HashiCorp’s freemium business model means they have rich stores of data at their fingertips. And not just on nameless leads—they can see how prospective buyers are already using their products for free. For Head of Growth Caroline Guo, that was an opportunity in the making. As she explains it:

“Anyone could decide to sign up for Terraform Cloud, which is a SaaS offering of Terraform’s open source tool, and they could access a free to use version of Terraform Cloud or decide to convert to a paid tier offering if that made sense for them.” 

If only they could identify those upsell opportunities at the right time, there was a chance to capitalize on product-led growth. But with 14 unique open source, enterprise and SaaS products, none of them speaking to each other, there was no way to reliably identify and signal the engagement triggers that suggested a user was ready to move up to their paid product. The sales team wasn’t able to identify the best time to reach out to users and they were missing out on sales opportunities.

If they could find a way to automatically identify upsell leads while they were still hot, Caroline believed, their sales team could act on them immediately and convert them from free users to paid subscribers. 

Caroline thought that they could achieve that by structuring their data to identify in-product user behaviors and signal opportunities ripe for upsell. But any strategy they employed would also have to take into consideration how users actually engage with their products.

“When someone signs up for our SaaS products, they either come in and adopt the product quickly because they’re familiar with our OSS products or they have an onboarding curve which  always runs the risk of user drop-off before activation. Product-led growth requires really quick data insights to drive decision making in the user lifecycle.”

Determine the right engagement signals 

If you’re going to automate a way to identify upsell opportunities, you first need to know when someone is showing signs they’re ready to move up to a paid model. For example, Caroline recognized that creating a workspace in Terraform Cloud, then building a certain amount of infrastructure, or running a number of applications, signalled users’ investment in their product and a potential readiness for upsell or conversion.

To get to that conclusion, they first studied user behaviors:

“We cohorted our users to understand usage patterns for people that convert or don’t convert into our paid tiers. We focused on the simplest user actions, then validated these actions with our sales team to make sure they fit what they were hearing in upsell conversations.” 

Clean up and consolidate your data

“For us, this was particularly complicated because HashiCorp has multiple products, and they don’t have common shared user identification between them.”

HashiCorp set to work consolidating user activity across different product lines into a single database. They associated user activity with organization activity, and merged in Salesforce information to create a complete view of a user and organization.

Build an automated Slack feed (or other notification system)

“We built a Slack feed that tags each individual sales rep when one of their accounts is ready to buy.”

Account matching in Salesforce helped Caroline and her team identify which sales rep owned each account. From there, it was all about building a bot on Slack that could send a notification to the appropriate salesperson when one of their engagement triggers was activated. 

This is what the flow of the system looked like:

While HashiCorp used Slack, though, email or Microsoft Teams could provide the same function. Two syncs a day make the process as real-time as possible, letting sales reps reach out while the user is still optimally engaged. 

This is an example of what HashiCorp’s Slack notifications looked like:

Follow up in real time

Once a sales representative is served up a lead, they can immediately click through to Salesforce and learn more about the account, how the customer is using the product, what campaigns they have engaged with and why they’re primed for upsell. From there, sales reps strike up a conversation, using personal research from LinkedIn and their knowledge of the account to create a personalized email. 

This is an example template the HashiCorp sales team uses for email outreach based on this notification system:

Learn from Brynne Burgess at Sprig how to approach segmenting your self-serve and enterprise website visitors.