How Sales Enablement Can Drive Revenue Growth in 2021 According to Crayon's Director of Sales

How did your leadership priorities change in 2020? If you started paying more attention to the sales enablement needs of your organization, you’re not alone.

According to recent HubSpot research, 65% of sales leaders who outperformed revenue targets in 2020 reported having a dedicated person or team working on sales enablement efforts instead of making it an initiative someone works on off the side of their desk.

For sales organizations that have been waiting to implement dedicated sales enablement measures — the time is now. With 2021 right around the corner, intentional sales enablement is a must-have for organizations that want to remain competitive in the future.

HubSpot recently sat down with Chris Pope, Director of Sales at Crayon, to discuss how companies can implement sales enablement strategies that can move the needle and drive revenue growth.

"Crayon defines sales enablement as providing our account executives with the resources and content they need to win more deals. Closing deals is more important than ever, especially in today’s competitive market where there are fewer deals to close," he says.

In 2020, Crayon placed even greater emphasis on sales enablement to support their sales force. "We've put even more effort into making sure that our sales teams have the resources they need, simply because every deal matters more than ever," says Pope.

Continue reading to learn Crayon’s sales enablement best practices to inform your 2021 strategy.

How to Improve Sales Enablement for Your Team

1. Use data to inform your sales enablement content.

Crayon uses data to inform sales enablement decisions. According to Pope, his team relies on "velocity reports" to determine what areas of the sales process reps need the most support with.

"Velocity reports tell us what our reps conversion rates are at every stage of the sales funnel. How many opportunities are turning into discovery calls? How many discovery calls are turning into demos? How many demos are turning into proposals? And how many proposals do we send out that turn into closed business?" says Pope.

"We leverage that data to inform us where each individual rep needs to spend the most time, and where managers need to spend time training individual contributors."

From an organizational level, this approach helps sales leaders know how to support sales managers and reps, and provides valuable insight into the type of training and content would be most effective.

Two examples of enablement content Crayon leadership has provided to their sales team include:

Call Recordings

"We love call recordings. We not only have call recordings of what the perfect call sounds like, we also have recordings of ideal discovery calls, effective demos, and successful closing calls. We share these recordings with reps who may need help in those areas, and we share them broadly across the organization so everyone is on the same page," Pope says.

Battle Cards

Battle cards are a valuable tool for preparing reps to speak to features and objections related to your product. Crayon relies heavily on battle cards to ensure sales reps understand what they’re selling inside and out.

"We use our own product to make sure that our individual contributors have the most up to date messaging on how we position against our competition. This knowledge has been crucial not only for our organization, but for our customers as well," says Pope.

2. Focus on sales team culture.

Chances are, you’re familiar with the term "company culture" — the idea that a company should have a shared set of beliefs, values, and practices. But when was the last time you assessed the culture of your sales team?

Sales teams are often dynamic organizations with motivated team members whose ability to sell is critical to the health of a company. Building strong rapport among members of the sales team and having a culture of open communication, especially in a remote environment, is an effective way to support sales enablement.

Feeling supported and included while selling remotely can be challenging for reps. For Crayon, sales team cohesion is a high priority.

"We’ve done our best to create a team atmosphere. We have daily calls where the entire sales team is on together, we have a peer program where our more experienced reps are paired with less experienced reps to offer coaching and mentorship, and we’re creating cross-functional opportunities for our pipeline generation team to work closer with our closing team," says Pope.

These activities build trust across the team, and strengthen communication among sales managers and reps, creating a better environment to tackle sales enablement issues as they arise.

3. Prioritize sales enablement at each level of the organization.

At Crayon, sales enablement is an all-hands-on-deck initiative from the top down.

"Sales enablement is a team effort at Crayon. It starts at the top with our Senior Vice President of Sales, who delivers insight on broad topics and training related to overarching sales themes such as a demo workflow, or how to run a closing call," says Pope.

"The managers and directors are responsible for individual training tailored to the needs of their reps. This can include listening in on at least a few calls for each individual contributor weekly, and providing regular feedback."

In addition to the sales enablement work of leadership, Crayon focuses heavily on team selling to get everyone involved.

"If one of our reps is great at positioning our product against a competitor’s or they’re strong at demoing a certain aspect of our platform, we’ll invite their team members to tune into their sales calls so they can learn from them."

Everybody within the organization plays a role in our sales enablement.

In 2020, sales managers at Crayon took a hands-on approach to coaching reps who had opportunities for improvement.

"We've really made it a focus to make sure managers are involved in more calls. Managers are putting time aside to give individual contributors and feedback that they need after calls, and benchmarking performance after every stage of the sales cycle," says Pope.

According to Pope, if a rep is struggling with a specific part of the sales process, Crayon’s team will "focus our training on the specific aspect of the process they’re struggling with to help them improve and get their overall win rate up."

4. Don’t wait to give feedback.

When sales managers and seasoned team members are coaching reps, the Crayon team makes it a point to provide feedback quickly.

For example, if Pope were to listen in to a rep’s sales call with a prospect, he would schedule 15 minutes with the rep right after the call to deliver feedback on how it went.

"When you let time pass, the call is not as fresh in the rep’s mind, and your feedback is not going to be as direct as it would be if you delivered it right away."

5. Make sure sales managers feel supported.

Sales managers often have a lot on their plate. They are responsible for coaching and leading their reps to success, and are accountable for their team’s performance to leadership. For growing companies, relieving pressure from sales managers is crucial for a healthy organization.

"As you continue to scale your teams you don’t want your managers to feel overwhelmed. You want to make sure they have enough time in the day to give every individual contributor the attention that they need to to perform their best." says Pope.

Pope says Crayon focuses on conscious staffing and resourcing to avoid sales manager burnout:

"If we know we're going to hire a new group of sales reps, we make sure we already have enough managers in place who have the bandwidth to lead.

So when those people start we don't have a new manager meeting new reps, we have experienced managers working with new reps, and we make sure that team members have the data they need to understand what their path to success will be as an individual contributor."

Improving Team Morale in 2021

Per HubSpot’s 2021 Sales Enablement Report, 40% of sales leaders expected to miss their revenue targets this year. That means sales enablement efforts are not only necessary for growth — they are critical for survival.

In a competitive landscape where sales teams are working with volatile markets and buyer uncertainty, keeping morale high is more challenging than ever. Pope shares why communication is Crayon’s greatest tool for keeping employees engaged.

"Morale has been all over the map for different members of the team. At Crayon, we never go a day without checking in on our reps," he says. "I try to at least have two times a day where I'm asking them how their days are going, what they've been working on, what calls have gone well, what calls haven't gone well, and asking how can I continue to support them."

This approach to communication happens at the organizational level as well.

"Crayon has done a really great job of communicating, being honest about when we might go back into the office, and making sure we're meeting with folks who are concerned about not having an office atmosphere to make sure that they're comfortable with their remote work setup," says Pope.

For more insight from Crayon, check out HubSpot's video interview with Pope below:

If you’re looking for more advice on boosting sales rep productivity and morale, check out this post for advice from an Aircall sales leader on navigating employee fatigue.