Pricing is a message, and if you price at the highest end of your competition and segment, that will send a message you are the most valuable vendor. It may well be easier to close large customers if you are the most expensive vendor in the space. But if you choose this strategy, you have to go all in. You have to truly be the most secure, the most redundant, the best integrated, the most enterprise vendor. You also need enterprise-grade approaches to customer success and deployment. So Anchor High if you can deliver. It can be the fastest way to increase revenue 50%-100% or more, if you can pull it off. But you can’t go half-in here. • With bigger customers, it’s total deal size that matters. If you can simplify this calculation (like Slack and Atlassian do), it can help. Bigger customers really want to know what it will cost to deploy you to their division, their team, their org etc. • No one wants to get ripped off. This is maybe the most important thing to think about in the end. To have happy customers that spread your brand through word-of-mouth. Pricing should seem fair. There should be pricing protection for renewals and later years. Upsell should be as organic as possible. Concerns should be addressed, and support should be as close to real-time as practical. • Finally, remember what really really matters is CLTV. The total lifetime value of the customer. And customers in SaaS can last decades. Think more about how to naturally grow the account over the years to come. And a little less about how to get every nickel on Day 1. SAASTR.COM 57