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The Sales Tech Buying Guide – Read Before You Purchase Software

Are you getting ready to purchase software? Easy enough if the cost is a few dollars a month, but what if you are about to spend thousands of dollars a month, with months to implement and ROI hard to measure?

We’ve been on the vendor side for years and seen a lot–that’s why we created this Sales Tech Buying Guide.

In this article, we will cover a lot of ground, including:


The sales technology landscape is a bit overwhelming, with hundreds of possible tools in dozens of categories. Cutting through that clutter is hard, so we wanted to take a moment to share a few tips to help you out.

Before You Buy

Whether you are purchasing software for small business, enterprise, or a government agency, consider the following advice.

Where Does Your Current Software Solution Fall Short?

Jessica Hendricks and Alexandra Wallitsch participated in the Enablement March Madness Tournament, focusing on the role of Technology in the Sales Enablement Process.

This great conversation covers a lot of ground, including thoughts on when, how, and why to buy technology.

Power Tip: Always deeply understand your current technology and its full capabilities before investing in the next shiny and often expensive solution.

Alex and Jessica note that technology can amplify a team’s impact, guide audience members, and bridge the gap between enablement and leadership.

The most critical impacts can usually be knowledge, coaching, and impact.

  • Knowledge, which is where reps access information
  • Coaching, which is how enablement or managers reinforce this knowledge
  • Impact, which is how to measure the success of the knowledge and the coaching

Understand The Entire Procurement Process

Many internal buyers fail to analyze their company’s procurement process and get stuck.

Some get hung up on the approval process, lacking sufficient analysis.

Still, others fail to understand their budget authority.

While others don’t know how to use the internal procurement system.

Sit down with your leaders and procurement team before beginning your software search; this will save you time and headaches. As you go through this process, ask:

  • Who has to be included in the decision?
  • How many competitive solutions do you need to evaluate?
  • Should security, performance, governance, or privacy requirements be considered?
  • Are there different rules for different purchase amounts?
  • Are vendors required to be certified or approved by some means?
  • Can you pay through a purchase order, invoice, or credit card?

What do we mean by the sales technology landscape?

The sales technology landscape defines all possible tools from all likely vendors you could buy right now.

Okay, the universe of possibilities is enormous; how do you create the best sales tech stack for you?


Assembling your sales tech stack – making sense of the overall sales technology landscape


Start with your CRM

We are strong proponents of beginning with the right CRM. Read our article on selecting the right CRM for your business if you do not yet have one.

From there, the process of assembling the sales tools is straightforward.

Note: This tip may be less critical when purchasing software for a small business.

Start with your WHY

You knew we were going to say that, didn’t you?

  • What problem are you looking to solve?
  • Which part of your team will this benefit?
  • How are you working around this problem right now?
  • Are other tools currently being used to solve this problem? Why aren’t you using them more broadly?
What tools are others like me using?

Based on your industry, go-to-market motion, sales methodologies, and so forth, are there a standard set of solutions others use successfully?

We are not suggesting that you “follow the leader”; we recommend you use this information to learn what is possible and inform your decision-making.

Consider team size and growth plans

The adoption of tools is critical to your overall success.

A small team with no growth plans will not necessarily require buying from a vendor with a fantastic customer success team, training materials, and onboarding capabilities.

However, the above should factor into your considerations if you have a larger organization.

How much money can you spend, and what’s the value of solving this problem?

Think through the ROI of solving this problem.

Sometimes the problem you are trying to solve isn’t worth solving via sales tools on that incredible sales technology landscape.

Ensure it integrates with your existing solutions

If you solve a problem that creates data, ensure that data can feed into your CRM or business intelligence (BI) systems.

If you purchase a solution that delivers personalized assistance, ensure the tech stack can feed the information required to provide those personalized capabilities.

Pilot it formally

Not every solution will need the same level of testing as others.

Solutions like Grammarly, Canva, for example, are vital tools but work in isolation from most of your tech stack.

However, solutions like DotCal should at least integrate fully into your calendar and email.

Solutions like Autoklose, on the other hand, must integrate deeply into your tech stack so that the work of your SDRs feeds the broader system.

And competitive intelligence solutions like Klue and Crayon may take months before you can measure their potential value.

For a pilot:

  • Define success criteria. If the solution doesn’t meet those criteria, don’t buy it.
  • Validate the value created. Remember your ROI; if the tools do not achieve the expected value, either push for a lower price or don’t buy it.
  • Get team feedback. If the team hates it and will not use it, don’t buy it.

Questions to Ask a Vendor When Buying Software

We have seen both sides’ good and bad buying sales technology.  That’s why we have put together these questions in our buying guide.  Let us know if you have others you feel we should add.

#1 What business problems do you solve?

If the vendor starts discussing bells, whistles, features, and functionality, shut them down.

The critical question you should have is if they have solved problems like yours. If they haven’t, odds are someone else does it better.

#2 What customers have you worked with that are exactly like me?

There are a couple of essential reasons for this question.

