Resilience is a skill – and Jason Hainsworth knows that about as well as anybody.

Jason is the VP of customer success and account management at Divvy, a FinTech company that offers a spending and expenses management platform for businesses. (Divvy was bought by last year for $2.5 billion.) He jumped into customer success about decade ago, during the early days of CS, and through hard work, ingenuity and his affable demeanor, quickly rose to the top of the industry.  

He recently discussed his career – and how other’s can build killer CS careers, too – with UpdateAI CEO Josh Schachter on LinkedIn. If you missed it, here are a few highlights from their conversation: 

1) Going the Extra Mile (Literally)

Sometimes you have to go the extra mile to deliver value to the customer – or, in the case of Jason’s first great CS memory, an extra few hundred miles. 

Let’s back up about a decade ago. Jason was working in Albuquerque, New Mexico fresh out of college, and managing about 30 clients for the company he was at. A few months into the job, he ran into an issue: one of his clients, who was based in El Paso, Texas, had put in a cancellation request. 

“I was like, man, this sucks,” Jason told Josh. “They’re not gonna renew their contract [and] I’m going to get dinged on my quarterly bonus. And so I’m like, I’m not going to let this guy shirk.” 

He didn’t just try talking to the customer about his issues over the phone, either. Instead, Jason jumped in his car the next day and drove more than 260 miles to talk to the customer face-to-face at his office in El Paso. After completing the 4 hour drive, Jason arrived at the company’s waiting room and told the receptionist he was looking to squeeze in 5 minutes with the customer; when the customer walked in and saw Jason, he wasn’t as excited about having a brief conversation. 

“He said, ‘I don’t want to talk to you,’” Jason remembered. “I sent your company a letter – I’m canceling. I’m going somewhere else.” 

Jason remained polite and said he’d drove several hours to speak with him about the reasons he was canceling. The customer said he didn’t have time and went to his office. Still, Jason continued to wait in the waiting room. Later, when the customer – a true “Texas gentleman” as Jason described him – left for lunch, he gave Jason a “weird look,” paired with a “couple expletives,” because he was shocked Jason was still there. 

Jason continued to wait, though. He was determined to talk to the customer about the roadblocks that he’d run into; at worst he’d learn why he was canceling, and at best, he’d be able to find a solution and keep the customer. Finally, when the customer went to leave for the day and saw Jason was still there, a little past 5:00 p.m., he started to give in. 


“He is like, ‘you are crazy… but I like it,’” Jason remembered. 

The customer told Jason to return the next morning at 9:00 a.m. and he’d give him his 5 minutes. Jason came back the following day, and their 5 minute chat turned into a 90 minute conversation. 

Jason listened to the customer’s issues with his company’s product, and he quickly realized the customer was canceling because the customer didn’t understand the technology or how it could help his car dealership. Jason trained him on the software immediately, showing him how it could help him both make and save more money. 

Ultimately, the customer not only rescinded his cancellation order, but decided to renew his deal for another 2 years. Jason’s persistence – and long drive – had paid off. 

It was a “light bulb moment” for the customer, Jason said, where everything snapped into place and he realized how Jason’s company could help him. Jason loved that. And at the same time, it was a light bulb moment for Jason, because it was early in his career and it was the first time he felt great delivering for a customer. 

“That’s where I was hooked,” Jason said, about making CS his career. 

Of course, this doesn’t mean every issue a customer runs into necessitates a multi-state drive and in-person meeting to help fix the problem. But it’s a great example of a customer responding well to a CSM going above and beyond to help them. That effort doesn’t guarantee success, but it certainly improves a CSM’s odds of achieving it.

2) How CS Can Change When The Product Is Free 

Jason brings a unique perspective to customer success because, unlike previous CS experts highlighted in this newsletter, Divvy is a free product. There is no charge, no renewal cycle and no time period that they’re managing. 

Divvy monetizes its business by having users on its platform. When people spend money on Divvy, the company gets a slice of the fee merchants pay to credit card companies and the issuing bank. That makes customer satisfaction with the product paramount. 

“At the end of the day, our job is to drive adoption [and] drive utilization,” Jason said. “We have to win our customer’s business day in and day out.” 

One huge benefit of the free or freemium model is that customers are more open. As Jason put it, their “guard seems to be automatically down.” That’s a nice contrast to other models, he said, where the customer may feel like you’re trying to sell them something. This allows the customer and CSM to get to the heart of the issue faster and work towards a solution. 

On the other hand, this model doesn’t come with the typical CS “playbook” many other companies lean on, Jason said, so it requires CSMs to be nimble. But the foundation remains the same: “All we want to do is help them solve problems and drive efficiency within their business,” Jason said.

3)  The 4 Essentials 

Jason shed some light on the four things in particular he looks for when hiring CSMs. 

Here’s what he told Josh he has his eyes on during interviews: 

1. A Track Record of Excellence 

 This typically includes promotions at previous jobs, which shows the interviewee is “comfortable in a performance-driven culture,” Jason said 

2. Self-Awareness 

The candidate can articulate their core values and professional goals 

3. Resilience

The ability to be persistent and push forward during difficult circumstances 

4. Proven Ability to Sell  

The candidate has sales success at their previous jobs – or they’ve shown an aptitude to learn to sell