Episode 108 : How to Build an Effortless Experience Using Conversational Messenger Platforms

Kaitlin Pettersen leads the global Customer Support team at Intercom – responsible for the performance and operations of 60 ICs and leaders out of Intercom’s Dublin and Chicago offices. Previously, she launched Yelp’s EU Customer Success and Account Management in their London and Dublin offices.


  • Could you share a little bit about yourself with us, a little bit about your journey, how it is that you got into customer success and just all of what led to where you are today?
  • Intercom is the name of the company that you are currently affiliated with; it’s a conversational relationship platform. So, for those persons that may be listening to this podcast, could you share with them exactly what does Intercom do?
  • Can you share with us what do you view as the major challenges and opportunities facing customer support right now?
  • Intercom recently launched Conversational Support. Can you tell me a little bit about how you are actually diving into providing conversational support from your end?
  • As a leader, as a customer support leader, what are some maybe one or two traits you think that you really need to be successful in this industry?
  • Could you share with us maybe what’s the one online resource, tool, website or that you absolutely can’t live without in your business?
  • Can you share with us maybe one or two books that have had the biggest impact on you? It could be a book that you read many, many years ago or even a book that you read recently. But it has really struck a great impact on you.
  • Could you share with us what’s one thing that’s maybe going on in your life right now – either something that you are working on to develop yourself or your people, but something that you’re really excited about?
  • Where our listeners can find you online?
  • Is there a quote or saying that during times of adversity or challenge, you tend to revert to this quote? It kind of helps to put you back on track and just get back on what it is that you are working on.


Kaitlin’s Journey

Kaitlin shared that she have probably her entire career since she joined the workforce at 15 at a local cafe, has always worked in customer facing roles, cafes, coffee shops, customer support representatives on up through the leadership track. So, across a variety of industries, including, of course, Intercom and Yelp, as well as some of the more traditional service industries earlier in her career. So, that’s sort of been a through line through it all.

She’s originally from California, she’s been with Intercom for about three and a half years now, and it’s been a real joy and something that she has found to be profoundly exciting and fulfilling to see really the rise of the customer. And she has seen sort of that transformation that she has heard talked about on the podcast in the past and she thinks that all of us have seen in the industry where what happens post sale it’s that, it’s an afterthought. And to see this new wave of call it customer centricity, call it something else, call it just good business practice has been really fun to watch and it’s certainly a change in the industry that her career has benefited from and she knows that the careers of so many.

So, very, very fortunate to lead a really amazing team of individual contributors and managers at Intercom. They are working and using their own product to support Intercom’s 30,000 customers, they believe in a messenger first approach but really stretching the boundaries of what she thinks people assume support means when they hear messenger or chat, this is asynchronous, highly segmented.

They’re leveraging technology, proactive support, and self service support. But that’s a little bit about her, her excitement for this type of work in industry and how they’re currently managing and running their team at Intercom.

What Does Intercom Do?

Kaitlin shared that Intercom is a conversational relationship platform; they offer a variety, a whole suite of products that are layered on top of their messenger. So, you may if you if you haven’t heard of intercom before, you’ve likely seen it, if you’re on your favorite website and in the bottom right hand corner, if you see a little messenger bubble that’s got the intercom smiley face and you’ll know it once you see it. And the messenger is really what sits on the front end that consumers and website users see.

But on the back end of that messenger, you’ve got a powerful platform and tools and a suite of tools and features that allow you to communicate with your customers, really every stage of the life cycle. So, whether that be kind of the work that’s more traditionally associated with, say, sales development that lead generation on through to the actual sales process itself, to the customer management, customer success, customer support, customer experience, whatever you want to call it. And then there’s, of course, the marketing element too.

She thinks so much of how we think about selling, supporting and engaging customers, there’s so much fluidity between those use cases and roles these days. And a tool like Intercom really empowers that fluidity and allows you to use one product to talk to your customers, sort of regardless of where they are in that lifecycle. Most folks would know them as a support tool that, of course, is their bread and butter and something that they’re very, very proud of.

