sales enablement torture chamber

9 Ways to Make Buying Sales Enablement Software Less Painful

If you’ve ever had to buy software for your business, then you’re probably familiar with the special brand of torture the evaluation process can entail: there’s the long period of reviewing multiple tools and scores of features. Then the proposal and paperwork once you select the right solution. And then comes everyone’s favorite–the implementation phase. Months go by before you know if the tool you selected is actually going to help your sales team or not.

As any seasoned B2B marketer can tell you, this process is a painful one, especially when it comes to selecting the right sales enablement tool for your team. But here’s the thing: It doesn’t have to be this way. Not if you’re willing to stay laser-focused on the key problems you need to solve throughout the evaluation period.

And, as is true for any software purchase for your organization, it helps to acknowledge these three (unofficial) universal truths:

  1. Every vendor is positioning their tool as a disruptive force in the market. (Shocker!)
  2. No tool does exactly what you are looking for. (Really, there isn’t.)
  3. But… a lot of them come pretty close. (Patience, grasshopper.)

So, in the midst of the evaluation process for sales enablement solutions, what should marketers and sales teams keep in mind?

After interviewing dozens of B2B product marketers, sales leaders, and individual contributors in need-finding interviews for product development at DocSend, as well as hundreds of hours of sales discovery calls, we’ve identified several common questions and concerns that you should use to guide the process of considering your next sales enablement solution.

Let’s dig in.

#1 – First off, define the problem(s) you’re trying to solve.

No two sales teams function the same way.

A tool that embeds itself into the fabric of one company may be inappropriate for another. To avoid a misguided purchase, focus on the key problems you’re facing with sales enablement. You’ll feel compelled to list a ton, but be realistic, and try to keep that list to 3-5 problems, maximum.

Populating your list isn’t going to be easy. You can’t run a report in Salesforce and exactly where enablement efforts are falling short. Your CRM is only as powerful as its instrumentation, and if you aren’t tracking specific activities like, “wasting time looking for slide deck,” or “following up with prospect to ask if they read the white paper,” (and who is?) then you aren’t getting the full picture of your team’s inefficiencies.

The best way to figure out where reps struggle is to ask them. Set up a quick survey in a tool like Google Surveys, or run brief 1:1 interviews with key players and department representatives to identify common themes around where they think they’re falling short. From there, you can make a more informed decision about what goes on your list of sales enablement challenges.

#2 – Decide what you want to enable.

Sales tends to be involved in a few key activities: outreach, consultation, follow-up, or closing.

While there are a broad array of sales enablement tools out there, pretty much all of the aforementioned activities revolve around content, either the creation of it or its distribution across your sales team, and ultimately, to prospects. That’s why so many sales enablement solutions tend to fall into one of two categories:

  1. Tools for content creation and collaboration
  2. Tools for managing, tracking, and connecting content to business outcomes

There are benefits to having a content creation tool. For one, approval workflows provide a iron clad system cutting out rogue content at the source. However, these tools can come with a learning curve and usually require hours of training for every user. If the system isn’t intuitive, and your sales team doesn’t feel like they can quickly and easily create and personalize sales content, they may not bother doing it at all.

Sales enablement solutions that focus on content management over creation tend to be more flexible for both sales and marketing teams within your organization. That’s because they allow teams to create collateral wherever they want, and upload only the final version to the platform for sales to use. Solutions like these tend to put more resources into the presentation and document viewing experience, as well as content analytics and CRM syncing, too. Which means marketers can see which content sales is really using, and sales can see which content really closes deals.

If you want to evaluate the role of content in your sales process, and find out if it’s an area in need of improvement, here are some questions you should be asking:

From the need-finding interviews we did with marketers, salespeople, and management, here are a few things we learned when developing DocSend:

Sales doesn’t know:

  • What approved content exists for them to send to spur sales conversations
  • Where that content is stored online
  • Which content to use for certain industries, deal types and stages
  • What content is current and what is out of date

Marketing doesn’t know:

  • What content the sales team is sending to prospects
  • What content is effective at turning prospects into customers
  • Which content resonates with prospects

Management doesn’t know:

  • How sales and marketing work together
  • If they’re aligned in their goals
  • The ROI of content that marketing makes for sales

#3 – Develop internal benchmarks for your solution’s success.

