Named after Section 409A of the US tax code, a 409A valuation establishes the fair market value of common stock so option grants can be priced compliantly. Failing to perform a 409A or pricing options below fair market value triggers severe tax penalties for option recipients.
409A valuations are typically refreshed annually or after material events (financing, M&A, significant operational change). The 409A FMV is almost always lower than the preferred-share price from the most recent priced round, usually a discount of 30 to 80% depending on stage and company maturity.