The Top 7 Questions to Ask Sales Technology Providers

Better questions get better answers. When purchasing Sales Engagement or Lead Generation tools, keep these topics in mind!

If you’re in marketing, sales, ops, or enablement, you’ll be a part of a sales technology evaluation as some point during your career. You might be leading it. Or, you might just be a part of it.

In our world of constant change, frequent revisions to the sales tech stack is a new normal. 

Here, we’ll be focusing on 3 particular categories of sales technology that you may be focused on.

Category 1) Lead Generation & Data Tools

Data and information comes in all shapes and sizes. Sales platforms in this category help by providing B2B emails to help alleviate the manual work of finding and validating emails manually. This can include a database of contacts that is updated on a regular basis or the ability to create a custom prospect list by leveraging an extension that can capture emails based on specific search criteria.

Category 2) Sales Engagement (Email Automation)

This allows sales reps to create email campaigns that will send automated follow ups. This functionality provides sales reps the ability to contact prospects at scale without having to track and send follow ups manually. Reporting across different tools in this category differ since Google recently gated their API. This means that only companies that complete and pay for a security assessment have access to all reporting and gmail tracking.

Category 3) CRM Syncing & Integrations

If your team has a CRM, than like many sales organizations, your leadership team wants to make sure all communication is logged in the CRM. Some tools sole purpose is to automatically sync inbound and outbound emails into the internal CRM which removes the manual work of doing this manually.

6 Questions to Ask

Now that we are on the same page, let’s take a look at the questions to ask sales technology providers during the evaluation process. 

Question 1) What do you offer outside of the 3 categories above?

Generally speaking, all-in-one solutions are more cost effective. This is because onboarding, training, process design, and overhead is consolidated. Usually, more tools means more complexity.  

Question 2) What does the implementation process look like? Does onboarding take days, weeks or months?

It’s important to understand the onboarding process and adoption rates to make sure the entire team adopts the tool.

The length of time it takes to train the team is valuable time that could pull you and sales reps away from other tasks.


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Question 3) How much day-to-day maintenance is required?

Some tools offer off-the-shelf reporting and dashboards which eliminates the work of setting these up internally. Figure out if your company needs custom dashboards since you’ll need the internal team to devote time building reports.

Question 4) Is technical support included or how much does it cost? How is your customer support rated?

Not all providers include technical support and it could come at an extra cost. Understand how often you may deal with bugs and troubleshooting.
Ask what channels you have available to you to reach an agent – email, chat, phone call, and/or support tickets.

Question 5) What makes you different from your competitors?

For a lot of companies, a trial is very important to validate the tool’s functionality. However, there are some providers that don’t offer trials which might be a red flag if your internal team needs confirmation before getting locked into a long term contract. Also, think of the negative business consequences if you purchase a year upfront to then find out the tool doesn’t something unique to your business.
A simple UI is sometimes overlooked by potential buyers, especially when they are new to the sales enablement industry. You want to make sure all reps, SDR’s and AE’s, are going to adopt and use a tool.

Service, service service… noone wants to deal with support when something is wrong but knowing that there is a quick and witty support team makes the experience so much better. Especially if it’s included at no additional cost.

Question 6) Are there any integrations that are required?

The most common integration with a sales enablement tool is syncing data to a CRM. If the tool doesn’t have a native integration, then ask if they have an open API. Be sure to include the cost of building the integration or outsourcing it through Zapier.

Question 7) Where do you see the product/offering being in 1 year? 5 years?

Last but not least, one of the best questions to ask sales technology providers is about vision. A strategic partner will have a quick, meaningful answer. A regular “vendor” will have vague, bland answers. When investing in a solution that you expect to use for at least 1-5 years, it’s important to have a general feel for the trajectory of the company. This helps you understand what your investment will return in the short, medium, and long term. 

Next Steps

If you’re exploring new solutions, you’re more than welcome to start a trial below. Also, feel free to book a tailored demo with us or simply request for more resources to be sent. We’re here to help however we can on your sales journey!



Director of Customer Success

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February 7th, 2020



Director of Customer Success

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