What was the problem/opportunity?

Our original platform only captured meeting recordings & provided post-conversation transcription/insight.

It was reactionary and mainly helpful to data-hungry sales leaders, not the sales reps running the meetings.

The platform was rough, but got us by in the early days (2020).

However, with the ever-expanding conversation intelligence space, we needed an edge to compete & differentiate.

Pickle became the first service to evolve our point of view from providing big data for revenue leaders, to being the meeting champion of the full-cycle Account Executive.

Our product roadmap changed with it. Prioritizing AE proactivity before, during & after meetings as much as conversation analysis across the team for sales leaders.

Enter Pickle’s AI Smart Notes for Zoom — One of the first in-meeting notetakers built to provide pre-meeting context & capture the important moments inside the Zoom app itself.

Zoom Meeting Notetaker App:

Post-Meeting Recording & Highlights:

This was our push into the free trial product-led growth model & a huge advancement in our positioning, integration capabilities, and pricing structure.

Here’s how I approached the product launch:

Who were we talking to?

After interviewing current & past customers, ideal prospects, past opportunities who didn’t buy from us, and our internal team; I built out these persona profiles:

User - B2B Remote SMB Account Executive

Decision Maker - B2B Hybrid SMB Sales Leader

How did I tell the story?

Here’s my typical storytelling framework for the internal team. It also guided messaging for external assets:

What teams were involved?

I worked with the product team to design the onboarding campaigns, with the engineering team to create seamless access to the platform & feature gates, and with the sales team to spread the word.

How was success measured?

Our north star was current customer conversions, new user trial sign-ups, and paid user conversions.

We tracked these KPIs via Intercom, Google Analytics, the Zoom Marketplace, and Stripe.

What was the outcome?

100% of our current customers converted after a month-long campaign push consisting of emails, in-app chats & webinar onboarding sessions.

We had 766 new user trials start and ~7% of those converted to paid plans.

What was the strategy/distribution plan?

Here is the rough PLG trial journey I sketched out initially:

Here's how that sketch came to life. I always plan from the bottom of the funnel & work up:

Customer Activation Strategy

We created automated onboarding sequences for new users and existing customers who downloaded the Zoom app.

Our goal was to encourage daily active log-ins with multiple touchpoints across their trial experience.

Each message contained explainer text & GIFs. Educating users on specific features and how they would benefit most.

We determined a few ‘aha’ moments in the platform that if users leveraged, they were 2x as likely to convert to a paid license or bring on their whole team. We prioritized those messages.

Here’s an example of one of the automated messages:

For power users, we launched an extensive helpdesk to dive deeper into feature sets and deliver even more value. This could be accessed in every email & in the app itself.

Bottom Funnel Strategy

The two channels you could start your free trial with were our website & Zoom App Marketplace listing.

Our Website

I created a conversion-focused hero section of the homepage that, in one scroll, connects:

• Tangible pain (can’t afford bad meetings)

• Trust (real user reviews)

• A visual explanation (clickable GIF that takes you to an interactive demo)

Here’s the interactive demo GIF, teasing the product & us drawing you to click the button:

I made the CTA buttons straightforward housing a Typeform popup with a simple, yet informative journey/flow for the user and our internal team.

Our pricing page explains the offering in more depth with each CTA button leading back to the same Typeform popup.

Used Google Tags to track which buttons were being clicked to access the form.

Zoom App Marketplace Profile

Here’s our Zoom Marketplace profile listing. We had a surprising amount of organic trials starting from random people clicking through this page. It was hard to control for ICP, but the bad fits would usually drop out pretty quickly.

After completing either form, you were funneled into our in-app account creation page. You could sign up with Google SSO or manually.

Once signed in, your free account displays an “Upgrade” tag & the in-app onboarding automation begins.

Mid Funnel Strategy

To capture organic demand further along in their awareness journey, I created some landing pages and blogs.

All were based on higher-intent keywords like ‘zoom call transcription software’, ‘automated meeting summaries’, ‘meeting notetaking software’, etc.

Top Funnel Strategy

Our mailing lists, LinkedIn, and outbound campaigns were the main demand generation channels.

I put together this launch video as a core asset with the help of some freelance designers.

We published multiple LinkedIn posts a week geared toward buyers in different journey stages. Each one is linked back to the website or Zoom App Marketplace profile.

I'm sure you're dying to know what that clip is. See the LinkedIn post here🔺

We had a large mailing list built from our Zoom app waitlist, past opportunities, and our newsletter. Giving us a solid owned audience to get in front of.

Here is one of the emails we sent out:

Also worked with our sales team to create Peer Prospecting campaigns that connected with fellow ICP Account Executives.

The goal was to talk about how it’s helped our team become better sellers & have the prospect start a free trial themselves.