Why Sales Onboarding and Upskilling Are Key to Closing More Deals

Sales reps need the right tools, resources and skills to reach their full potential. Here’s how to prepare them to sell more even as buyers tighten their budgets.

Written by Kelly Lewis
Published on Sep. 20, 2023
Why Sales Onboarding and Upskilling Are Key to Closing More Deals
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Sales is a critical bridge between companies and customers, but right now that bridge is teetering. Less than 25 percent of salespeople at technology companies hit quota in Q4 2022, compared to more than half in Q4 2021, according to a report from Bravado.

The problem is multifaceted. Reduced budgets, aggressive competition, bigger buying committees and slower sales cycles have formed a gauntlet for salespeople to navigate. 

2 Metrics to Track Sales Onboarding and Upskilling Success

  1. Ramp Time: New hires who go through comprehensive onboarding programs report proficiency in their work four months sooner than those who were rushed through the onboarding process.
  2. Attrition: Organizations with formal onboarding and upskilling report higher rates of employee engagement, which leads to increased retention and creates an opportunity to keep top talent for longer periods of time.

During a time when sales is anything but easy, how can companies empower their sellers to succeed? It all starts with onboarding and upskilling. To bring home the revenue, sellers need the right tools, resources and skills to perform their jobs to their full potential. Let’s examine what good looks like when it comes to onboarding and upskilling and how you can prepare your team to make the most of every sales opportunity. 


Sales Onboarding Is the Foundation for Success

Sales success is built on a foundation of exceptional onboarding, and that starts with a competency framework, which is a guide that outlines the skills, values and behavior that are important for a given role. This equation provides a basis for your onboarding program and defines which skills you want to foster in your sellers. 

During this process, ask yourself: What are five areas of focus where we want our talent to be experts? What skills do they need to succeed? Who should we hire to maximize the success of our sales team?

From there, you can design your onboarding program with operational rigor. And although this looks different for every company, it should always include strong project management and cross-team collaboration. These important pieces of the process are often overlooked, and can help clearly define a front-line manager’s role in the onboarding process — another critical concept.  

You also need to plan ahead. For long-term success, your onboarding program must be scalable. This means approaching the creation of your program with a “crawl, walk, run” mentality that progressively ramps up and builds on itself.  Deciding where you want to be two years from the start date will help you strategically drive in that direction over time, as well as prevent your teams from doing too much too soon. 

For example, hiring 20 reps off the bat will deplete your resources and burn out your people even if that’s where you eventually want to be. In challenging economic times, this is especially important. The significant cost of failing to properly onboard a rep can make reaching revenue targets even more difficult.

Using a combination of facilitated learning and asynchronous learning can also help with this process. Certain aspects of learning are best taught by a facilitator. For instance, managers can provide valuable feedback and conduct role plays. Other learning can be left to the reps to complete in their own time, serving to reinforce concepts and continue building on skills.

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How to Upskill Your Sales Team

While onboarding prioritizes starting employees off on the right foot, upskilling focuses on business outcomes. This means figuring out exactly what the majority of your sales reps need to do differently based on the market’s fluctuation or the company’s growth. We call this “thawing the frozen middle.” It involves developing core performers and scaling the best practices of top performers. 

When you increase quota attainment across the team, it unlocks revenue previously left on the table. Investing in upskilling your reps empowers sales enablement teams to create consistent execution, which leads to predictability within your models.

Just as sales reps have to think about their audiences, you have to think about your sellers as the audience for your training and upskilling programs. Where are your reps struggling? And how do you address these challenges without over-correcting or overwhelming? Advanced sales enablement tools are your secret weapon for evaluating individual rep and team performance, identifying areas of opportunity and training and coaching your salespeople to close deals with confidence. 

One specific way to make the most of your upskilling efforts is to focus on practical learning. Bring education to the field. We’ve found that more than 70 percent of real learning in sales happens on the job. Practical application reinforces the behaviors you want your reps to exhibit and teaches them how to use these skills in their everyday buyer conversations, as well as ensures that your managers can coach to the behaviors you want to drive.


Metrics to Gauge Onboarding and Upskilling

Your investment is only as meaningful as its return. With onboarding and training, two metrics indicate value: ramp time and attrition.

Ramp time, the amount of time it takes for a new sales rep to reach full productivity and provide value, reflects onboarding success. During times of economic uncertainty, your instinct might be to shorten the ramp time and push the rep to start generating revenue faster. But that will only end up having the opposite effect. New hires in companies with comprehensive onboarding programs report proficiency in their work four months sooner than companies with short programs, according to a report from Highspot. 

The second major measure of success is attrition. Good onboarding makes a difference in how long employees stay at a company. Organizations with formal programs saw that 89 percent of employees felt more engaged in their work, which leads to increased retention and creates an opportunity to keep top talent for longer periods of time, according to a report from BambooHR.  A positive onboarding experience makes 69 percent of employees more likely to stay at their job for at least three years, reducing the risk of expensive churn, according to a report from Highspot.

Securing leadership buy-in is critical to ensuring you have the means to continuously invest in your programs. Numbers don’t lie – strong metrics help you build a strong case for the value your programs provide the company. And what matters most to leadership? The bottom line. Research shows that sales onboarding specifically can improve win rates by 14 percent and quota attainment by 6.6 percent, the Highspot report found. The payouts can be massive – companies that invest in training see more than a 350 percent ROI.

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Sales Onboarding and Upskilling Are Investments that Pays Dividends

In an ever-changing sales world, onboarding and upskilling prepare your salespeople to succeed. These strategic investments act as the compass that equips your sales force to navigate emerging challenges while expertly maneuvering through familiar obstacles. 

Devoting time and resources to onboarding and upskilling initiatives fosters a resilient and adaptable team that not only thrives in the present, but also embraces the future with unwavering confidence. 

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