But there’s a lot more to that. And most recently they launched a new system that they really believe in, which they’re calling the conversational support funnel, which really allows growing companies to do what previously has been very challenging or nearly impossible, which is to maintain a high quality, high level of support for your customers, but to do it at scale and to ensure that you don’t have to compromise that quality experience for the inefficiency that growing companies with big commercial ambitions need to prioritize.

Me: Brilliant. I was actually looking at some of the examples of the interfaces that you have on your website while you were speaking. And it reminds me of I’m assuming that the platform I use for my webinars is Demio, they probably are one of your customers because this is exactly how their interface looks when I am conversing with them. And I’ve had many conversations over the last few months, definitely since Covid-19, where I speak about the fact that I love that their platform integrates across different channels, so it’s an omni channel experience. So, whether I speak to them through their website or through Facebook Messenger or through Instagram, all of the conversations are connected. Does your platform facilitate that? Clearly it does.

Kaitlin agreed that it does and that they are one of, as Intercom support team; they’re one of Intercoms biggest customers. And so, she can certainly speak to how they use it. And for them, it is that omni channel experience. So their customers can email them, they can send them a tweet, they can open the messenger on their help center, for example, if they couldn’t find what they were looking for. And all of that flows through into what they call their team inbox. And then her team communicates with their customers through that inbox, sort of regardless of that initial point of contact, it all flows through to that inbox.

And then there’s a variety of features and functionalities to better understand some of the themes coming up in that conversation that would then inform what might be a follow on proactive communication that they would send to you kind of in that customer engagement space or what material, what might be helpful to you is that customer that was seeking something from them. What can they serve you proactively that’s going to be useful to you?

So, there’s a lot that goes on behind the scenes there, behind that little messenger. 

But you are right, it is an omni channel experience and that customers, regardless of their entry point, it all flows sort of through that messenger on the front end into the back end to their team and support teams like her own team who have the great responsibility and joy of talking to customers.”

Kaitlin Pettersen

Me: I love it. I talk about them all the time. As a matter of fact, that was my deciding factor. So even though the platform that I use for the webinars doesn’t have maybe as many features as some of the more established webinar platforms, I chose Demio because of their responsiveness and their customer experience, because that was extremely important to me. So, I definitely give you and your team kudos and an applaud and recognition for partnering with them, having them as a customer and definitely providing that experience for me because I’ve spoken about it so many times.

What are the Major Challenges and Opportunities Facing Customer Support

When asked about challenges and opportunities facing customer support and Kaitlin shared that the list is long but she’ll focus on maybe the top two or three. She had a former leader who called them “problemtunities”, which is probably a silly phrase, she thinks that’s what you got to do when the world is shifting around you and support teams are up against new realities, how do you lean into solve them but also identify what opportunities might be there?

But to answer your question more directly, major challenges, it’s hard to talk about this year without talking about the impact of Covid-19, either directly or indirectly. So, she thinks if we look back to say like let’s call it March through maybe June, everything was changing.

The travel industry is the one that always comes to mind for her as an example, you just have this surge of customers with needs and questions and they’re time sensitive and in some cases panicked and pick your vertical, pick your industry, some version of that happened on the back of Covid-19.

And for some businesses, it was a positive surge. Many, many businesses saying, goodness, our doors are closed, but we can still sell our great products online. How can we leverage the technologies out there to do that?

So, whether it’s a positive thing or a challenging thing, Covid has certainly accelerated change that we’re seeing in customer support. To Yanique’s point in particular, the webinar platform, customers expect a high quality but also convenient experience and they won’t stick around or they won’t say yes to you if they don’t get it.

And she says high quality and convenient intentionally, she doesn’t necessarily say fast. Now for you, you might also say, “Nope, for me, fast, faster is better for Demio.” But she thinks that something that is also changing is like historically people have associated online support or chat support with real time support.

But there are technologies and workflows and processes that you can leverage in chat and in messengers to offer a great asynchronous customer experience. And they can get into some examples of that, of course, if and when helpful. But, again, you can imagine the travel industry business, let’s say an airline, they’re getting a big surge of questions and as people are navigating to their website to grab their phone number to jump and chat or to grab an email address, you can pop up a messenger that serves some information to that customer right there when they need it that says, “Hey, are you looking to understand your options, to change your flight?” as an example.

