Linear Enterprise pricing becomes highly negotiable at enterprise scale. For a 500-user deployment, list pricing runs approximately $239,735 annually, but Vendr's data reveals significant discount opportunities that most buyers miss. Benchmark targets based on Vendr intelligence: 500 users, 1-year term: Target 16-20% discount ($191,788-$201,378); 500 users, 3-year term: Target 21-32% discount ($163,000-$189,000 annually); The 95th percentile of successful negotiations achieved 32% discounts ($163,000 vs. $239,735 list). Key negotiation levers: Linear's Enterprise tier has substantial margin built in for large deployments. Companies with 300+ users represent their highest-value segment, and our data shows they're willing to discount aggressively to win these deals. The sweet spot for maximum leverage is 400-600 users—large enough for significant discounts but not so large that you trigger their most complex approval processes. Multi-year strategy: Three-year Enterprise contracts show the highest discount potential. A 500-user, 36-month deal at the 75th percentile pricing ($291,890 vs. $359,470 list) saves $67,580 over the contract term. Factor in annual price increases of 8-12% that you'll avoid, and total savings approach $85,000-$95,000. Competitive leverage: Reference Asana, Monday.com, or Notion pricing during negotiations. Linear typically matches or beats competitive offers by 5-10% to close enterprise deals.