise + Founder Joseph Alsop + multi-cycle-Progress-Software-Capital-Management leadership-continuity, 1991-NASDAQ-IPO + 2017-Telerik + 2019-Ipswitch + 2021-Chef + 2023-MarkLogic + 2024-ShareFile transformational-platform + multi-cycle-disciplined-bolt-on-M&A, emerging-Application-Development-and-DevOps + emerging-Data-Management + emerging-Content-Collaboration + emerging-Government-and-Public-Sector structural-tailwinds. Multi-cycle reliable-and-emerging-growing-dividend (~$0.72/yr ~1.0-2.0% yield ~7+ year continuous post-2018-restoration) + multi-cycle-disciplined-share-buyback ($60-150M/yr). Multi-decade compounder thesis combines Progress-Software-and-Burlington-MA ~44+ year heritage (founded 1981 + 1991 NASDAQ-IPO + 2016-Yogesh-Gupta-CEO), ~2,000+ employees + ~globally-positioned-Application-Development-Software-development-facilities, 2017-Telerik + 2019-Ipswitch + 2021-Chef + 2023-MarkLogic + 2024-ShareFile + multi-cycle-disciplined-bolt-on-M&A, Yogesh Gupta + Kaseya + Sungard + Progress-Software expertise, multi-cycle reliable-and-emerging-growing-dividend + multi-cycle-disciplined-share-buyback + Sub-IG-emerging balance-sheet, emerging-Application-Development-and-DevOps + emerging-Data-Management + emerging-Content-Collaboration + emerging-Government-and-Public-Sector structural-tailwinds. Capital position is Sub-IG-emerging (Ba3/BB-), dividend-reliable-and-emerging-growing + multi-cycle-disciplined-share-buyback, conservative-and-multi-cycle-leveraged-post-2024-ShareFile-acquisition: net debt ~$1.30-1.55B (~3.0-4.0x leverage), Ba3/BB- equivalent, $0.05-0.20B liquidity, $0.72/yr dividend (~1.0-2.0% yield, ~13-16% payout, ~7+ year continuous post-2018-restoration) + ~$60-150M/yr buyback + multi-cycle-disciplined-bolt-on-M&A + emerging-Application-Development-and-Data-Management-and-DevOps capex + multi-cycle-2024-ShareFile-acquisition-debt-paydown, ~43-46M shares. At ~$50-80 per share, equity value ~$2.2-3.5B, EV ~$3.5-5.0B, ~11-17x EPS and ~9-14x EV/EBITDA. Base case: Application-Development-and-DevOps constructive + emerging-MarkLogic + emerging-ShareFile + emerging-Government + revenue $810-910M + adj. EBITDA $340-410M + adj. EPS $4.95-6.05 + dividend hiked + ~5-15% return. Bull case: Application-Development-and-DevOps accelerates + emerging-MarkLogic inflects + emerging-ShareFile inflects-substantially + emerging-Government inflects + revenue $860-960M + adj. EPS $5.50-6.75 + dividend hiked + selective-M&A + emerging-strategic-acquisition-target (Microsoft + Oracle + Salesforce + ServiceNow + SAP + IBM + Atlassian + GitLab + Cloud-Software-Group + MongoDB + Snowflake + Databricks + Elastic + Splunk + Cisco + Couchbase + private-equity-Thoma-Bravo-Vista-Bain-Apollo-Carlyle-KKR-Blackstone-Francisco-TPG-Permira-CVC-Hg-Genstar-Insight-Sumeru-Mainsail-Marlin-Haveli interest) + re-rate 13-20x + 25-50%+ return + takeout-premium-upside. Bear case: Application-Development-and-DevOps stresses + emerging-MarkLogic-and-ShareFile-integration disappoints + adj. EPS $3.00-3.70 + de-rate 7-11x + flat-to-substantially-negative.

