How to Choose the Right Tools for Your Sales Stack in 8 Simple Steps

October 5, 2016

In the quest for the perfect sales stack, one is reminded of Icarus, who overestimated the power of his waxen wings and flew too close to the sun. During the final moments of his fatal plunge toward earth, the mind of Icarus must have swum with regrets, the chiefest among them of course being: “Why did I settle for the first wings I found? Sure, they were flashy and new and TechCrunch just wrote an article about them, but maybe I should have given this a little more thought.”

While a robust sales stack can be a powerful tool in the fight for more sales, the sales stack is not a cure all, and simply loading your shopping cart with the latest and greatest sales tools won’t get the job done. In fact, it may just weigh you down. To build the optimal sales stack for you and your company, here is how to choose the right tools.

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1. Define Your Pain

You may be thinking, “But pain points are for customers! I’m a salesperson!”

I hate to break it to you, but when you’re shopping for sales tools, you’re just as much a customer as the rest of them. And as a customer, it’s important to define your pain before making a purchasing decision.

So, what problem or problems are you hoping a sales tool will solve? Perhaps you’re:

  • Dissatisfied with the current visibility into your pipeline
  • Struggling to analyze customer data in a meaningful way
  • Concerned that your sales funnel clogs too easily
  • Worried your sales cycle is too slow
  • Upset by your disorganized workflows

2. Define Why You Need To Solve Your Pain

A what without a why is like a supervillain with no origin story. If you don’t know what makes a supervillain tick, how will you ever hope to defeat them?

At this point you’ve established the what. Now it’s time to understand the why. So ask yourself:

  • Why is it important for me to analyze customer data in a meaningful way?
  • What will I accomplish if I gain more visibility into my pipeline?
  • Why do our workflows need streamlining?

3. Define How Solving This Pain Will Affect Everyone

Before you toss aside your dictionary, you need to go one step further by understanding how solving your pain points will affect your company.

For example, if more visibility into your pipeline leads to a more efficient sales cycle, then perhaps a more efficient sales cycle will save people hours, increase morale, and cultivate a happier work environment.

Or, if analyzing customer data in a meaningful way will help fine tune your marketing tactics, then perhaps a better marketing strategy will bring in more qualified leads, increase productivity, and allow your company to expand its reach.

4. Put It All Together

By now you should have a holistic understanding of your pain points, which might look something like this:

One of our company’s top priorities is to streamline our team’s workflows to increase productivity, giving our team room to improve their skill sets, grow as a group, and do better work.

There are many tools that help streamline your team’s workflows, but in this specific circumstance, the most optimal tool would also help your team evolve their skills. Therefore, something like might be the best fit, as it not only helps organize and streamline workflows, it also provides performance insights to increase your team’s effectiveness.

5. Research with Strangers

By defining all aspects of your pain points, it’s easier to narrow down what sales tools you might need, and arrive at a more curated set of options. But creating a sales stack is a big investment, which is why it’s important to do your due diligence. Researching your tool options before making a purchase is crucial, and crowdsourcing your research can be incredibly effective.

So start your research process by talking to people you DON’T know.

Leverage the social power of LinkedIn Groups, Twitter, and Facebook to gather unbiased opinions of certain tools. What does the hivemind think? What do the outliers think? What is the overall perception of the tool? Of the brand?

6. Research With Friends

After gathering the opinions of strangers, look to friends for feedback. Their feedback may not be objective, as they know you and understand your interests, likes, and dislikes, but combining their opinions with those of strangers will result in a much clearer picture of which tools will and will not work for you.

7. Define Success

With a curated list of sales tools coupled with a comprehensively researched overview, the final step in choosing the right sales tools for your sales stack is to ask yourself the following 5 questions. The answers to these questions will help you confirm you are focusing on the right improvements and increase your commitment to improving them.

  1. Once we implement [name of sales tool], the sales reps should be able to do ______, ______, and _______ better.
  2. We will be able to measure ______, ______, and ______ for improvements.
  3. We have / do not have baselines for ________, _______, and _______ measurements from #2.
  4. It will take us ______ weeks come up with baseline measurements based on #2 and #3.
  5. Our hypothesis for success will be an increase of ______% for ______, ______% for ______, and ______% for ______ above our baseline numbers.

8. Intelligent Trials

In most cases many of the tools for your sales stack offer free trials. By all means take full advantage of them. In fact one of the smartest things to do is to assign certain tools or tool categories to your reps for testing. It’s a great way to get real feedback from the user. Additionally it gives all parties an opportunity for professional development.

As a manager it allows you to learn to delegate and accomplish more. As a rep it allows them to feel empowered and learn what it takes to be a manager. This fosters a stronger sense of teamwork, camaraderie, trust, transparency.

If you gone through your eight steps you are now able to make a smarter decision. You have data to support your decision and a plan in place to set you up for the best possible chances of success.


Richard brings over 20 years of technology and SaaS experience in sales training, operations and sales leadership into his role as a Sales Consultant. He is the Founder of <a href="">Harris Consulting Group</a. He has built, led and consulted with a wide range of organizations including start-ups, mid-size companies, and global organizations. Richard is also the current Director of Sales Consulting and Training for <a href="">Sales Hacker</a> and is a regular speaker at the various Sales Hacker events, workshops, and SalesStack conference. Some of the companies that Richard consults for include Mashery (aquired by Intel), Spanning (acquired by EMC), Outbound Engine, TopOpps, Village Voice Media, Riverdeep (acquired by Houghton Mifflin Harcourt), PC Guardian (acquired by Acco Brands), DotNext Inc., Telecom Inc., and Yozio.