Enterprise deals are a different beast. They’re more complex, require more people involved, take more time to come to fruition, and can be very volatile. 

On the flip side, they’re home runs that can skyrocket your business to new heights. 

The ultimate expression of Product-Led Sales (PLS) done right is when you can close enterprise deals from initial bottom-up product adoption. 

As exciting as it can sound to have self-serve adoption turn into huge deals, it’s not an easy process to master. 

Lucky for you, Riley, Harbour, Head of Business Development at Grammarly, shared with us the sales playbook that Grammarly’s product-led sales team follows to close enterprise customers who start using their product for free. 

Take out your notebooks, this is a good one! 📓 Now from Riley himself… 

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Before I get started, let’s address one caveat 👇

You can’t rely on a bottom-up motion for enterprise sales

Atlassian or Shopify won’t hop on your enterprise plan without talking to your sales team. 

Not going to happen. 

Chances are, even their usage of your free plan might become limited from a scale perceptive due to security or compliance requirements. 

Even if end-users adopt your product for free initially, they will need to go through managerial loops and approval processes if they want to dive deeper into your product’s value. 

Therefore, you need a strategy for capturing enterprise adoption! 

Our enterprise sales process has 3 components: 

➕ Identifying accounts that qualify for enterprise expansion

➕ Running our enterprise playbook 

➕ How other functions support the playbook’s execution

The meat of this sales playbook will be to break down our enterprise playbook. In other words: how we go from identifying opportunities to closing them. 

🔍 How Grammarly’s sales team identifies expansion opportunities

Weekly meeting between SDR and AE. 

Every week, our SDRs and AEs on the enterprise team meet to review new opportunities that have been flagged by our system as qualified for enterprise expansion.. 

Which accounts qualify for enterprise deals? 

Our tool is used by such a wide range of people that it’s important for us to prioritize efficiently. 

First, we look at product usage. 

We stack rank based on free users, premium users, and weekly active users within a given account, as well as recent sign-ups within the last 30 days. We monitor trends, such as increases or decreases in active users, over time. 

We combine all of this data to create our product-qualfiied account (PQA) score – a key part of our GTM strategy.

Second, we look at whether or not the account’s firmographics match our enterprise criteria, meaning that the account either has a revenue potential over $X of annual revenue or the employee count is greater than 5,000.

More on PQLs and PQAs at Grammarly in this article. 

Once reps find a qualified account, they get to work! 

Here’s the PQA enterprise expansion playbook we run ⤵️

📋 Grammarly’s enterprise expansion playbook 

TLDR?

Our team focused on 2 things throughout the Product-Led Sales process:

😍 Making users more successful 

🤝 Expanding accounts into enterprise customers  

The sales cycle has 4 phases: 

1 - Understanding end-user value

2 - Understanding management value and priorities 

3 - Crafting a case for business-wide value

4 - Getting to executives and closing the deal 

Let’s explore HOW we execute each step ⤵️

Phase 1: Understand end-user value 

Marketing fires sequences to end-users. 

The intention here is to support users through their journey and gather data about the value that they’re getting from Grammarly. This data is paramount to back up claims made to decision-makers down the line. 

Examples of what our marketing campaigns gather from end-users: 

• Direct ROI: “I’m saving 5 hours a week”
• Before and after: “My articles readability has increased from basic to expert in a few days”
• UX: “Grammarly is so much easier to use than other alternatives” 
• Big swings: “I avoided a huge mistake in an email last week because of Grammarly”

To pull this off efficiently, our marketing team leverages product usage data to send hyper-personalized marketing emails. 

For example: 

Sending an email based on product triggers rather than generic time-based triggers.

The chances of your email resonating with users are slim if you send everyone a one-size-fits-all campaign. Our sales teams fire emails right after users hit specific milestones in Grammarly. 

Utilizing product usage to make emails contextual and personalized 

Every week, we send our users a written update with a summary of their progress and contextual tips and best practices. This helps maintain user success. 

Reps research the account’s product usage

BDRs do not reach out to end-users because of the sheer volume of Grammarly’s user base. The financials of involving our reps too early simply don’t make sense. 

We’ve found that the best way to understand user value is to research how they’ve been using the product. Reps leverage product usage dashboards similar to the one shown below in Calixa, where it’s easy to find which features are utilized, and by whom. 

Phase 2: Understand management-level value

BDRs go after directors and managers 

While our marketing nurtures end-users and gathers the value end users achieve as well as ROI statements, BDRs start reaching out to managers. 

The relevancy of BDR emails and sales calls comes from product usage. Not only does product data make outbound messages super personalized and timely, but it also raises trust with prospects.  

It validates that we’ve done our homework and are experts on their business then proving why we believe that we can provide value. 

📨 Sales angles reps can take to make outbound relevant to prospects ⤵️ 

More examples here 👈

Email templates for enterprise sellers here 👈

Hand-off to AEs 

Once a few conversations with prospects are underway and end-users have provided feedback, BDRs gather the value that managers are getting from Grammarly as well as their objectives with the tool. 

