The No-Regrets Guide to Evaluating GTM Tools in 2025
The 2025 global tech spend is projected to grow by 5.6%, reaching a whopping $4.9 trillion. That’s $700 billion more than the global automotive market.
This acceleration represents significant investments largely driven by the increasing reliance on SaaS applications, cloud solutions, and investments in generative AI within go-to-market (GTM) teams.
As someone who has been in the front seat of vendor evaluations, I know a lot about the pressures that come with making high-stakes technology purchases. Choosing the wrong technology partner isn’t just frustrating, but it could be a very costly decision that impacts your business for years.
That's why I've done the groundwork to help you make a confident and well-informed decision. Follow this complete guide to create a structured and repeatable GTM software evaluation process that will make your next purchasing decision easier.
1. Define Strategic Objectives
At the center of any evaluation process are the business objectives that make up your north star. If tightly defined, these are 2-3 critical objectives that directly contribute to the organization's strategic goals.
Whether I was focused on aligning GTM teams or reducing churn and driving net revenue retention, I learned that strategic objectives only drive impact when they are clearly defined and measurable. It's not just about vision; it's about aligning the right metrics with the outcomes that matter.
2. Identify Evaluation Criteria
Once you have your strategic objectives defined, it's time to establish the criteria your organization will use to assess vendors. This includes identifying key criteria such as cost, security, service reliability, and functional fit.
These criteria will serve as the foundation for building your vendor scorecard. Here are five common criteria that span across most industries:
Strategic alignment and partnership
Too often, evaluators focus so narrowly on solving today's challenge, they forget to evaluate how a vendor's strategy or product roadmap aligns with the long-term business goals. My advice?
Functional Fit
Simply put, technology must meet the day-to-day functional needs of your team. Functional fit is a key consideration, making sure the tech you purchase fully supports your use cases, workflows, and the goals of your end users.
A strong functional fit doesn't need to check all the boxes, but it does need to hit the mark on the top 2-3 functional use cases and workflows. This will accelerate adoption and help you hit the ground running with fast results.
Interoperability
Interoperability is just a fancy way of explaining how systems work with other systems.
It's a bit of a no-brainer, but any tech purchase must integrate with low effort into your current tech ecosystem. If not, you run the risk of creating data silos and building inefficiencies.
Start by looking for native out-of-the-box integrations. Second, consider API capabilities to connect to different data sets. Don’t worry if the technology doesn't play well with every piece of tech in your stack. Rather, focus on the key integrations such as CRM, marketing automation, BI tools, and your ERP platform.
Scalability and flexibility
Business needs change over time, and the tech you select should be able to grow with your evolving needs. You should consider your organization's size today and your expected headcount in 2-4 years.
Consider how your plans for regional expansion or the forecasted increase of data volume over time will impact system stability. Flexibility is equally important. Technology needs to be adaptive to different business models, workflows, and user needs without having huge overhead costs to make changes.
Adoption and change management
Something that is near and dear to my heart and often the least scrutinized element of any evaluation. As part of your evaluation, you need to know how your selected vendor will support both short and long term adoption.
A true technology partner doesn't just hand over software. They partner with your business to ensure your investment is successful. That's how you get the best ROI on GTM software.
Here are some questions that you should be asking prospective partners:
What is your change management methodology?
Look for a consistent methodology. Do they follow formal frameworks like ADKAR, or do they have their own proven framework?
How do you drive adoption in organizations like ours?
Ask the vendor for industry-specific experiences and customer success stories.
Can I speak with a customer reference about their onboarding and adoption experience?
Make sure they provide you with relevant customer references at the right level, i.e., Director and/or VPs.
How do you handle lagging adoption?
Look for specific playbooks for addressing this. If they don’t have designed playbooks, this could be a huge red flag.
3. Develop a Vendor Scorecard
Now that we’ve discussed some key criteria you should pay attention to, it's time to start putting together a structured scoring system that allows for consistent measurement across your criteria and each vendor.
Scorecards are Really Important
Building scorecards into your process allows you to practically execute your evaluation. It ensures that each vendor is consistently assessed based on pre-defined criteria and not on how a group of people feels.
Make your Scorecards Effective
To make the most out of your scorecards, start with specific scoring guidelines. For example, use a simple grading scale of 1-5 (1 for below, 3 for meets, 5 for exceeds). Provide your evaluation committee with examples of what constitutes a 1 versus a 5.
The CRO Club has a CRM evaluation scorecard that could easily be used to evaluate any GTM tech.
Once you have your scoring mechanism in place, identify how your criteria will be weighted. As an example, if you are in a highly regulated industry, security and compliance might be weighted higher than innovation. Apply weighting based on what is most important to your organization.
Common Pitfalls to Avoid
Lack of clear business objectives
Pitfall: Going into evaluation cycles without defining your north star business challenges or outcomes.
Solution: Spend the necessary time needed aligning with stakeholders on business goals, metrics, and the priority of use cases.
Evaluating too many vendors
Pitfall: Attempting to assess too many tools leads to evaluation fatigue and analysis paralysis.
Solution: Do an initial screening using third party research or write an RFP, then narrow your evaluation down to 2-3 vendors.
Over-indexing on demos
Pitfall: Do not get overly impressed by cool demos or bells and whistles that you may never actually use.
Solution: Score vendors against your prioritized functional and non-functional requirements.
Underestimating integration complexity
Pitfall: Selecting a solution that does not integrate well with your existing tech ecosystem
Solution: Involve platform owners and IT early. Score the vendor on data architecture, API access, and compatibility with existing tools.
Overlooking TCO (total cost of ownership)
Pitfall: Only evaluating licenses cost and some potentially larger costs, such as data storage, admin/developer overhead, and ongoing maintenance cost.
Solution: Attempt to do a rough calculation (won't get this perfect) of the total cost of ownership over 3-5 years, including all the significant downstream impacts.
Lack of stakeholder engagement
Pitfall: Evaluations that are done in silo and excluding key business partners are destined to fail.
Solution: Build a cross-functional evaluation committee with users from different business units.
No Evaluation Criteria
Pitfall: Making purchasing decisions based on gut feel instead of a structured comparison.
Solution: Establish a vendor scorecard based on the criteria we discussed above!
Skipping the Pilot
Pitfall: Deciding to purchase a solution before actually testing it in the “real world”.
Solution: Run a pilot program with actual users and different use cases to validate some of your decision-making criteria
How I Bring It All Together
My most successful evaluations always started by tying my organization’s strategic objectives to a clear and repeatable process. Without this connection, it's too easy to chase new shiny tools instead of solutions that actually have a business impact.
If there is one thing I can leave you with, it's to always involve the right cross-functional stakeholders early. I find having their valuable input early in the process helps surface real pain points and ensures our purchase not only addresses today’s challenges but will scale as we grow.
When everyone has a seat at the table, you are far more likely to make a decision that sticks and delivers.
Need more help evaluating GTM tools?
Our software advisors can help you find the right fit for your tech stack.
