Shepherd vs IBM
Side-by-side comparison of AI visibility scores, market position, and capabilities
YC-backed construction insurance MGA with technology-enabled underwriting for GC general liability and workers' comp; $22.3M with $13.5M Costanoa Series A achieving 5x GWP growth for construction sector insurance.
About
Shepherd Insurance is a New York-based insurance technology company providing technology-enabled commercial insurance specifically for the construction industry — writing General Liability, Commercial Auto, Workers' Compensation, and Excess Liability policies for general contractors and construction enterprises. Founded in 2021 and backed by Y Combinator with $22.3 million raised including a $13.5 million Series A led by Costanoa Ventures, Shepherd achieved five-fold growth in Gross Written Premiums year-over-year and expanded from one to four commercial insurance product lines serving the high-risk and underserved construction insurance market.
Armonk NY hybrid cloud and enterprise AI (NYSE: IBM) at $62.8B revenue; $6B+ generative AI bookings, record $12.7B free cash flow 2024, DataStax acquisition for watsonx vector database competing with Microsoft Azure for enterprise AI.
About
International Business Machines Corporation (IBM) is an Armonk, New York-based global technology and consulting company — publicly traded on the New York Stock Exchange (NYSE: IBM) as an S&P 500 component — providing hybrid cloud infrastructure, artificial intelligence software, and enterprise IT consulting through approximately 270,300 employees in 170 countries with $62.8 billion in annual revenue. Founded on June 16, 1911, as Computing-Tabulating-Recording Company through a merger orchestrated by financier Charles Ranlett Flint, renamed IBM in 1924 under Thomas Watson Sr., IBM has undergone multiple strategic transformations over its 110+ year history: building the System/360 mainframe platform (1964), launching the IBM PC (1981), selling the PC division to Lenovo (2005, $1.75B), and completing the $34 billion Red Hat acquisition (2019) that repositioned IBM as a hybrid cloud platform company. CEO Arvind Krishna (appointed April 2020) has focused IBM's strategy on three areas: hybrid cloud (powered by Red Hat OpenShift, the enterprise Kubernetes platform), AI (the watsonx platform for enterprise AI model development and deployment), and enterprise consulting. Under Krishna, IBM recorded $12.7 billion in free cash flow in 2024 (a company record), surpassed $6 billion in generative AI bookings since June 2023, and saw the stock price double — trading at all-time highs through 2024-2025. IBM announced the DataStax acquisition in 2025 to deepen watsonx's data layer with AstraDB (vector database for AI applications), DataStax Enterprise (Apache Cassandra), and Langflow (low-code AI agent development).
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