Chapter, an AI-driven Medicare navigation platform, has raised $100 million in a Series E round led by Generation Investment Management, valuing the company at $3 billion. Fifth Down Capital, 8VC and existing investors including Stripes and XYZ Venture Capital participated. The company has more than doubled its valuation since its previous funding round less than a year ago. Chapter achieved $100 million in annual recurring revenue in 2.5 years whilst tripling revenue in 2025 and maintaining flat headcount. Chapter reviews every Medicare plan nationwide, combining AI technology with licensed advisors to provide unbiased recommendations for seniors. The funding will support expansion into additional financial products aimed at retirees' health, wealth and wellbeing. The company recently launched tools including a provider directory and prescription cost calculator.

Oyster, a global employment platform, has raised $150 million in Series C funding at a valuation exceeding $1 billion. Georgian led the round, joined by Salesforce Ventures, LinkedIn, Base10 Partners Advancement Initiative and others, including existing investors Stripes and Emergence Capital. The funding makes Oyster a unicorn less than two years after launch and one of the few B Corporations to reach this milestone. In 2021, the company grew revenue by over 20-fold and the number of team members on its platform by 17 times. The platform now pays more than $200 million annually to global talent across over 180 countries, with 25 per cent of that talent in emerging economies. Oyster has raised $227 million total and will use the funding to develop its platform and invest in the People Ops community.

/PRNewswire/ -- Today, Pomelo Care, the national leader in evidence-based healthcare for women and children, announced it has raised $92 million in Series C...