Episode 092 : How to Revolutionize Your Digital Transformation with Ryan Lester

Ryan J. Lester, Senior Director of Customer Experience Technologies at LogMeIn. Ryan and his team own the strategic development and implementation for the go to market plan for Customer Experience and Digital Engagement offerings across their platforms, Chatbots, Virtual Assistant and Workforce Optimization (WFO) products.

He is passionate about making new technology easy and helping any sized company unlock the potential of AI and bots. Prior to his role at LogMeIn, Ryan held various sales, marketing and product positions at Intel Corporation, Cisco Systems, and Eaton Corporation. He has a passion for making new technology accessible and approachable.


  • Could you share a little bit about yourself? You seem to have a diverse background, sales, marketing, product development and now you’re into customer experience technologies. Tell us how your journey has been and how it has gotten you to where you are today.
  • So could you share with us maybe three to five things based on your experience that if you have a digital platform, that you are facilitating to your service deliver or product delivery through, how you can make that an effortless are frictionless experience for your customer? What kind of things do you need to look at in your journey to manifest that kind of result?
  • Could you share with us maybe a few things that companies could do to find out what the problem is? Is it case where they need to ask, how would you know what a problem is?
  • Could you tell us a little bit about LogMeIn, what it is that they do? What problems are they solving for their customers?
  • How do you stay motivated everyday?
  • Can you share with us what’s one online resource, tool, website or app that you absolutely cannot 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 recently or maybe something you read a very long time ago, but it still left a very indelible mark on your success, on your journey.
  • Can you share with us one thing that’s going on in your life right now – either something that you’re working on to develop yourself or your people?
  • Can you tell our listeners where they can find you online?
  • Do you have a quote or saying that during times of adversity or challenge, you will revert back to this quote are saying, it kind of helps to refocus you on just keep you channeled.


Ryan’s Journey

Ryan shared that even though he’s an only child, he’s very much a people person, energized by people. He loves solving problems, the way he really describes himself is kind of the head of an engineer and the heart of a marketer or a customer centric person.

So, he loves tackling new challenges, but he also loves staying close to the customer, because at the end of the day, you want to solve their problem and you want to make their life better. And that’s what keeps you in business and drives your organization.

And so throughout his career, he started out in the world of sales and really learned a lot there. And he started spending more time in the product world and then really kind of landed on this intersection of customer experience where understanding the customer’s journey, the friction points, why they buy from you, how you can make that experience better really is something that drives his passion.

And so he has been doing this for a number of years, and he really loves doing that at LogMeIn, really helping them as a company, one, create better experiences for their customers, but two, create technology that customers of theirs can use to deliver better experiences.

So, it’s really a wonderful space. He finds there’s lots of big challenges to solve and it gives him a lot of interesting work to do each day.

Me: So everybody pretty much, globally, many businesses are forced to even if they didn’t have a digital presence, they’re pretty much forced to create some level of digital presence or if they had digital presence, but they maybe weren’t optimizing it in its best form. They pretty much have to be putting a lot of energy in that space now because people want to minimize on their face to face interactions just for being safe.

I found, just based on my experiences, sometimes these digital experiences that we have, they cause you to have to exert a whole lot of energy and it’s not a smooth experience. It’s not effortless.

How to Deliver An Effortless Experience Digitally

Ryan stated that that’s an excellent question.

“He thinks it’s spot on that there’s two reasons why digital really maybe hasn’t kept up or often can feel like a second class experience. And the one reason is because oftentimes it’s under invested or it’s not a top priority. So, we focus on things like in-person and phone and email because those are all the more established, higher volume.”

Ryan Lester

But too often we don’t approach the right problem. So, we often say, well, we have this new technology, we have chat or we have messaging channels or we have AI and we try to just take the technology and then go just apply it versus being very specific about the problem we’re trying to solve.

And it goes back to just good customer experience practice. At the end of the day… What is the thing that the customer needs help with?

Where are those friction points or where is that high customer effort?

And let’s go understand the problem first, and then try to understand the solution.

And so he thinks that’s often where companies get caught up, is they’re taking technology and just looking to apply it versus saying rather, what’s our problem and how can technology make it better?

So, to give some real examples of that, one really simple thing we’ve seen in the challenges around COVID-19 is that information and policies are changing at a very rapid pace and something as simple as maybe the hours of your office or what are the rules around coming into a physical branch or a physical store or even of your return policies change or your shipping policies changed?

In the current state, that’s not really a great thing to have somebody to call in to find out. People don’t wait on hold. They don’t have to go through the effort. So either you have a customer that’s churning because they don’t want to go through the effort or you have an upset customer because they went through the process and they can’t figure out an answer.

So one simple thing you could do is to say, let’s modernize our FAQ page, we all have that kind of old grandma’s attic, we all have that part of our website where it’s like frequently asked questions and it’s meant to be helpful, but oftentimes it’s really not focused on, it’s under invested. And so, now we can take a technology like AI, maybe even something like a like a simple bot and we can really spruce that content up.

