12 Tips for a Successful Sales Enablement Rollout You Can’t Miss

12 Tips for a Successful Sales Enablement Rollout You Can’t Miss

As companies understand the importance of sales enablement, they invest more time and resources to set up a robust sales program. There are always many hiccups when you roll out the program.

It could be a lack of adoption of a sales enablement tool, ineffective training methods, or a lack of alignment between leadership and sales. Ultimately, it negatively impacts your deal cycles and client churn—preventing you from reaching your revenue goals for the year.

In this article, we’ll review 12 expert tips to help you roll out your sales enablement program and maximize your investment.

1. Get leadership buy-in and marketing-sales alignment early on

The biggest challenge you’ll face while rolling out a sales enablement plan is getting executives' approval. Typically, leadership needs to know precisely how a strategy will play out and the expected ROI. Your efforts go to waste if you can’t speak their language and convince them.

“If your executives and sales leaders are not in agreement on the strategy, it doesn’t matter what you do next,” notes Meredith Jung, founder and principal product marketers at Amplified Edge LLC. “You need the executive team and sales leaders to introduce, push and enforce the strategy. When enablement does these three things themselves, sales teams ignore the new strategy and continue to do things the way they always have.”

Also, when leadership is actively involved, it signals the importance of the initiative, ensuring that the required resources and support are provided.

Do this by interviewing sales, marketing and product teams to understand their challenges and develop a tailored strategy. Explain how the plan will benefit the company and contribute to its goals to align them on the enablement initiative.

2. Evaluate your current sales processes to determine challenges and gaps

This process involves analyzing the entire sales cycle, from lead generation to closing deals, and pinpointing inefficiencies, bottlenecks, or areas where sales reps struggle. It lets you find out what works well and what doesn’t, allowing you to focus on the right areas.

Start by asking the hard questions:

  • Is the customer journey changing?
  • Are there any major industry trends that impact the sales cycle?
  • Are your sales reps prepared to tackle different objections?
  • What are the main points of friction in the sales process?
  • Do you have the right workflows in place to empower reps?
  • Which content assets do sales teams need for better conversions?
  • Are you able to expand your outbound motion using different channels?
  • What are the major bottlenecks that sales reps face every day?

An excellent understanding of your sales teams and their needs is crucial. Lee Brooks, a revenue and product marketing manager at Multiply, describes them as “front-liners who’ll deliver your act.” Whether it’s the need for specific tools, training, or internal alignment, find out their issues and address them in your rollout.

She says, “It’s about orchestrating each element, so when the curtain rises, your team performs seamlessly, leaving the audience—in this case, the customers—thoroughly impressed.”

3. Hone in on the ICP and build sales processes around that

“Know your customers” — that’s one of the most common pieces of advice marketers and sales reps receive. But despite that, many companies struggle to define who their ideal customer is clearly.

They might have a detailed buyer persona document to help their enablement teams, but that’s about it. The real gold comes from understanding your buyers' main challenges and how your product/service rectifies them.

In 2023, buyers asked about 18 questions on average in a sales call. In 2022, it was just 13. Buyers spend more time researching their products or services now. So, conduct deep research using surveys, interviews, and focus groups to understand how they go about the buying process.

Use those insights to build your sales funnel and processes around that. This lets you increase conversion rates across the funnel and retain customers in the long run.

4. Focus on the bigger picture before creating the strategy

Sales teams are pressed for time as it is. Additionally, marketing and product teams who support sales are also short on time and resources. This is one of the reasons why they’re more resistant to trying out a new plan, as they don’t understand how it impacts.

So, keep the focus on the organization’s goals and objectives. Show them exactly how the current sales enablement strategy will help them achieve the company’s long-term vision. In the same way, reps have to show a customer the ROI of their offer, you need to show reps the ROI of your plan. And that involves including them from the get-go—not after the strategy is ready for rollout.

5. Involve the sales team while creating the sales enablement strategy

Sales reps have firsthand experience with what strategies, tools, and resources are most effective in engaging customers and closing deals.

When you involve them initially, your strategy remains grounded in real-world experiences—not theoretical possibilities. It also ensures that when you roll out the plan, there’s a level stance and better adoption rates, as they already know why this activity is being conducted.

6. Conduct personalized training sessions for sales reps

Recognizing that each sales rep might have unique strengths, weaknesses, and learning styles is key. Use that as a guide to tailor your sales enablement plan accordingly.

“Take the time to understand your sales workforce,” recommends Abid Salahi, co-founder and CEO of FinlyWealth. “While small teams benefit from an individualized strategy, larger teams demand an approach focusing on harmonization and scalability. Here, systems and tech tools that allow standardized, repeatable processes while tracking metrics help balance individual performance with overall team targets.”

