Contrary to common belief, closing the gap between top- and bottom-performing salespeople isn’t effective sales enablement. 

Instead, creating a conducive selling environment where everyone can win more is a better option.

Meaning: as sales leaders, our focus should be more on increasing the size of the pie as a whole instead of trying to divvy it up as-is. The recipe for success is developing a sales development strategy that prioritizes consistent wins and sales productivity. 

In this guide, we — Kyle Asay, the Regional Vice President at MongoDB, and Braxton Carr, UserGems’ Director of Revenue Enablement — share our collective experience in coaching reps to improve sales performance.

Before we get into the nitty-gritty of creating a results-driving sales enablement program though, we’ll look at what’s wrong with the typical sales training programs.

The typical sales enablement process and its shortcomings

Most sales decision-makers take a reactive approach to sales enablement. They read about interesting, potentially results-driving training initiatives and get their sales reps to adopt them.

This kind of ad hoc implementation doesn’t consider the initiative’s value or purpose in your sales process, driving little to no results and leaving sales managers wondering what went wrong.

The problem here: The lack of a rep-centric sales enablement strategy.

Even if there’s a sales enablement strategy in place, it uses a one-to-many framework to train salespeople. In doing so, reps never get coaching specific to their needs, which prevents companies from building a conducive selling environment.

Here are some of the steps you can take to address this issue:

1. Create a data-driven sales enablement strategy

This strategy should identify:

👉 Skills essential to your team’s high performance

👉 Skills currently lacking in your sales teams

👉 Ways to improve the highlighted skills

👉 KPIs to measure the results of your enablement efforts

2. Use a one-to-one training framework

Despite what you may think, a one-to-one training framework isn’t all that time-consuming. Instead, it requires you lay the same coaching foundation for your team but tweak the training style based on the: 

👉 Salesperson’s job requirements. ADRs and AEs, for example, need different training based on the requirements of their work.

👉 Size of the business you’re targeting. For instance, selling to an audience of small and medium-sized businesses is different than selling to an enterprise buyer.

What is a productive selling environment?

A successful selling environment is one where all reps do their best work, consistently meeting their sales quotas and growing the bottom line without hitting burnout. 

It’s an environment where reps focus on self-improvement and learning from team members. And, at the heart of it, it’s a culture of sales coaching that aims to empower and boost reps’ confidence. 

In short, a conducive sales environment promotes reptonomy (read: gives rep the autonomy to take risks, try new tactics, and learn by doing and getting feedback).

Here are some of the foundational elements of developing a successful sales enablement environment for your sales team. 

1. It starts with understanding the product and target buyer

Results-driving sales teams have an in-depth understanding of the product they’re selling, who they’re selling it to, and the entire buyer journey.

Be careful though: you don’t want your reps to only have a superficial understanding of the ideal customer. They should also understand the target buyer’s challenges at each step of the customer journey and the dream state they want to reach.

2. It empowers reps to try new tactics and get feedback on them

A successful seller environment encourages reps to try new tactics and refine those that work for them using feedback.

Such an empowering environment makes reps feel like they’re consistently learning and growing, which, in turn, is crucial for increasing their engagement at work.

3. It prioritizes professional development 

Sales leaders can employ a number of different strategies to show they’re invested in their sales enablement team’s professional development and career growth (not just ‌in revenue growth). 

These include:

👉 Offering tailored coaching to help reps recognize their strengths and overcome weaknesses

👉 Providing relevant content in a knowledge base that is easy to access and navigate

👉 Removing ambiguity around the path reps can take to get promoted

7 steps to creating a successful seller environment

From empowering reps to coaching them on the skills they lack, there’s a lot that goes into creating a results-driving strategy. 

Follow these sales enablement best practices to streamline your strategy and build a seller environment that encourages high win rates and bigger deal sizes all while keeping sales reps engaged and happy. 

1. Start with buyer persona mastery

The first question to ask the reps that are part of your sales force is: how well do we know our buyer?

Ask them to bring you a list of personas you’re selling to. Then review how much they know about them.

At this point, you may find that the information they have is extremely surface-level. Most reps typically only have a high-level marketing overview of their target customers, which isn’t much better than the generic information you can find on a website or social media profile. 

That means you need to help your sales and marketing teams better understand your personas, to the point where they can be emotionally relevant to them.

Be sure to educate them about what these clients’ pain points are and what their ideal fix would be. But don’t stop there. Talk to your reps about what potential customers want to avoid, and what their best-case scenario is. 

Reps can then use this vital information to offer potential buyers a solution that enables them to steer clear of their nightmare state and guides them toward their dream state.

