Introduction: Don’t Waste Your Free 30 Days
Starting a new CRM can feel overwhelming, and too many businesses waste most of their Pipedrive Free Trial simply trying to figure out where to begin. Instead of unlocking the full power of Pipedrive, they spend days tinkering with settings and end up making their decision based on half the features.
The good news? You don’t have to fall into that trap. With a clear roadmap, you can use your 30-day trial to test real sales processes, automate daily tasks, and even close deals before your trial ends. At The Prairie Group, we help businesses like yours transform a simple free trial into a powerful sales accelerator.
This step-by-step guide shows you exactly how to get the most out of your Pipedrive Free Trial — day by day, week by week.
Why Start Your Pipedrive Free Trial With The Prairie Group
Pipedrive is designed to be simple and intuitive, but every CRM has a learning curve. Signing up for the trial on your own gives you software access — but without guidance, you’ll likely spend weeks exploring features instead of generating results.
By starting your Pipedrive Free Trial with The Prairie Group, you get more than just access to the platform. You get:
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Certified setup support to ensure your account is structured correctly from day one.
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Onboarding guidance so you don’t waste time reinventing the wheel.
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Training resources to help your team adopt Pipedrive quickly.
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A partner who has been a Premier Pipedrive Partner since 2020 with decades of CRM experience.
In other words, we turn your trial into a true test drive of how Pipedrive will work for your business.
Days 1–7: Setup and Onboarding
Your first week is critical. This is when you lay the foundation for success with your Pipedrive Free Trial. Focus on these steps:
1. Import Your Contacts
Bring in your leads, clients, or past deals. Pipedrive allows easy CSV imports so your data is ready to go.
2. Create Your First Pipeline
Pipedrive’s visual pipelines are at the heart of the CRM. Set up stages that match your sales process (for example: Lead In → Contact Made → Demo Scheduled → Proposal Sent → Won).
3. Connect Your Email and Calendar
Sync your work email and calendar to log every message and appointment automatically. This saves time and ensures nothing falls through the cracks.
4. Automate a Basic Follow-Up
Even in the trial, you can set up automation. A simple workflow like “send a follow-up email 2 days after contact” helps you see the power of automation early.
By the end of Week 1, you should have a working CRM that mirrors your sales process.
Days 8–15: Customize Workflows
Now that your basic setup is done, Week 2 is all about making Pipedrive fit your business like a glove.
Add Custom Fields
Capture the information that matters most to your team — such as industry, lead source, or contract value.
Build Automations for Tasks and Reminders
Create workflows that assign tasks automatically when deals move stages. For example, when a deal moves to “Proposal Sent,” you can automatically schedule a reminder to follow up in 3 days.
Integrate With Your Existing Tools
This is where The Prairie Group makes a difference. We specialize in connecting Pipedrive with tools like Apollo.io, PandaDoc, and JustCall. During your trial, we’ll show you how integrations streamline everything from lead generation to e-signatures.
By the end of Week 2, your trial account should feel like it was built for your exact workflow.
Days 16–25: Train Your Team and Drive Adoption
A CRM is only as powerful as the people who use it. In Week 3, shift your focus to team adoption.
Assign Roles and Permissions
Set up user roles so your team members see only what they need. This keeps things clean and secure.
Train Reps on Deal Stages
Walk your team through how to move deals through the pipeline. Reinforce the importance of keeping data up-to-date.
Use Insights to Track Activity
Pipedrive’s Insights dashboards show calls, emails, and activities by rep. Use this to coach your team and identify bottlenecks.
When your team is actively using Pipedrive, you’ll quickly see where deals are stalling and where you’re winning.
Days 26–30: Measure Results and Plan Next Steps
Your last week in the trial is about measurement and decision-making.
Run Reports
Use Pipedrive’s Insights to see how many deals were created, how many moved stages, and how many were won.
Measure Pipeline Value
Calculate the value of your active deals. This gives you a forecast of what could close in the next 30–60 days.
Forecast Your Next Quarter
Look at your pipeline by stage to see if you’re on track to hit your sales goals.
Decide on Your Plan
At the end of your trial, you’ll have a clear picture of how Pipedrive supports your team. Most businesses choose to upgrade at this stage — and with The Prairie Group, we’ll help you select the right plan and keep your setup intact.
Common Mistakes to Avoid During Your Pipedrive Free Trial
Many businesses don’t get the full value from their trial because they fall into these traps:
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Waiting Too Long to Set Up → Don’t spend the first 20 days exploring menus. Get your pipeline live immediately.
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Skipping Training → If your team doesn’t know how to use Pipedrive, you won’t see results.
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Not Testing Automations → The trial is the best time to see how automation saves time.
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Making the Decision Too Late → Don’t wait until day 29. Plan your decision by day 25 so you’re ready to move forward.
Avoiding these mistakes ensures your trial delivers maximum value.
Conclusion: Turn Your Trial Into Real Sales
Your Pipedrive Free Trial is more than just a chance to test software. It’s a 30-day opportunity to transform how your business manages sales, automates tasks, and tracks results.
When you start your trial with The Prairie Group, you don’t just get CRM access. You get a trusted partner with decades of experience in CRM implementation, training, and integrations. That means your free trial becomes a true business test drive — one that leads to real results.
👉 Ready to get started? Start your 30-Day Pipedrive Free Trial with The Prairie Group today.
