Letting the Prospect Drive the Sales Conversation | Jason Rozenblat, CRO at CallRail

Letting the Prospect Drive the Sales Conversation | Jason Rozenblat, CRO at CallRail

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Historically, it's been difficult for sales teams to know how and when to reach out to current users of their product either for conversion or expansion. But, with access to product data, sales teams can be both proactive and reactive at the same time. So, how do things shift when sales, marketing, and customer success all work together to make for a great user experience?

According to CallRail's VP of Sales, Jason Rozenblat, that's a daily reality for their product-led company. With a constant feedback loop of data, it's easy to spot problems in the process to brainstorm solutions in real-time. Since the company can see exactly where drop-offs and disconnects happen, they can pivot their efforts quickly. 

With a heightened focus on storytelling from the treasure trove of data seen in trial and new user cases, Jason helps his sales team work with other departments to give customers a great experience from the very first time they hit the free trial button. 

In this episode of the Product Led Revenue podcast, Jason joins host Breezy Beaumont to discuss how a user-driven trial process connects to better conversions, why success must evolve as a definition throughout the company's history, and how serving in a sales role at a product-led company is truly different.


💡 Name: Jason Rozenblat

💡 What he does: Vice President of Sales

💡 Company: CallRail

💡 Noteworthy: Jason has experience in both product-led and traditional sales-led companies.

💡 Where to find Jason: LinkedIn

Key Insights

Overwhelmed by data? You're not alone.

There's so much data available to sales and marketing teams today that it can be hard to tell where the results are coming from. That's the entire premise behind CallRail so that teams can more effectively dig into the data. "We're always trying to figure out additional ways to get more data out of the app and into either product marketing's hands or product's hands, sales' hands, or success. We're always looking for ways to understand what they're [users] doing in there and how we can help them."

If you have multiple products, treat each one individually with lead scoring.

Jason points out that the data CallRail collects internally helps them decide when someone is a perfect fit for one product. That more personalized outreach drives better conversion numbers. ''We look at some other product usage data points that help us determine whether we think they might be a good fit for one or three of the other products. There's a certain level of outbound efforts to those existing customers. But we also generate a lot of marketing-qualified contacts and engagement in QCs and hand-raisers that will say, 'You know what, I do want to try this additional product."'

There are many different ways to offer free trials. Find what works for your customers.

For example, CallRail doesn't require a credit card when the trial starts to make things easier for the prospect at that time. It also matches their sales approach and usability efforts, where the goal is for the prospect to fall in love with the product. "That has led to a much better experience for the prospect. We're trying to meet them where they are and create a great buyer experience. Hopefully, they're buying the software at the end of the 14 days, but we're not trying to sell them anything; we're just trying to make sure that we can get them to that point where they can make that decision on their own."

Episode Highlights

Aim for a frictionless trial process 

The CallRail team knows they don't want to bombard their prospects with too much follow-up. With an end goal of letting the product be the star, their team makes it simple for someone to sign up and get a taste of how things work by themselves. 

"Our founders very much believe in the product-led movement and letting the product do all the talking and the ease of use, ease of setup, and that starts with a free trial experience." 

The team focuses on making it an easy and intuitive experience so that the product adds to the user's work in a meaningful way rather than leaving the user feeling like it's one more thing to be mastered. 

When it comes to customer service and offering help, Jason says they focus on being available without being pushy. "It's more of a support function or an implementation function where we are there to assist you throughout that 14-day trial process to make sure your account is set up properly." 

Use your data and build your systems and sales teams in response to it 

To know whether that trial is working, Jason's team captures a lot of data and then uses it to drive who focuses on what and which systems should be changed. The team also uses various sources of their own to find out how the process starts and where it drops off, especially with the help of Pendo and Looker. 

"We're getting data into Pendo. So we have a lot of in-app experiences that have created a custom view. The way that someone is interacting with our product, that data is fed directly into Looker so that we have visibility into how customers from different industries are using the product. Are they onboarding themselves properly? How much do we need? It guides a lot of the decisions that we make on different types of messaging in-app. And then also, a lot of that data is pumped from the app directly into Salesforce and then from Salesforce into Outreach. 