So it doesn’t necessarily have to be this back and forth real time, faster is better, in many circumstances faster is better. But she likes to be very specific about saying high quality, convenient and in their experience; they also believe conversational, people are using messengers at a faster and faster rate these days, WhatsApp, iMessage, Facebook messenger, Instagram messenger, this is how people communicate now.

And so, making it as easy as possible for your customers to communicate to you. I text my family, I check something else through messenger, and then I message a company with a question and I’m able to interact with them in a way that’s rather familiar to me.”

Kaitlin Pettersen

So, she thinks the need for that sort of personal, convenient meeting customers where they are when they need you, she just thinks the need for that has really accelerated. And then to the volume point she talked about, customers expectations are not changing, but their needs are perhaps increasing.

So, customer support teams, and this is certainly impacted them, have felt overwhelmed by the volume of inquiries they need to manage. And that not only can lead to challenges for customers, but also challenges for your team. Burnout is a real thing. Front line support as you call it, it can be a bit gruelling. And so, as the months roll on, you’re not only thinking about how do we continue to adapt our experience to meet the needs and expectations of our customers but how do we also maintain this great, highly motivated team that we worked so hard to hire and retain? So, she thinks we’re seeing increased needs and volume from customers, we’re seeing increase pressure on support teams.

So, businesses need to adapt faster than ever to adapt to all that change and they need that personalized human way to connect with customers. She also thinks one of the greatest needs of this year in and outside of the customer world is empathy. Everyone is just going through something or multiple things, big and small.

And so how can you empower teams and customer facing folks to connect with customers in a way that empathy can transfer through and everyone can still do their job and get done what they need to get done for the businesses. But sometimes when you’re just dealing with like forms and these more traditional methods of communication, you’re not really able to bring in that element of empathy, which she thinks is also sort of a unique need.

So, all that to say, she thinks big change, lots of transformation, businesses running as fast as they can to keep up. And from her and their perspective, they think that this is creating a movement towards these conversational experiences. So, again, it doesn’t necessarily have to be real time, but how can you meet people where they are? How can you connect to them in an empathetic and real way? And most importantly, how can you meet their needs efficiently?

Launching and Providing Conversational Support

Kaitlin shared that firstly, just to define Conversational Support, it’s probably obvious that just to be clear here, so they believe that conversational support is the next generation way to resolve customer questions. And really what they mean by that is this is a messenger based experience, as she mentioned, showing up for your customers where they are, when they need you, that’s to speak again to some of that omni channel experience that you talked about.

And so, they started to wrap their heads around what is conversational support mean and how can they package this in a way where it really makes sense to the market where they can say, “Hey, we think there’s a better way to do this and here’s how to think about it.” So, in June of this year, which in 2020 terms feels like 9 months ago, but it was just a few months ago, they launched a framework for delivering this conversational support and they call that the conversational support funnel. She mentioned that earlier.

And so, this is really a blueprint to show businesses how to increase efficiency, because that’s certainly a need, it’s always been a need in the support space, but has increased in importance this year. How can you improve your customer experience and then how can you improve the morale of your team? Let’s not forget about these teams that are doing such great work out there.

And so, this funnel is a concept for how they think modern support should look like and how it empowers customers to scale these messenger based experiences. Because, again, in the past, she thinks folks associate messengers or chat experiences with very expensive one to one real time support when it doesn’t need to be that way.

So, to bring that funnel to life, you can picture your little upside down pyramid here, at the top you have proactive support. So, again, to her airline example, what are the known questions that you know are coming in that can be answered proactively using targeted content?

And so, for them on their team, this looks like a deep partnership with their product education team that owns their help center and produces materials that help their customers. How do they partner with them to surface the right content, at the right place at the right time? And this is a balance, you don’t want to overwhelm customers with information that they don’t need. So you need to be really thoughtful here about surfacing the right again, the right thing at the right time, at the right place.

But that’s that top of the funnel is get to the customer before they even have the question. And she’s sure we can all imagine these really delightful experiences we’ve had unfortunately they can be few and far between them. But you’ve got a need/question, maybe it’s time sensitive and you jump onto the website or you pull up the email and it’s like there it is, there’s what you need. And you just saved yourself 30 minutes and that feels really good.

Going on down the funnel, you got self-serving report. So these are those repetitive questions that can be answered automatically using chat bots or the knowledge base or help center.

