Subscribe to Modern Selling on the app of your choice!

From Loom, to Dropbox, to Grammarly, and even Calendly – there are hundreds, if not thousands, of productivity management software tools on the market to choose from. Although these tools often draw millions of free users every year – the question often becomes how do product led growth companies truly scale and become profitable sales engines?

That’s the topic of discussion in this episode of the Modern Selling Podcast.

With our expert guest, we dive deep into the sales side of product led growth, what it means, what metrics sales leaders should be tracking, and the proven strategies to use to not just scale – but to grow efficiently and profitably as an organization.

In this episode we welcome Kate Ahlering, the Chief Revenue Officer at Calendly – the modern scheduling platform for high-performing teams and individuals. Kate currently leads sales, partnerships, and revenue operations for one of the fastest growing product led growth companies in the world.

Prior to joining Calendly, Kate was the Chief Sales Officer for Glassdoor, one of the world’s largest jobs and recruiting sites. She led a team of 600+ globally across new business acquisition, account management, customer success & support, channel sales, and revenue operations. Reporting directly to the CEO, she was responsible for Glassdoor’s go-to-market vision, strategy, and execution.

Download the episode to hear the proven sales strategies Calendly and other large product led growth companies are using to drive sales.

How does Product Led Growth, or #PLG, drive #sales for an organization? 🤔 Learn the answer in this ep of @GoModernSelling #Podcast w host @M_3Jr and guest @KKreags CRO @Calendly Click To Tweet


What are the challenges that sales teams are facing?

With such a digital world, sales teams have had to transition rapidly to meet the modern buyer on a host of online platforms. I wanted to get Kate’s perspective on what sales teams are facing right now in the post-pandemic space.

Kate shares, “Now, more than 80% of transactions of the B2B buying process have some sort of digital component or online touchpoint. This has made the sales experience and expectations far more complex. I think the challenges that a lot of sales teams face are around how to interact with prospects and customers. How do you engage with your audience and bring value to them as often as you can? That’s a constant question sales teams are trying to answer every day.”

I’ve seen this too, with Vengreso, over the past two years. Instead of relying on face to face communication, our sales teams now have to figure out what is the best route to reach out to and engage with prospects. Is it by phone? Video chat? Email? Text message? Social media? These are all avenues now that we have to explore when we reach out to modern buyers.

Join in the conversation with Kate to hear what other challenges she sees sales teams facing and how she recommends sales leaders help them move beyond the obstacles.

How does Product Led Growth differ from Sales Led Growth?

We often throw out these “buzzwords” without truly defining them. So, I wanted to spend time with Kate getting clear on the difference between product led growth (PLG) and sales led growth (SLG). 

Product led growth is all about getting more users into your product to rapidly grow your user base. The focus here is on building value to get people into your product.

Whereas sales led growth is just that – focused on monetizing your products or services to grow revenue. Once you’ve grown your product to a critical mass of users, now the conversation has to shift to getting these users to pay.

At Vengreso, we experienced this transition ourselves when we made the major decision to move away from being a video sales training company to becoming a SaaS company, with the rollout of – our innovative, text expander tool for knowledge workers.

It’s in this transitional period that we had to focus on how to bring value to our FlyMSG users to both grow our audience base AND to convince them to upgrade to a paid subscription, to ultimately drive sales.

I know Kate has had a similar experience with Calendly, so we spent some time diving into the details of how to make this transition from PLG to SLG and what that means exactly.

Her insights are spot on, “With PLG, the salesperson’s job has to evolve from solely focusing on outbound, prospecting strategies to instead focusing on looking at the user data for actionable trends. For example, if we see that an organization has 100 free users, then it’s the salesperson’s responsibility to find the key decision maker at that organization, reach out to them, and clearly convey the value in an Enterprise account.”

Listen in this ep of @GoModernSelling #podcast, as host @M_3Jr and guest @KKreags CRO @Calendly, dive deep into the #sales side of product led growth, what it means, what metrics #leaders should be tracking, and more! 👏 Click To Tweet

Listen into the full conversation to hear what specific user data points Kate highly recommends that every salesperson tracks to know when and how to drive sales.

What are the steps to transition from PLG to SLG?

This transition often takes time and a strategic approach. For example, even though Calendly has been around for a decade, their monetization model is still in its infancy. In fact, when Kate joined Calendly, they had not yet monetized their product. 

I was curious to know what steps she took to help Calendly make the transition to sales led growth to get a large portion of their free users to upgrade. 

According to Kate, there are three key steps to take:

  1. Optimize inbound leads. With a robust user base, the key is to enhance their experience. Getting free users to absolutely love your product and see the immediate value in it makes it a lot easier to pitch paid upgrades.
  2. Drive value for large target accounts. To accelerate growth, it’s critical to look at the data for user trends and identify those large target accounts that could convert to Enterprise sales. However, to do this well, you have to get clear on the value your product brings to not just the individual users, but to the organization as a whole.
  3. Establish a sales structure. When you focus on product growth, other key sales systems may not be in place. That’s why it’s important to get sales methodologies and playbooks established so you can standardize the sales process to easily track sales and success.
How do #PLG #companies truly scale & become profitable #sales engines? Listen now and learn the proven #strategies to use in order to grow efficiently and profitably as an #organization💡 @GoModernSelling w @M_3Jr & @KKreags CRO… Click To Tweet

Want to know more about making this transition? Tune into this episode to get the sales gems that Kate shares related to how she’s scaling sales within Calendly.

This episode of the Modern Selling Podcast is brought to you by Korn Ferry. Korn Ferry transforms sales teams using their world-class Miller Heiman, methodology, employee assessments, benchmarking and talent advisor capabilities to increase win rates and quota attainment. Korn Ferry offers Korn Ferry Sell, a sales effectiveness app available in App Exchange and app source that helps your sales team develop and replicate powerful sales strategies that help sellers win more deals and crush their quotas. Learn more at  

Watch the video version for this episode here:

Table of Contents
Add FlyMSG to Chrome. It's Free!