🔥 How Grammarly closes enterprise deals

With real examples and templates from their team.

May 6, 2023

Zoom, KPGM, Caterpillar and Netflix all have one thing in common: they won’t hop on your enterprise plan without talking to your team.

You need a process for enterprise expansion. I have one for you ;)

Here’s what you missed in PLG in the last 2 weeks👇

🚀 How Grammarly turns users into enterprise deals

🦉 How Hootsuite transitioned from sales-led to product-led

😒 Prospects think your sales content is useless

🏈 Play of the week: Usage spike

Scroll to the end for 🎁 Cheat sheets & templates, 📊 New data, 🎧 Podcasts, 📺 Videos and 🔥 Hot conversations.

🚀 How Grammarly turns users into enterprise deals

You might think of Grammarly as a tool for individuals. Yes, but they also have great success with Fortune 500 companies. Riley Harbour (Grammarly’s Head of BD) spilled the beans on their strategy (download their playbook infographic).

Source: Calixa.io

Before running the play: they identify enterprise opportunities by looking at usage patterns and filtering by firmographics (details here).

Phase 1 is understanding user value: Marketing fires campaigns based on product usage with the goal of gathering insights from end users and fostering adoption.

At the same time, BDRs start researching how the account has been leveraging the product.

Phase 2 is understanding management’s objectives with Grammarly: While marketing nurtures end-users and gathers insights, BDRs start reaching out to managers.

“Our curated BDR outreach comes from leveraging product usage signals. Not only does it make outbound messages super personalized and timely, but it also builds trust with prospects.

It validates that we’re experts on their business - we’ve done our homework, understand their pains and challenges and how we can provide real value.” (Read the blog for email templates).”

Phase 3 is building a business case.

2 choices:

📈ROI claim: “Based on an account’s usage of Grammarly, we can calculate time savings and extrapolate through an expansion proposal.”

📉Loss aversion: “We’ve worked with a research firm to calculate the cost of not implementing Grammarly. It creates urgency for prospects.”

At phase 4, AEs pitch executives: traditional sales execution applies here. One thing to note at this phase is that our reps can also submit lists of accounts to be supported by ABM. That’s been key to raising executive awareness and earning the right to pitch.

🦉 How Hootsuite transitioned from sales-led to product-led

A successful transition from a sales-led focused business to product-led isn’t easy. One success story is Hootsuite. Kyle Poyar broke down the details of their shift ⬇️

Source: Growth Unhinged

1. Focus on improving your PLG motion in the same sequence as your customer’s journey.

Setup moment: The user has performed necessary actions to set up the core value proposition.
Aha moment: The user has experienced the core value proposition for the first time.
Habit moment: The user has established habits around the core value proposition.

2. Experiment against your conversion funnel for KPIs like:

F:P (Free to Paid);
T:P (Trial to Paid); and
Paywall Conversion (in-app expansion).

💳 Credit card-gated trial won at Hootsuite

3. Segment your Product-Led Sales motions

Self-serve-always customers. Bought through self-serve and wanted to continue using self-serve. Could range from our lowest-priced plan up to “enterprise” ACVs.
Product-qualified leads (PQLs): Hit a certain set of product usage metrics and would be a fit for a self-serve paid trial or a sales-assist motion.
Product-qualified accounts (PQAs). Self-serve customers that meet criteria to be reached out by sales and helped through a sales-assist motion.
Demos. Pretty simply, prospects that asked for a demo first on our website, get directly routed to sales.

4. Build the right organizational structure to support PLG.

Build a “PLG army” in your organization and find the right change agents to transition your company.

5. Bring in the right PLG tooling.

“There’s an app for that” they say and usually, they’re right. Here are 3 resources to help you through the PLG tooling process:

Should you build or buy?

What is a Product-Led Sales platform? How to pick one.

😒 Prospects think your sales content is useless

Alarming new data from Gong. 91% of prospects think that what you send them isn’t personalized or relevant to them. More data and a few suggestions below ⤵

Source: Gong labs

🕜 Sales reps customize 58% of all outgoing content, and spend up to 12 hours each week personalizing these messages by customizing pre-defined templates or manually creating outreach from scratch.

🤖 78% indicate they would like tools to personalize outreach for each prospect and organization using generative AI.

✅ 2 solutions to speed up outbound and make it personalized:

Leveraging product data. 9 examples here.
Using generative AI to summarize account context.

🏈 Play of the week: Usage Spike

Great sales execution comes from adjusting to what’s happening with your account in the product. That’s why we’ve introduced PLG Sales Plays. This week, we highlight what sales need to do when they see a qualified account with a usage spike ⤵

Source: Calixa Plays

💡 Product trigger

Target account’s usage grows > 50% month over month

🔺 Context

A qualified account is showing great momentum in your product. Openness to sales outreach will be high. Engage active users to understand how the spike can be tied to a business goal.

⚡ Actions to take/Tasks

Research the account. Are there any external trends that can explain the spike?
Review the account’s product usage.
Add the most active users to a sequence.
Identify a decision-maker and add him/her to a sequence.

🗯️ Recommended message

Offer an upgraded plan with a lower unit cost and more predictable billing.

✉️ Email template

Subject line: User Growth in [Your Company Name or Product]

Email copy:

[FirstName], I see that [User Growth].

Considering [Product Usage Context], you can [Added Value of Paid Plan] with our [Paid Plan or Paid Plan feature]. We’ve seen that outcome with [Customer 1] and [Customer 2].

I have the green light to give you discounted seats if that’s top of mind for you.

[Interest-based CTA]?

[Sales rep’s signature]

🎁 Cheat sheets & templates

Grammarly’s enterprise playbook
7 questions to ask before writing content
How to write good email subject lines
A framework for building trust within your organization

📊 New Data

Take 3 min to answer the Product-Led survey
Gong’s State of Sales Engagement
2023 State of Product Onboarding

🎧 and 📺

(📺) Save this for the next time you have to explain PLG
(📺) Growth won’t fix your problems
(🎧) The active content repurposing process
(🎧) How to achieve hypergrowth in your business and career

🔥 Hot conversations

5 pivotal shifts in Appcues’ 10-year PLG motion
Humans should be amplified by AI, not replaced.
Speed-to-lead is real and it’s hurting your pipeline.
Benefits of LinkedIn for B2B executives.

📅 Upcoming PLG events

The only event for product-led GTM (I’ll be there)