Use different approaches like 1:1 coaching, role-playing scenarios, or workshops to get sales representatives up to speed.

7. Create and document your sales enablement strategy

Implementing a sales enablement strategy is not a one-time task. Unless you document your strategy, it’s hard to figure out how it helps the company, how you’ll roll it out, and what metrics you’re held to.

Documenting it forces you to have a clear-cut roadmap for the entire process and clarifies the what, why, and how at every stage. For example, having unclear goals like “We need to sell more” won’t make a difference. But saying “Increasing closed-won rates by 15% for APAC in Q1 via rep coaching” is a more specific plan.

This also acts as a reference point for internal teams in the future so that they can adjust plans based on how the current one performs.

8. Perform beta tests with smaller groups before rollout

Beta testing with a small focus group lets you test the value of your plan and its feasibility in achieving its goals. It also enables you to assess the ease of integration into existing workflows and the overall user experience.

Jung usually gets buy-in from leadership and sales leaders to align the strategy with long-term goals and address current challenges. Once she creates the strategy, the first step is getting the sales team’s feedback.

”I pilot the initial strategy with a smaller group,” explains Jung. “This allows me to do two things: Test and refine the strategy before rolling it out to the broader organization and find champions who can advocate for the strategy with their colleagues and coach them through implementing it successfully. I like to feature these champions in the rollout.”

In the final rollout, she includes the following:

  • Context from a high-level sales leader or executive around why this is important and what’s in it for the reps
  • Case studies or testimonials from pilot champions
  • Training or an overview of how to implement the strategy

This makes the rollout process easier and reduces any roadblocks you might face.

9. Encourage an open dialogue, especially in smaller teams

In smaller teams, each member’s role is often more significant. Regular meetings, feedback sessions, and informal discussions can help maintain this open dialogue and address issues before they become a significant bottleneck.

“With fewer reps, you can easily tailor the enablement strategy to individual needs, encourage open dialogue, and quickly iterate on the strategy based on direct rep input,” says Matias Rodsevich, founder of PRHive. “This personal approach ensures the strategy is well-integrated into their daily workflow, leading to better adoption and more effective use of sales enablement tools.”

10. Create a custom suit for small teams but a “school” for larger ones

As your sales team grows, so should your enablement approach. For smaller teams, adopt an individualized approach, but for larger teams, adopt a structured playbook-style approach to ensure uniformity.

Michael Chen, head of growth at Notta, says, “If I’m working with a small sales team, I say, ‘Keep it personal.’ Talk to each rep, see what tools and training they need, and make sure they get it. It’s like making a custom suit—it should fit just right for each person.”

“But for larger teams, it’s like setting up a school. You need the same good books and clear rules so everyone knows what to do. Make sure everyone’s on the same page, and use numbers to check if the plan’s working or if you need to switch things up.”

11. Invest in conversion-oriented sales content creation

Most of the content that marketing teams create is focused on the top of the funnel. It generates awareness and brings people into the sales funnel. But sales teams need more middle and bottom-of-the-funnel content to convince prospects to buy from them.

This type of content directly addresses potential customers' needs and pain points, increasing the likelihood of converting prospects into buyers. Some examples include the following:

  • Product demos
  • Case studies
  • One-pagers
  • Battlecards
  • Whitepapers
  • Product/service brochures
  • Datasheets
  • Buying guides
  • Pitch decks

So, when you’re including content creation as part of your sales enablement plan, create more conversion-oriented content that talks about your offer.

Also, monitor its conversion potential over time and see if you need to make any adjustments. Depending on the analytics, you can streamline your content library, too.

12. Continuously measure and iterate your enablement efforts

It’s a fact that no matter how many feedback cycles you use, you’ll still have to adjust your enablement efforts as you get more data.

Chen says, “I start by analyzing our sales data and pinpointing where our team typically hits snags. Throughout the rollout, I’ll keep an eye on the KPIs, ready to adjust as needed. It’s about laying the groundwork, being attentive, and always ready to fine-tune our approach.”

For example, if your goal was to reduce sales cycle length by creating the right content assets, measure how long it takes for newer deals to close once they’re in the pipeline. Choosing the right KPIs lets you keep track of what’s working so you can adjust as needed.

Sales enablement requires sustained efforts in the long term

The success of your sales enablement rollout depends on how well you plan it and how well you foresee potential challenges. It’s not just about implementing new tactics or workflows, it’s about meeting the needs of your sales reps and empowering them to do better faster.

Understand that it’s an ongoing process, and be ready to implement feedback as and when you implement each phase. This creates a culture of continuous improvement—leading to better sales outcomes in the future.

If you’re looking for a tool to manage all your content during the rollout process, learn more about how Content Camel can help you.