Progress Software Thesis 2026: An App-Dev + Data-Management + DevOps Compounder

Key Takeaways

Progress Software Corporation (NASDAQ: PRGS), the Burlington-MA-headquartered Application-Development-and-Data-Management-and-DevOps-Software + emerging-multi-cycle-MarkLogic-and-Telerik-and-Sitefinity-and-emerging-ShareFile-acquired leader, closes FY2025 (Nov-FYE) with selected various aggregate revenue ~$770-870M (~~5-12% YoY-growth driven by Application-Development-and-DevOps + emerging-multi-cycle-MarkLogic-and-ShareFile-from-Cloud-Software-Group), adjusted EBITDA ~$315-385M (~~38-44% margins reflecting Application-Development-and-DevOps-Software economics), adjusted EPS ~$4.55-5.50, net debt ~$1.30-1.55B (~~3.0-4.0x leverage post-2024-ShareFile-acquisition), and ~~43-46M shares under President & CEO Yogesh Gupta (since 2016, ~~9+ year longtime-Progress-Software-and-Kaseya-and-Sungard entrepreneur); Founder Joseph Alsop + Progress-Software-historical-1981 + multi-cycle-Progress-Software-Capital-Management.
Operates substantial multi-cycle ~~2,000+ employees + ~~globally-positioned-Application-Development-and-Data-Management-and-DevOps-Software-development-and-distribution-facilities + emerging-multi-cycle-MarkLogic-and-ShareFile providing distinctive multi-cycle Application-Development-Software + emerging-Data-Management + emerging-DevOps + emerging-Content-Collaboration platform.
Distinctive multi-cycle Progress-Software-and-Burlington-MA-and-Application-Development-Software heritage: founded 1981 by Joseph Alsop + 1991 NASDAQ Progress-Software-IPO + 2016 Yogesh Gupta President-and-CEO + 2017 substantial Telerik-and-Kemp-acquisitions + 2019 substantial Ipswitch-acquisition + 2021 substantial Chef-Software-and-Kemp-Technologies-acquisitions + 2023 substantial MarkLogic-acquisition (~~$355M) + 2024 substantial ShareFile-acquired-from-Cloud-Software-Group (~~$875M).
Distinctive multi-cycle Application-Development-and-Data-Management-and-DevOps-Software (~~95-99% revenue, distinctive multi-cycle-Application-Development-Software-largest-business + multi-cycle-emerging-Data-Management-MarkLogic + multi-cycle-emerging-DevOps-Chef-Software + multi-cycle-emerging-Content-Collaboration-ShareFile + multi-cycle-emerging-Telerik-and-Sitefinity-and-Kemp) + Emerging-Other (~~1-5% revenue) platform.
Customer base: substantial multi-cycle US-and-emerging-multi-cycle-international Enterprise-Software-Developer + Mid-Market-and-Large-Enterprise + Government + emerging-multi-cycle-Healthcare-and-Financial-Services-and-Manufacturing-and-Public-Sector + emerging-multi-cycle-Content-Collaboration-ShareFile-customer.
Sub-IG-emerging (Ba3/BB-) balance sheet (multi-cycle-leveraged-post-2024-ShareFile-acquisition), multi-cycle reliable-and-emerging-growing-dividend (~$0.72/yr ~~1.0-2.0% yield ~~7+ year continuous post-2018-restoration) + multi-cycle-disciplined-share-buyback ($60-150M/yr), FY2026 turns on Application-Development-and-DevOps + emerging-multi-cycle-MarkLogic-and-ShareFile + emerging-multi-cycle-Government-and-Public-Sector + multi-cycle-disciplined-bolt-on-M&A + Yogesh Gupta-strategic-execution.

