The right CRM does exist: a step-by-step CRM evaluation guide

Running a business requires essential tools—but when is the right time to invest in a CRM? The right system can streamline operations and boost growth, but choosing one can be overwhelming.

Do you go with the biggest name? Stick to the basics or pay for premium features? And how do you know if a CRM will help—or just add complexity?

Jordan Robers, an Account Executive at Streak, has helped thousands of companies navigate the CRM selection process. But he doesn’t just follow the usual sales pitch—he takes a consultative approach to help teams cut through the noise and find a CRM that actually works for them.

We had a conversation with him to get his expert advice for taking the guesswork out of CRM evaluation so you can proceed with confidence. 

1. Evaluate your CRM readiness  

The first moment of truth is to understand why you are searching for a CRM in the first place. 

Yes, we sell a CRM solution here at Streak. No, we don’t believe every team needs one (or that ours is the right fit for everyone). Instead, we believe it takes a more consultative approach to determine what you do and don’t need. 

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Is a CRM investment right for you? 

First off, you shouldn’t adopt a CRM because you think you are “supposed to have one.” A CRM is worth the investment when it solves a specific problem, fills a gap, or addresses a pain point in your business.

Without that clarity, you risk investing in a CRM only to abandon it later—leaving you stuck with the same inefficiencies.

“The first thing you should do is take a step back and identify your top priority,” Jordan advises. “It’s not just about recognizing challenges or gaps—it’s about understanding which problem is most important to solve.”

Start by considering what problems or inefficiencies you want to solve. 

“Often these issues exist because of poor task management, the inability to scale outreach, or because you need a better way to capture data and interactions,” explains Jordan. “That’s when finding a CRM becomes a business-critical decision.”   

Signs that you need a CRM now  

Certain business needs make a CRM investment a clear decision. If you're struggling to keep up with customer interactions, manage data, or scale your outreach, your current tools may no longer be enough. 

“Many teams we work with struggle with manual processes. They're often piecing together two or more solutions at once, which means data goes missing,” says Jordan.   

Some of the most common signs that it’s time for a CRM include:   

• Time-consuming manual data entry and processes
• Disorganized task and follow-up management
• Deals or emails slipping through the cracks
• Limited visibility into customer interactions

• Poor internal communication

• Desire to scale and improve outreach  

• Lack of a single source of truth

For example, you may have mastered Google Sheets or developed a well-organized email labeling system—but when your team grows, manually entering and extracting data becomes tedious and inconsistent.  

“Without a single source of truth, it’s hard to hold everyone accountable for their responsibilities and track what’s being worked on,” Jordan explains.

2. Identify the CRM that will solve your pain points 

The better you can define your needs, the easier it will be to find the right CRM for your business. 

Instead of choosing a platform based on name recognition alone, focus on what each CRM can help you accomplish and whether it aligns with your specific challenges.

Understand CRM specializations 

While many CRMs offer the same core functionality, each one may have certain strengths and weaknesses.

The key to successful CRM evaluation is finding one that not only addresses your pain points but also fits seamlessly into your team’s workflow. 

“Each CRM solution has its niche, often shaped by the specific pain points or workflows it was originally designed to solve,” Jordan explains. “Over time, these specializations have made them particularly strong in certain areas.” 

Based on what you want to accomplish, different CRM specializations will fit the bill better than others. 

A few examples of CRM specializations within the current market include: 

• Project management CRMs – Designed for organizing tasks and team collaboration for project-based work (e.g., Monday, Asana)
• Marketing-focused CRMs – Strong in inbound marketing automation and email campaigns (e.g., HubSpot)
• Email-integrated CRMs – Integrates directly with your email inbox to streamline communication, pipeline management, and workflow automation without switching tools (e.g., Streak)

For example, Streak is designed for teams who primarily work in Gmail, allowing them to manage pipelines and track communication without switching between tools.

“Not only does Streak offer CRM functionality,” says Jordan, “but because it’s integrated into Gmail, it allows teams to track deals and conversations in one place and get the full picture.”

A CRM that fits naturally into your team’s workflow increases adoption and makes it more effective in solving the challenges you set out to address.

Pick a CRM that solves your current challenges first

Just like you should consider a CRM’s specialized nature, you should also keep in mind that some CRMs are very robust and geared towards enterprise-level companies.   

“When stakeholders tell me they're a team of two and they’re trying to decide between Streak and Salesforce, I can usually tell them why they don’t need to invest in an enterprise-level solution,” Jordan says.  

Salesforce is highly complex and works well for large organizations, but it’s often too clunky and difficult to customize for small and medium-sized businesses. Most smaller teams need something more intuitive, customizable, and user-friendly.  

“When you adopt a CRM, you don’t want to be overwhelmed with complex features. The first priority is to fix your broken system,” says Jordan. 

Even at Streak, we recommend starting with the simplest pricing tier and plan when it makes sense. While some businesses need advanced automations and integrations right away, others just need a better way to track engagement and activity.

Taking a Goldilocks approach to CRM evaluation means you can pick the one that’s just right for you. When you choose well, the CRM platform or subscription tiers will support you as you grow. 

3. Understand (the real) pricing and scalability 

Price is an obvious factor when evaluating CRMs, but it’s important to look beyond the upfront cost. Consider what you're actually paying for now and how pricing will change as your business grows.  

Look beyond introductory pricing 

We’ve all seen internet and TV providers lure customers in with low introductory rates—only to raise prices later. The same thing happens with CRMs if you don’t look beyond the starting price. 

“Some CRMs have better introductory pricing than others, but that pricing isn’t always static,” says Jordan. “This often means paying extra for essential features you thought were included—resulting in a much higher total cost.”

