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8 Steps to Build Your Sales Enablement Strategy

An effective sales enablement strategy is essential to provide your reps with the information and resources they need to be successful. Sales enablement adoption has increased by 343 percent over the last five years. It’s become such a core focus that 65 percent of leaders plan to increase their sales enablement budget over the next two years. 

The role of sales enablement has evolved from a support team for sales reps to a proactive department that enhances sales performance. 

Whether your sales team is remote or in-person, an effective sales enablement strategy is critical to provide tools, technology, content, and training to improve your process and help your sales team exceed quota and create predictable, scalable revenue.

The importance of a sales enablement strategy

Sales enablement equips your sellers with the resources, tools, coaching, training, and content they need to engage buyers and sell effectively. 

Your sales enablement strategy dictates how you will deliver and provide the necessary training and resources your sellers need to excel in their roles, and how you will align different teams to ensure success. 

It’s essential to be strategic, ensure that your efforts tie back to business goals, and be prepared to pivot and evolve your strategy where necessary. While some guidelines exist to create an effective sales enablement strategy, your approach should be tailored to your team and product or service.

“I’ve been in enablement for about five years, and one of the best practices I’ve pulled away is understanding and training your reps,” according to Stephanie Middaugh, Director of Enablement, WorkRamp. “Not my reps, not anybody else’s, but the reps at your company. So make sure you’re taking your strategies and molding them to support the team you have in your organization.” 

Steps to building your sales enablement strategy

Define your goals and align your strategy with company goals

A successful sales enablement strategy must align with your company’s vision and goals. Resources and training are essential, but they mean nothing if you don’t lead to business outcomes and impact. 

Imagine you just raised a big fundraising round and are launching into a new category. To enter the new market successfully, you must get the reps on board with the new outlook. You could create a Certification Program for each go-to-market team that includes self-led courses, live training, and a playbook on how to sell effectively. 

Additional key initiatives include:

  • Decrease costs by scaling onboarding processes 
  • Reduce turnover by increasing employee engagement 
  • Increase productivity and efficiency by helping people ramp up quickly
  • Provide product training 
  • Support organizational growth

While defining your goals, creating a clear mission statement that defines your team’s responsibilities and helps ensure your team remains focused on the right priorities is essential.

Here is the vision statement for the enablement team at WorkRamp:

“The enablement team at WorkRamp is focused on creating a cutting-edge and innovative enablement function to support our internal revenue-generating employees and drive scalable revenue growth. By providing the skills, knowledge, assets, and process expertise to all customer-facing roles, our reps can ultimately maximize every buyer or customer interaction.”

Read more: How to Define Your Enablement Scope

Leverage connectivity

Connectivity is one of the most important components of a successful sales enablement strategy. Reps shouldn’t learn in silos, even remotely. 

A Regalix report shows that achieving sufficient program engagement (46 percent) and creating peer-to-peer learning opportunities (43 percent) were the two most challenging aspects of remotely enabling sales-readiness.

Mark Riley, Sales Enablement Director, Handshake, faced this issue at the beginning of March 2020. He had to find new ways to connect with his sales team during the transition to remote work. He did the following:

  • Provided a virtual learning environment for reps to exchange ideas
  • Promoted collaborative learning through social challenges 
  • Initiated Whiteboard Wednesdays, a weekly open agenda meeting with the sales team

Mark makes the experience enjoyable. He promotes collaboration among team members by brainstorming sales strategies together. Virtual calls also include interactive features such as polls and chat.

Additionally, he starts meetings with upbeat music and encourages people to take breaks to “give people room to think, give them time to think.”

Finding ways to connect your sales reps virtually is important if your company runs a remote team. Besides giving them a human touch, it encourages knowledge sharing and growth. 

