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5 Ways Salespeople Can Upskill

5 Ways Salespeople Can Upskill

Here are five ways upskilling your salespeople can look like in practice.

Most experienced sales reps have no trouble jumping on the phone and making cold calls. They know how to get past the admin assists and other gatekeepers to reach the customer or prospect they want. They’re savvy in putting together pitch decks to persuade buying committees and when they close, they’re often good at upselling or cross-selling to generate a bit of extra revenue.

As with any other key role in a business, though, being a successful salesperson means committing to lifelong learning. Some of that learning will happen almost by osmosis through the day-to-day lessons they get by doing their job. In some cases reps might also pursue more formal professional development in their spare time. Neither of those approaches are quite the same thing as upskillling.

Upskilling defined

When companies offer sales reps opportunities to upskill, they’re not just ensuring everyone is maintaining the competencies necessary to do their regular duties.

Upskilling represents a chance to learn skills that will take a salesperson’s performance to a higher level. This could include the ability to sell a wider or more premium range of products. It might mean they can sell into a different vertical market.

In some cases upskilling allows reps to tackle more complex sales configurations or bundles. Then there are upskilling initiatives designed to help reps achieve a more ambitious target or sales quota.

It’s important here not to confuse upskilling with reskilling. There are plenty of jobs that, for one reason or another, become obsolete or change so dramatically that reskilling is required.

Even when reselling is successful however, it means an employee has learned to either do the same job or one that requires a similar level of training.

Upskilling means they are ready to stretch themselves further and achieve more than they ever have before. This is critically important given the digital transformation that’s happening across almost every kind of business.

Companies that upskill sales reps aren’t just in a better position to grow their business. They’re also likely to drive a more engaged employee experience and benefit from reduced turnover because reps see their company as committed to their success.

Here’s what upskilling can look like in practice:

1. Stage A Super-Sized Virtual Buyer Committee Meeting

Reps are probably used to walking into a boardroom filled with the various stakeholders who might weigh in on a big purchase. They might have once gone around shaking hands or making small talk right before or after the meeting with the final decision-maker and their influencers. Doing the same thing in a virtual setting might seem more daunting because they’re just looking at a screen filled with faces.

Bring a dozen or more of the reps’ coworkers together — whether they’re also in sales or another department — for a video call. Have them take on the roles of the buying committee members. Let the rep practice making eye contact with specific individuals on screen, asking questions or making their pitch relevant to different representative buyer personas. If you’re the manager, use chat functionality to coach them through the mock call on how they might improve their performance.

2. Offer Guidance On Conference Sessions With The Biggest Value

It might be standard practice for reps to go to an industry event for their professional development, and for managers to sign off on it without a lot of discussion. Upskilling means taking a more active role in helping reps set objectives around educational opportunities and ensure they walk in ready to learn.

Consider sending a rep to a conference like Dreamforce, for example, with a goal of learning how to improve their ability to visualize data by taking in a session about Tableau. Have them sign up for a session on alternative purchasing models, like subscriptions, and let them run a pilot project afterwards. Encourage them to bone up on low-code development platforms like Heroku so they could build their own sales app, or at least play a bigger role in one the company develops.

3. Build Greater Alignment By Job Shadowing Across Functions

Reps usually learn the value propositions of their company’s products by heart. They are often ready to talk about them with any of the leads that come their way. Ask them to tweet about it or write a post on LinkedIn, however, and they might look panic-stricken.

Pair up a rep with someone on the marketing team for a day and let them learn what it takes to tell compelling brand stories on social media. Or bring them into a meeting when you’re developing your next ad campaign. It will help them work more closely with their counterparts and deliver a more holistic experience for your customers.

You could do the same thing with your customer service team. Have an agent take on the role of customer and lob common questions or troubleshooting issues to a rep. As they learn how to providing top-tier service and support, they may be able to better prepare customers to be successful with their products when they’re selling them.

4. Identify Credentials And In-Demand Expertise To Earn Career Advancement

Beyond conferences and events, courses give employees great time to dig into skills in more depth. Even if attending in-class isn’t an option, there are plenty of online courses available that are relevant to those in sales.

Trailhead is a perfect example. It offers an extensive library of courses that range from highly technical optics to soft skills that could prepare someone to become a sales manager one day. As with signing off on conference registrations, talk with reps early on about the kinds of badges they should think about earning. Or, to put it another way, discuss their performance to date and create a vision of what kind of Trailblazer they could become.

5. Open Up Avenues To Contribute To The ‘Triple Bottom Line’

Selling has typically been all about financial performance, but that’s just one aspect of how successful businesses are looking at the impact they create today. The “triple bottom line” also takes into account how an organization contributes to society, as well as how it helps address urgent environmental issues.

Assign reps to task forces or committees within your company that are driving sustainability. Have them sit on advisory councils or work on projects that benefit your local community. By looking beyond revenue numbers, they’ll be able sell in a way that aligns as much with customers’ values as their burning needs and pain points.

There’s an old adage in sales that reps should “always be closing.” For employers, it might be “always be upskiling.” When you do, you’ll find sales teams can always reach greater heights.

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