Many CRMs structure their pricing around add-ons, meaning essential features could cost extra as your needs evolve. Before committing, check what’s actually included at your current tier and how much it will cost to upgrade when you need more features.

At Streak, our simple pricing is structured to scale with your business without hidden costs or confusing add-ons:

• Pro Plan – Offers core CRM functionality in Gmail with pipeline management, email tracking, mail merge, and team collaboration features at a straightforward price.
• Pro+ Plan – Adds advanced reporting, workflow automation, and AI-powered insights to help growing teams streamline processes.
• Enterprise Plan – Built for larger teams with more complex workflows to include custom roles, data validation, and priority support.

Instead of gating off essential features or making you pay for add-ons, make sure your CRM is designed to support your business as it scales—without unexpected costs down the road.

Ensure your CRM will scale with you

Having a clear vision for your growth will help you choose a CRM that fits long-term. As a starting point, Jordan recommends considering where you want your workflows and CRM usage to be six months from now.

One useful exercise is to identify your team’s repetitive tasks—things a CRM could automate down the road to improve efficiency.

“Is there something your entire team does repeatedly? That’s likely something we can automate,” says Jordan. “And if we can automate it, we’re already setting a goal to be more efficient.”

Tracking these patterns will help you see where a CRM can save time and effort as your business grows.

Jordan suggests asking each CRM provider what your best-case scenario would look like after six months of using their tool. Then, clarify what it would cost to reach that ideal setup.

4. Ask your sales rep the right questions  

Are you ready to go all-in on CRM evaluation? Start by preparing a list of questions for the sales reps you speak with. Be direct, specific, and don’t hesitate to ask follow-ups throughout the process.

Here are some key questions to consider as you evaluate CRM solutions:

• My main problem is [X]. How can this CRM solve for that?  

• Why should I choose this CRM over [X]? 

• What plan/tier makes sense for my team to start with and why? 

• Will this CRM allow my company to scale as we intend to?  

• When and how would my pricing change?  

• What is the ideal trajectory/best-case scenario if we adopt this CRM?  

• I am still on the fence because [X]. What are your thoughts?  

A good sales rep will answer these questions honestly rather than deflect. Selling you the wrong solution won’t keep you subscribed for long, so they should be transparent about fit. They may even offer additional support or an extended trial to help you make the right decision.

5. Test drive the CRM as a team

While key stakeholders often lead CRM evaluation, the entire team needs to adopt and use the tool for it to be effective. A CRM should fit naturally into your team’s workflow—not feel like extra work.

Team buy-in is key to CRM success

A CRM only works if your team actually uses it. If it’s clunky, unintuitive, or adds extra steps, people will avoid logging information—leaving you with incomplete data and missed opportunities.

“If you want successful adoption of a CRM, the best approach is for everyone to learn and evaluate the tool together,” says Jordan. “New systems fail when one person makes the decision without input or support from the rest of the team.”

Even if you’ve been assigned as the CRM point person, involve as many team members as possible. Their feedback will help ensure the tool meets everyone’s needs and increases adoption.

Streak, for example, eliminates friction by integrating directly into Gmail. This way, your team doesn’t have to switch between tools or go elsewhere to log or find deal information. The easier a CRM is to access and use, the more likely your team will adopt it—ensuring you get the full benefits of automation, lead tracking, and streamlined outreach.

Choose a CRM that enhances team communication

A great CRM should improve collaboration by keeping conversations and information easily accessible. Ask yourself:

• Can your team collaborate in real time?
• Can they easily find updates and track progress?
• Is all key information stored in one place?

“When a CRM has failed me or the team I’m working with, it’s because there’s no place for real conversations,” explains Jordan.

Many teams start with simple tools like Google Sheets or Excel because they’re easy to use and widely accessible. But as your team grows, you may need a more integrated solution that serves as a single source of truth.

If communication and deal tracking feel disjointed, you’ll want a CRM that centralizes everything—so no one has to dig through emails or multiple platforms to get the full picture.

6. Make the most of CRM trials and support resources

The first few weeks with a new CRM are critical to long-term success. Jordan estimates that most teams know within 10 days whether they’ll stick with a new tool. That’s why onboarding is so important—using support resources early ensures your CRM is set up for immediate impact.

Maximize your trial period

Most CRMs offer free trials, but simply signing up isn’t enough—you need to actively test how it fits into your workflow. During your trial, make sure to:

• Set up a test pipeline or process relevant to your team
• Have multiple team members try it and provide feedback
• Identify any bottlenecks or missing features
• Check if the CRM improves efficiency or adds unnecessary steps

Lean on CRM support and training

“The best way for a CRM to help you with your core problems is to lean on support from your provider. They are the experts in what they've sold to you, and they should be able to guide you in the right direction to ensure you receive the best possible outcomes,” says Jordan.

Many CRM providers offer training resources that can significantly improve adoption. For example, Streak offers teams:

• Live, expert-led classes to walk teams through setup and best practices
• A self-serve Streak University video library for on-demand learning
• 1:1 support to answer specific questions and help with implementation

Taking advantage of these resources can make the difference between a CRM that sticks and one that gets abandoned after a few months.

By testing thoroughly and leveraging support, you’ll ensure that your CRM doesn’t just look good on paper—it actually works for your team.

Select a CRM that will position you for lasting success  

Vetting CRMs can feel daunting at the outset, but with the right approach, you’ll quickly recognize which options solve your unique business needs and challenges. 

Focusing on your organization’s specific challenges—not just flashy features—will help you choose a CRM with meaningful capabilities that drive real impact. Before committing, talk to a sales rep and ask the tough questions—pricing, scalability, and how it actually solves your challenges.

Once you have full team support and have set up your CRM for lasting success, you’ll be positioned to improve efficiency, strengthen customer relationships, and scale with confidence.