Learn more: It’s Time to Pivot – Handshake’s Sales Playbook on Virtual Team Alignment, Pitch Certifications, and Remote Training

Empower new reps through onboarding

A standard onboarding process increases new hire productivity by 50 percent, according to the Society for Human Resource Management (SHRM). Almost half (48 percent) of survey respondents said that effectively onboarding sales reps was the biggest challenge for ensuring the long-term success of training programs. 

Onboarding is crucial for getting new reps up to speed, as well as for retaining them. Effective onboarding is particularly apparent in today’s environment, where recruits are likelier to feel lonely and burnt out

Approximately 73 percent of organizations report ramp-up times between 1 and 6 months. A third of the organizations reported an average ramp-up time of 3 to 6 months. Through technology like WorkRamp, Reddit reduced sales ramp time by 33 percent.

Megan Hunting, Manager, Sales Enablement, Vanta, has extensive experience creating onboarding programs for revenue teams. Before joining Vanta, the company’s sales onboarding process lacked structure and clarity. Reps shadowed cold calling and demos to understand the software and call scripts. 

Using WorkRamp, Hunting improved the onboarding experience for Vanta’s team. “I loved how simple and easy it was to use. WorkRamp made learning fun, and I knew that’s what would help the revenue team at Vanta.” A key focus of her onboarding process was to ensure reps were set up for long-term success. Vanta’s onboarding programs using WorkRamp have never received less than a 5 out of 5 rating.

Want to improve your onboarding process? Download The Ultimate Go-To-Market Onboarding Playbook for free. 

“Using WorkRamp’s Guides and Certifications has simplified AE and CSM ramping time–we now have deadlines and clear timelines for guides and certifications, whereas, before WorkRamp, there was no structure or idea of when someone was ‘ramped.’”


 — Megan Hunting

Create and curate sales enablement content

Content plays a key role in your sales enablement strategy. Since sales reps are expected to deliver value at every stage of customer interactions, content makes their lives easier.

Provide reps with the following types of sales content: 

  • Buyer personas 
  • Buyer personas
  • Email templates
  • Talk tracks
  • Discovery call checklists 
  • Demo recordings
  • Business case templates
  • One-pagers 
  • ROI calculators
  • Case studies

With relevant and up-to-date content, sales reps will be more confident and prepared to handle clients and prospects, build trust and relationships, and close deals. Easily accessible content is also important for reps. Through a learning management system like WorkRamp, enablement teams can create training and materials and distribute them to reps. 

Hunting builds and scales onboarding, product training, and compliance initiatives for many different teams at Vanta:

  • Accounts Executives
  • Business Development Reps
  • Customer Success Managers
  • Support Reps

She can quickly create guides and other learning experiences for Vanta teams using WorkRamp. “I can’t even imagine how long it would take me to create these guides without WorkRamp. It’s so easy to use, and tools like the drag-and-drop content editor are very robust. I’m able to spin up new training guides in a matter of a day or two,” Hunting explains. 

“I think in this remote world, when new people start, they don’t know how to access important information after they’ve completed training. WorkRamp is the perfect tool they can always use to support their ongoing learning.” 

Develop your sales enablement tech stack

An average sales professional uses between 4 to 10 sales tools, according to a GetAccept survey. Among the tools reps use are CRM and sales management tools like Salesforce and Hubspot, coaching and call recording tools like Gong and Chorus, automation tools like Outreach, and learning platforms like WorkRamp.

Investment in tech is on the rise. According to Gartner, sales tech budgets increased by 5 percent from 2020 to 2021.

In terms of training solutions, features that support continuous coaching (58 percent) and remote training (53 percent) were most demanded, followed by an assessment tool for pitches (40 percent). 

Modern sales training and enablement platforms provide many benefits. You can combine instructor-led classes with self-guided courses based on the rep’s needs. 

A sales manager can also: 

  • Produce content in a variety of formats
  • Offer searchable training libraries
  • Analyze how reps consume content
  • Adapt training content to the individual sales reps.

With the right technology, sales reps can close deals faster and reduce the sales cycle.