Company Background

Progress Software Corporation (NASDAQ: PRGS), headquartered in Burlington, Massachusetts (corporate HQ + Burlington-MA-Progress-Software + emerging-multi-cycle-Burlington-MA-Progress-Software + multi-cycle-Progress-Software-and-emerging-multi-cycle-Progress-Software), is an Application-Development-and-Data-Management-and-DevOps-Software + emerging-multi-cycle-MarkLogic-and-Telerik-and-Sitefinity-and-emerging-ShareFile-acquired leader providing distinctive multi-cycle Application-Development-Software + emerging-Data-Management + emerging-DevOps + emerging-Content-Collaboration services to substantial multi-cycle US-and-emerging-multi-cycle-international Enterprise-Software-Developer + Mid-Market-and-Large-Enterprise + Government customer base. The company has a distinctive multi-cycle Progress-Software-and-Burlington-MA-and-Application-Development-Software heritage: founded 1981 by Joseph Alsop + multi-cycle-Progress-Software-historical-entrepreneurs; 1991 NASDAQ Progress-Software-IPO; 2016 Yogesh Gupta President-and-CEO; 2017 substantial Telerik-and-Kemp-acquisitions + 2019 substantial Ipswitch-acquisition + 2021 substantial Chef-Software-and-Kemp-Technologies-acquisitions; 2023 substantial MarkLogic-acquisition (~~$355M); 2024 substantial ShareFile-acquired-from-Cloud-Software-Group (~~$875M).

Multi-decade strategic-evolution: 1981 Progress-Software founding by Joseph Alsop; 1991 NASDAQ Progress-Software-IPO; 2016 Yogesh Gupta CEO + multi-cycle-disciplined-bolt-on-M&A; 2017 substantial Telerik-and-Kemp-acquisitions; 2019 substantial Ipswitch-acquisition; 2021 substantial Chef-Software-and-Kemp-Technologies-acquisitions; 2023 substantial MarkLogic-acquisition (~~$355M); 2024 substantial ShareFile-acquired-from-Cloud-Software-Group (~~$875M providing Content-Collaboration-platform); 2020-2025 substantial multi-cycle post-COVID + emerging-multi-cycle-Application-Development-and-DevOps + emerging-multi-cycle-MarkLogic-and-ShareFile + emerging-multi-cycle-Government-and-Public-Sector + multi-cycle-disciplined-bolt-on-M&A.

Under President & CEO Yogesh Gupta (since 2016, ~~9+ year longtime-Progress-Software-and-Kaseya-and-Sungard entrepreneur providing distinctive multi-cycle-Progress-Software-and-emerging-multi-cycle-Progress-Software + 2017-Telerik-and-Kemp + 2019-Ipswitch + 2021-Chef-and-Kemp-Technologies + 2023-MarkLogic-and-2024-ShareFile-acquisition-integration execution + multi-cycle-strategic-execution + multi-cycle-emerging-Progress-Software expertise; Founder Joseph Alsop + multi-cycle-Progress-Software-Capital-Management), FY2025 (Nov-FYE) closes with selected various aggregate revenue ~$770-870M, adjusted EBITDA ~$315-385M, adjusted EPS ~$4.55-5.50, net debt ~$1.30-1.55B (~3.0-4.0x leverage post-2024-ShareFile-acquisition), and ~~43-46M shares outstanding.

Deep-Dive 1: Application-Development-and-Data-Management-and-DevOps-and-Content-Collaboration Franchise

The first deep-dive — Application-Development-and-Data-Management-and-DevOps-and-Content-Collaboration franchise — covers entire Application-Development-Software + emerging-multi-cycle-Data-Management-MarkLogic + emerging-multi-cycle-DevOps-Chef-Software + emerging-multi-cycle-Content-Collaboration-ShareFile business + distinctive multi-cycle Progress-Software-and-emerging-multi-cycle-Progress-Software positioning.

Geographic + Employee composition: distinctive multi-cycle ~~2,000+ employees + ~~globally-positioned-Application-Development-and-Data-Management-and-DevOps-Software-development-and-distribution-facilities providing distinctive multi-cycle Progress-Software-and-emerging-multi-cycle-Progress-Software across:

US (Burlington-MA-HQ + Multi-Office) (substantial multi-cycle largest-business).
Emerging multi-jurisdiction-international (emerging-multi-cycle): emerging-multi-cycle-Progress-Software-International-Multi-Office (EMEA + India + Asia-Pacific).

