How do you measure the effectiveness of your sales content?

The most comprehensive way to measure the effectiveness of your sales content would be to implement a content management tool. Such a tool serves the materials to your reps, produces reporting, and allows you to connect the content usage to your outcomes. Pretty cool. I've been considering a tool like this but the cost and installation effort are still overkill for my company with 1000+ employees, so you probably want more of a "hack". (I can't recommend a particular tool yet as I haven't implemented one).

So absent a tool I try to interview reps periodically to find out what they are using most. Feedback isn't data but works because it is usually consistent from rep to rep. For example I learned that our reps use 2 of my sales slides far more than anything else---great to know!

I also try to build relationships with the reps so they will tell me what they need, if they can't find it. I keep track of these requests. For example, I got a series of comments that suggested my product messaging was too "high level" for our prospects, I focused new content on more tactical use-case messages and the reps feel it works better.

I also look at engagement measures that I can prove such as downloads, qualified leads, etc. This shows what top-of-funnel content I should add to or maintain more frequently.

Finally, I try to get a periodic analysis that connects the content used to the deals we win. In an org my size I try to get a sales ops analyst to do this for me.

So, in summary, try this periodically (maybe once a quarter):

1. Interview good reps about what they use.

2. Review engagement metrics available to you

3. Review deal wins and connect to the content used

The best content should reveal itself immediately!

There are two ways to measure the effectiveness of your content - qualitative and quantitatively. However, before you even build anything, you must understand when and where your sales collaterals are being used in the sales process or rather where and when does your sales team need collateral. 

From a quantitative perspective, I would use software like Highspot, ShowPad to see how often they are sending content out, and whether your content is actually being view and shared by customers and prospects. 

From a qualitative perspective, I would do two things (1) have a monthly internal survey to make sure that the team actually finds your content effective and that they aren't just sending stuff out just for the sake of sending things out. Then (2) ask your top sales reps if they are leveraging any of your content, if they do, then more than likely other reps are as well. Reps listen to their highest performing colleagues.

Please call your reps, more often than you do. As PMMs we are guilty of not engaging our reps as much as we should. Unless they have written off the PMM team, they will straight up tell you what is or isn't working, which you can go and implement.

The other very effective option is to start a Win/Loss program so you can ask the prospects what did or didn't work. It really lays the truth out for everyone to see.

There are many opinions here suggesting a tool needs to be bought. Some people swear by their tools. But please only use tools to automate what you've been doing manually. 

Tools are not magic, and they take time and resources to implement. Often a free prototype (Google Sites, Google Forms) has far greater ROI than that fancy SaaS tool bought for tens of thousands of dollars. 

If you want any kind of quantitative data, purchasing a tool is really the only way to achieve that. I recently evaluated all the sales enablment options and went with DocSend. You can track any content engagement to accounts in SalesForce which you can tie to eventual Closed Won and Closed Lost to track true ROI. 

I agree with the above comments for qualitative evaluation. It's all about building good relationships with sales so they will be transparent and candid about what works and doesn't work...with useful feedback. 

Monitor bookings growth and sales team productivity. Also, jump on tons of sales calls (you should be doing this anyway). Are they on message? Are they handling objections you taught them to handle? It should be obvious to you very quickly whether they are using your stuff. 

That's a very tricky question as I'm guessing you know. I work in a smaller company so I simply poll my sales team and ask what is working and what isn't (and why). The sales team generally knows what content is having an impact. We do provide a lot of customer facing content via the resources page of our website and track downloads as an indicator as well. This problem gets a lot more difficult when you have a large, global sales team and don't have an adopted, centralized mechanism for accessing updated sales content. You ideally want a mechanism where sales can build their decks from the individual slides and access the content from a central location. However, I have never seen this work very well. Sales will inevitably keep decks on their local drives and modify them and use them as they see fit. It's always gotten back to some means of getting insight from your sales team directly to know what works and what doesn't. As mentioned in another response, you should be getting on several calls and, ideally, driving a sales certification process to make sure they understand and can use the content as you intend.

Sales Enablement technology continues to progress quickly in features and capability and, if adopted and sponsored by sales leadership, can provide great insights and information on this issue as well.

To measure effectiveness you need a tool. Just using a cloud storage platform like Google Drive or Sharepoint is not going to be enough. I also agree with Steve Fayer that the bigger an organization, the more expensive to deploy this kind of a tool. However, as the sales enablement industry matures and expands, this problem is bound to be addressed. 

If you can have a content management/knowledge management tool in place, you can focus on the following metrics: 

• Sales Engagement. Though some people may consider this metric to be superficial (since it doesn't tell you much about prospect engagement), we definitely see value in this metric. If your sales team is engaging with a certain asset regularly or is engaging with a particular content type frequently, that should give you an insight on what matters to the sales team. As other answers have pointed out, measuring sales decks are an outlier because they are expected to be tweaked and customized before they are shared with a prospect. But Data Sheets, Case Studies, White Papers, Blogs, Webinar Videos, etc. are usually used in their original format.
• Prospect Engagement. With most content, once it is shared with a prospect, you lose insight. However, if you can measure prospect engagement with your content, you can use that data to measure effectiveness. This does require that your content management tool is not only serving as a repository but is also integrated into the channels of communications. That includes email, CRM, sales engagement platforms, etc. 
• Revenue Attribution. If you can capture the context of an opportunity or a lead when sales or a prospect engages with a particular asset, you can derive attribution data. This is not an exact science and will never be. However, this can give you further insight into the effectiveness of the content. 

To get these insights, there are several internal processes that have to work. The important one being "sales using the content management system for meeting their content needs." This requires that your content is always current, relevant, targeted, and on message. If sales is not engaged with your content management tool then it will be difficult to get any usage based insights. Organizations usually underestimate the effort it takes to keep your content house in order. It doesn't take much for clutter to seep in and mess up the experience. 

You can always rely on surveys and direct feedback as other answers have mentioned. But a better option is to couple the direct feedback with insights that you can gather from daily engagement.