Then, they pass that information to our AEs. 

These findings are added to the account notes in the CRM and discussed during weekly meetings.

AEs reach out and meet with managers before they pitch executives. 

Mainly to understand: 

• What do executives care about? 
• Who needs to be involved in the decision-making process?
• Who are the gatekeepers to enterprise adoption? (Security, compliance, legal, IT). 
• What type of pitch resonates more? ROI or loss aversion, or both? (more on this below). 

Reaching out to users, non-users or both 

90% of my team's outreach is to current Grammarly users (all management levels). 

We surface managers, directors, and VPs that are end users to our GTM teams as PQLs and high-priority contacts for outreach. 

Note that Grammarly can deliver value to pretty much everyone within an organization, so we benefit from having a high % of adoption throughout all management and non-management levels.

If that’s not the case for your product, you can still leverage what users are doing in your product to make cold outreach to non-users contextual and relevant.  

Here’s an example from Calixa’s named account signup GTM Play ⤵️

Phase 3: Build a case for business-wide value 

Executives’ goals are always tied to business goals. So Phase 3 is all about taking insights from Phase 1 and Phase 2 and making hypotheses about how Grammarly can help the organization as a whole. 

Tying end-user value to business value is one of the crucial requirements in the buying process of PLG companies in 2023. 

To do so, our AEs analyze overall product adoption across teams and pick a sales angle to use in their pitch.  

Depending on the context and data at hand, they can anchor their business case on: 

📈 ROI 

--> The value that the prospect can gain from upgrading to Grammarly’s enterprise plan.

📉 Loss aversion 

--> The cost of not upgrading to Grammarly’s enterprise plan. 

🎯 Both. 

What does the actual business case look like? 

A business case is a story, backed by facts. It can take many forms, such as presentations, infographics, what reps pitch during demos, proposals, emails, etc. 

Here’s an example ⤵️

👎 Identified problem

👍 Our provable solution

Back your business case with data

You have a business case. Great! It won’t fly if you can’t back it up with quantifiable proof. 

Execs are busy. They follow data, not opinions. If you want their attention, you better be able to back your claims. That’s why proving ROI or loss aversion is so important. 

Here’s how we do it: 

📈 ROI: Leverage product data to quantify ROI

We're able to basically aggregate all of the words typed across the entire account, as well as the suggestions that have been accepted. Based on the % of suggestions accepted by a prospect’s team from Grammarly, we can work that back to time savings. 

So we'll actually be able to say: “Hey, just from using Grammarly free, your team's saving 23 minutes per day on average”.

📉 Loss aversion

 You can pitch ROI all day, but in tough economic times, what’s the cost of not doing anything?

Our team at Grammarly worked with a research firm to calculate the real cost of NOT improving your writing communication. 

Turns out that bad writing is costing your employer a chunk of cash! 

Furthermore, if your business is struggling, you want your sales teams to spend less time writing and more time they’re spending with customers! 

Grammarly has the data to back it up 👇

Phase 4: Getting to executives & closing the deal

By this phase in our playbook, account executives have: 

✅ Full understanding of the account’s product usage and goals with Grammarly

✅ A compelling sales narrative to present to executives

✅ Data to back up their claims and be credible to decision-makers

Now, how do you get in front of the right executive, cold? 

Traditional sales techniques apply here. I won’t go into details. 

It’s worth noting, however, that product data heavily support how our reps execute PLS deals.

💻 How we use end-user insights & product data to curate demos

Because we have the bottom-up context and we understand the value of Grammarly business for multiple stakeholders, we're able to thread that through our sales activities like demos. 

For example, if accounts tell our sales reps that they're on G Suite and they use HubSpot, we show HubSpot marketing integrated into Grammarly.

Similarly, if we know that they’ve been using a specific functionality like plagiarism detection, sales reps lead demos with a use case that leverages it. 

Sales leaders: there’s one other non-intuitive technique that’s super effective when nurturing an enterprise account that’s already using your product. 

ABM. 

How ABM supports our sales process

Every week, our reps submit a list of accounts to marketing for ABM. Once an account is in an enterprise ABM campaign, decision-makers will start seeing more of Grammarly’s ads and content.  

It raises buyer awareness throughout the sales cycle and improves our chances of initiating conversations and closing deals.  

I believe that over is the time when marketing’s responsibilities end at passing leads to sales. In PLG, marketing supports the whole customer journey.

This sums up our enterprise sales playbook. Here’s a visual summary👇. Feel free to download the PDF and share it with your team. 

Enterprise sellers, I hope I’ve laid out a good framework for you to get started on driving enterprise expansion and become successful with Product-Led enterprise sales. 

Spoiler alert: There's no finish line. Product-Led enterprise sales is a very iterative process, but following a sales playbook like this one has been proven to generate great results. 

Follow sales processes like this one and you’ll see more deals, larger deals, improved deal velocity, and an ability to create opportunities with large enterprises. 

If you want more from me, read 5 questions to fine-tune your sales motion and connect with me on LinkedIn.