Revenue mix:

Application-Development-and-Data-Management-and-DevOps-and-Content-Collaboration (~~95-99% revenue, distinctive multi-cycle-Application-Development-Software-largest-business + multi-cycle-emerging-Data-Management-MarkLogic + multi-cycle-emerging-DevOps-Chef-Software + multi-cycle-emerging-Content-Collaboration-ShareFile + multi-cycle-emerging-Telerik-and-Sitefinity-and-Kemp).
Emerging-Other (~~1-5% revenue).

Customer base: substantial multi-cycle US-and-emerging-multi-cycle-international Enterprise-Software-Developer + Mid-Market-and-Large-Enterprise + Government + emerging-multi-cycle-Healthcare-and-Financial-Services-and-Manufacturing-and-Public-Sector + emerging-multi-cycle-Content-Collaboration-ShareFile-customer.

Distinctive multi-cycle 2023-MarkLogic-acquisition (~~$355M) + 2024-ShareFile-acquired-from-Cloud-Software-Group (~~$875M): substantial 2023 MarkLogic-acquisition + 2024 ShareFile-acquired-from-Cloud-Software-Group providing distinctive multi-cycle Progress-Software-and-emerging-multi-cycle-Progress-Software.

Emerging structural-tailwinds: emerging-multi-cycle US-and-international-Application-Development-and-DevOps + emerging-Data-Management + emerging-Content-Collaboration + emerging-Government-and-Public-Sector demand environment.

FY2026 catalyst is Application-Development-and-DevOps + emerging-multi-cycle-MarkLogic-and-ShareFile + emerging-multi-cycle-Government-and-Public-Sector + multi-cycle-disciplined-bolt-on-M&A + Yogesh Gupta-strategic-execution.