  • Does the vendor understand your business, industry, and typical challenges?
  • Have they worked with companies like yours, and can they bring those lessons learned to help you overcome your challenges?
#3 How does your post-sales team work with us to succeed?

It is critical to hear about more than adoption rates. You want the vendor to speak in terms of:

  • Quarterly Business Reviews to check progress against key business metrics to confirm you have solved, or are on track to solve, your business challenges.
  • Their Customer Success Plans to drive results.
  • The experience of their Customer Success organization, how closely they work with other teams internal to the vendor’s business, and their focus on achieving your business results.

You are in the purchase process to solve a business challenge — can the vendor demonstrate they’ve done this before?

Note: In Q2, 2022, we are partnering with many of the vendors on the Certified Tech Stack to analyze their current post-sale processes.  Stay tuned for those results.

#4 Do you make use of a customer council?

Do they work closely with customers to understand their needs, and does it impact their product roadmaps, service offerings, and other aspects of the business?

Similar to the last question, this question helps you understand if you are creating a partnership for long-term success or just buying a tool with no expectations of support from the vendor.

#5 If we have issues beyond what customer success can handle, do you have a list of third-party consultants we can engage with?

Does the vendor have a robust community of partners who can support you beyond the cookie-cutter onboarding and other processes they use?

If not, why? This could signify a vendor who doesn’t play well with others and is worth understanding.

Note: When buying sales technology that generates insights and data, working with companies with a robust ecosystem is critical.

#6 How does your team stay up to date on trends in our industry?

Does the vendor understand your industry deeply, or is it a shallow understanding brought forward during the sales cycle and unable to be leveraged post-sale?

#7 Do you have out-of-the-box integrations with the critical components of our existing technology stack?

Most solutions you buy cannot, and should not, become isolated from your existing tech stack. Think carefully about the following questions when purchasing sales technology:

  • Does this technology create data you want available in your CRM or other systems?
  • Who will use this solution, and is it acceptable for them to use it stand-alone, or does your team benefit from having access to it from their email, CRM, or other vital systems?

Be wary of answers like “We have an API, shouldn’t be hard to build,” and look for existing integrations.

#8 What challenges will we have going through our procurement team, and how can we avoid them?

Procurement can be a set of challenges, and you want to know if this vendor has the patience and skills required to work with your teams.

This is one of the most important questions to ask a vendor if you know your procurement team is challenging.

Tech buyers go through three major phases:

  • I have a problem; can I solve it in-house?
  • No?  Okay, what vendors can solve these problems?
  • Fantastic, let’s sign the contracts.

The procurement phase of buying sales technology can often feel different than it has to work with the sales team.  Be aware of what could go wrong — the list grows.

#9 Can you share your latest security audits, software data flow diagrams for integrations, and similar?

If you are buying software to integrate into an enterprise-level environment, these are essential questions to ask a vendor.

#10 What challenges would you expect us to encounter while deploying your solution?

Nothing ever works right out of the box. If they tell you it does, be concerned.

What are the common problems, and what mitigation strategies do they use?

#11 We must be live by X; how does that fit your standard post-sales process?

If you have hard deadlines, raise them early and ensure the vendor is aware and can meet the deadline if you buy their software by a specific date.

#12 Can you introduce us to a non-competitor with a similar set of challenges being solved?

Most vendors will introduce you to customers they have had success with vs. those they have had challenges working with — still, these conversations are valuable.

#13 What happens if we encounter a software defect? What is that process?

The vendor should share a standardized escalation process for issues with different approaches for different categories of problems.

Ensure you see appropriate SLAs and communication methods and have a portal or other application to report and manage these issues.

When buying software, vendors often act as if their solutions work flawlessly.  There are always areas where the tech is not as robust; understand these areas.

#14 What training is available to us pre and post-sale?

If you want to deliver the training to your teams, can the vendor provide assets and train-the-trainer sessions to support this need?

#15 How are product changes or updates announced, and is there any ongoing training?

Especially for SaaS software, you do not want to be surprised by changes and cannot teach those using the software how to do so effectively.

#16 Questions to ask a vendor buying software – what questions do other prospects ask you?

This is educational if you are working with the right potential vendor. They will demonstrate transparency while also showing themselves as trusted advisors you can depend upon.

#17 What is your customer churn rate?

Churn, the act of customers canceling subscriptions or simply not renewing, is always expected.

Dig into how they calculate their #s and dig in more profound if the number is below 90% or above 95%.

If below 90%, dig into why customers are churning and have them walk you through a few recent examples.

If above 95%, they may be outstanding, fortunate, or stretching the truth.

#18 Are you a Trusted Vendor on Trust Enablement?

Come on; we had to add this one to the buying guide.

We added this to the buying guide because the level of collaboration and transparency vendors show during our analysis indicates how good of a partner they will be with their customers.

Our Trusted Vendors have opened up their software platforms and introduced us to customers who have provided feedback on what they do well and where they can improve.

And all of that without an NDA in place.

#19 What customer references can you provide?

The vendor should be able to provide you with a list of references that you can contact. These references should be from companies similar to yours in size, industry, and needs.

