79. What are some of the biggest mistakes you made with enterprise SaaS sales? Boy a lot. A list of some of the bigger ones: • Not mapping out — and getting to know — all the stakeholders. This is a skill you need to learn quickly in the enterprise. The person that inbounds is often just one of many stakeholders in the purchase. Don’t assume whomever you are currently talking to you is the buyer, or even in the end, the decision maker. • Not being responsive to every key concern. I remember my CTO once arguing with a Fortune 500 company on a “security” concern they had which really made no sense. Didn’t matter. They were concerned. That meant we had to be concerned. You can’t do everything. But you can be responsive to every concern. • Not visiting enough customers in person. I never lost a customer I visited in person. But the ones I didn’t, were the ones that silently churned. Even / often when the usage was high. • Not hiring a full-time RFP person. If you are going to do a lot of RFPs, they need an owner. They are too much work to just dump on a product person, success person, sales leader, etc. • Not hiring a full-time Chief Security & Compliance Offer. Hire a CSO way early if you are truly going enterprise. It just makes the customers so much more comfortable. And then security audits, reviews, etc. go so much faster and easier. • Not opening an EMEA/London office and field offices earlier. Enterprise customers expect you not just to get on jets (see the point above), but to be there. Wherever you have $2m or more in revenue — you should have an office. • Not investing earlier in customer marketing and corporate marketing. Enterprise customers expect a brand to be presented in a certain way. You need to be at their events, sometimes with a red carpet. You need to pamper them the right way. You need the right types of collateral and case studies. The quicker you do this, the SAASTR.COM 76