If you already have a few bigger deals under your belt, but most are smaller … and you want to build on that and close more “bigger” / enterprise deals … 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:
- 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 post-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:
- 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:
- Get on a jet. And get on a LOT more Zooms. A lot more. Yes, you can close bigger deals on Zoom for now. But, especially when the customer doesn’t really get to know you, they will often 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. For now, the best hack is having the CEO join more prospect and customer calls. Customers love, love, love to talk to the CEO. And later, when we come out of this, if your competition won’t get on a jet, and you will — that’s magic. More on that here: And listen to Stewart Butterfield, CEO of Slack, describing how customers were shocked how many more Zooms he joined since Covid:
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.
So 4 more tips to levelling up here:
- Build an enterprise-only sales team. Even if it’s just 1 or 2 reps at first. Round-robin of leads gives everyone a shot, but you also have to specialize. Have the folks who can close the big deals — get those leads. We all wait too long to do this. More on that here.
- Once you have 1 top logo in a segment, put an amazing outbound team on everyone in that space. This works. Everyone will take a call in the space to learn who Zoom, who Shopify, who Google just picked.
- Continually raise prices at the high-end. Not forever. But do it consistently, and you will learn. You’ll learn what you have to do, and build, to drive up your ACV.
- Do all the “enterprise stuff”, from SOC-2 to HIPPA to DR Policies to Hybrid Cloud to 100% Uptime and more. Just do it all. Todd McKinnon CEO of OKTA shares below in the video how they stopped all feature development for almost a year to build a service that just wouldn’t go down. That let them win in the enterprise, even when they were feature-poor vs. some of the competition for a while.
(note: an updated SaaStr Classic post)