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- Climb's M&A Weekly: F5, DigiCert, and Sheridan Capital all feature
Climb's M&A Weekly: F5, DigiCert, and Sheridan Capital all feature
F5 acquires CalypsoAI and DigiCert acquires Valimail
Climb Advisors Weekly
September 21, 2025
Welcome back to the Climb Advisors weekly newsletter with five deals from across the B2B tech landscape.
Climb Advisors focuses on sell-side advisory for B2B Software and services companies generating $5m-$15m in revenue. We also advise on credit solutions for companies of the same profile & in select cases engage in retained buy-side processes for quality buyers. We love to talk markets and make introductions - please don’t hesitate to reach out if you’re a founder or investor looking to transact.
F5 acquires CalypsoAI from Paladin Capital Group for $180 million
Overview: F5, the Seattle-based application delivery and security company, purchases CalypsoAI, an AI security startup, from Paladin Capital Group for $180 million in cash. F5 will acquire all issued and outstanding shares of CalypsoAI, a private company with major operations in Dublin, Ireland for $180 million financed primarily with cash. CalypsoAI's platform provides AI guardrails and helps companies secure their AI infrastructure against cyber threats and data leaks. Read more here.
Climb Comment: CalypsoAI was founded in 2018 and has raised over $40 million prior to its acquisition from investors including Paladin Capital Group, Lockheed Martin Ventures, and Hakluyt Capital. The acquisition comes as companies are rapidly introducing AI workflows while trying their best to minimize security threats against the company. CalypsoAI's platform, powered by proprietary AI agents, provides a strategic advantage to companies by continuously red-teaming, stress testing, and protecting GenAI systems. F5 plans to integrate CalypsoAI's capabilities into its application and security platform.
DigiCert backed by a host of PE firms acquires Valimail
Overview: DigiCert, backed by Clearlake Capital, Crosspoint Capital, and TA Associates, acquires Valimail, a market leader in zero trust email authentication as a service. The acquisition adds email authentication capabilities to DigiCert's digital trust platform and expands the company into the Domain-based Message Authentication, Reporting, and Conformance (DMARC) solutions market. Read more here.
Climb Comment: The deal sees DigiCert enter the market for DMARC solutions, which is valued at ~$4 billion. Email is still the main platform for phishing and spoofing attacks, and Valimail's zero trust email authentication platform helps individuals and organizations protect against these attacks. The acquisition strengthens DigiCert's platform strategy by adding email authentication as a new capability alongside its existing PKI and DNS security solutions. DigiCert plans to integrate Valimail into its DigiCert ONE platform to provide unified protection for websites, software, devices, and email.
Sheridan Capital Partners acquires National Care Systems, a billing and payroll platform for nursing and assisted living facilities
Overview: Sheridan Capital Partners purchases National Care Systems, a provider of billing and payroll solutions for nursing homes and assisted living facilities. National Care Systems offers comprehensive back-office solutions like payroll processing, billing management, and compliance tools. The acquisition expands Sheridan's portfolio in the healthcare technology space. Read more here.
Climb Comment: The healthcare administration software market continues to consolidate as providers are looking for specialized solutions for regulatory and operational requirements. National Care Systems' focus on long-term care facilities addresses a niche market with specific billing complexities around Medicare, Medicaid, and private pay arrangements. Sheridan Capital has been active in healthcare services investments and this acquisition fits their strategy of building platforms in fragmented healthcare verticals. The aging population and increased demand for long-term care services should drive growth for National Care Systems' solutions.
GrowthCurve Capital acquires PlanHub
Overview: GrowthCurve Capital, a growth equity firm, acquires PlanHub, a construction project management and bidding platform. PlanHub connects general contractors with subcontractors through its digital marketplace and provides project management tools for the construction industry. The platform streamlines the bidding process and helps construction companies manage their project workflows more efficiently. Read more here.
Climb Comment: The construction technology sector has been experiencing significant growth as the industry digitalizes its manual processes. PlanHub's platform addresses inefficiencies in the subcontractor bidding process. GrowthCurve's investment will likely be used to expand PlanHub's customer base and strengthen its technology. The construction industry's ongoing digitalization creates a favorable environment for PlanHub's continued growth.
Collaboration software company, Atlassian, acquires AI startup, DX for $1 billion
Overview: Atlassian acquires DX for $1 billion in cash and restricted stock. DX specializes in engineering intelligence and helps firms measure developer productivity and identify bottlenecks in their software development processes. The acquisition strengthens Atlassian's position in the developer tools market and adds AI-powered analytics capabilities. Read more here.
Climb Comment: The acquisition comes as organizations increasingly invest in AI tools for software development and need ways to measure their effectiveness and ROI. DX's platform provides insights into how AI coding assistants and other productivity tools are impacting team performance. As the coding world changes rapidly, these insights are extraordinarily valuable for management teams. Atlassian plans to integrate DX's capabilities into its existing portfolio of collaboration and project management tools, creating a more comprehensive platform for engineering teams.
Article of the week
The article this week is an excellent case study from Dirt Cheap Stocks.
Thanks for following along & hope you found something useful or interesting. Please don’t hesitate to reach out if you’re considering a sale this year - we’re always glad to chat & share perspective.
All the best,
Nick