How do you develop a sales enablement roadmap?

I love Agile practices for this...my teams have always followed a process of Intake prioritization, and constant backlog grooming to feed a roadmap.

A roadmap typically is a combination of the absolute must haves (e.g. events like SKO or infratsructure projects like getting an LMS in place or what not), and should haves (e.g. key strategic goals, new product launches requiring enablement, etc.) and some white space for all those things you can't possibly plan in fast growth companies. 

Your sales enablement roadmap should be one piece of your larger PMM roadmap. If you can flight out upcoming product launches, new research reports that will be launching, etc… then you can tie an enablement approach and cadence to each of these. Aside from new enablement, it’s good to monitor and notice when your sales teams might need re-enablement on existing sales plays or content. Often times if salespeople have been around for a while they might stick to their approach out of familiarity and comfort, but the market and competitors may have shifted. Recognize when sales teams are not making the most of every opportunity and run re-enablement sessions that make each person “stand and deliver” their pitch and earn “certification” from PMM, their sales leaders, and their peers.

This is done in conjunction with your sales enablement team, if you have one. Ideally you will look at the key priorities for sales enablement which you gathered directly from the sales team either via surveys (if you have a big team) or informally during a feedback session (great for smaller orgs).

Part of the prioritization process involves looking at:

1. What are the most requested enablement topics or needs

2. Which of those will have the highest impact in a seller's ability to meet their quota

3. How much effort is required to deliver it

From there you plot along the timeline the projects you will take on and work with the enablement team on the best way to deliver them. In some cases you could just record a video and make it available for on-demand consumption, in other cases you will want an in-depth training session. These should also be thought about and scheduled in advance.

And, of course, you should try to avoid the last month of the quarter when the sales team is fully focused on closing deals.

Love this question. Here is my 5-stepper

1. Identify your corporate dates. sales offsite, management offsite, product launches etc. are time based anchorpoints. Key decisions get made or updates occur. Execs get together etc. (pro tip: avoid end of quarter)

2. Identify your key business priorities (more coverage, more sellers, increase avg ticket size, new CRM etc.)

3. Identify the steps to complete the key priorities and estimate how long they take

4. Reverse engineer from your anchor dates, baring in mind iterative and parallel efforts

5. Align sales leadership around roadmap

Here are some of the guiding principles I like to use when developing a sales enablement roadmap:

- Map out the product launches for the coming quarters and use these as anchors in the enablement calendar. Consider tier 1/2/3 launches and the format/audience for each. 

- Identify key areas of focus for the coming year like value selling & ROI, persona/use-case/industry playbooks, positioning refresh, demo academy, etc., and align them to different quarters by order of importance or urgency. You might be expanding into new verticals or geos or going up/down market and these new motions will determine the areas you'll need to focus on. 

- Understand what are the key selling skills and techniques that the team needs to master from prospecting to discovery or negotiation skills and work with the enablement team to determine when and how these are showing up in the enablement calendar 

To create your sales enablement roadmap identify the opportunity you need to capture, uncover the barriers to adoption, and then deliver new materials and activations that address those barriers.

1. Identify the Opportunity: Which segment or customers do you need to drive action from? And what action do you need them to take? If you start from a clear target (who + what), you will be able to craft tactics that get you to that outcome.

2. Uncover Barriers: What is holding back your target customers from taking the desired action? This can be identified for qualitative research with customers and sales teams. Be sure to fully evaluate your pitch / sales motion. Are customers struggling with implementation and require new set-up materials? Do sales team members struggle to pitch you product and need more education? Are sales teams unable to prove to customers the value of your product and you need new proof points?

3. Address the Barriers: Create a plan to launch your new materials and education programs. Once you know what you need to build, this is typically the easy part. Don’t forget to build measurement into your plan.

I like to start by:

1. Interviewing and/or surveying the sales team on needs/wants.
2. Listening to sales calls - how are they pitching? What are they using to pitch? How is it resonating?
3. Audit for the basics: Can sales speak/show how we compare to competitors? Are the top objections and responses documented? Is there an up to date pitch deck? Is there any/enough social proof the sales team can share with prospects?
4. Prioritize what will improve the sales pitch first, then what you think will be used the most by Sales, then work down the list from there.