Now that you know the problems you need to solve, the next step is to think about what success would look like for your team if they used a specific product. Instead of being open to endless possibilities and miscellaneous features from sales enablement vendors, guide your purchase around what you imagine success looks like for your team and organization. For example, your goals could be:

  • 90% of sales reps know where your content lives (based on follow-up surveys)
  • You’ve made it impossible to send outdated content to sales prospects
  • Sales content is fully integrated and tracked in the CRM
  • Management has visibility and reporting into sales content related activities

Again, these will likely be a bit different for every organization, but if you want to stay focused, use benchmarks to guide your consideration process.

#4 – Determine who is going to own this software and how it will impact their workflow.

Sales content management software isn’t just used by sales reps. Everyone from sales ops to leadership, to marketing and beyond is going to get their hands dirty, so it’s important to get buy-in on your solution early on.

Make sure every department stakeholder knows, and agrees with, exactly what they’re expected to contribute to the ongoing management and maintenance of the your new sales enablement system while the purchase process is going on, not after the solution has been bought.

#5 – Know the difference between sharing links versus attachments.

All sales content management solutions allow sellers to send content one of two ways:

  1. Regular, old school, attachments (throwback to 1992!)
  2. Links

If you’re looking at a system that uses attachments, be forewarned that this means you likely won’t get data on how and when prospects engage with your content. It’s also unlikely that you’ll be able to track the performance of your sales content all the way to a purchase through your CRM with an attachment-based product. You won’t know your content’s performance, and you can’t use it to identify what’s working. Many attachment-based sales content management tools may tell you how many reps accessed a piece of content, but it can’t track when a prospect opens that content, how long they read it for, or who else they forward it to.

Link-based systems allow users to track the performance of sales content. By tracking which content prospects are viewing and when they do so, sales and marketing can create a feedback loop of sales content performance data.

#6 – Create real success metrics for the product you choose.

If you don’t think you’ll be able to hit specific outcomes with a product, take it out of the consideration process. After all, if you’re owning the process of evaluating sales enablement solutions, your management team is going to want to know how it’s performing once it’s implemented.

Whatever success looks like for your organization, make sure it’s something you can objectively measure. It could be a revenue based goal, like:

  • % increase in content related activities per rep.
  • % increase in pipeline per rep.
  • % increase meetings booked per rep.
  • % increase deals closed-won per rep.

Or it could be a binary goal like:

  • Successfully integrate sales content into the CRM.
  • Provide management with a dashboard on sales activities that includes content engagement.
  • Determine the 10 most and least effective pieces of sales content in the company’s content library.

Whatever success looks like for your company, make sure it’s being tracked, because just, “feeling really good about where our content is at,” doesn’t tend to hold up in the QBR.

#7 – Identify how your prospects engage with sales content.

Over 80% of the US has a smartphone. That means prospects are going to read sales collateral on their mobile devices. If your sales content management solution has a clunky mobile viewer, or worse, requires reps to send attachments, you’re adding friction to the buying process. While going through the trial process, make sure to test your content on multiple mobile devices to understand what the prospect content experience will be like on mobile.

#8 – Make sure your goals align with the solution you’re selecting.

Although you’re buying the tool for your team today, you could be using this solution for years to come. Always ask vendors about their plans for the future. Learn their product roadmap, know their vision, and ask what features they’re committed to building. If their product direction isn’t aligned with how you envision utilizing the solution, it may work for the next few months, but fall out of favor in the long term.

#9 – Be certain your solution works where your sales reps do.

Almost all sales content management solutions integrate with Salesforce, but the levels of integration, and the workflows they require very greatly from vendor to vendor. Some solutions require that reps send content and emails directly from the Salesforce interface, other solutions allow users to send content from inside Gmail and Outlook, but send all that data back to the CRM. Depending on your sales team’s current workflow and preferences, one may be a lot easier to implement and achieve adoption with.

Don’t Be Afraid to Be Thoughtful

Nothing about selecting a sales enablement solution is easy or quick, and the wrong choices do get made. But by taking these nine considerations seriously, you stand a better chance of buying the right sales enablement solution for your organization the first time around.

Want more help with sales enablement software?

Download our guide:

Finding the Right Sales Enablement Solution for Your Business.

image via chrisd90