If the product is easy to use and not expensive, use a light touch instead 

CallRail wants users to become fans and not feel interfered with during the trial process. Their basic premise is that these users are looking for a solution that meets them right where they are at to make things simpler. Jason says that means they don't want a phone call right away. 

"It's a pretty straightforward product; it's not too expensive. It's month to month, 'I don't need to talk to anybody, I can figure this out on my own,' so for that prospect, they don't want to talk to anybody, and we're not going to force them to talk to us." 

For Jason, that's like a gold medal in sales when a prospect goes through the entire process and signs up because they've self-educated and self-selected because that helps the sales team put their focus elsewhere. 

"I would love to have sales just work on the situations or the scenarios where someone really needs additional help, like more custom solutions, custom pricing, a more in-depth demo, something that's not ordinary or out of the box." 

The success definition should evolve 

Growth in the team is one metric by which you can tell that the product is pushing the company forward. But what success looks like might change over time, and Jason says that's a process many should embrace. 

"It's not just the team size, but their involvement, their seat at the table. I think, historically, they were sort of viewed as glorified support, so the level of support for larger accounts was all relative. Most of our customers are SMB and mid-market, and then we have some enterprise customers; we would basically say, 'Oh, who has the highest MRR? Let's draw a line in the sand. You're now going to be given a success account or a success rep.'"

With that early approach, the company wasn't thinking about the potential size of the account or the real role of the account success rep. Today, the customer success team doesn't sell things directly to customers but instead uncovers new opportunities and passes them over to the sales team. That protects the trust of the customer along the way, too. 

"Customer success reps can tee up one of my reps with a customer that is interested in trying one of our additional products or upgrading or more licenses on one of the products." 

Build systems to capture long-term value 

As the company grew and added more products, they didn't want to forget about the simplicity of determining their best customers. They've also chosen to divide and conquer when it comes to helping those clients so that certain teams are laser-focused on the long-term winnable areas. 

"We did an analysis a few years ago, and we know that certain industries that we work with have a significantly higher LTV than other industries that we work with. So we basically are putting our best, most tenured reps on the higher LTV industry. We route all the leads for those verticals directly to certain reps and then sort of our lower LTV verticals, we'll give to our more junior account executives that have just moved up." 

Along with long-term value, the company makes an effort to cross-sell when it makes sense. Identifying when someone is ready for a different product is determined through the usage data CallRail collects. 

"If we know that our customer has call tracking, one of the four products, we take a look at a ton of different variables. We look at how much money they spend with us a month, how long they've been with us, whether, obviously, whether they have the other products or not, their industry, and other product usage data points." 

They can do this successfully because they use lead scores around individual products rather than the whole suite. "[Leads] may score up specifically for that one additional product, which allows for a much easier conversation instead of saying, 'Hey, are you interested in products?'"

[...] We also have a constant feedback loop. We use Slack, and there is a lead feedback channel where all my reps are in, and all the domain marketers are in, and reps in real-time are providing feedback to the marketing team to say, 'Hey, this was a really great lead.'"

Collecting all that data and looking at it is the only way to know when changes need to be more or when another department needs more help. "The ability to have that much data allows you to make changes and learn very quickly and fail fast. One of my favorite quotes is you win, or you learn, so if things are going well, and we want to know why it's going well." 

Top Quotes

[10:53] "We're trying to meet them where they are and create a great buyer experience."
[17:59] "We have a large team dedicated specifically to selling back to our existing customer base, cross-selling and upselling back to our existing customer base, and it's not named accounts. It's purely reactive based on a lot of this usage data."
[28:59] "We're looking at every possible angle and every different way, every different factor or variable that could impact conversion rates." 

Interested in learning about how Correlated can help your PLG company uncover expansion and upsell opportunities?

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