The Seller’s Guide to Moving Upmarket and Closing Bigger Deals

As Proposify continues to go upmarket, it creates a lot of challenges for me as a marketer.

I was curious…what sort of struggles has our sales team gone through? How did they become comfortable and skilled with closing bigger deals?

For our first episode of the Closing Show Live, I sat down with our own Customer Growth Manager, Scott Tower, and Clearbit Account Executive Al MacLeod to get their experience with moving upmarket.

The Seller’s Guide to Moving Upmarket and Closing Bigger Deals

Whether your organization is just starting to sell upmarket or you’re new to a company that forges a lot of big deals, we’ve got some great advice straight from the trenches.

Check out the full episode of the Closing Show Live on closing bigger deals:

What counts as a “big” deal

Everyone has a different calculation, but a big deal is usually considered to be 2 to 4 times your average deal size.

“Whenever I’m working a deal that’s more than double my normal contract size, that’s a big opportunity. And a small deal would be something under my typical annual contract. When I started Proposify, $3000 was a big deal, but now that’s small as we’ve moved upmarket.” - Scott Tower, Customer Growth Manager at Proposify

And as you move upmarket, your average deal size will increase, and so will what constitutes a “big kahuna.”

The top 3 challenges with upmarket sales

There are a lot of challenges that sellers face when they need to move upmarket and cater to the needs of larger customers.

Here are some of the top struggles:

1. Helping champions get buy-in from their company

Having one super-champion doesn’t mean you’ll close the deal. You need to help them convince other decision makers to give you a chance.

“You might have your buyer saying everything you want to hear, but then you don’t realize how much work is ahead of you to actually make your solution a priority for the entire company.” - Scott Tower, Customer Growth Manager at Proposify

2. Keeping buyer committees aligned on the same priorities

It can be extremely difficult to make sure that all buyers are on the same page. If they aren’t, the deal with fall through.

“As you bring more people into the conversation, they might have competing priorities, so you need to pay attention to what these people care about and make sure it all aligns with the common goal you’re trying to solve. I remember a couple of deals that went by the wayside because I wasn’t focusing enough on the decision maker’s main goal.” - Al MacLeod, Account Executive at Clearbit

3. Satisfying more complex review and validation processes

When selling software to large organizations, the review process gets complicated. Buyers might expect to see detailed MSAs and responses to their security questionnaires. Some hands-on work might be necessary to validate the effectiveness of a mission-critical integration.

Solving these challenges presents yet more complexity because sellers need to collaborate internally with solutions engineers, customer success managers, cybersecurity engineers, and others to gather the information and materials that prospects need.

How to sell upmarket

So how do you successfully sell upmarket?

Try these tips.

Tip #1. Know which selling model to use

You need to know which method to apply to which opportunity.

“What clicked for me was understanding the different selling models. Transactional works for smaller deals. But for larger deals, you either need the solutions selling model—where the prospect will buy from you if you can satisfy their solution criteria—or the consultative selling method, which is more about understanding their business. As a seller early on, I didn’t understand those differences. And sometimes you have to crash and burn to learn that you can’t sell the $10,000 opportunity the way you sell the $1,000 opportunity.” - Scott Tower, Customer Growth Manager at Proposify

Tip #2. Have patience

Without patience, you’ll be stuck in a transactional-selling mindset that absolutely won’t work on bigger fish. This can be tough for new sellers or for sellers who are used to closing a certain amount of deals. But the patience can pay off big time when it comes to deal size.

“The biggest thing I’ve learned is that you need to have the patience to advise your prospects on what they should be thinking about when they enter their buying cycle and to foster these relationships.” - Al MacLeod, Account Executive at Clearbit

Tip #3. Understand the lead’s buying process

With a clear understanding of what the buyer’s side looks like, you can better assist them with that process and move through it faster.

“I remember with one deal, we had three or four calls, and at the end of every call I was asking for the signature and then finally I was like Wait, what do you need to get done to make this happen? And the champion laid out all the next steps for their decision-making process. And then I mapped out my process to theirs and realized I should be asking those sorts of questions for all larger-scale opportunities.” - Al MacLeod, Account Executive at Clearbit

Tip #4. Build relationships and add value at every step

When you are a patient seller, it’s easier to build real relationships. You’re focused on their needs, not your own. Make sure to find ways to add value throughout the sales process.

For example, if you’re going 3 or 4 weeks between calls, you could send a Loom video with insights that are tailored to the concerns they’ve already shared.

Tip #5. Get creative

The slower the economy gets, the more creative you have to be. Don’t be afraid to find ways to give customers a taste of your solution, so they can get it approved easier.

“Being more flexible and creative is important in these times. If you haven’t done a paid pilot yet, maybe it’s time to try that out. Or if you haven’t done quarterly billing yet, maybe let them sign up for one quarter and then renew.” - Al MacLeod, Account Executive at Clearbit

Recommended books for learning how to sell upmarket

Al and Scott shared some of their favorite books for learning how to close big deals. The insights within are also relevant for every deal size.

The SaaS Sales Method for Account Executives

Book cover for The SaaS Sales Method For Account Executives by Jacco Van Der Kooij

“This book covers the different frameworks and models for SaaS sales. I reference all of Jacco Van Der Kooij’s sales playbooks on a daily or weekly basis.” - Scott Tower, Customer Growth Manager at Proposify

Find it on Amazon.

Gap Selling

“Gap Selling is a great refresher (especially in this market), when you need to go back to the business impact because people aren’t really buying something just because it might look cool.” - Al MacLeod, Account Executive at Clearbit

Atomic Habits

“Atomic Habits is applicable to anyone in any role but it really speaks to salespeople. It’s great for building consistency with sales and finding ways to build your own systems.” - Scott Tower, Customer Growth Manager at Proposify

Large deals may differ in their number of buyers, calls, and requirements, but without working off a strong foundation of real business impact, you can’t even get your foot in the door.

Proposify has tons of features to help increase your proposal closing rates. Check us out.

The Seller’s Guide to Moving Upmarket and Closing Bigger Deals

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