Boost sales pipeline with the free to paid conversion playbook

A template to launch your free-to-paid conversion playbook. This playbook prioritizes free accounts or users, based on ICP-fit and conversion likelihood.

Alexa Grabell
Alexa Grabell
Co-Founder & CEO at Pocus
Playbook Overview

When should you run this playbook?

Once your self-serve flywheel is up and you're looking to turn those users into qualified pipeline for sales.

Who to target?

New freemium or free trial users 

Playbook goal?

Convert free users into paying customers.

Responsible team(s)?

SDR or Sales-Assist/Product Specialist.

  • Consider a free to paid conversion playbook when you have tons of free users on your product but account penetration is low.
  • Your sales team should triage high ICP-fit leads for high touch follow ups as their top priority. Use a combination of product usage (what they did in the product) and ICP fit (who they are/who their company is) to align when to reach out and how.
  • This playbook helps you bring forward revenue from high-potential customers by engaging with them early and providing additional support on the free tier.

The PLG monetization journey usually looks like this:

Stage 1: Get lots of users on the product via a self-serve free trial or freemium model.

Stage 2: Track feedback, requests, and interactions with your product to guide your roadmap, your ideal customer profile, and ensure product-market fit.

Stage 3: Start to prioritize revenue growth. 

At this stage, if not earlier, most PLG orgs add sales to the mix — product virality can only get you so far. It’s time to scale revenue by optimizing self-serve conversions, with a human touch.

Enter stage 4: Layer in Product-Led Sales playbooks like sales-assist and free-to-paid conversion, so that your GTM team can fill the gaps the product can’t, ensuring your best-fit sign-ups get to value and convert into paying customers!

Today, we’re focusing on the free-to-paid conversion playbook. This playbook helps you generate more qualified pipeline for the sales team, improve their efficiency, and accelerate conversions, aka more ARR in the bank. The challenge? Identifying opportunities that are ready for sales, so your team spends time on leads that need a human touch. Companies just starting their PLS motion will often put sales resources on every self-serve sign-up, potentially creating a lot of unnecessary friction for users. The goal of a free-to-paid conversion playbook is to pinpoint users or accounts ready for sales based on their product usage and other intent signals like firmographics.

What is a free-to-paid conversion playbook?

Free to paid conversion is one of the most popular playbooks for Product-Led Sales beginners, especially those struggling to monetize their free user base. The goal of a free-to-paid conversion playbook is to turn free users of your product into paying customers. This conversion playbook identifies customers that might need a human touch to accelerate their conversion. This playbook fills your sales team’s funnel with qualified leads that have strong intent signals like high product usage and strong ICP-fit.

Marketing, growth, and product teams have their role to play in free to paid conversion, but this playbook focuses on the incremental value of a sales team (aka human touch). The point is to insert human touch points at just the right moments — which, in this case, tend to be activation milestones or other product usage signal that mean the account is ripe for conversion.

bottom-up product-led sales motion: sign-ups, PQLs/PQAs, opportunity, closed won

Like all PLS Playbooks, free-to-paid conversion can look different depending on your product, market, and ideal customers. However, the goal of this playbook isn’t to reach out to every free user with better-than-average product usage. Your sales team should triage high ICP-fit leads for high touch follow ups as their top priority. Use a combination of product usage (what they did in the product) and ICP fit (who they are/who their company is) to align when to reach out and how

For example ,you might want to focus on high ICP-fit sign-ups that aren’t showing signs of activation within the first 7 days on your product, so you can get them to value, before they drop-off.

All reps running PLS Playbooks should be mindful of helping, before selling. By digging into product usage data as the first point of discovery, reps can tailor their outreach according to user behavior on the product— recommending additional use-cases, highlighting relevant features, and of course, outlining the benefits of upgrading.

Here are some example of how sales can add incremental value at this stage of the customer journey: 

  • Offer help choosing the best plan them when they hit a paywall
  • Give some technical support to deepen their product usage and increase the value they are getting
  • Get alerted when a decision-maker signs up to offer white-glove onboarding and support

Pro tip: Do a regression analysis of usage and other factors like, industry and job function, of your best customers and how they got there. For free-to-paid conversion target similar users who are a step, or two, behind those.

