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6 Sales Onboarding Best Practices from Top Sales Enablement Leaders

Every organization wants to reduce the amount of ramp time new hires need before they can meet sales quotas. Many don’t realize that you can create an onboarding process that quickly brings reps up to speed, increases new-hire retention, and helps you build a team that hits business goals in the long term.

With effective onboarding, 65 percent of your reps can be effective within 24 months, compared to 49 percent otherwise. Also, only 41 percent of companies with effective onboarding reported too-high turnover, compared to 57 percent of companies overall.

Studies have shown that effective onboarding can also lower ramp times by two months, so you can’t afford to overlook the impact of your new hire process. Here are some steps you can take to improve your onboarding.

How long should sales onboarding be?

The sales onboarding process takes about 3.1 months, and onboarding can cost $4,700 per new hire. Sales onboarding can be both a time-consuming and costly mistake for your organization when done wrong. 

Sales teams may be tempted to rush through onboarding to maximize value. If new hires hit the phones too quickly, their lack of preparation will be evident. However, if new hires are in training for too long, they drain their trainers and fail to generate revenue. The key is identifying ways to streamline onboarding without sacrificing the quality of education for new hires.

In practice, we talked with three sales enablement pros who employ smart strategies to get the most value out of their sales onboarding programs to show you what that looks like. While onboarding looks different for every organization, stand out by implementing sales onboarding best practices that make companies like Zoom, Divvy, and Handshake successful.

What should be included in sales onboarding?

Your sales onboarding process helps a new hire understand your company and learn your sales process.

Some of the steps you need to include are:

  • Introduce company culture early and reinforce it often
  • Have an assigned buddy or coach for each new hire
  • Train new hires using a variety of methods, including experiential learning, role play, self-paced learning, and more
  • Use assessment tools to measure the results of training and provide follow-up material to those who are struggling
  • Showcase your knowledge database and help new employees understand how to find the sales materials they need
  • Use surveys to learn more about the new hire experience from the new employees themselves

For more information about how to create a comprehensive onboarding process, learn how to take onboarding from good to great.

How can the sales onboarding process be improved?

All companies have a process for onboarding new hires, and you may have been doing things the same way for a long time. However, that doesn’t mean your process can’t be improved—potentially in significant ways.

By looking at other organizations’ best practices, you can see what changes could make a difference in your training. 

Sales onboarding best practices

To show you what that looks like in practice, we talked with three sales enablement pros who employ smart strategies to get the most value out of their sales onboarding programs. While onboarding looks different for every organization, stand out by implementing sales onboarding best practices that make companies like Zoom, Divvy, and Handshake successful.

Audit your sales onboarding frequently

Performing an audit can help you identify what you’re doing well and some of the most prominent areas that need improvement in your sales onboarding process. Without regular updates to your program, you risk relying on onboarding methods that instill bad habits and leave sales reps underprepared.

Stephanie Middaugh, Director of Enablement at WorkRamp and previously at Divvy and Zoom, suggests starting your audit by surveying team members while onboarding new sales reps: “The first survey is right after they complete the boot camp. Then again, after they have been in the program for 30 to 60 days because inevitably, they have been on the sales floor long enough to realize what’s going on.”

Consider some of the questions below.

  • What did you find most helpful in the onboarding process? What do you think are areas of opportunity?
  • Do you feel like your manager and team support you?
  • Is there anything you wish you knew before starting?
  • Do you have the knowledge you need to do your job correctly?

Once you clearly understand the onboarding challenges and areas of opportunity, “see what the low-hanging fruit is and where you can come in with some quick wins and big impacts.” For instance, Stephanie used these insights to realize sales enablement content and resources were all over the place. Whether in an email, on a desk, or a PowerPoint slide, the sales reps spent a lot of time trying to find information. She then made it her mission to find all the information and collapse it into one space. This small change made a massive impact on productivity and company morale.

Make virtual onboarding sustainable and scalable

Virtual onboarding allows sales reps to learn whenever convenient for them, without pulling other team members away from their regular duties.

In today’s digital world, a lack of remote and immediate learning opportunities causes slower onboarding and a loss of productivity. Employees can spend up to five hours a week waiting on others for knowledge. Stephanie learned early on when Divvy was still doing their onboarding in person that adults like to learn independently. Therefore, it was essential to bring learning opportunities online so that reps could access them where and when it works for them. For example, if sales reps are in their CRM and have questions, WorkRamp has a Chrome extension that can help them quickly search for training.

Learners and companies alike prefer asynchronous learning because it’s efficient and scalable. Stephanie encourages managers to record their training so their insights are repeatable and attainable. “It’s vitally important to get that muscle built sooner rather than later. If you have new hires coming in every month or every couple of weeks, it’s going to be essential that you start creating content that’s going to be repeatable,” she says.

