Learning enterprise sales for the first time leads to a lot of mistakes.  A lot of them.  Then you learn the playbook.

A list of some of the bigger ones I made learning how to sell into the enterpriser:

  • Not mapping out — and getting to know — all the stakeholders in a deal.  And after the deal. This is a skill you need to learn quickly in the enterprise. The person that contacts you often is 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 decisionmaker.  Every deal is at renewal risk if you don’t get to know, and map out, all the key stakeholders.  
  • 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.  It literally made no sense, and in fact, their app did the same thing.  But that 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 key, top concern.  If you have to build a check-the-box feature for a top enterprise customer, just build it.  Another top customer will also want it.
  • 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. More here: I Never Lost a Customer I Actually Visited | SaaStr
  • 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 more 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 more comfortable prospects and customers will be that you are “enterprise-grade.”
  • Not getting the company to move to a Big Customer-centric culture faster. This is #1. If you go upmarket, if you move from SMBs into mid-market and then the enterprise … your culture also has to change. From one of users to one of the broad needs of 1000s of customers to one almost of … clients. Your very big customers aren’t just customers, they are clients. They deserve client-level service and attention. Many of your team that hasn’t done that before won’t enjoy it. They’ll bristle at their seemingly one-off requirements. They’ll struggle to deal with the drama around the big deals. But the folks that have been in that environment before and know what to do will solve most of the problems above for you.

Just a few of many.


(note: an updated SaaStr Classic answer)

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