Presented by Chargebee

The subscription space is booming, but organizations still need to find new ways to engage and retain customers. In this VB Spotlight event, you’ll learn how to boost subscriber growth and sales velocity with data-driven insights, powerful automation and more.

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Though subscriptions are wildly popular in the consumer and B2B space alike, churn and retention are taking center stage in the shifting global economic landscape. Marketers are critical not only in acquiring customers but for influencing lifetime value (LTV) and customer acquisition cost (CAC). In this quest, automation is delivering real-world ROI.

In this recent VB Spotlight, Guy Marion, CMO of Chargebee, Patricia Rollins, head of marketing at Typeform and Jessica Gilmartin, CMO at Calendly discuss the way automation is transforming how marketers engage with customers, why data is so critical and more.

Automation, data and the customer experience

“Automation is definitely improving efficiency, but it’s also making us be smart and targeted for when we reach out,” Rollins says. “As we think the credit card is expired, we’re reaching out. As we think they’re approaching their limit, we’re reaching out. It’s letting us be smarter as we start growing and scaling the company.”

Automation also offers efficacy, Marion says.

“The performance, the engagement and the conversion of the campaigns that are being run tend to be higher when they’re better targeted,” he explains. “You’re solving a customer’s problem with a very specific offer. Or a buyer’s problem. One thing we’ve experimented with this year is introducing a usage-based pricing plan for our startup segments, for companies that don’t yet know exactly their growth horizons ahead.”

Automation and personalization at scale

“Both Calendly and Typeform have been successful because one thing they do is extend the individual customer experience at scale in an online fashion, leveraging personalization and better targeting to do so,” Marion said. “We see that’s more important now than ever, when automation and scaling more efficiently is now a key buzz phrase, as the IT tools budgets across the industry are being scrutinized and reduced. Keeping the customer first is critical during those times.”

It’s also crucial to develop working committees and partner with the data science team to identify opportunities for better onboarding, loyalty programs or retention offers — particularly at key moments in the buyer’s journey, when companies are considering downgrading or churning, or introducing new pricing models, Gilmartin says.

“One thing we’ve done successfully is create personalized home pages for our customers based on where they are in the trial process,” she adds. “That understanding combined with downstream information around what creates long-term happy customers that retain and monetize well, is really important to us. We’ve seen a significant uptick in our activation and conversion metrics by using some of that intelligence.”

Not only is the data important in making sure you’re personalizing well and creating the right automated experience, but it’s also invaluable in serving the right content, Rollins said.

“An effort we’re also looking at here at Typeform is making sure that the content, from the minute that you acquire a customer, all the way through the funnel and the life cycle, stays true to them,” she says. “As you talk through the content, through the personalization and automations, you’re using all the subscription data to help trigger and automate the expansion, the churn prevention campaigns, your payment failure campaigns and so on. You can trigger the coupons and incentives for automated billings. As you go through their life cycle, you’re really bringing them along the journey, and trying to upsell them or expand them, and also making sure they find you the best partner to work with.”

Subscription data and successful targeting

The subscription billing platform and the subscription life cycle bring an entirely different set of targeting parameters to the marketer that, coupled with demographics and firmographics, can help personalize that message and develop the right copy and content for the user at that stage in their journey, Marion says.

“When we think about targeting customers and being more effective in marketing campaigns, it starts with, who is the audience you’re trying to engage? Are they new prospects and leads that fall within a certain vertical or company size or region of the world?” he explains. “Obviously we think about the world in terms of core customer segments and multiple products. Each of those have their own ICP that we map out closely, and then we categorize that in our CRM so we can drive effective startup-focused nurturing, with messaging, ads and a customer journey designed for, say, an SMB SaaS company.”

Critical data comes when a customer purchases or tries a service, as well as from the billing platform — for instance, the customer’s plan type, MRR (monthly recurring revenue) or billing cadence. And offers can be more finely tuned based on the life cycle stage, from trial to 90-day honeymoon period, mid-life cycle or long-term loyal power customers who should be rewarded and incentivized with memberships and loyalty bonuses.

Getting automation up and running

“I’m happy with where we’ve gotten very quickly,” Gilmartin says. “I think it’s because we have a steering committee that’s a combination of the relevant people in marketing as well as customer support. Those are the two groups that have to be very involved, as well as product. For Calendly, it’s driven by the growth marketing team. Having a clear owner with accountability for metrics is core to them, but also is having a close partnership with product, customer support — the foundation of data — to enable quick decision-making.

Rollins agrees, saying, “we have to work hand in hand with our CSM team and support team, because as they get the triggers, they’re also having to make sure they connect with the customer and ensure that it’s a proper experience.”

It’s easier than ever to get started, because today’s tools are built to focus on providing personalization and targeting.

“My recommendation is thinking forward about the data stack and the integration with the automation stack that go-to-market leaders in both marketing and other areas need in order to effectively target,” Marion says. “That means having a CRM with good hygiene that integrates with marketing automation, outbound ABM systems, customer data platforms and your subscription billing platform. With that core set alone, it opens tremendous opportunities to build a strong view of the customer, where they are in the life cycle, their usage depth, breadth and frequency; it then triggers different types of engagements, both in product, by email and via humans around that customer journey.”

For a deep dive into automation strategies with proven ROI, how to integrate automation into your marketing stack and more, don’t miss this VB Spotlight event.

Watch free on-demand now!


  • Streamlining sales velocity via trials, easy upgrades, and more
  • Developing a customer-centric approach to subscription management
  • Leveraging data-driven insights to boost subscriber growth
  • And more


  • Patricia Rollins, Head of Marketing, Typeform
  • Jessica Gilmartin, CMO, Calendly
  • Guy Marion, CMO, Chargebee
  • Art Cole, Moderator, VentureBeat