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Choices, Choices: Selecting the Right Sales Tools Can Make or Break an Organization

choosing the right sales tool

choosing the right sales tool

When I tell people that I’m a director of sales enablement, the typical response I get is, “Oh, so you’re a sales trainer?” While true to an extent, sales training is only one responsibility of sales enablement professionals.

If I broke down my typical daily activities and weekly operating cadence, I probably spend more time on strategic sales enablement. Those responsibilities include building thoughtful and scalable enablement and readiness programs that not only address the foundational and continuous learning needs of the sales organization but also directly tie to sales rep performance, results, and revenue achievement.

But one of the most important skill sets a sales enablement professional can master is the art of effective communication (because we communicate all the time). Whether we’re channeling all the communications that go to the sales team, collaborating with multiple departments, or presenting to senior leadership and executives, being able to efficiently communicate value and positive business outcomes is essential, and how we communicate externally is equally important.

Understanding Sales

Enablement’s Role

In an article titled “The Sales Enablement Doctor Is In” that appeared in the Winter 2020 issue of The Pragmatic, I wrote that sales enablement is the “ultimate sales psychologist.” One reason is, it’s literally our job to gain credibility from the get-go and become a trusted advisor for sales leaders, sales reps, and many other peers. When we achieve the coveted status of “trusted advisor,” we become a true advocate.

As we build out the scalable programs our sales organization needs, we also must consider which tools will enhance these programs and allow our sales reps to succeed. Many times, as a trusted adviser, sales reps will come directly to enablement to request these tools.

However, full ownership of sales tools might not fall under sales enablement’s list of responsibilities—I often see sales tools directly under sales or business operations. But even in these cases, sales enablement should work closely with these teams to ensure that the right tools are selected and implemented internally and that they’ve launched in a way that ensures adoption, use, and return on investment.

Enablement’s biggest stake in the game is building sales tools training into a formal launch plan for the existing sales team as well as into the strategic onboarding program for new hires.

Enablement is also the best representative for sales reps’ experience. We understand when a sales tool will be used in the sales process, the person who’s using the tool, and how the tool fits into their overall operating rhythm.

While sales operations may focus on business intelligence and integrations with processes or other systems, sales enablement focuses on selecting a tool that has a simple user interface and provides upfront value to the rep.

Sales reps face two potential problems: Either they don’t have the right sales tools, or they have too many. The sales tools we select must address sales reps’ pains and frustrations, and no one understands those pains and frustrations better than sales enablement.

Because enablement has this “insider” understanding of sales and the challenges reps face using sales tools, we’re the perfect candidate for establishing vendor relationships and defining the sales team’s needs.

And remember that sales enablement is one of the top personas that sales tool vendors regularly prospect. It makes perfect sense for enablement to be engaged in the dialogue.


I always remind my sales reps that customers complete a good portion of the buying process through their own research—before they even speak to a rep about a product or service. This same concept applies when I’m the buyer who is considering potential sales tools.
I start by conducting an internal review of all existing sales tools and outlining details like:

* How each tool is used

* How the tool affects the business

* Who will access the tool

* At what stage of the sales cycle the tool is most likely to be most effective.

It’s also important to identify which department owns and/or maintains the tool, including the primary point of contact, any system administrators, and when the last contract was signed with the vendor.

Looking at the copy of the most recent contract will help identify key players and influencers—both internally and with the vendor. This review also helps clarify the technical requirements, integrations, and any customized functionality associated with the tool. All of this helps you proactively prepare for upcoming renewal conversations and avoid potential surprises that may negatively affect the sales team’s productivity and access to the tool.

This initial exercise also provides the foundation needed to create content for new hires to educate them and set the right expectations for sales tools. Plus, if tool ownership or key influencers change or leave the company, transferring ownership of the tool is easier because everything is documented.


Once I have a good handle on the existing tool stack, I then look at the current efficacy of each tool and how it’s used to drive business. In this phase of the review, focus on the adoption and usage of each tool and whether there is a correlation back to top sales rep performance.

This also is a good time to engage the vendor (usually a dedicated customer success manager) and ask for deep analytics and quantifiable metrics that show a return on investment. This allows you to define what “good” looks like with the current tool stack as well as uncover any gaps or areas where additional tools are needed to meet business requirements and help sales reps succeed.

Gauging efficacy begins the transition into the research and education phase of the tool-selection process, and a good portion can be handled online before ever speaking with a vendor rep. A simple Google search returns pages of information on every tool available, plus company reports and recent business news. Navigating to different vendors’ websites can deliver data sheets, blogs, articles, analyst reviews, testimonials, and product demonstrations. And peer-to-peer review sites like G2 Crowd and Capterra provide real-time consumer insights. Just make sure the site you use has high ratings and a reputation for reliability and accuracy.

I use the qualitative details these sites provide, as well as feedback from other reviewers with a similar professional background as mine. Finding feedback from companies in the same industry with a comparable size to my sales team is a bonus.