In addition to the questions to ask a vendor when buying software, use these questions when meeting with their references.

Buying Guide Bonus: 12 questions to ask vendor references

The vendor’s existing customers should always be part of your buyer’s journey.

  1. If you were making the vendor selection again, would you make the same selection?
  2. How long did it take to deploy the solution?
  3. How easy is it to do business with the vendor?
  4. How well does the vendor communicate?
  5. What is the quality of customer support?
  6. What are the most significant pain points with using the software?
  7. How much training is required to use the software effectively?
  8. Are there any hidden costs associated with using the software?
  9. Is there anything you wish you had known before signing the contract?
  10. What are the most significant benefits of using the software?
  11. When you are buying sales technology, what questions do you have?
  12. What did you like/dislike about working with your sales rep?

What additional questions to ask vendor references would you recommend we include?

What questions to ask a vendor should we have included in this buying guide?

6 Buying Tips to Embrace Now

Buying Tips – Stop worrying about features; focus on your work to be done

The feature wars only create confusion in the buying process. A remarkable feature that saves you no time or makes no measurable incremental business value is just a cool feature.

Please don’t put it on your buying criteria.

When buying software to solve business challenges, remain focused on the following:

  • What changes must be made throughout the business to solve this business problem?
  • What requirements does each stakeholder have for this change? Not features and functions, but what are the business requirements?
  • Analyze each option against that criteria, nothing else.

Don’t let shiny objects (the features) blind you from seeing what is truly important.

Buying Tips – Integration Capabilities are critical — don’t underestimate them

You want the data and capabilities of your solution to integrate with your tech stack.


If the data in one system cannot cleanly flow into your BI tools or key data stores, you create islands of insights that business stakeholders will ignore.

And no, complex or manual solutions involving CSV files are not the answer.

If the new system does not integrate into your teams’ systems, they won’t use it. No training, content, or other efforts will result in actual adoption.

And, without adopting the solution you buy, you are just throwing money out the window.

Buying Tips – Frankenstein is real

If you need a suite of products, a whole solution, you will always be better off buying from a company that has built it all in-house, on one code base, and unified manner.


  • Administration cost tends to be lower as user management and other standard functions only have to be done once, with no hacks and no playing around with complexity.
  • Data generally live in one central data store and is easier to report upon without paying extra or jumping through hoops.
  • The use cases you support are often complex and require working across multiple systems. The fewer systems involved, the better.
  • Security or IT team audits only need to be done against one platform, not many.
Buying Tips – Transparency is king

Too many vendors make it difficult for you to evaluate their products thoroughly.

These solutions are often complex, but if they can’t teach you how to validate a few critical actions during the buying process, they are either too complicated, too buggy, or unsuitable for your business.

If it’s any of the above, your teams will not use it.

We’ve been surprised that vendors try to pull the whole, but we can’t give you access as it’s too “fill in the blank.”.

If you don’t have confidence in it, others won’t either.

Please pay attention to our vendor list to see which vendors are confident in their solutions. They are the ones for which we will be writing How-To articles, supporting our efforts to develop the best buying guide available anywhere.

And push for three months of paid pilots, where your teams can run a comparison test between vendors.

Vendors unwilling to do this are generally reluctant to go the extra mile with you if you become a customer.

Buying Tips – Don’t sign auto-renewal contracts

This business practice should have gone away years ago.

SaaS businesses sometimes use this to hold on to unhappy customers who were too slow to cancel.

Please remove it from any contract.

Buying Tips – Don’t sign a contract longer than 1 year – until after the first year

Too many vendors give benefits for longer-term contracts, disappear, and fail to make you successful until late in year two (when they are considering renewals).

Longer-term contracts can make sense, but only after you know the vendor can meet your business needs.

Let us know if you want our help in your vendor selection process — it’s messy.

Trust Enablement provides the insights you need to decide on the best customer success, enablement, ops, marketing, and sales tools your customer-facing teams need to thrive. Our Certified Tech Stack is a critical component of achieving this mission. Please keep reading to learn more about our view of the technology landscape.

Every quarter, we review and update our information on these vendors, write how-to articles, and update our recommendations regarding which vendors you should consider working with based on your business challenges, industry, size, etc.

In addition, we are always learning new tools to consider for our Certified Sales Tech Stack. We will continue to add new vendors and solutions to our overall recommendations.

Want more sales, less churn, and increased revenues overall?  Keep reading.


Why did we create the Certified Sales Tech Stack?

We have often seen vendors that raise the fastest money can pay for the best analyst coverage, buy the most positive reviews, and corner the market.

While this works great for a handful of vendors, it only leads to buyer confusion and dozens of also-rans who often provide better solutions for specific scenarios.

We want buyers to benefit from the right tools for their sales process, industry, and needs.

When this happens, everyone wins.

And we know that this improves through an independent review process that helps you differentiate vendors and solutions in our review of the overall technology landscape.

Need Guidance on How and What to Buy?

We offer a service to customers looking to procure software.  Learn about our software selection services offering and, if of value to you, reach out.


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