The New Wave of Customer Service #7: Colin Flanigan from Pingboard

Customer service is evolving at a rapid pace, so having a conversation about the field’s major trends and topics has become particularly important. 

Zowie’s New Wave is a series of interviews with trailblazing experts from the customer service industry. They’ll be offering insights and laying out their vision for the future. 

Today, we meet Colin Flanigan, Head of Customer Experience at Pingboard.


About Our Guest

Colin has been a customer experience professional for 10 years and a customer enthusiast for much longer. He is currently the Head of Customer Experience at Pingboard.

As Head of CX, he’s responsible for the planning, management, and inspiration of Pingboard’s customer-facing teams. These include Customer Support, Customer Success, and Technical Support.

He also works cross-functionally. Along with key Growth and Product team members, Colin makes sure CX is supporting the organization’s growth. He helps Product make informed decisions based on customer insights.

When he’s not empowering his organization to bring excellent experiences to customers, he’s probably reading, roasting coffee, or exploring nature with his family.


What does excellent CS mean to you?

This is such a tough question to answer. To me, excellent CS functions as something of a nice surprise to customers.

But I’m not talking about that sort of played out “surprise and delight.” I’m thinking of something similar to the way that finding a $20 bill in the back pocket of your favorite jeans when you didn’t know it was there feels. The fact that it was already there keeps you from being completely shocked, but it’s a nice little bonus to your day. And it really cements those jeans as your favorite pair.

That’s what great CS should feel like—taking an already enjoyable experience and enhancing it. What customers don’t often realize (which is totally fine) is that when great service is paired with a great product, CS influences their total experience of a product, whether or not they’re contacting support.

What do you spend the most time on as a Head of CX and what would you like to spend more time on?

We’re a smaller team, so I spend a lot of time on enablement: tweaking this feature of our software stack here, modifying this process there, that sort of thing. I love it, and I think it’s an essential part of what I do.

There’s nothing that I feel I need to spend a bunch more time on, but two areas that I’d love to work more on are external research (what solutions are companies in similar spaces to us implementing?) and internal communications guidance.

Our CX team is situated in the Growth Department, so I get a lot of chances to work with Marketing. However, I think there’s always more opportunity for collaboration presenting itself, and I know I don’t have time to focus on all of it—at least right now.

What are the biggest challenges in CS/CX?

We have a decent amount of complex issues we solve for our customers, so I find that one of the biggest challenges is closing the gap between the time it takes to troubleshoot an issue and find/create a solution (especially when working with the engineering team) and keeping in contact with the customer.

We make sure we follow up on long-running issues very often so that nobody is left in the dark, but I think that actually holding the customer’s attention is the most difficult part of those conversations. By day three of a pending solution, a lot of customers may have already lost interest. It can become difficult to follow up with them.

More broadly, something I’ve been trying to keep in mind as a challenge is remembering that while my high standard of CS/CX is second nature to me at this point, it may not be for some others on our team.

Sometimes, you just forget how to deal with certain situations if they haven’t come up in a while. Our customers tend to be pretty happy, even when they reach out to us for help. That’s why it can be jarring when someone reaches out and is really upset. I’ve been working on coaching our CX department on capturing, recording, and remembering those instances so that we’re not caught unprepared (strategically or emotionally).

In your opinion, what will change in CS/CX within the next 5 years? What are the main trends?

Automation is an obvious one. I feel like I’m getting a sales email from someone in the CS/CX and AI space every other day. While it’s great, I wonder how customers will actually feel about that trend as time moves on.

There are a lot of wonderful, helpful implementations of AI in the CS space that I’m really excited about, but most of them are transparent about when a customer is working with AI vs. when they’re working with a human. I think that’s key. For instance, any AI or bot presence in our Live Chat software is explicitly marked as a bot, and those bots are explicit when they’re pulling in a human to assist if they haven’t done their job properly. That helps customers trust that we’re not just using AI as a budgetary measure or as a tool to avoid talking to people.

Another trend I see, especially post-pandemic, is people wanting to talk a little more than they used to. We all know the kind of customer who hangs out longer on a call or on the live chat for some chit-chat, and I’ve seen anecdotal evidence that the number of those conversations is increasing.

People are finding the isolation they’re dealing with exhausting, and they’re looking extra hard for that human touch in their CS/CX experiences. They miss interacting with humans in a neutral space. I see that trend increasing a bit more before it decreases.

How could CS and CX teams work together better?

I suppose that depends on how we’re defining CS and CX. On our team, the global label is CX. Billing, Customer Support, Customer Success, Technical Support—all of those are considered CX because they all weave into the customer’s overall experience.

In fact, even though they’re not on our team, I consider everyone at our organization an honorary member of the CX team because, as long as we have customers, there are very few actions any of us can take that won’t influence the customer’s experience one way or another.

In general, the best way to improve work between CS, CX, and any other team within a company is to get people working cross-functionally, talking to each other, and regularly having conversations about the experiences customers are having. For example, while our Customer Success Managers work with a very specific, higher-paying segment of our customer base, they join the same CX meetings as Tech Support, Customer Support, and Billing. That helps our team look at problems holistically.

Often, the various segments of the team will have advice for one another on how to approach a particular issue or process. Customer Support Team members also join CSM calls with customers (especially new ones) to introduce themselves as a representative of the support team and to learn from the CSM’s talking points on the product during account reviews.

What are the challenges around automation in CS/CX?

For a lot of teams, one of the chief challenges is time investment. Like any other resource, be it a Help Center, a video guide, an FAQ, or a product tour, every implemented solution needs to be well-built from the start.

Then, it must be well-maintained. Depending on what solution you’re working with, AI can be particularly challenging when it comes to time management. It has to be well-trained. It has been my personal takeaway that solutions which claim to require no training (as long as they can view previous conversation data and knowledge base articles) can be clunky.

More customized solutions provide a better customer experience. If you want a sophisticated, well-trained AI solution for your customers, you’re going to have to sink in some time training it in the same way you might a new employee—complete with a 30/60/90-day plan and everything. For smaller teams like ours, making this work can be a serious time investment.

There are other challenges, of course—customer perception, fine-tuning over time, software stack fit, etc. However, the time needed at the front end of implementation feels like a particularly high hurdle for a lot of teams.

We want to thank Colin for his valuable insights.

For more pioneering perspectives on customer service, check out our other New Wave interviews.