When should you run a free-to-paid conversion playbook?

The best time to launch this playbook is once your self-serve flywheel is up and you're looking to turn those users into qualified pipeline for sales.

However, your data infrastructure and sales workflow need to be ready. In order to run free-to-paid conversion playbooks, GTM teams should be able to create PQL/PQA scores combining ICP-fit (firmographic data like, industry, deal size, and job function) with usage data (signals like milestones reached, invites sent, and feature usage.) 

Playbook complexity model: product-led sales beginner, intermediate, advanced

To get your PLS plumbing up to the task, you’ve got three options:

#1 Custom build: Data teams build custom data models and dashboards for go-to-market teams.

Primary challenge: Slow feedback loops. Having a data team build dashboards is great, but getting on their backlog isn’t always easy. Go-to-market teams constantly evolve and need new data, but they can’t immediately access a data engineer’s time. 

#2 Pipe data into CRM: RevOps teams pipe product usage data from the data warehouse into the CRM. 

Primary challenge: Not seeing the full picture. You'll miss insights if you try to push your product usage data into Salesforce’s prescribed model. Salesforce is built for point-in-time data and makes it difficult to see data trends across a time horizon. Because of the rigid data model, you won’t have the same level of granularity as the data warehouse, just aggregations.

#3 And option three… Engage with a vendor (hint, hint: it’s us) that can set you up with a single source of truth for customer and usage data, enabling your go-to-market team to surface and action the best opportunities in seconds.

Primary challenge: You’ll need budget approval — and for that, you have to make a case internally. Luckily, we’ve got a few tips (and a template) on getting buy-in for your PLS motion.


Playbook overview: Grammarly example

Let's take a look at the free-to-paid conversion playbook with a real life example. Grammarly has simple packaging and pricing, with clear differentiation between tiers. Teams looking to collaborate on writing assignments fall into the Business tier, while users who need more advanced features like full-sentence re-writes would benefit from the Premium tier.

The virality Grammarly has achieved through their freemium model means they have tons of potential paying customers already on their product, so free-to-paid conversion playbooks are an opportunity to generate qualified pipeline from their existing base of users.

Grammarly pricing page - opportunities for product-led sales playbooks

Here are two free-to-paid conversion playbooks they could run:

#1 Target account conversions: Reach out to new users (from target account companies) within the first 14 days to provide support and white-glove onboarding to speed up sales cycle.

#2 Freemium conversions: Surface long-time loyal users who haven't yet made the upgrade and convert into paying customers.

Playbook 1: Target account conversions

With thousands of users signing up daily, Grammarly needs a quick way to spot high-priority leads for a more personalized experience. AEs should start engaging target account sign-ups early (within the first 14 days) to make sure the user gets to value and understands the benefits of the higher tiered plans, for themselves and their team.

  • Target: ICP-fit sign-ups in the past 14 days
  • Goal: Convert to paid customer
  • Team responsible: Account Executives

Why deploy this playbook?

Accelerate conversions from target accounts. Bring forward revenue from high-potential customers by engaging with them early and providing additional support on the free tier.

PQL signals

  • Active usage > 4 days
  • Frequent feature use: tone detection
  • Domain = target account

Recommended actions

High touch: Since this playbook is surfacing target account sign-ups, personalized outreach is the best action. Reps should craft messaging around helpful tips to better leverage tone detection and highlight the benefits of re-writing full sentences according to your desired tone — a feature available by upgrading to the Premium plan.

Playbook 2: Freemium conversions

Since Grammarly offers frictionless access to their product via a freemium tier (free forever), they have massive volume of sign-ups. This amount of users makes it challenging to know which of those are likely to convert into paying customers, but it's also a huge opportunity to dig into usage data (the best intent signal) to uncover high-potential leads.

  • Target: Active freemium users
  • Goal: Convert to paid customer
  • Team responsible: SDR or Sales-Assist/Product Specialist (depends on the company)

Why deploy this playbook?

Do more with less - Optimize monetization by helping loyal free users get more value, while incentivizing them to try the Premium plan.

Focus reps’ effort - Instead of flying blind chasing after every free user, effectively deploy SDRs to target only the customers who are likely to convert.

