Strategic Pricing: How SaaS Companies Should Ask for $1M+ Annual Contracts

Jason Lemkin advises SaaS founders to aggressively increase pricing targets when moving upmarket, starting by doubling their highest ACV and eventually targeting $500k-$1m annual contracts. He provides two concrete exercises: challenging prospects with double the previous highest price point, and proposing expanded solutions to existing customers at significantly higher price points. The strategy works because enterprise customers have flexible budgets that flow to important solutions, and founders often underestimate what the market will pay.