Freshworks (FRSH) announced a $400 million share repurchase program on February 26, 2026, supported by $844 million in cash and $223 million in adjusted free cash flow generated in 2025. This move follows CEO Dennis Woodside's significant insider purchases and a period of accelerated insider buying. Despite these efforts, the company's stock declined 16.5% after its 2026 adjusted EPS guidance of $0.55-$0.57 missed consensus estimates, leading to analyst target cuts. Freshworks is navigating a critical transition from per-seat pricing to outcome-based AI pricing, with revenue growth decelerating from 20% in Q2 2024 to a projected 13.5%-14.5% in 2026, raising concerns about margin economics and customer base adaptation amidst the evolving AI landscape.