PQL signals

  • Weekly active user
  • 20% higher rate of words analyzed than the average in freemium plan  
  • ICP-fit: potential for expansion to larger ACV 

Recommended action

Low touch: Automated email sequence rewarding high usage and highlighting the value-add of Premium plan — tailored recommendations according to tone, full-sentence re-writes, and the potential to bring on the rest of your team. Include plenty of CTAs to get them back on the product! 

Free-to-paid conversion playbook template 

Step 1: Define your sales goal for free-to-paid conversion

free to paid conversion inbox - Pocus

To set up a free-to-paid conversion playbook in Pocus, first create a goal for your playbook. In this case the goal should be to go from free to paid. 

In Pocus, you can have multiple playbooks aligned to each goal. Create multiple playbooks based on different triggers and measure their performance towards your goal.

‍Step 2: Define the segment of users to target

Pocus playbook set-up: goal and segment

In this case, we’re including all free accounts from companies with over 500 employees. We’ve set up the goal at the account level, but we’ll create specific playbooks for individual users, accounts, and teams.

Pocus playbooks

‍Step 3: Set up your playbooks

Once you’ve got your goal and desired outcome you’re ready to define your playbooks.

Accelerate new user conversion: active usage, excellent customer fit (target account domain), signed up in the last 14 days.

Convert high potential accounts: good or excellent product engagement, good or excellent customer fit, are nearing a paywall.

Pocus playbook - free-to-paid conversion

Convert teams with use-case incentives: active use of X and Y feature  —  since we know customers who use X and Y together, also tend to get value from Z in our paid plan. 

Pocus playbook - free to paid conversion

This is just a start, you can keep experimenting by creating more playbooks with different triggers and actions. Track performance and iterate as you learn. 

Step 4: Define next actions for reps

  • Accelerate new user conversion: personalized outreach providing white-glove onboarding, support, and education on upgrade benefits. 
  • Convert high potential accounts: personalized outreach with upgrade incentives and paywall call-out.
  • Convert teams with use-case incentives: automated sequence with feature education about how best to use X and Y. 
from insights to action - Product-Led Sales playbook Pocus

Sales leaders can leave a detailed description for reps, so they know exactly what to do with the qualified leads in their free-to-paid conversion Inbox. This way you can create a repeatable process for all team members — and fast-track sales training of new hires.

Then, select what metrics your reps need to see in their PQL alerts. Choose the ones that will help reps in their outreach efforts, as well as prioritize the highest potential opportunities.

‍Step 5: Arm reps with highest priority PQAs and product usage data 

Pocus drilldown view - user level - playbook set up

Surface PQLs to your reps according to their workflow. 

Inbox: Your reps can check in to their Pocus inbox every day to see a prioritized list of opportunities organized by playbook. 

Slack alerts: Your reps can get instant alerts each time a new PQL is surfaced.

Push data to CRM:  Ensure that any updates in the customer lifecycle are automatically synced to CRMs like Salesforce, HubSpot, or anywhere else your reps are looking.

Pocus Inbox - 360 degree view into users, teams, workspaces, and accounts,

Now, all they have to do is their favorite part of the job: sell to customers who are genuinely excited about the product.

Power up your self-serve pipeline with Pocus

Ready to fill  your pipeline with qualified opportunities? 

First: Define your PQLs: usage signals, firmographic data, outreach triggers.
Surface high-potential opportunities from your existing base of free users.
Craft personalized messaging or automated sequences to help them get more value, while providing incentives to upgrade.
Measure results, iterate.
Fifth: Rinse and repeat!

About the Author

Alexa Grabell is Co-Founder and CEO of Pocus, the Revenue Data Platform built for go-to-market.

What our customer say...

I can log into Pocus and see a holistic picture of our users and insights about their product usage with a few clicks. It’s a game-changer having access to data that was previously locked in the data warehouse. 

Casey Bertenthal

Head of Sales

50% percent of our incremental sales revenue comes from our PQL leads. With Pocus, we’ve been able to reliably uncover high priority sign ups faster. These sales-assist leads convert 10% higher with a 32% higher ACV  because our team is able to reach out at the right time.

Giancarlo Gialle

Head of Sales and Success, OpenPhone

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