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Podcast Recap: Customer Success - The Answer to Scaling

Updated: Jan 31

Customer Success is one of the fastest-growing careers right now!

Since 2015, LinkedIn reports that the role has grown by 736%, especially amongst the Software and IT industry, showcasing how pivotal the position is for subscription-based business growth*.

And it’s because we’re relying more on tech but people still buy from people.

One of those software giants is Dropbox. In their 2019 third-quarter results, they beat their market expectations due to growth in their customer base. Luckily, there’s a podcast out there that breaks down their customer experience setup!

Hey everyone 👋, in this post I’ll be recapping an episode from the Build Podcast along with Lisa Ashcraft, the former head of Customer Success over at Dropbox.

The Details

Lisa Ashcraft started her professional career over at Cisco in some very deep domains within Engineering and Analytics. She went on to jump around a bit within Cisco and found a place in something she says she had no business in, UI/UX. Throughout all this time, she learned so much from her journey within large enterprise IT. She made her move over to Dropbox when someone she climbed the ranks with at Cisco gave her a call and said: “We have this need and you’re the right fit”. She accepted and went on to lead the Success team there!

Build is a Podcast hosted by OpenView, a venture capital company focused on the expansion stage. If you’re in SaaS, this is a newsletter you WANT to sign up for. They go deep into topics about market research, product-led growth and so much more!

Okay, so top three takeaways from this episode, let’s go ↓

  1. How to decide who gets a CSM?

  2. Scale around the repeating patterns

  3. Retention is not always the priority

How to Decide who gets a CSM?

It’s the question that has a lot of us scratching our brains and gracefully disagreeing with each other.

scaling with customer success

Which customers have access to a Customer Success Manager?

Dropbox offers a freemium model and they also cater to enterprise-grade companies so drawing the line has involved teams outside of Success. Their Support and Success team both sit within the Customer Experience team and while the Support team handles reactive customer interactions, the Success team focuses on a specific segment.

To draw this line, Lisa stresses the importance of getting “clear and clean on where to play and how to win”.

This means creating clear segments which include factors like:

  1. Size of the company

  2. Location

Yet she admits that there was still some confusion internally around the size of the company vs. the amount they purchased (we all wish things were more black and white when drawing this line).

Their first stab at drawing the line was offering Success services to companies with 100 employees, then that number jumped to 250. The line has evolved several times over the years and has been assessed annually.

At the time of the podcast, the support and channel teams work with companies with less than 250 employees and companies over 250 with 100 licenses purchased are eligible for a Customer Success Manager.

Of course, there’s always a gray area…

Like companies with large logos–you know, the ones that could be worth a pretty penny down the road. For those companies, Lisa says that, yes there’s a framework in place to help them operate but exceptions will definitely be made!

Scale around the repeating patterns

Blake asked a great question around scaling:

“For customers under 250 employees, how do you scale Support/Success?”

Lisa points out that clearly, there’s an investment of staff and intimacy with top of market customers. But what she’s looking for are some repeating patterns. These are the pain points and tactics used to solve that pain.

To find these repeating patters, she recommends we keep an eye out for the playbooks (how we’ve been solving the pain points). Once that’s done, we need to decide if these activities are something we need to keep doing because it’s core to our relationship with our customers or if we should source and scale it and give it to SMB/smaller teams within our portfolios.

scaling with customer success

Lisa and her team learned that teaching these larger companies how to use Dropbox through 1:1 training was a context, not a core activity. They sourced this by bringing on some agencies to build out this experience and help them scale. A Customer Success Manager was averaging 20 – 50 touches with customers a week and training 10 – 15 of them depending on how they organized it. With the agency’s help, they were touching 3,000 a week!

Here’s an example of a specific scaled training program with two offerings:

  1. Web-based training/self-guided training – A three-module training which includes 1) end-user training, the main focus is “what do you need to know as an end-user to use the product?” 2) Admin training, admins need to need to know the product and how to set it up for their team 3) Help desk for larger enterprises that need to abide by certain regulations.

  2. Virtual instructor-led training – This is a training is a bit more on-demand. A team requests a date and time for their training and enter a “learning classroom”. The training is offered in 6 different languages and the instructor follows a script. Everything covered in the web-based training is also covered in this training.

There are other repeating factors outside of training which we should be inspecting. Training just so happens to be a great example 🙃

Retention is not always the priority

Customer Success paves the way to customer retention* This quote resonates with many of us as it’s probably tied into our KPI’s in some way or another.

And while retention is useful, it shouldn’t always be the North Star. Lisa urges leaders to inspect the behaviors that need to drive at a certain time.

For example, if retention was always the focus, Dropbox would’ve gotten a different set of behaviors. Back in the day, it was important for them to drive the advocacy externally of their customers. They needed their customers to talk about Dropbox’s product value, in particular, they needed enterprise leaders to talk about them publicly.

So at this time, getting these customers to renew was good but getting them to speak publicly was even better.

This very thing was what helped Dropbox move into the enterprise market. The transition from servicing consumer-grade products over to enterprise wasn’t entirely smooth. There were some gaps in their enterprise capabilities and gaps in support. And it was the Success team that helped them cross that chasm!

By leveraging really strong relationships with customers, they were able to manage these gaps. The customers knew what they were getting from the product and in return, Dropbox also knew what they wanted to get from these customers…

Them speaking publicly about the product!

So be thoughtful about what you need right now especially when it comes to the relationship you want your Customer Success team to have with that target market.

scaling with customer success


  1. Get clear on where to play and how to win – draw a clear line for when CSMs are involved

  2. If an activity is not part of your core identity as a company, consider outsourcing it to help you scaling

  3. Think about what your company needs at the moment and define your Success KPIs based on this

Shout outs

Thanks to the Build podcast for hosting Lisa! Go follow Build them on Twitter

And if you want to hear more from Lisa, connect with her on LinkedIn



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