James Carbary

Founder at Sweet Fish Media

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4 Questions to Ask When You’re Evaluating Sales Technology

James Carbary

Founder at Sweet Fish Media

Full Profile »

A fine-tuned sales machine is every sales exec’s dream.

Imagine a set of processes—from prospecting to productivity—all running seamlessly, reps working efficiently and hitting their quotas, and you not micromanaging every stage of the funnel.

Ah…can’t you just feel the freedom?

If this is the dream, then what do you need to do to make it happen?

The secret ingredient in every fine-tuned sales machine is the set of tools behind it.

There are tons of sales tools out there, so in order to choose which ones will drive the most growth, you must understand the intricacies of your company.

You must ask digging questions and find every missing link and gap in your funnel.

In a Sweet Fish Media interview, Fred McGill, VP of Marketing and Business Development for Redox, shared how he took a company with zero sales processes and created a high-functioning sales machine from scratch.

These were the questions he asked.

What Is the Culture of My Sales Organization?

Based on the culture, what tools will your sales and marketing reps actually adopt and integrate into their workflow?

Typically, reps newer to the game are quicker to grab hold of a tool and run with it. On the flip side, more seasoned reps might not be as receptive to new software.  They typically have their particularities, and aren’t always gung-ho about change.

If you do have resistors in your bunch, it’s highly beneficial to have an executive sponsor driving the “why” behind the change.

Sometimes it takes a CEO or VP communicating the 50,000-foot goal to employees working on a more granular level.

It’s also important that you’re bringing in technologies that make your reps’ lives easier. That way, when the resistors see other reps using the tool and being more efficient at their job, they are more likely to get onboard.

What Integrations Need to Be Considered?

The next question to ask when building a sales machine is, “What integrations need to be considered?”

This deals with understanding and considering your existing IT landscape.

If you have a complex IT landscape, it may be more challenging to integrate a sophisticated CRM or marketing tool. Don’t integrate a sophisticated CRM into a complex IT landscape.


In this case, steer towards lightweight tools. Particularly if you don’t have an administrator or experienced IT rep.

Otherwise, you’ll be managing the administration of the tool. No one wants that.

What Degree of Administration Is Required?

A well-built sales machine doesn’t just shift administrative tasks from your rep’s plate to yours.

It makes everyone’s lives easier and more efficient.

As a sales leader, you don’t want to be micromanaging the tools that make up your sales process. You want things to be intuitive, which will make your sales team feel empowered in the process.

Lean toward the tools that require little to no administration on your end.

What Is My Budget?

Now, efficiencies are important, but we all know your executives are going to be saying, “Show me the money!”

They might not be screaming it to Cuba Gooding Jr., but you can guarantee they’ll be asking for ROI.

Before heading into that exec meeting, have answers to these questions about your proposed technologies:

  • Does this tool provide new channels for people to find you?
  • Does it provide you a better understanding of trends and how to predict business?
  • Does it help you identify and prevent funnel leakage?
  • Does it automate aspects of the sales process?
  • Will it drive best practices that are common among leading sales organizations?

Technologies That Help Map the Buyer Journey

Fred also shared a list of tools that will help you in each stage of the buyer journey:

Lead Sourcing and Data Intelligence: In this day and age, your data integrity and governance is so important. You want to have clean, organized data. A few great tools are Data.comDatanyze, and Hoovers.

Prospecting: In order to create a fine-tuned, quality email for your targeted persona, you have to do some heavy lifting in terms of prospecting. It’s best to have tools like SalesloftClearbitPersistIQ, and LeadFuze to support the process.

CRM: CRMs are now being designed to automatically collect data, so the more your CRM can provide this feature the easier your life will be. Some of the top-performing CRMs to check out are SalesforceHubSpot, and PipeDrive.

Marketing Automation: You want to choose an automation tool that compliments your selling style and process (e.g., inbound vs. outbound). Between PardotMarketo, and HubSpot you can find software that fits your needs.

Sales & Gamification: Sales gamification tools have made a big splash in inside sales. Ambition is a great tool for gamifying sales.

Productivity: The more productive your team is, the more time they have to close deals. Tools like CalendlyUberconference, and FollowUpThen are clutch when it comes to saving hours in your week.

When you’re looking through all these tools, make sure to check out G2Crowd, a site that offers over 80,000 business software reviews.


Nobel Prize writer Naguib Mahfouz once said, “You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions.”“You can tell whether a man is clever by his answers. You can tell whether a man is wise by his…


This quote couldn’t reign truer in your business. When you’re building a sales powerhouse, you’ll find that wisdom is found through the questions you ask.

If you’re looking for further information on inside sales, best practices for driving leads, and automating your funnel, check out Sales Acceleration Formula by Mark Roberge and Predictable Revenue by Aaron Ross.

You can find this interview, and many more, by subscribing to the B2B Growth Show on iTunes. If you don’t use iTunes, you can listen to every episode by clicking here.