Yesware increases free-to-paid conversion with behavioral analytics

Ann Johnson

Yesware is a sales productivity tool built from the ground up to help salespeople sell more. Yesware connects directly to a salesperson’s inbox and calendar to help them manage their opportunities with features like email tracking, reminders, and templates.

Yesware is kind of an invisible software,” said Jake Levirne, who is Vice President of Product at the company. “Yesware works where salespeople work, so they never have to learn another tool or switch applications. Instead, Yesware is just there in an ambient way for the eight to ten hours a day that they’re using the tools they’re familiar with.”

Unlike enterprise software tools where visibility into usage data is limited, Yesware’s software as a service (SaaS) design makes it easier to get real-world data about how users interact with their tool. “We’ve always had this notion of capturing usage data about our users,” Jake recalled. “By having a product that’s fully instrumented, we can quickly get answers to a lot of questions that before we used to have to go out of our way to interview and survey users to find the answers.”

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Ad hoc SQL queries couldn’t scale

In the beginning, the product team set up their own reporting against a SQL database to capture important metrics like the total number of users and the total number of new users on a weekly basis. To answer any questions outside of that fixed report, the team would have to ask Yesware’s CTO to craft custom SQL queries.

The dashboard reporting and ad hoc queries worked while the team was small, but as the team grew and took on more projects, it became harder and harder to carve out time to manually write SQL queries. And as new features were introduced to the product, the team realized that they needed a greater visibility into usage and feature adoption than what the static dashboard could provide.

Why analytics solutions need to be flexible

Jake and his team evaluated several analytics solutions and ultimately decided to partner with Interana to better understand user behavior. Jake said, “Compared to the other analytics tools we looked at, Interana’s flexibility was the game changer. Being able to report on ten different things that a user is doing versus hundreds of different things, and then being able to craft the actual question that you want to answer as opposed to a rough approximation you can modify. That’s the big difference.”

While many analytics tools provide out-of-the-box dashboards and metrics, predefined metrics don’t always line up with benchmarks and success criteria. “As we build out features, we have to carefully think ‘what type of feature is it? Is it a feature that everybody is going to use? Is it a feature that people are going to use infrequently? Is it a feature that only our power users would use?’ There are different curves of adoption you’d expect for different features,” said Jake.

One example is Yeware’s Team Reports feature, which provides sales managers with metrics regarding their sales teams’ performance. Just looking at the overall usage percentage of subscribers who used that feature would show an incredibly low adoption rate since there are far fewer sales managers using Yesware than salespeople. With customizable metrics and the ability to build out cohorts based on attributes like title or frequency of use, Yesware is able to more accurately understand whether or not a particular feature is successful.

Optimizing for conversion

In addition to measuring the success of new features, the Yesware team uses Interana keep a pulse on real world usage by their users and understand how effectively they’re converting people from trial users to paid subscribers.

“At our weekly executive team meetings, each executive is responsible for one number,” Jake said. “On the sales side, it’s new business closed in the past week. For customer success, it’s the total amount of renewed business. Then for product, the one number I bring to bear is usage of the product in the four-week trial to understand how effectively we’re converting people.”

To understand how effectively they are converting users, the Yesware product team set up funnels to see how users interacted with different features from starting a trial all the way through subscribing. John Billington, senior product manager at Yesware, shared how he used Interana to A/B test the onboarding process for new users.

“Salespeople can also install Yesware from our website or from the Google Chrome store. Our website had a form that asked new users to provide us with information like their role and title, whereas on the Google Chrome store we didn’t. We tested implementing a similar form on the Google Chrome signup process, but found that it became a major barrier. With Interana, we were able to see that the percentage of those who ended up subscribing without the form in their onboarding experience was much higher than those who had the form.” With insights like this, the Yesware team is able to continuously optimize their signup process to make it easier for users to install the tool.

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Analytics goes beyond the product team

It’s not just the product team that uses analytics at Yesware. Engineering, design, customer success, sales, and even the executive team use Interana to better understand behavior.


  • Understand feature adoption and utilization
  • A/B test and prioritize new features prior to mass rollout
  • Optimize the onboarding experience to convert free trial users to paid subscribers


  • Identify, troubleshoot, and resolve bugs and issues


  • A/B test user interface and user experience changes to the product
  • Complement user survey and user research data with real world usage to create a great user experience


  • Work with customers to ensure that they are maximizing the value of their entitlements


  • Understand usage data to give a detailed quarterly review of the Yesware product to key customers
  • Identify power users at key customers and work with them to become Yesware ambassadors at their companies


  • Create and share dashboards to use at executive team meetings
  • Expand on high-level metrics and reports by digging deeper and exploring behavior

Jake concluded, “Interana has increased my confidence level when I make recommendations to people and has helped me make sure that people actually use our product. I can see how many users are using our product in any given hour, day, or week. That’s the biggest thing for me: knowing that our product or a specific feature – especially a new feature – is actually getting adopted.”

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