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Onebrief has raised $220 million in Series D funding, increasing its valuation to $2.15 billion, with investments led by Battery Ventures and Sapphire Ventures. The funding will enhance its AI Assist product and facilitate the acquisition of Battle Road Digital, which will improve military command software by integrating simulation capabilities for better decision-making. The company plans to expand its workforce to over 500 employees while serving most U.S. combatant commands.