Calendly

Calendly's SSO add-on costs $36 per user annually. For a 50-user team, this adds $1,800 annually. Discounts can be achieved during negotiations, with top negotiators securing up to 35% off.

For a 100-user deployment, Calendly Teams costs $4,800 annually ($48/user), while Enterprise pricing starts at $30,000 annually ($300/user) - a 525% increase per user. Enterprise becomes cost-effective at around 150+ users. Enterprise discounts can reach up to 51% off list price.

Negotiate 'bridge pricing' that phases in Enterprise features while maintaining Teams-level costs. This can save 35-50% compared to immediate transitions.

Calendly Standard pricing is rigid, with virtually no discount opportunity. Focus on negotiating contract terms and upgrade paths instead.

For 100 users, median discounts are around 14%, while for 250 users, they can jump to 20% or more. A 250-user deal could drop from $75,000 to as low as $25,200 annually.

First-time renewals typically see 5-15% discount improvements, while second renewals can achieve 20-35% better pricing. Start discussions 90 days early and introduce competitive alternatives.