Getting my first deal into Pipedrive

Pipedrive's homepage says "Full access. No credit card required." I signed up, answered ten fields of questions, and got a pipeline tailored to my industry. It had nothing in it.

In this story I run a one-person consultancy. My deals live in my inbox and I keep losing track. I want a simple CRM, and I want to see it working today.

So I recorded my screen from the homepage to the end of the setup guide, and timed how long it took to get one real deal into Pipedrive.

What I found:

1. No card and a Gmail address that gets in: the sign-up is easy.
2. Ten fields and a goals screen, and none of the answers shows up in the product.
3. A pipeline "Tailored for your industry" with no deals, a tour of empty screens and an 11-task to-do list. Three and a half minutes in, zero deals.

Let's get into it.

Meet me. I run a one-person consultancy. My deals live in my inbox and I keep losing track of who I owe a reply. I want a simple CRM, and I want to see it working today.

Pipedrive's homepage is built for me:

"Pipedrive is the easy, intelligent CRM loved by growing sales teams." Try it free. Full access. No credit card required.

An easy, intelligent CRM, and no card. Let's see. I click "Try it free".

"Sales management that's actually simple." It asks for a work email. I type my Gmail and it still lets me in. Good.

Then a 6-digit code by email. Off to Gmail and back: 23 seconds. Behind the pop-up, a blurred pipeline full of deals.

"About you." Name, password, job title, "Have you used a CRM before?", phone number. The phone number isn't optional: "Please add your phone number."

"About your company." Company name, size, industry, how many people will use Pipedrive. I skip the size and get a red error.

Then "Your goals: What would you like to focus on during the trial?" I tick "Improve customer communication" and "Optimize and automate my sales process". Then "Creating your account…" for 11 seconds.

To be fair, some of these fields aren't for me. Pete Kazanjy suggests adding "some fields to your initial signup form that helps characterize the potential value of an account" (Lenny's Newsletter), so sales knows who to call. The phone number makes sense now. The goals screen is different: it asks what I want from the trial.

"Welcome to Pipedrive, Edijs!" A sales pipeline, with a blue label: "Tailored for your industry". New Deal, Contact Made, Qualified, Meeting Completed, Negotiations started, Contract Signed. Six empty columns. "No deals added yet."

Remember the blurred pipeline behind the code? This is the same screen with the deals taken out. The fastest way to see value is a small button in the middle: "Try with sample data".

I click Continue. "Bring your contacts into Pipedrive": "No people added yet." Continue. Activities. Then a pop-up: "You've now covered the basics." And a rating: "How easy was the setup for you?"

I haven't added a single thing. I've seen three empty screens and been told I'm done.

"Hi, Edijs! Let's get you set up." A progress bar: "1/11 suggested tasks completed". Four groups in the to-do list, more under "More to explore", and an "App recommendation" pop-up in the corner, two minutes in.

My inbox, where my deals live, is group two: "Connect your communication tools", 0 of 4 tasks, under a collapsed row.

I go looking for the price. Billing. Credit where it's due: Premium, €74 a seat, shown as €0 during the 14-day trial, no card, billed monthly. Clear.

And on top of it: "Would you like to skip the remaining trial period? Subscribe now." Two and a half minutes into a 14-day trial.

Back to the setup guide. Task group one: "Make your CRM switch with confidence." I click. "See how your previous setup maps to Pipedrive." A dropdown: HubSpot, Zendesk, Salesforce, Zoho, monday.com, Freshworks.

I pick one, and get… a help article in a new tab: "How is Pipedrive data organized?" Task marked done.

It already asked "Have you used a CRM before?" at sign-up. I said yes. Three and a half minutes in: zero deals, zero contacts.

Each one puts a deal in the pipeline before the to-do list.

🧪 Start with sample deals

Make "Try with sample data" the default, with deals that fit the industry I picked, and let me clear them later. Shopify put "pre-generated things based on what we know about you" into the real editor, and saw the payoff in merchants selling (Archie Abrams, Lenny's Podcast).

📥 One task, from my goal

I said customer communication. Make connecting Gmail the first and only task, then show me the deals it finds in my inbox. "Driving all attention into one seeded task for guided completion" is one of the answers in Lenny's activation survey (Lenny's Newsletter).

🔁 Import, don't link

When I pick my old CRM, start the import, or offer a call. Jeff Weinstein: "Turn those moments during your self-serve process into not self-serve" (Lenny's Podcast).

The goal: a first deal in the pipeline within five minutes.

Pipedrive gets the hard parts right: a fast sign-up, no card, a clear price. The leak is what comes after: a pipeline tailored to my industry with nothing in it, and a to-do list instead of a deal.

The whole journey, from my recording:

• 0:00 · "Try it free" · ✅ No card
• 0:15 · 6-digit code by email
• 0:38 · About you, company, goals · ❌ Goals never used
• 1:39 · Pipeline "Tailored for your industry" · ❌ No deals
• 2:00 · "You've now covered the basics"
• 2:06 · Setup guide: 1/11 tasks
• 2:33 · Billing: "skip the remaining trial period?"
• 3:13 · "Switch with confidence" · ❌ A help article

The fix: Put one deal in the pipeline before anything else: sample deals by default, then my own from Gmail.

The six lessons

• No card, and let any email in · ✅
• A full pipeline behind the form · ✅
• Ask for my goals, then use them · ❌
• "Tailored" should mean deals, not column names · ❌
• A tour of empty screens isn't onboarding · ❌
• When I say I'm switching, that's the product · ❌

A CRM has a hard job in a trial: most people who try one already have something. Pipedrive's own question, "Have you used a CRM before?", says so. Karri Saarinen, Linear's CEO, put it plainly for any tool like that: "The tool eventually replaces their other solution, which means there isn't a real activation until that happens." (Lenny's Newsletter).

By that measure, my three and a half minutes got me nowhere near activation. Not because Pipedrive was slow, it wasn't, but because nothing I own ever made it inside.

If you run a trial for a product people switch to: find the first moment they see their own data in it. Then take everything else out of the way.

What's the first thing a new user sees in your product: their data, sample data, or an empty screen? Leave a comment. I read every one.

Further reading:

1. Lightfield's CRM trial teardown, the previous teardown, about a CRM that asks for the card before the inbox
2. How to accelerate growth by focusing on the features you already have, Ken Rudin in Lenny's Newsletter
3. What is a good activation rate, Lenny Rachitsky and Yuriy Timen

I break down real free trials and show where they lose paying users. If this helped, send it to someone who owns a trial.

Want a teardown of your trial? DM me "teardown" on LinkedIn.

Eddy