Starting his career in Product-Led Sales as an early employee at a growing PLG Company, Grammarly’s Head of Business Development, Riley Harbour, knows a thing or two about driving high-performing product-led growth strategies. In this blog, he shares five questions to help others fine-tune their own selling motions.

Moving careers from GoSite to Grammarly, the contrast between markets, install bases, and product intent signals couldn’t be starker. While their ticket sizes may differ, both experiences taught me valuable opportunities and skills for strengthening the Product-Led Sales (PLS) motion. If you’re a leader looking for new ways to refine (or simply define) your PLS strategy, here are five questions to get you started.

How are you measuring value for your ideal customer?

Defining your ideal customer profile (ICP)—who they are, what they do, where they work, etc.—is key to helping your reps prioritize their outreach and hit sales targets. When building this profile, make sure you can measure (and substantiate!) the value you deliver to these customers. For example, two of our ICPs for Grammarly Business are customer experience and marketing leaders, and we’ve nailed down the value that our AI-enhanced communication assistance provides to these two distinct functions. 

These ICPs are successful because we can tie our value directly to their revenue attribution, connecting the likes of decreased ticket resolution times to better customer experiences and improved efficiency. Compared to, say, sales, this line to revenue attribution becomes less direct. While Grammarly certainly helps sales teams mitigate risks, it’s challenging to definitively say it’ll help them increase win rates by X percent.

Does your GTM strategy include product qualified leads and product qualified accounts?

There isn’t a one-size-fits-all solution for product qualified leads (PQL), and it varies across different spaces. At GoSite, high product usage was a key indicator, with us reaching out mostly to power users. At Grammarly, our top indicator is the use of a business domain. If someone logs in with a business email, it’s a high indication they’re using Grammarly in their day-to-day work. Here, we’re looking for weekly active users on a business domain who’ve accepted a Grammarly suggestion within a given time period. 

That said, I’d say our biggest indicators are product qualified accounts, which we use to aggregate users within a certain company or account that’s ready for sales assist or outreach. 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 before layering in firmographic data at the end. This includes information such as whether an account is commercial, enterprise, or a key sales target. We combine all of this data to create our product-led account score, and it’s a key part of our GTM strategy.

What hidden intent signals or opportunities are you overlooking?

While a business domain is our top signal, we’ve also found that a strong giveaway is finding power users who self-identify in the product. These are folks who log in using a free domain, such as Gmail or Yahoo, but self-identify during the onboarding flow. We ask them what they’re using Grammarly for, and if it’s for work, we ask for their company name, department, and seniority level. We can then connect with them on LinkedIn, reach out over email, and consolidate users within an enterprise account.

Another opportunity we focus on is collecting stories and feedback from different power users. Because Grammarly serves both the enterprise and the consumer, we must be careful not to mix signals. Many power users don’t hold influence at the enterprise, which means they’re not ideal folks for sales reps to reach out. Instead, we collect stories to form a narrative around why a specific team, pod, or department is using our product, which we leverage with the decision-maker. This might be a director, VP, or IT leader who hasn’t used Grammarly but is willing to buy it on behalf of the 200 people who love and use our product every day.

Do people have enough time to reach their a-ha! moment?

Giving people the freedom to unlock the a-ha! moment in the product on their own is the magic of any PLS motion. But knowing this doesn’t mean that sales reps aren’t tempted to reach into the cookie jar for leads that aren’t quite ready—especially when booking numbers and quotas start to get tight. This will only make the PLS motion more challenging. Not to mention, sales reps who come in too early can quickly lose a deal or turn it from a consultative sale to a hard close. 

You also want to ensure your sales team doesn’t come in over the top, make empty promises, or sell value that simply isn’t there yet. Think about your overarching PLG strategy as a combination lock between product, marketing, and sales. Your product should deliver the story your marketing team is telling, which should match what sales is providing in the PLG atmosphere. If one of these components is off-kilter, it will lead to a clunky user experience.

Where can you augment product insight with human insight?

While product insights can take you far, augmenting them with human insights can take you further. This is where layering thoughtful sales touches into the user journey can help you better understand gaps and iterate on free offerings. For example, when we started a 30-day trial at GoSite, we noticed a drop-off in usage after 14 days. At the time, we weren’t sure whether it meant the power user had been properly onboarded or the person had lost interest in the tool. 

So, we decided to implement sales touches at days 3, 7, and 10 to check in with users during their activation period. We were able to tell which folks were going to convert based on how many messages they sent, the amount of reviews they managed, and their active transactions in the first 14 days. We also found that someone who didn’t use two or three of these tools in the first 14 days had a churn rate of 85-90%. We shortened our free trial to 14 days, knowing the additional two weeks of nurturing didn’t make economic sense for us.

If there’s one thing I’ve learned about selling at PLG companies, it is that product-led sales is not a linear process and there is no one-size-fits-all approach. As your product grows and your ICP evolves, so should your GTM strategy, sales tactics, and, most importantly, how you leverage product data. Start small, track patterns, and experiment.

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