2. Teach your reps effective messaging

All your efforts will go down the drain if reps understand exactly what the buyer wants but can’t communicate about it effectively with them.

Whatever your approach to selling — cold calling, video prospecting, or social selling — teach reps to write succinct outreach messages that get folks to take the next step. 

3. Build a “good day” framework

A “good day” framework outlines what a good day, week, and month looks like for a rep in your sales organization including various metrics to aim for, such as the number of cold emails sent and LinkedIn connections made.  

Make sure you collaborate with your team on creating this framework. Then use it to hold them accountable for daily progress against these metrics.

For instance, if you see lead generation metrics going down for a week in comparison to the metric on a good week, you can start course-correcting your team member in real-time. 

4. Audit and improve your current seller ecosystem

Next, create a list of skills that are essential for reps’ success using your sales strategy and existing workflows.

For example, at UserGems, we take a relationship-building approach to selling, which is why we value the following skills:

• Pre-call research
• Storytelling
• Active listening and selling
• Forecasting
• Nurturing
• Multi-threading
• Give to get

Based on the list you come up with, grade reps on a 0-2 scale where two is amazing, one means there’s room for improvement, and a zero means you’ve identified an area of focus.

Using this method, you can hone in on specific areas for development for each sales representative to provide them with tailored coaching sessions.

Another idea is to co-pick coaching themes with your team. Give them suggestions for focus areas (from the list of skills you identify above) and ask them to vote for what they want to learn more about.

You can also review reps’ recorded sales calls to find out what they’re struggling with. 

For example, if your review shows reps struggle with opening their cold calls, you could make improving cold call openers the theme for one of your training meetings.

To track progress, go back to the recorded calls and see how well reps are implementing the suggestions you provide during coaching sessions.

5. Create an ongoing, two-way feedback loop

As you coach and provide sales content to reps on the selected theme, proactively source and address their follow-up questions.

Often, after a coaching session, reps are directed to find answers to whatever follow-up questions they have in a knowledge base.

Most of the time, these knowledge libraries are hard to navigate, making it nearly impossible for them to find the answers to their questions. The result? Incomplete learning and a coaching program with no feedback loop.

The better option is to:

• Create easily navigable knowledge libraries that share resources related to your training sessions.
• Embed the knowledge base in the tools reps are already using (such as the customer relationship management platform) to remove friction from accessing the resources.
• Track the types of search queries that are coming through the knowledge base. This way, you can follow up with training sessions based on real questions reps have.

6. Empower reps to self-review their work

It’s common for managers to listen to their team’s calls and nitpick issues. But that does little to encourage reps to improve since there’s no focus or specificity in the feedback.

What we do, however, is quite the opposite. We ask reps to listen to their own calls with us and comment on what they could’ve done better. This works well for two reasons:

• It prompts reps to better recall shortcomings to work on
• It instills a habit of introspection among reps which pushes them to keep learning by reflecting on how well they’re doing

7. Give hands-on coaching in a short time frame

The goal of this last step is to teach reps what to do and who to involve in each stage of the sales funnel.

But rather than taking 60 days to coach reps using mid-to-late funnel execution examples, use UserGems to train reps on quick-to-close deals after their general onboarding.

Essentially, UserGems tracks customer job changes. This gives reps easy-to-close leads to convert since alumni customers have already used your product (and hopefully enjoyed it) which makes them more likely to convert than new leads.

As a result, these bluebirds quickly build reps’ confidence. They also lower the time-to-first close, which means you can coach reps across multiple areas of the buying process within a few short weeks.

Over time, the high-quality, likely-to-close UserGems leads compound with the typical leads, providing reps with an easier way to quote attainment. 

Level up your sales enablement today

Focus your sales enablement efforts on creating a culture of coaching and empowering reps.

Remember, it all boils down to one simple concept: ensuring your team gains confidence quickly.

Thankfully, leveraging UserGems as one of your sales enablement tools lets you grow reps’ confidence by giving them bluebird deals to close. It also speeds up your post-onboarding, in-person coaching.

And by using UserGems as your pipeline generation tool, you can also equip your team with the right software to quickly achieve their quota — growing their confidence even more.

So what are you waiting for? Book a free UserGems demo today.

Why UserGems

UserGems is a pipeline generation software that helps revenue teams generate and protect revenue efficiently. With UserGems, companies can track and automate outreach when their champions change their jobs, and capture the buying groups to find the warmest path into every account.

Companies like Mimecast, Greenhouse, Medallia use UserGems to reach their revenue goals, quickly and efficiently.