Competes in Application-Development-Software-and-Data-Management-and-DevOps space with Microsoft (MSFT + Azure-and-DevOps-and-GitHub-and-Power-Platform), Oracle (ORCL + Oracle-Database-and-Application-Development), Salesforce (CRM + Salesforce-Platform-and-MuleSoft), ServiceNow (NOW + ServiceNow-Platform), SAP (SAP + SAP-Application-Development), IBM (IBM + IBM-WebSphere-and-Red-Hat-and-OpenShift), Red Hat (IBM-subsidiary), Atlassian (TEAM + Jira-and-Confluence-and-Bitbucket-and-Trello), GitLab (GTLB + DevOps-Platform), GitHub (Microsoft-MSFT-subsidiary 2018), HashiCorp (IBM-2024-acquired ~$6.4B + HashiCorp-Terraform-and-Vault-and-Consul-and-Nomad), Cloud Software Group (Bain-Vista-Equity-take-private 2022 + Citrix-and-TIBCO + 2024-ShareFile-divested-to-Progress-PRGS), MongoDB (MDB + Atlas-and-Database), Snowflake (SNOW + Data-Cloud), Databricks (private + Lakehouse), Confluent (CFLT + Apache-Kafka), Elastic (ESTC + Elasticsearch-and-Observability), Splunk (Cisco-CSCO-acquired 2024 ~$28B + Splunk-Observability-and-Security), Cisco (CSCO + 2024-Splunk-acquired), Couchbase (BASE + 2024-Haveli-Investments-take-private ~$1.5B + Couchbase-Database-and-Capella), Dynatrace (DT + Observability), Datadog (DDOG + Observability-and-Security), New Relic (Francisco-Partners-and-TPG-take-private 2023), AppDynamics (Cisco-CSCO-subsidiary), Solace Corporation (private + Event-Streaming), DBT Labs (private + Analytics-Engineering), Fivetran (private + Data-Movement), Informatica (Salesforce-CRM-2024-acquired ~$8B + Informatica-Cloud-Data-Management), Talend (Thoma-Bravo-and-Qlik-acquired 2023 + Talend-Data-Integration), Qlik (Thoma-Bravo-private + 2023-Talend-acquired); Application-Development-Mid-Market Telerik (Progress-Software-PRGS-subsidiary), Sitefinity (Progress-Software-subsidiary), Outsystems (private + OutSystems-Low-Code), Mendix (Siemens-SIE-DE-acquired 2018 + Siemens-Industrial-Software-Mendix), Pegasystems (PEGA), Appian (APPN), nintex (private + Nintex-Workflow), ServiceMax (PTC-acquired 2023 + PTC-and-emerging-emerging-ServiceMax), Boomi (Francisco-Partners-and-TPG-take-private 2021 + Boomi-iPaaS), Workato (private + Workato-Integration); Content-Collaboration-and-File-Sharing Dropbox (DBX), Box (BOX), Microsoft (MSFT + SharePoint-and-OneDrive-and-Teams), Google (GOOG + Google-Workspace-and-Drive), Citrix (Cloud-Software-Group-private + Citrix-ShareFile-divested-to-Progress-2024); DevOps-and-Configuration-Management Red Hat (IBM-subsidiary), Puppet (Perforce-Software-private-acquired 2022), Chef (Progress-Software-PRGS-acquired 2020-2021 ~$220M), Ansible (Red-Hat-IBM-subsidiary + Ansible-Automation), SaltStack (VMware-Broadcom-AVGO-subsidiary), HashiCorp (IBM-2024-acquired + Terraform-Vault-Consul-Nomad); Government Software Tyler Technologies (TYL + Tyler-Government-Software), Verint Systems (VRNT + Verint-Customer-Engagement), Booz Allen Hamilton (BAH + Government-Consulting), CACI International (CACI), Leidos Holdings (LDOS), SAIC (SAIC), General Dynamics (GD + GDIT); private-equity-Enterprise-Software Thoma Bravo (private + emerging-Thoma-Bravo-Software + 2023-Talend-acquired + 2024-Coupa-emerging + 2024-J-D-Power-emerging), Vista Equity Partners (private + Vista-Software), Bain Capital (private + Bain-Software), Apollo Global Management (APO + Apollo-Software), Carlyle (CG + Carlyle-Software), KKR (KKR + KKR-Software), Blackstone (BX + Blackstone-Software), Francisco Partners (private + Francisco-Software + 2023-New-Relic-take-private), TPG (TPG + TPG-Software + 2023-New-Relic-take-private + 2024-Couchbase-emerging), Permira (private + Permira-Software), CVC Capital Partners (CVC-AMS + CVC-Software), Hg Capital (private + Hg-Software), Genstar Capital (private + Genstar-Software), Insight Partners (private + Insight-Software), Sumeru Equity Partners (private + Sumeru-Software), Mainsail Partners (private + Mainsail-Software), Marlin Equity Partners (private + Marlin-Software), Sumeru Equity Partners (private), Haveli Investments (private + 2024-Couchbase-take-private ~$1.5B emerging); Enterprise-Software-customer JPMorgan Chase (JPM), Bank of America (BAC), Wells Fargo (WFC), Citigroup (C), Goldman Sachs (GS), Morgan Stanley (MS), UnitedHealth (UNH), CVS Health (CVS), Walmart (WMT), Apple (AAPL), Microsoft (MSFT), Google (GOOG), Amazon (AMZN), Meta (META), Tesla (TSLA), Nvidia (NVDA); Government-customer US Department of Defense (US-government), US Department of Veterans Affairs (US-government), US Department of Homeland Security (US-government), US-state-government (multi-state).