For example, I have more than 200 sellers worldwide. If a different company with a U.S.-based 50-person sales team provides insight that their implementation of a tool was seamless and the cost was relatively low, I can’t assume my company will have the same experience. Being in a larger, global organization with varying seller roles and a more complex sales process could mean higher costs because of the need for more licenses and a more intricate and customized implementation.

Peer-to-peer review sites also provide side-by-side comparisons of like vendors with competing products. In looking at these comparisons, remember to:

* Look at the most recent feedback. Feedback from two years ago may not be helpful if a company has updated and enhanced its product.

* Ignore one-sided feedback that only focuses on the negative—unless you see the same feedback multiple times from different reviewers.

* Look for honest and authentic reviews that highlight the best features of the product or company and provide constructive feedback about functionalities or services that could be improved. These are the most effective and useful reviews.


After the education and review phase, it’s time to select the top contenders that may address your organization’s needs and start engaging with vendors directly.

It’s also time to form an internal buying committee to assist in the selection and buying process. In recent buying scenarios, I’ve had between four and 12 internal colleagues involved in the vendor selection and buying process.

Democratized buying and multiple levels of internal approval needed have made decision-making more challenging than ever.

Oftentimes, ensuring budget for a solution depends on having several departments contribute.

Collaborating with a dedicated buying committee that includes cross-functional groups and departments eliminates the risk of missing important details. It also helps ease a solo purchaser’s anxieties. Ensuring every group’s interest is represented is a great way to create additional champions who will help build a solid business case.

For example, along with benefitting sales reps, sales tools also need to provide insights for sales managers to drive the business, coach reps to better performance, and make informed decisions.

No sales tool should be chosen without first obtaining buy-in and support from sales managers. Think of it this way: If sales leadership isn’t brought in on the value of a tool, they won’t require and enforce its use.

When you’re evaluating vendors and tools, there are a few helpful questions to ask:

* What are the most inefficient processes in our business and how will the sales tool address them?

* Are there any internal operational processes or workflows that the tool will optimize?

* Can this tool be used globally?

* Who in our company will use the tool? How many user licenses are required? (Remember to include licenses for new hires.)

* How does this tool fit into the overall systems and tools landscape? Are integrations with other applications required?

* What is the budget?

* Will customers benefit from this sales tool?


Next, create a sales-tool matrix that defines technical and business requirements. This will help you track each requirement against vendor features and functionalities—and it’s the foundation for building a business case that will eventually be presented to the economic buyer before final sign-off. When possible, have the economic buyer meet the vendor you prefer.

It’s also wise to proactively ensure that you understand your organization’s and your vendor’s paperwork processes. Companies commonly require things like legal and security reviews or IT risk assessments.

Finding out about these checks at the last minute could delay the close of the deal and the implementation date. If you’re working with a vendor that’s new to your company, you’ll likely have to complete a new vendor process, too.

As you build the business case, demonstrate why the sales tool is needed, its benefits, and the risks of not having it.

You can ask the vendor to help you create the business case, too (and if they’re unwilling to help, it’s a good indication of the type of partner they’ll be). Some organizations may have in-house experts who can help you prepare your case. For larger projects, you may need to use an independent consultant.

A strong business case makes a compelling recommendation for implementation and will resonate with what the economic buyer cares about most.

Remember to include:

* Project scope

* Financial benefits

* Productivity or performance benefits

* Alignment with sales strategy

* Overall fit with the existing tool stack

* Proposed implementation plan

* Risk

Include screenshots of key capabilities and tie them back to the business need.

For added “wow,” create a future vision of how things will improve and provide examples of the positive impact to the business.

Also, show a thoughtfully developed launch and training rollout plan for the new tool. This shouldn’t be an afterthought! Use it to get your “yes.”

Create a pilot test group representing different roles and geographies and define initial measures of success.  This will ease concerns sales leaders may have around rolling out a new tool to the sales organization that hasn’t been tested or proven.

The pilot period should be a set duration that allows enough time for testing and fine-tuning as needed. Sales leaders want to know you’re doing everything in your power to make a great first impression when the tool is formally launched.

Work with your vendor to deliver sales tool training—after all, they’re the subject-matter experts who can answer technical questions.

After the initial training, remember to bring them back for reinforcement or new feature training.

Record these sessions and build them into your new-hire onboarding program.

Also, ask if the vendor has a regular newsletter that shares tips and tricks with your team.

Finally, schedule monthly or quarterly recurring meetings with your account manager and/or customer success manager. This is when you can address any open items you have with the tool or focus on a usage discussion.

Tool administrators typically have access to reports, but the vendor usually can obtain deeper analytics and compare them to industry trends.

This is the best way to correlate the impact of the tool to increased productivity or performance. Make sure you’re getting the tools and support you need to achieve your goals.


Choosing the right sales tools can be a daunting task that requires a lot of effort. But when it’s done right, the result is a sales team that outsells the competition and succeeds—and that makes the time upfront worth it.



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