So, they have a product called Resolution Bot that they use, but there’s a lot out on the market that allows you to kind of programmatically recognize, “Hey, this is a repetitive question and we’ve got the answer and let’s serve that up to this customer.” We’ve seen this go wrong in the past and what’s exciting about the chat bot space is we kind of saw this. If you kind of think about technology, there was like the boom and then the bubble burst and then this new wave tech, she thinks similarly with chat bots there was like chat bots are the next generation and it really didn’t work.

And you can imagine the like stock photography photos and you know you’re not chatting to a person, you know you’re chatting to a robot and you keep trying to get out of the loop and you can’t. That’s the past. The technology is moving very quickly and they believe in making people know if it’s a bot, tell them it’s a bot, “Hey, while you wait for Yanique and her amazing team, does this maybe help to answer your question, thumbs up or thumbs down? Thumbs down. Okay, no problem. You want to wait for the team? It’s going to take us about X hours or whatever it is to get back to you.”

So, you’ve got to do it right, leave the objective stuff to the bots, leave the empathy to the humans, and then that gets us to the third and final point in the in the funnel, which is the human support.

So, complex questions that can only be answered by a human. But it isn’t just about like whittling the volume down to your great smart humans, but also making it easier for them to work more efficiently. How can your system help them do their job more effectively, more efficiently and maybe even more delightfully.

So, conversational support is this idea of using a messenger, meeting customers where they’re at. And you’ve got this funnel, which is this framework that’s like, Okay, I’m into this conversational support thing, but how do I do it?

And they think that that’s the proactive piece, the self-serve or automated piece and then there’s the human piece. And then the last component here and you could tell she could probably go on hours here because this is really exciting.

The last thing she’ll say is in August they announced a whole bunch of new features and tools to bring enterprise grade efficiency and scale to customer support for the first time.

So, traditionally businesses have had two choices, old school email ticketing forms and these allow teams to work efficiently, it organizes your customer’s needs into a nice and tidy queue and they’re just going to wait as long as they wait but they’re transactional. And then on the other end of the spectrum, you’ve got that fast personal messenger based experience that delighted customers. But synchronous is expensive and it lacks the under powering flexibility or underlying power to keep up with how larger teams work and scaling businesses, that gets really expensive and unmanageable really quickly.

So, they built this whole suite of tools to enhance this funnel or this model. And they think that they’re more powerful and efficient than your traditional ticketing system, that they take that messenger experience, they unlock all components of that funnel and enable businesses to not have to make that tricky choice between clunky ticketing, old school or modern but expensive, finding that happy medium.

Traits for Being a Successful Customer Support Leader

Me: So, Kaitlin, what are some important considerations for customer support leaders like yourself to be successful? So you spoke a lot about conversational support and a lot of these people that are working in your different teams with different organizations, they literally have to be out there in the battlefield every day offering that level of empathy, offering that level of understanding with customers, even if it’s situations or circumstances that they’ve never experienced themselves. As a leader, as a customer support leader, what are some maybe one or two traits you think that you really need to be successful in this industry?

Kaitlin shared that she loves this question and she thinks Yanique hit on such an important point, which is sometimes as a leader, you don’t know what it’s like. And something that always comes to mind for her is to know the difference between what she would call knowing the material and then leading.

And she thinks as the support or experience leader, it’s our job to do the latter, to lead. Our discipline in this wild world of customer support more than most means that your frontline employees are likely to know how to do their jobs or at least have the answers to your customer questions much more than you ever will. She jumps in to talk to their customers every now and again because it’s the right thing to do and it’s a great way for her to connect with their customers and team and it is the most humbling experience.

She mentioned that she is the most rookie person on their team when it comes to knowing their products and talking to their customers. Whereas if you think about, say, like the sales world, which she has a background in prior to post sale.

A leader can really coach those core sales skills and then you apply that philosophy to how your team approaches their book of business or their prospects. So, she thinks….

It’s really important as a support leader to recognize you’re very likely not going to have all the answers and so your value doesn’t come from that, your value comes from building a strategy that allows your team to always be improving what they do for your customers and to feel for themselves that they’re always advancing, that they’re learning more, they’re doing more, that they’re developing in their own careers.”

