For those of you in more complex sales targeting larger companies, what are the go-to pieces of content/collateral that you encourage sales to send? More specifically, what do you like to send to help a user convince their economic decision maker?

Bulk of my career has been in mid-to-large enterprise solutions -- from engineering to marketing and sales enablement. I agree with Mike's commentary, it is super important to understand what is solution selling and the challenger framework can be very helpful. There's other tools that have come in -- I recently heard about MEDIPPIC at my previous company, believe SAP uses this methodology. 

It is less about content because many of the folks you are targetting like senior executives (CIOs, Managing Directors) are less likely to come to your website and even give information for gated assets. I have said this so many times, I feel like many PMM leaders and even campaign managers don't get it. So you have to find their watering holes -- aka Thought leadership pieces in industry magazines, like NEtwork World, CIO World or something of that nature. 

I also advocate, PMMs being on sales calls and visiting customer sites to see how the product is being use post-installation. Because the deployment cycles can also be bit longer than when your product is selling into SMB space. 

Complex enterprise sales are more about relationships and solution selling than they are collateral. So, if anything, content and collateral becomes less important the farther up market you go. These sales are about face to face presentations, conversations, solution selling and discovery.

The problem with collateral and content is that it's a one way transfer of information. Enterprise sales requires two way interaction. And the farther up market, the less time real decision makers have to read collateral. I guarantee you a G2000 CIO is absolutely never going to read your datasheets and whitepapers. 

So, if you put a gun to my head and said "what three assets would you create for an enterprise sales rep," I'd probably say a killer solution presentation, a great demo and a compelling enterprise case study. But I'd focus way more time and attention into sales enablement than buyer content and collateral. 

As an aside, I'd highly recommend to any PMM in the enterprise, or even mid-market, go through a challenger solution selling course at some point. It's tremendously useful on two fronts

• Obviously, it will help you tailor your sales enablement materials to facilitate this type of solution selling
• More importantly, these skills are super useful for you. Your customer conversations will be much more detailed and meaningful and you might even help your bottom line by bringing in a few deals yourself. 

I agree with Mike above. Complex enterprise sales is about relationships and solution selling. There are multiple stages of selling and it should be part of your challenger solution selling course. These stages need collateral, marketing assets that excite, educate and enable the customer/user at that stage. 

Sales folks will benefit from this collateral (internal or external) in value selling at each stage and having one voice at each stage. 

I have spent my entire career selling into large enterprises. Now I work with our enterprise sales team executing complex enterprise sales, and enabling them with tools and content. My two-cent is that there is no such thing as go-to pieces content and collateral. More important is the sales process and qualification methodology. I think Savita mentioned MEDIPPIC. Taking a step back, the buying process which informs the sales process and the qualification method will determine the content and collateral that you will need. For example, if the security review is bigger than usual, then you will need a security one-pager. Because complex sales require so many stakeholders, the tools will depend on the market you are selling into and the sales motion that you have to execute against that market.