If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions:

    • Hire a Very Good VP of Sales that has sold at your “high end” price point. She will be much better at you than this. At getting the High End of Normal, the Most Without The Customer Feeling Ripped Off. You aren’t great at it. If you can make this hire now — you will do much, much better. More here: The 48 Types of VP Sales. Make Deadly Sure You Hire the Right One.
    • Be aggressive — but be patient. Eventually, you’ll figure out how to get better at closing “all the seats”, all the revenue, up front. At least more often. Salesforce is now routinely doing nine figure deals, Box and Slack are now routinely doing many seven figure deals. They didn’t start there. Push. But don’t push the customer and prospect to a breaking point before you’ve “earned” the right, from a brand perspective, to ask for all the seats up front.
    • Lean in >heavily< on customer success. The best way to make pos-initial sale land-and-expand happen organically is engaged, happy customers. Not just happy customers. But engaged, happy customers. You need human beings to do this. Try to have as much as one CSM per $500k in ARR if you can afford it. More on that here: The $2 Million Dollar Man/Woman: How to Think About Scaling Your Customer Success Team and in this great video with Gainsight here:

  • Get zen about longer sales cycles. It’s just a fact that bigger deals take longer to close. A great VP of Sales will shrink that as much as possible. But you can’t close a $1m deal in 30 days. Certainly, you can’t as a new-ish start-up. Be zealous about shortening sales cycles. But don’t let the length of the sales cycles of bigger deals get you down. More on that here: Two SaaS Metrics That Actually Don’t Matter That Much: Absolute Churn and Sales Cycles
  • Get on a jet. Finally — GET ON A JET. Yes, you can close bigger deals on the phone. But. They will be smaller. They will take longer to close. They will be more at risk. The human element matters even more in sales and customer success in the age of software eating everything. And if your competition won’t get on a jet, and you will — that’s magic. More on that here: I Never Lost a Customer I Actually Visited

Going upmarket is a process. It’s well understood. Bring in at least 1 or 2 veterans that have done it as your aspirational high-end price point for next year … and magic will happen.

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