And it’s not to say we need to update all of it, so we don’t need to take every single article, every piece of content and breathe new life into it, but maybe we take our top 10 intents or questions coming into the contact center or to our customer service teams and we put that into a better, more AI powered support center page or a simple bot. Now, all of a sudden, all those questions are being answered in more real time. So, people are getting faster, more consistent, 24 hour answers. And now our teams are freed up to spend time on more interesting things.

So it really comes down to think about what’s a problem you want to solve and how can this newer technology, digital technologies make it better. And there’s other examples, for example, leveraging things like messaging channels.

So, WhatsApp is very popular, Facebook Messenger, it’s very easy to stand these channels up and put something like a very simple bot or even have your live agents leverage those channels so rather than making the customer find your website and look it up and wait on hold, they can ask some simple questions over a messaging channel they’re already in that they’re conversing with their loved ones who maybe they haven’t seen or that they’re posting the latest image of them making maybe something fun in their kitchen.

How to Understand and Be Clear on Solving the Customer’s Problem

But they’re already there. So now, rather than forcing the customer to come to where you are, you’re going to go where they are today. There are lots of these great examples of once again, understanding the problem, is the problem access to information? Is it engaging the customer where they are today? Is it consistency, being clear on what’s the problem and then applying that right technology to solve it?

Me: So, Ryan, could you share with us maybe a few things that companies could do to find out what the problem is? Is it case where they need to ask, how would you know what a problem is? Should I just sit down in my office as a customer experience strategist/specialist at my company and say, “Okay, I’m going to think of what I think the problem is and make a solution or should it be a case where the customers, you’re kind of watching what they’re saying, listening to what they’re saying, identifying based on previous conversations, what they’re asking for, and use that data to inform your decisions to solve problems.”

Ryan shared that both are correct, it’s probably more 80% the second and 20% the first. So he thinks certainly there’s lots of information out there. We can take call records; we can take survey information. If you have something like web chat already, you can take all those web chat logs and look through that data. So there’s a ton of information that we already often have around our organization.

And then now becomes using that data to then drive our decision. And it’s not always that the data will tell us the answer, it’s sometimes that the data will just tell us what’s the next test we want to do in the world of scientific method. It defines our hypothesis.

So we say, “Oh, based on what we’re hearing from our customer service agents, our customer service employees, these are the top five things that they feel like are the most friction, that they get a lot of call volume on or that customers feel frustrated.”

And then we can say, okay if that’s what you think is the problem, let’s build a hypothesis. What do you think could be causing it? And then let’s go try and test that, both validating that the problem is really there. And then two, ways we can correct the problem. So he thinks it’s spot on that things like NPS scores, post interaction surveys, transcripts. There’s a ton of information that often we already have or are very easy to stand up that can help point us to that challenges.

To the original point, it also isn’t back to just sit have those moments of reflection to say, well, here’s something I think is a problem because often times we’re very much in the middle of things, we’re kind of in the weeds and so, it can be nice to say, “I think there’s a problem, let’s go once again, try and test it.”

So, he thinks we have a challenge maybe around how we do traditional customer service or how we do returns. It feels like there’s a lot of effort and energy around that from a customer’s perspective. Let’s go set up a test and try that out. So, it’s not always going to come to light immediately from the data we have, it’s also okay to kind of have as an expert your perspective and then go test and learn.

Me: And in terms, you mentioned just testing and developing a hypothesis, it’s critical for us to solve the problem because all businesses go into business to solve a problem. If you see a product or service, you’re really solving a problem for someone. So we’re operating in his new realm and employees play a critical role, especially if you have employees in the business, they are a lot of times the front facing persons who interface with the customers on a daily basis.

How about integrating them into the solution as well? Asking them to help you solve the problem? Because I think a lot of times they have the solutions themselves, but then they’re not the change makers or the policymakers.

Ryan agreed and shared that there’s an interesting project they had done with a white goods retailer, so someone that sold like refrigerators, ovens, etc, in the U.K. they’re called AO.com and they’re rapidly growing. And many of their frontline employees, to your point, the people working with those customers had a really good perspective.

They had really good sense of where the challenges were, where it was hard for them to get their job done, where the customers felt pain, and they created a project where they got them actively involved and what they did, this is a little more advanced, it’s certainly something most people could do. But it would be more for like a mid-sized business is they created a technology that faced the agents, so an improved knowledge base.

And they actually put a chatbot in front of it. So, rather than having something that faced the customer and the customer question this answered their frontline employees’ questions. So, if someone said, “Hey, I have a question around the return policy for this product.” or “Does this product come in stainless steel?” or “I see it comes in electric does it also come in gas?”

As they’re on the phone or they’re interacting with these customers, they could quickly interact with this bot and get a very quick answer, it’s wonderful. And so one, to your point, they identified the problem, they started to find the solution but then two, was really nice out of this is they also started to curate the content.

Everybody has great experts across the organization incur what it’s often like, you go but bumped your elbow up to the person and say, “Hey, I got this really tough question, I know you’re going to have the answer.” That doesn’t scale. So the nice thing is by leveraging something like AI or a knowledge base is now all of a sudden when that expert enters the right answer. Now, everybody, not just the person next to them that can bump them with their elbow has access to that information.