Deep-Dive 2: Yogesh-Gupta + Multi-Cycle-Disciplined-Bolt-on-M-A-and-2024-ShareFile-Acquisition + Multi-Decade Compounder Thesis

The second deep-dive — Yogesh-Gupta + multi-cycle-disciplined-bolt-on-M-A + 2023-MarkLogic-acquisition + 2024-ShareFile-acquisition + multi-decade compounder thesis — covers distinctive multi-cycle Yogesh-Gupta-CEO (~~9+ year longtime-Progress-Software-and-Kaseya-and-Sungard entrepreneur) expertise + Founder Joseph Alsop + multi-cycle-Progress-Software-Capital-Management leadership-continuity, 1991-NASDAQ-Progress-Software-IPO + 2017-Telerik-and-Kemp + 2019-Ipswitch + 2021-Chef-and-Kemp-Technologies + 2023-MarkLogic + 2024-ShareFile transformational-platform + multi-cycle-disciplined-bolt-on-M&A, emerging-multi-cycle US-and-international-Application-Development-and-DevOps + emerging-Data-Management + emerging-Content-Collaboration + emerging-Government-and-Public-Sector structural-tailwinds.

Yogesh Gupta CEO leadership: CEO since 2016 + ~~9+ year longtime-Progress-Software-and-Kaseya-and-Sungard entrepreneur providing distinctive multi-cycle-operational-discipline + multi-cycle-strategic-direction + multi-cycle-disciplined-bolt-on-M&A execution + multi-cycle-Application-Development-and-DevOps + emerging-multi-cycle-MarkLogic-and-ShareFile + emerging-multi-cycle-Government-and-Public-Sector expertise.

Multi-Cycle-Disciplined-Bolt-on-M-A + 2023-MarkLogic-Acquisition + 2024-ShareFile-Acquisition transformational-platform: distinctive substantial 2017 Telerik + 2019 Ipswitch + 2021 Chef-and-Kemp + 2023 MarkLogic-acquisition + 2024 ShareFile-acquired-from-Cloud-Software-Group providing distinctive multi-cycle Progress-Software-and-emerging-multi-cycle-Progress-Software.

Multi-cycle reliable-and-emerging-growing-dividend + multi-cycle-disciplined-share-buyback: distinctive multi-cycle reliable-and-emerging-growing-dividend (~$0.72/yr providing ~~1.0-2.0% yield, ~~13-16% payout providing multi-cycle reliable-and-emerging-growing dividend-track-record ~~7+ year continuous post-2018-restoration) + multi-cycle-disciplined-share-buyback ($60-150M/yr providing multi-cycle-disciplined-share-buyback discipline).

Multi-decade compounder thesis combines distinctive multi-cycle Progress-Software-and-Burlington-MA ~~44+ year heritage (founded 1981 + 1991 NASDAQ-IPO + 2016-Yogesh-Gupta-CEO), ~~2,000+ employees + ~~globally-positioned-Application-Development-and-Data-Management-Software-development-and-distribution-facilities, 2017-Telerik + 2019-Ipswitch + 2021-Chef + 2023-MarkLogic + 2024-ShareFile + multi-cycle-disciplined-bolt-on-M&A, Yogesh Gupta + Kaseya + Sungard + Progress-Software expertise, multi-cycle reliable-and-emerging-growing-dividend + multi-cycle-disciplined-share-buyback + Sub-IG-emerging balance-sheet, emerging-Application-Development-and-DevOps + emerging-Data-Management + emerging-Content-Collaboration + emerging-Government-and-Public-Sector structural-tailwinds.

Consolidated Capital Position + Balance Sheet

Capital position is Sub-IG-emerging (Ba3/BB-), dividend-reliable-and-emerging-growing + multi-cycle-disciplined-share-buyback, conservative-and-multi-cycle-leveraged-post-2024-ShareFile-acquisition: net debt ~$1.30-1.55B (~3.0-4.0x leverage), Ba3/BB- equivalent (Sub-IG-emerging), $0.05-0.20B cash + undrawn revolver liquidity, $0.72/yr dividend (~1.0-2.0% yield, ~13-16% payout, ~7+ year continuous post-2018-restoration) + ~$60-150M/yr share-buyback + multi-cycle-disciplined-bolt-on-M&A (2017-Telerik + 2019-Ipswitch + 2021-Chef + 2023-MarkLogic + 2024-ShareFile) + emerging-Application-Development-and-Data-Management-and-DevOps capex + multi-cycle-2024-ShareFile-acquisition-debt-paydown, ~~43-46M shares + multi-cycle-disciplined-share-buyback.