Personalize the sales onboarding process

Not many people get excited about onboarding or trust it is useful, yet it falls on sales enablement to encourage participation and ensure successful outcomes.

While sales enablement professionals know how indispensable onboarding is, a recent study showed only 11 percent of sales reps think their company’s onboarding program is effective. So the challenge for sales enablement professionals becomes how to ensure reps feel that training is worth their time. Stephanie has experienced this previously in her sales enablement career: “Creating a culture of learning is not an easy task. To earn the trust of the team you are supporting, make whatever content you present relevant to them. Especially training salespeople, anytime you’re taking them off of the phone, off of LinkedIn prospecting, off of demos, they need a valid reason.”

Beyond personalizing training, another sales onboarding best practice is to personalize incentives to maximize motivation. Find out what incites their best work, get their buy-in, and think creatively when encouraging them to learn. Mark Riley, Sales Enablement Manager at Handshake, shared that he empowered his team by tying their compensation plans to their performance during onboarding. He knew they were motivated by money and used WorkRamp’s onboarding features to track performance: “Certifications, courses, and everything we are teaching has a measurable impact on what the reps care about, which is money. If you can make the incentive what you know they want, it helps show them why they should care.”

Automate sales onboarding

Many sales enablement professionals take advantage of automation features in their learning management systems to reduce admin time and let new sales reps learn at their own pace.

A structured onboarding program is essential for several reasons:

  • Consistency: Provides automatic guarantees that new hires are learning the same information and reduces the likelihood of human error.
  • Saves company time: Employees do not have to take time out of their weeks to prepare and present in training meetings. Nor do HR professionals have to organize paperwork or ensure the new hire is on the right track. An automated system will do it for them.
  • Higher retention: New hires are more likely to stay at a company with a formalized onboarding program.
  • Quicker competency: Employees like to learn on their own when they are most focused. Automation allows new hires to learn at a comfortably, never be in the dark about the next steps, and return to previous training as needed.

There is a lot for sales reps to understand when coming into a new role, and automation can be a valuable tool to manage the tasks and content they need to work through. “Start figuring out your sales reps’ journey through onboarding and try to stagger out content as they go. That way, they get the information they need but not all at once,” Middaugh advises. One of her sales boarding best practices is to think about onboarding automation as a funnel. Start high level initially and funnel it down by what they need to know to do their day-to-day jobs as they progress through the process.

Set clear guidelines for team communication

New hires won’t automatically know who to turn to for questions, collaboration, and hand-offs. So during onboarding, don’t just focus on external communication; build skills and establish expectations surrounding effective internal communication.

Chad Dyar, Senior Sales Enablement Manager at Zoom, said his approach is all about the team: “When you are in a long sales cycle, there will be many people involved. The challenge is ensuring all the plays are organized across the team. It’s not just about doing the job; you must communicate that to the right people at the right time.” Failure to communicate updates or critical information can lead to confusion on the team and lost deals.

Bring communication to the forefront of your onboarding program by having regular synchronous touchpoints for new hires and distributing resources with clear communication guidelines. For example, many sales enablement experts, like Riley, hold weekly sales meetings to discuss updates and challenges. These mandatory meetings are times when he can get everyone on the same page and insert additional training. At the beginning of onboarding, it is also beneficial to show off your internal communication resources, whether a messaging platform like Slack or an LMS like WorkRamp, to get new sales reps acquainted with your expectations for communication.

Participate in the interview process

If you aren’t taking part in interviews, you miss vital insights that should inform the new hire’s onboarding strategy. Riley agrees, “sales enablement starts at the interview. The best interviews are not just what that person is good at, but what that person needs to learn.”

Sales enablement experts often look for a different skill set than an HR professional might. Some notable attributes to look for when interviewing a candidate include:

  • Ability to collaborate
  • Experience with your tools
  • How they learn best
  • Relationship building experience

By identifying strengths and weaknesses during the interview phase, you can more precisely meet new hires’ training needs during onboarding. For example, if you know a new sales rep is excellent at building relationships and making deals but struggles to stay organized, you can have them spend extra time getting to know your tools and their importance. This saves time reviewing concepts the new hire is familiar with and allows them to focus on learning needed skills.

Extend learning beyond onboarding with a sales enablement platform

While sales onboarding best practices are often unique to an organization, one commonality these sales enablement experts share is their use of sales enablement software to enhance onboarding. From automating your process to tracking engagement and progress, sales enablement software can take productivity to the next level.

Additionally, learning doesn’t stop after the onboarding period is over. Continued learning and onboarding go hand in hand. For example, new hires and long-term employees should be notified of process changes or new leads. Sales enablement software allows for company-wide communication of updates, announcements, and continued learning opportunities.


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