Kaitlin Pettersen

And she thinks that’s what’s really important to hire and maintain great talent. And so, she’s really big on that one and she kind of had to learn that in the hard way, because really in her experience at Yelp. She had done everything in sales and post sales support except maybe sweep the floor that they sat on.

And so, understanding what is leading the team look like, how do I enable them to be and feel more successful?

And how do I really own delivering great experiences for our customers and how do I leverage our team to do that?

So, she thinks that’s a really important one. And then the second one, she’d say would be finding the balance between maximum efficiency for your customers and then maximum delight.

And she touched on this a little bit earlier as part of the funnel. But this is really going to look different for different businesses and brands. Ritz Carlton, they’ve got the bank account and the brand to air on delight.

But a lot of businesses out there, that isn’t what you need and so regardless of where you sit on that spectrum, do we need maximum efficiency?

Do we need maximum delight?

Everyone should probably fall somewhere in the middle. But being intentional about understanding where your experience for your customers should sit and then what you can do to drive for those outcomes.

So maybe you’re going from bootstrap startup to scaling up business that wants to go public, you’re probably going to need to lean a little more on the efficiency side because you’re going to need to tighten the belt and button up costs.

And so, again, she thinks it changes as the business grows. But being really intentional about understanding where do we fall on the spectrum and then how do we leverage our tool, stack, our team, workflows to help us achieve that outcome.

App, Website or Tool that Kaitlin Absolutely Can’t Live Without in Her Business

When asked about online resources that she can’t live without in her business, Kaitlin shared that she always feel bad because they’ve got a lot of favourites. So, she will cheat by saying they, of course, couldn’t live without Intercom. They drink their own champagne, as they say. She doesn’t like the dog food phrase, so she likes champagne, so they drink their own champagne.

But aside from that, she would say that your sales team, too, but certainly your support team, especially in a remote working world, which that’s a whole other element of Covid that we didn’t even talk about.

A knowledge management tool and process, and so they are super fans of Guru, which is a knowledge management system for all sorts of teams. And what she loves about it in particular, they all know what it’s like to try and tackle an outdated internal wiki or to go look for an answer only to find that it’s a year or two outdated. Is they have really smart AI and machine learning and great kind of powerful technologies behind the scenes that really make it very easy for teams to keep their internal resources updated.

And they also, in that spirit of proactive support, they kind of help to surface the right content to your teams at the right time. So, she’s got a long list of products and tools and companies that they love. But she’s a big believer in your team, especially in a remote working world is only as good as is, it’s the quality of its knowledge management system. And for them, they’re big fans of Guru.

Books That Have Had the Greatest Impact on Kaitlin

When asked about books that have had the biggest impact, Kaitlin shared that she always struggle with this one and she will put her hand up and own it. Inside of working hours, she is diving into, throw her a white paper/sheet, throw her an article, throw her a podcast, she is into it. Outside of work, she is a fiction lover, but in the space of customer experiences and support, she will share a book that stayed with her.

One is The Effortless Experience: Conquering the New Battleground for Customer Loyalty by Matthew Dixon. Into that scale she talked about between efficiency and delight. She thinks that long held belief that you got to go above and beyond for your customers and be the Zappos and the Ritz Carltons of the world, which if that aligns with your brand and you’re intentional about it, then right on. But don’t just assume that that’s what you need to do. She doesn’t remember what the stat is, but that in Effortless Experience, it talks about like channel switching.

She was having a conversation this morning with their community manager about someone bouncing from their messenger to their community and then bouncing them back to messenger. They want to avoid that, they don’t want to bounce them around. So Effortless Experience really stayed with her because she loves that it challenges this long held notion of striving for delight when really ease and effortlessness is what customers need. So, that would certainly be one.

And then this is probably when she got her first “real job” which was Yelp back in 2009 which was Crucial Conversations: Tools for Talking When Stakes are High by Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler, and she has probably leveraged the learnings from that book more in her personal life, even though her professional.

Front line, post sale, pre sale, you’re having some tough conversations for a variety of reasons and understanding and she thinks the framework that stuck with her from that one is identifying a common goal and partnering with the person you’re speaking with to achieve that goal.