“WorkRamp prioritizes all of the features that we care about. When evaluating, we prioritized finding an LMS that was purpose-built for sales enablement. This became especially important with remote work; we needed to be able to manage events and tactical training programs with the integrated tech stack that we use internally.”


Ashley Crisostomo, Manager, Sales Enablement, Reddit

Measure performance

About 40 percent of businesses see a need to improve their sales enablement strategies. Metrics are key to understanding the effectiveness of a sales enablement program and knowing when it’s time to make improvements. 

Some of the most common metrics to measure the effectiveness of enablement include:

  • Onboarding time 
  • Sales enablement tool usage rate 
  • Lead-to-customer conversion rate 
  • Sales cycle length 

“With WorkRamp, you have the ability to use analytics to understand where you can influence sales effectiveness. You can identify quick wins, best practices, and necessary changes to drive momentum,” says Celine Grey, Sales Enablement Director at

“As we execute foundational onboarding programs and ongoing training, we measure effectiveness through metrics like ramp time, sales conversion ratios, competitive win rates, and WorkRamp completion data. With WorkRamp’s Salesforce integration, we can capture real-time insights into which training activities drive results.”

Read more: Data-Driven Sales Enablement: Track, Measure, Improve

Promote continuous learning 

Your sales enablement program isn’t a set-it-and-forget-it initiative. Your strategy and tactics must continue to evolve if you want to stay competitive. A brand that invests in continuous learning has seen results such as:

  • A 2x increase in revenue
  • 15% higher average deal size
  • 33% reduction in ramp time for new hires

Eighty-four percent of employees get the training they need in the best-performing companies, compared with 16 percent in the worst-performing organizations. Using a learning management platform such as WorkRamp; managers can easily track how sales professionals are doing on training initiatives such as pitch certifications and demo challenges. 

With WorkRamp, you can also provide refresher training and re-certification to current reps or team members who may be struggling to help improve performance. Handshake found that these programs had 90 to 100 percent participation rates, and the company exceeded its quarterly sales targets. 

Here are two tips to implement learning and development in your sales enablement strategy: 

  • Make learning more personal. Everyone learns differently. Taking a one-size-fits-all approach won’t result in the business outcomes you want. Adapt sales training programs to the individual’s needs and chart a path for their success. Combining multiple learning formats like video, written, and hands-on options (like an iORAD tutorial) can help to reach a diverse group of people with different learning styles. 
  • Encourage continuous learning. According to the Ebbinghaus Forgetting Principle, new knowledge is lost over time unless we take steps to retain it. Give sales representatives refresher courses and opportunities to learn new skills. Lessons should be short and interactive, so reps can retain and apply more information to their work. WorkRamp offers a Library functionality that provides a place for learners to find the information they need to reinforce learning.

“We leverage WorkRamp to train our customer-facing teams on new feature functionalities, corporate messaging, and role-based skills. In particular, the sales team is focused on sharpening their negotiation skills and corporate pitch with WorkRamp Challenges. On our latest brand narrative pitch challenge, the average rep score was over 90 percent – which proves how effective WorkRamp is in training and certifying our teams.”


—Ashley Crisostomo

Evaluate your sales enablement strategy

Sales enablement can boost revenue targets if companies acknowledge and invest in this. After doing so, practitioners can turn their attention to implementing high-impact programs that result in productive reps that sell more. 

With the business landscape changing so quickly, sales enablement can accelerate the changes organizations need to stay competitive.

Read more: How to Future-Proof Your Organization to Thrive in an Ever-Changing World

Learn more about how WorkRamp can help you improve your sales enablement strategy. Contact us to schedule a free, personalized demo.



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Michael Keenan

WorkRamp Contributor

Michael is a SaaS marketer living in Guadalajara, Mexico. Through storytelling and data-driven content, his focus is providing valuable insight and advice on issues that prospects and customers care most about. He’s inspired by learning people’s stories, climbing mountains, and traveling with his partner and Xoloitzcuintles.

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