WorkRamp Communities is now available.

The Customer Success Goal You’re Getting Wrong with Jon Herstein, Box

 We all know that creating an excellent customer experience helps you retain customers, build loyal brand advocates, and increase revenue. 

But in the fast-moving SaaS industry, creating successful, scalable customer success programs is more than delighting the customer–and this seems to be one of the biggest challenges for organizations of all sizes.

Jon Herstein, Chief Customer Officer, Box, joined the LEARN podcast sharing his extensive Customer Success experience. During his chat with our CEO & Co-Founder, Ted Blosser, Jon reveals his approach to delivering substantial value to customers.

SaaS platforms have transformed, making it significantly easier for customers to switch providers. SaaS allows for more fluid transitions than the on-premise mainframe days with hefty upfront investments. As a result, it’s more important for customer success teams to ensure continuous high-value use cases and proactively measure customer health.

“Because of the nature of STAs as a platform, it’s much easier to switch than it used to be,” Jon says. “I’m old enough to have been around in on-premise mainframe software deployments. [They were a] huge upfront investment, so a customer was incentivized to stick around on that platform for a long time. In SaaS, switching costs are much easier. And so there’s a lot more worth that has to happen on the customer success side, ensure high-value use cases, etc. 

“So a lot of what we do is focus on doing our best to measure customer health. And you can think of health from a vendor’s perspective as a value from a customer’s perspective. So if I believe you as a customer are deriving great value from Box, I will give you a high health score. If I think you’re not deriving great value, you will have a low health score. So the battle for us is less about, we’ve gotta fend off these competitors all the time. Really, if you think about it proactively, our job is to deliver as much value as we possibly can.”

Read more: 3 Customer-Led Growth Strategies to Stop Churn with Kevin Chiu, Catalyst

The customer delight paradigm

Jon shares that his mantra at Box was all about creating delightful user experiences. However, he realized the need to evolve this approach, recognizing that delight alone is insufficient. 

“It’s not enough just to delight your customers,” he says. “Your customers can love working with you. They can think you’re a great partner; they can think you’ve got great people, values, and all that. But at the end of the day, people buy software products or services in general because they believe it will provide some business benefit to them. 

“In the world of B2B, people don’t buy products because they like you. They buy products because they think they will solve a problem in their business and generate some ROI. And so you have to couple delight in creating a delightful experience with your customer, for your customer with providing real business value, solving real business problems.” 

It’s not the customer success team’s job to make customers happy but to ensure you’re delivering value. True success lies in delivering value and solving real business problems.

Navigating competition in the SaaS arena

Discussing the competitive landscape, Jon highlighted the coexistence of SaaS providers like Box with giants like Microsoft. 

Rather than viewing it as direct competition, Jon emphasizes positioning Box as part of the customer’s ecosystem, showcasing the added value of using Box alongside other platforms. This approach requires proactive engagement and clear communication on the product’s distinctive value proposition.

“The reality is it’s not just a competitive situation; it’s a coexist situation,” Jon says. “Every one of our customers is also a Microsoft customer, a Google customer, or both. So it’s not a question of whether my CSM is trying to convince a customer not to use Microsoft or Google. That’s never going to happen. It’s more about how we position ourselves as part of the ecosystem for the customer and why there’s a value-added in using us plus those other products as opposed to us instead of those other products.

“You must look for high-value, deeply embedded, highly integrated use cases. And that’s the benefit we think of having a platform is that we can deeply integrate into other things.”

Scaling customer success

With Box serving a diverse customer base, including around 120,000 paying enterprises, Jon shared the complexities of customer success at scale. He emphasized the shift toward a digital-first engagement model, leveraging automation and programmatic approaches. 

“It doesn’t matter how many accounts you have in your pool because you’re never going talk to all of them, so you have to pivot from a human-first engagement model,” Jon says. “You have to pivot to a programmatic or automated first model and then figure out where the touchpoints are where it’s essential to have a human.”

Jon shares some examples of how to blend digital engagement with human relationships:

  • At-risk customers. Build an early warning system to identify at-risk customers, then have a human reach out or automate outreach to these customers. Just ensure that a human has the actual conversations with these customers.
  • Software scheduling. Automate the process of scheduling meetings and consultations. Once it’s scheduled, your CSMs handle the call.

“It’s not one or the other,” Jon says. “I think for too long we probably thought it was, we have digital customers and we have human customers and it’s not that black and white.”

Read more: Expert Interview: How to Do More With Less and Scale Customer Success

Continuous learning and networking

Continuous learning and development are essential to success in any industry. Jon highlights the value of seeking insights from people outside of your company and from people with diverse perspectives. 

“A lesson from my career is learning from others trying to do the same thing you’re trying to do,” he says. “Networking with other people outside of your company who are trying to accomplish the same things you’re trying to accomplish. Some of the best things I’ve learned about customer success were from other CS leaders who don’t even work at Box.”

Jon’s journey from consulting to customer success leadership at Box offers insights for navigating the complexities of the SaaS world. As the landscape continues to evolve, it’s even more essential to deliver value and master customer success at scale. 

Listen to the full episode for more insights from Jon, and subscribe to the LEARN podcast on Apple, Spotify, or YouTube to learn more from top leaders in tech. 

Complete the form for a custom demo.



Maile Timon

Content Strategist, WorkRamp

Maile Timon is WorkRamp’s Content Strategist. She has over 10 years of experience in content marketing and SEO and has written for several publications and industries, including B2B, marketing, lifestyle, health, and more. When she’s not writing or developing content strategies, she enjoys hiking and spending time with her family.

Ready to Explore Online Learning Platforms?

Get in touch to learn how WorkRamp can help you achieve your training goals.

Request a Demo