Key Core Metrics

Metric	FY2025E Range	Notes
Revenue	~$770-870M	Application-Development + Data-Management + DevOps + Content-Collaboration
Revenue YoY Growth	~5-12%	Application-Development-and-DevOps + emerging-MarkLogic-and-ShareFile
Adjusted EBITDA	~$315-385M	~38-44% margins Application-Development-Software economics
Adjusted EPS	~$4.55-5.50	Multi-cycle-Application-Development-Software
Employee Count	~2,000+	Burlington-MA-HQ + Multi-Office
Application-Development-and-Data-Management-and-DevOps-and-Content-Collaboration Revenue Share	~95-99%	Largest-business
Emerging-Other Revenue Share	~1-5%	Emerging-multi-cycle
Net Debt	~$1.30-1.55B	~3.0-4.0x leverage post-2024-ShareFile-acquisition
Credit Rating	Ba3/BB-	Sub-IG-emerging
Dividend	~$0.72/yr	~1.0-2.0% yield, ~13-16% payout, ~7+ year continuous post-2018-restoration
Buyback	~$60-150M/yr	Multi-cycle-disciplined discipline
Shares Outstanding	~43-46M	Multi-cycle-disciplined-share-buyback

Market Evaluation

At ~$50-80 per share, equity value ~$2.2-3.5B, EV ~$3.5-5.0B, providing ~~11-17x EPS and ~~9-14x EV/EBITDA — typical-mid-cap-Application-Development-Software multiple consistent with multi-cycle 1991-NASDAQ-Progress-Software-IPO + multi-cycle-disciplined-bolt-on-M&A + 2023-MarkLogic-and-2024-ShareFile-acquisitions + emerging-multi-cycle US-and-international-Application-Development-and-DevOps + emerging-Data-Management + emerging-Content-Collaboration + multi-cycle-reliable-and-emerging-growing-dividend (~~7+ year continuous post-2018-restoration) tailwinds.

Base case: Application-Development-and-DevOps constructive + emerging-MarkLogic + emerging-ShareFile + emerging-Government-and-Public-Sector + revenue $810-910M + adj. EBITDA $340-410M + adj. EPS $4.95-6.05 + dividend hiked + multi-cycle-disciplined-share-buyback + ~5-15% return.

Bull case: Application-Development-and-DevOps accelerates + emerging-MarkLogic inflects + emerging-ShareFile inflects-substantially + emerging-Government-and-Public-Sector inflects + revenue $860-960M + adj. EBITDA $370-450M + adj. EPS $5.50-6.75 + dividend hiked + selective-M&A + emerging-strategic-acquisition-target (Microsoft + Oracle + Salesforce + ServiceNow + SAP + IBM + Atlassian + GitLab + Cloud-Software-Group + MongoDB + Snowflake + Databricks + Elastic + Splunk + Cisco + Couchbase + private-equity-Thoma-Bravo-Vista-Bain-Apollo-Carlyle-KKR-Blackstone-Francisco-TPG-Permira-CVC-Hg-Genstar-Insight-Sumeru-Mainsail-Marlin-Haveli interest) + re-rate 13-20x + 25-50%+ return + takeout-premium-upside.

Bear case: Application-Development-and-DevOps stresses + emerging-MarkLogic-and-ShareFile-integration disappoints + adj. EPS $3.00-3.70 + de-rate 7-11x + flat-to-substantially-negative.

FY2026 turns on Application-Development-and-DevOps + emerging-multi-cycle-MarkLogic-and-ShareFile + emerging-multi-cycle-Government-and-Public-Sector + multi-cycle-disciplined-bolt-on-M&A + Yogesh Gupta-strategic-execution.

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[PRGS] Progress Software Thesis 2026: An App-Dev + Data-Management + DevOps Compounder