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Tips for booking meetings and closing deals in an upsell role?

I was recently promoted from newco BDR to SMB upsell AE. We sell a B2B SaaS product that can be used by most departments. Customers can buy an entry-level license directly from our website (max of 5 seats), and my job is to convince these companies that purchased our entry-level website plan to upgrade to a commercial plan. Our commercial plans allow for more seats, higher transaction limits, a myriad of extra features, and 3rd party integrations.


The minimum price for our commercial plans is the equivalent of 5 seats on our website plans (they don't actually have to have 5 users though, they just have to pay at least that much). I've been doing a lot of prospecting around various extra features they can only get with a commercial plan, and have booked a decent number of meetings that way. The problem is that the vast majority of my accounts have just 1 or 2 seats purchased, so I usually lose them when they find out upgrading to a commercial plan is going to cost them 2.5x - 5x what they're paying now. I try to do discovery with them and use that to highlight how we can integrate with their other software, how their current processes can be eased by added features, and other use cases for our software they could use us for with higher transaction limits. But the vast majority of the time they decide they're happy with how they're already using our software, and can't justify 5x-ing their cost to get the 1 or 2 features they had expressed interest in.


Also been trying these approaches for setting meetings, which have had mixed success:


  • Prospecting to people at the company not using our software already - ex. if ACME's HR team is using our software, I'll reach out to a VP of Sales with something like "Hey Name, not sure if you're aware but ACME's HR team is using our software to solve X problem, curious if ACME's sales team also faces X problem, or Y and Z problems we also help with. Open to discussing ways we can help your team too?"
  • Annual renewals - "your plan is renewing next month, want to review how you're using our service and see if we can be a further resource for ACME"
  • Approaching transaction limits - this actually works well but usually they're pissed off about it, I really dislike these conversations. Kind of feels like if Comcast asked you for a meeting because you're close to hitting your data cap. (Our transaction limits are actually pretty reasonable but admittedly buried in the fine print.)
  • Using ZoomInfo/LinkedIn to figure out other technologies they're using, then prospecting around our integration. (Good for setting meetings, but hard to close them on it with the up to 5x cost increase for upgrading)


Any ideas on what else I can be doing to upsell more accounts? All of my experience in prospecting is NewCo, so I'm not sure if there's other things I could be doing I haven't considered. Also as a new AE I'm struggling to drive home the ROI of these added features/integrations - they want them, but usually they don't think it's worth the cost increase.

πŸ‘‘ Sales Strategy
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3
1nbatopshotfan
Politicker
+5
Senior Director, Enterprise Technology
Prospecting to additional users is your best bet, and has worked for me. You’ve passed any security and procurement review. You can leverage that since your technology is already onboarded. Profile additional users across departments and push them to reach out to your buyer. Building internal momentum is your best bet to unlock additional budget.Β 

Once you’re familiar with the additional users at a few clients, you’ll be able to repeat this across your portfolio.Β 
Fo
FormerStartupJobHopper
Contributor
+2
AE
My previous role was exactly like this. The basic license was free, so customers saw no need to upgrade to the paid version and I honestly didn't usually disagree with them. I flamed out and got the sack in 5 months along with about 10 other reps over the prior year, and about 15 people total. All this to say, no clue on your question but good luck lol
ADudeBeingAGuy
Opinionated
+3
Account Executive
Well hello there fellow traveller...Β 
We literally have the same job at the same company.Β 
We should connect and talk through some of this.Β 
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