Sales Enablement Strategy and Roadmap: A 5-Phase Framework

Nearly all sales teams have their sales process documented, but only 36% of reps consistently follow it. This enablement execution gap is one of the biggest variables in sales performance.

The good news is that you can close this gap. What it takes is an effective enablement strategy that guides your roadmap, and leadership reinforcement along the way. (So easy, right?)

What is sales enablement? 

Sales (or revenue) enablement is a dynamic organizational capability. It’s the ability to anticipate what reps need, and to get that support to them in a way that sticks. And it has to continuously adapt as the industry changes (that’s why it's a dynamic capability). 

Sales enablement is often the responsibility of a small team or individual reporting into sales leadership, a sales operations team, or corporate learning and development (I’ve seen all of the above). 

Did you know, the term sales enablement was coined by John Aiello and Drew Larsen in 1999? They built a platform to improve communication between the people creating customer-facing assets and the reps using them.

The three layers of effective sales enablement

Effective sales enablement requires three things working together: diagnostics, operations, and development. (Or, if you prefer the academic jargon: insight triangulation, enablement infrastructure, and sales support envelopment.) 

First, you need to diagnose what’s happening in the field: what’s working and what isn’t. Then, you need a system to take those insights and do something with them. Reps need the right support at the right time. Finally, you need a way to give feedback to reps, whether that’s through coaching or practice opportunities, so they can change their behavior. 

Most organizations have one of these layers working well (usually, it's the operational one). Few have all three working together and continuously adapting. That's what an enablement strategy and roadmap are for.

Why you need a strategy and a roadmap

An enablement strategy is a vision for bringing together the three layers as a system. It should be aspirational, but achievable. For instance, your vision might be that “All sales reps consistently follow the sales process.” That’s something you can build a roadmap around, and importantly, it’s something you can measure. 

A roadmap is a plan to execute the strategy. It's how you can manage your team's capacity and sequence work. Most importantly, it's how you get managers on board to support your work.

How to build your sales enablement roadmap

The scope of your roadmap will depend on the maturity of your sales organization. If you're at a company that's quickly scaling, you might build a roadmap one quarter at a time. If your company is well-established, you can likely build a roadmap for the fiscal year.

Here's why it matters what you're planning for. A roadmap is your way to be accountable for work. It gives you permission to push back when someone comes to tell you what you need to do for them. It's how you reconcile your expert analysis of what the team needs with what the business is asking for.

Phase 1: Assess 

When I'm building a roadmap, I find it helpful to think through a series of questions (ideally, with your team, or if you're running solo, a trusted sounding board). That starts with:

What problem are we really solving?

At this point you likely have two lists: one of support requested by stakeholders, and one of support you think is needed based on your strategy. Your goal is to pressure-test both of these against the data you have access to, such as:

• Call recordings or conversation intelligence
• CRM stage analysis
• Manager feedback
• New hire surveys
• Performance reviews
• LMS or LXP records

An LLM can help you identify patterns across these data sources (try the prompt below). You're looking to surface behavioral gaps, and then come to an evidence-based conclusion about what support you need to prioritize.

If you're in an industry where most sales interactions are happening in person (e.g., medical sales), you will need to augment your data with direct field observation (things like completed observation rubrics, debrief surveys, or manager scorecards).

Phase 2: Prioritize

Hopefully you now have a shorter list of priorities. It's time to decide:

What are we committing to this cycle, and what are we not doing?

By cycle, I mean the length of time your roadmap covers: a quarter, half a year, the fiscal year.

I think of this like a children's seesaw (a teeter-totter). On one end you have your team's capacity, on the other end you have the list of priorities. You'd like to find a balance between the two, so you don't send your team flying off (metaphorically).

For each item on your list, I want you to think through a few things:

1. The importance or time sensitivity: rank it low, medium, or high
2. The team resources needed to execute: a time horizon in weeks or months
3. The additional resources needed to execute: anything required to make this happen, from existing tools and resources to net new budget asks

With this information you can start to map out what's feasible, and what is dependent on things like approval from Finance.

Phase 3: Plan 

Once you have a better understanding of what you're committing to, it's time to plan the work. Every stakeholder conversation eventually lands on the same question: 

Why are you doing this work now, instead of something else?

Your roadmap is your answer.

The first step is to map out the rhythm of the business work you already support, like regular onboarding, quarterly sales kick offs, or annual leadership gatherings. Anything consistent you know you need to plan around. Your new work maps onto this calendar, not the other way around.

Don't forget to include holidays, flagship marketing events requiring sales presence, performance review cycles, hiring surges, and product launches. 

You'll be glad you didn't try to launch a major initiative the same week the entire team is in Vegas for a conference or heads-down trying to close out the quarter. 

Phase 4: Share 

When you have a working draft of the roadmap, it's time to get feedback from your stakeholders. You're asking:

Are we aligned on what this means?

Depending on your organization, you'll likely want to share the draft with your leadership, SMEs who will support content development, and L&D or HR partners.

You're walking a fine line between creating alignment around your roadmap, and opening yourself up to too much input. That's why I recommend carefully structuring how you share any draft:

1. Never share a draft without context. If your leadership asks for a pre-read, share your strategy document or the decision-making process leading up to the draft, including a summary of the data you reviewed.
2. Prepare structured feedback questions to ask, like: are we solving the right problems? Is there something we've missed?
3. Identify what the roadmap means for the stakeholders in question. Is there anything you're compromising on in their eyes?

You want to make it as easy as possible for stakeholders to get on board with your plans. Successful enablement depends on reinforcement, and you'll need it from your entire org. Approach this accordingly. The feedback you receive here won't always change your current roadmap, but it will shape the next one.

Phase 5: Iterate 

Throughout the year, something will shift. Maybe managers are inconsistently reviewing call transcripts, so only some team members are getting feedback. In that case, you'll need to figure out:

What do we change based on what we're seeing?

This is where measurement comes into play. For every deliverable on your roadmap, you'll want to define how you'll evaluate its success. Enablement can be challenging to measure. It's hard to isolate whether better coaching causes more deals to close, or whether the two are simply correlated.

When you're determining measurement criteria, I recommend going back to the data sources you started with in Phase 1. What repeatable evidence do you have access to? Could you confidently create a baseline to determine a before and after an enablement intervention? This is impact measurement. You can pair this with snapshot data — things like how many people participated in coaching sessions, and how often.

Your goal is what I call good enough measurement. You want evidence that the work is having an impact and that it is a worthwhile investment, or if it is not having the intended effect. That way you can confidently adjust your roadmap.