Balancing Users and Buyers in Product-Led Growth

How to Get (and Keep) Users Hooked While Winning Over Decision-Makers

DEAR STAGE 2: Our product serves different types of users—some are heavy users but not buyers, while others are decision-makers who don’t engage with the product. How do we tailor our PLG approach to reach both groups ~Balancing User Types

DEAR BALANCING USER TYPES: This is a common challenge for companies moving into product-led growth, especially when user and buyer personas differ. It’s tricky to keep both groups engaged without overcomplicating the product or missing out on revenue opportunities.

I recently had the chance to discuss this topic with Jessica Gilmartin, who was most recently CMO and CRO at Calendly. Jessica has a wealth of experience when it comes to building PLG engines that balance user delight with strong revenue generation, especially in complex ecosystems where the person writing the check is not the daily user.

Here is some advice that Jessica shared that can help you manage this and keep both users and buyers happy.

1. Build for Delight First

Jessica emphasized that a PLG product’s foundation should always be ease of use and fast value delivery—regardless of who the user is. “You need to make sure the product experience is simple and delightful for every user, even if they’re not the ones paying,” she said. If you over-engineer the product for decision-makers or gate key features too early, you’ll lose out on organic adoption.

In other words, don’t lose sight of your power users, even if they aren’t the ones writing the checks. They’re the ones who will champion your product internally. Start by ensuring that the product is usable, delightful, and solves a specific problem within the first 10 minutes. This gets people excited and keeps them coming back. A common mistake is overcomplicating features too soon, which can cause users to disengage before they experience value.

"For me, PLG really means a democratization of product. It feels 90% like a consumer product and 10% like a B2B product. The only way that you are going to get success is if users find value right away." - Jessica Gilmartin

2. Create Clear Triggers for the Buyer

While the product needs to work seamlessly for the everyday user, Jessica also pointed out that you need to create natural upsell moments for decision-makers. This is often where the PLG and sales-led growth models come together. “You need to reverse-engineer what drives enterprise adoption. For example, at Calendly, connecting Salesforce was a key indicator of future upsell. It allowed us to proactively target decision-makers when they saw the product becoming indispensable,” Jessica noted.

This is where you should focus on data triggers and product usage signals to alert you when an organization is ripe for monetization and expansion. For instance, once you see multiple users from the same company on your platform or when they hit certain usage thresholds, you can introduce higher-value features that require approval from the buyer.

3. Nurture Both Personas with Specific Messaging

Jessica’s team spent a lot of time experimenting with persona-based messaging, both in-product and through external marketing. “One key realization was that a broad, one-size-fits-all message doesn’t work in PLG. You need to segment based on who’s using the product and who’s likely to pay for it,” she explained.

For your everyday users, focus on retention and the “hero” experience. They need to feel like the product makes their job easier and even makes them look good in front of their peers or managers. On the other hand, for decision-makers, your messaging should be about strategic impact and value at scale—how the product can save time, increase efficiency, or solve a larger business problem across the organization.

This tailored strategy will help you nurture both sets of users without diluting the experience for either group.

4. Let the Product Do the Selling

Finally, let the product do the heavy lifting when it comes to expansion. Jessica emphasized, "Don’t rush to have sales reach out just because someone with the right title signed up," she advised. Instead, let the product guide them to discover more valuable features, and only when you see significant engagement should you introduce human touchpoints.

For example, when users start leveraging integrations or sharing the product with colleagues, you know the value is sinking in. That’s when you can nudge the decision-maker to expand the usage or upgrade to a higher tier. But remember, patience is key—PLG often takes 12 to 18 months to fully expand within an organization. Jumping in too soon can feel invasive and even drive people away.

Ultimately, balancing different user personas in a PLG framework takes a mix of data, timing, and patience. 

Until next week!