She uses it in her marriage; she uses it when working with folks on their team. And back in her kind of frontline days, she certainly used it when talking to customers.

 And at Yelp when they were talking about really sensitive things for small businesses like one star reviews. So, Crucial Conversations definitely an oldie but goodie and one that she thinks is helpful in and outside of the professional world.

What Kaitlin is Really Excited About Now!

Kaitlin shared that now more than ever, she thinks is important for all of us to find something we can get excited about, that’s something we all need this year. So, she loves that Yanique is asking folks this question.

So for her at work and she thinks as a leader, you need to strike this balance between guiding your team through the problems that are right in front of you. And this year, has presented more than maybe many of us were ready for and putting out fires.

Especially as a strategic leader, a few levels up, you really need to be building out what does success look like for us next year? And what about the year after that? And what is our target? What big, audacious, ambitious goal is our company targeting in the next few years? And how does the work of my organization contribute to that? And so, she thinks that’s always the balance of enabling your team in the moment and leading them through challenge of challenges present and also mapping out the future.

And nothing goes according to plan, of course, but building the vision, building the strategy to help get there, making sure that the work that your team does isn’t just purely reacting to what’s coming in, but also contributes to this larger goal for the company.

So in the spirit of that, she will be very transparent and say that they took a kick in the bum this year in terms of their support volume, and they found themselves in a place they’d never been before, which was sort of upside down and offering much slower wait times than they ever had.

And so, supporting the team and getting through that and coming up with big, bold strategies and ideas to help them do that is something she’s currently excited about and is the top priority because their customer experience is number one and how that impacts their team, because those things go hand in hand.

But longer term, like any company at Intercoms stage, she’s looking ahead and for them, that looks like building the future of their upmarket support offering. So startup early stage, you’ve got founders talking to customers, you’re going above and beyond for every single one to not only just retain them and keep them in the door, but also understand their needs and use that to inform your product roadmap.

And then you get to the next stage where you’re hiring a support team and you’re scaling it out, but you’re offering that one size fits all experience to every single customer and you’re trying to make it great.

And then you get more customers and you start to set your eyes on some ambitious targets in terms of like funding or liquidity events. And she mentioned this earlier; you got to tighten up your belt. And so, for them, the inflection point that they’re really at now is their enterprise segment and their upmarket segment is really swelling.

And so, their offering to them has been, “We’ll move you to the top of the queue. If you’re a premium customer, we’ll get to you faster.” That is so rudimentary, it lacks nuance, and it lacks sophistication. So she’s having some really fun conversations with folks on their sales team, with some customers, as well as folks in a variety of other departments to help her understand what they’re building, the future of the market support at Intercom look like not only in terms of the speed and quality of experience that they’re offering, but what does it look like on, say the availability side of the house and bug escalations and proactive partnership opportunities.

And so, that’s her sort of looking ahead of her toes out across the next few years and she’s really excited about it because building is really fun to do and she’s finding the conversations she’s having all over the place to be rather energizing and inspiring. So watch this space for what they built, but she’s pretty excited about it.

Where You Can We Find Kaitlin Online

Kaitlin shared listeners can find her at –

LinkedIn – https://ie.linkedin.com/in/kaitlin-pettersen-9a315215

Twitter – @kpetterman

Website – www.intercom.com

Quote or Saying that During Times of Adversity Kaitlin Uses

Kaitlin shared that there is a quote that carries her through personal and professional challenges and is really, for her, a North Star or a guiding principle as a leader. And it is the amazing Maya Angelou’s, “People will forget what you said, they’ll forget what you did, but they will not forget how you made them feel.” And she gets tingles when she thinks about it and when she thinks about her. When we think back in our lives, on the leaders, on the companies, on the brands and the people, the exes, the friends, you don’t remember the words; you don’t specifically remember the actions, maybe unless they were really good or really bad.

But you remember the feeling, it stays with you. And she thinks that’s true in business, but certainly outside of business as well and through adversity. She hopes that their team and their customers will look back on this time and say, did Intercom nail everything?

Of course not, because who would? We’re all just adopting and doing our best and working really hard. But did they lead with empathy and transparency and heart? So that’s one that she’s so glad she had the opportunity to talk about, because she thinks it’s such a great quote.

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