So to your point, he thinks you really hit on something critically important one, they know where the problems are. Two, they often have the energy and enthusiasm to fix it. And three, they often have the expertise to fix it. And then the question becomes, how do you turn that into a micro fix versus a macro fix where it impacts every employee?

Me: Agreed. Wow. That’s a beautiful knowledge base and having that resource material and you’re right. Sometimes it’s just that one person who has all the information, but sometimes they’re not always accessible. So why not have that information accessible to every single person in the organization that they can type in and get that information in real time on pass it on to the customer, I love that!

Ryan stated that what’s exciting too is there’s this great reinforcing loop that happens where one, now every frontline employee has access to that so they feel like their job is better and easier and they’re getting what they need to be successful. But two, as employees enter in that information, they’re feeling empowered because they’re helping the whole organization. So it’s a great flywheel effect of people feel empowered, they feel energized. They’re getting what they need to do their job better.

But then they also can help the next round of employees as they’re making that content more accessible and better over time. So, they’ve seen really great results of that. And once again, that could be an employee facing a sort of content; it could be customer facing content. And it’s relevant to the digital world; the physical store is that kind of reopens and certainly the contact center. So, there’s lots of great directions as a CX practitioner you can kind of point this technology and these capabilities to drive improvements.

Me: So in relation to chat bots, I was listening to a webinar recently, some of the panelists were customer experience practitioners, as you mentioned. And one of the things they’ve said, I’ve never had to experience myself, but I can see it happening where you start a conversation on someone’s website along your journey into experience with the chat bot and so it has gotten to a point now where it needs to be escalated, the bot can’t continue that interaction anymore.

And so when it’s escalated to human interaction, it’s almost like the customer has to repeat everything they told the bot, all the information that the bot would have asked them for they’re basically having to regurgitate all of that information over again.

LogMeIn | Go to Meeting | Go to Webinars | Bold360 | LastCall

How can companies ensure that when they implement these systems, they implement it in such a way again, that you don’t feel frustrated? Because that would be the equivalent of me calling a company, speaking to somebody on the phone, being transferred to somebody else and I have to repeat myself all over again. It’s just happening now in digital experience to human.

Ryan shared that it’s spot on. They use the term at LogMeIn called harmony. And it’s a harmony between the bot, the agent and the customer.

And you have to have all of them kind of singing the same song or working off the same sheet of music. Yanique is spot on and so that’s a terrible experience. And just to your point, it’s just like if you call into a call center and you talk with someone and it’s like, “Oh, I need to transfer you.” And then you get to the next person and they’re like, “Hi, how can I help you?” It’s maddening.

So, what they specifically do at LogMeIn, that’s actually one seamless conversation. So as you’re in that little chat window and that could a chat window that’s Facebook Messenger or WhatsApp or could be inside of an app like, for example, if your bank had an app or it could be on a website. If the bot starts a conversation and it’s set to do certain things and if it can’t accomplish those, it can then pull in a live agent.

What’s nice is when a technology is done correctly is that agent then can see the transcript of all the things that have happened previously and they can look through and say, “Oh, I see where we’re at now.” Also, what what’s interesting about technology is it also should be working in the background so the bot doesn’t go away. It’s just that when the agent’s talking to the customer, the bot now is working behind the scenes helping the agent.

So if a customer asks a question around, “I have a question about a certain type of checking account.” The bot has information, it knows about that account and can pull that information up. So one, that can just be a good reference for the agent so they know or if they’re chatting in chat, they can copy and paste that information in and not have to go look it up for themselves.

So, Yanique’s spot on that the right way to do this is how we all have one seamless conversation and that when the agent is pulled in, they’re given the context and the background on how that customer’s doing, where they’re at in their journey and what problem they’re trying to solve. So that is the best way to do it.

And really, if a platform doesn’t offer that capability, he would really kind of second guess them because really any of the kind of best in breed platforms offer this capability around that seamless integration between bot and human.

Ryan shared that LogMeIn, it’s a fun company. It was founded in Boston where he lives and went public in 2013, a little before that. And they have three different businesses.

They focus on communications and collaboration. So products like Go To Meeting and Go To Webinar, really focus on how they help people work better together. They have an identity and access business which is focused on how do you connect to devices securely and that has a product call LastPass, which maybe you’re familiar with, but it’s a great product for organizing all your passwords across all different websites you go to, it’s called Last Pass.

And then he works in their customer engagement support business is really focused on technology around helping brands better engage with their customers. And so, they have a product called Bold360, which is focused on digital engagement.

So, in many cases, people have phone capabilities, they have maybe e-mail capabilities but digital is still new and emerging. And to an earlier point, Covid-19, is accelerating that.

But they have a platform that really helps companies rapidly accelerate digital. So that could be chat, it could be messaging, it could be AI based support center pages or dynamic search bars. But basically it’s saying there’s all this wealth of capabilities that comes in digital and the nice thing about them is they’re usually more readily available. They’re available 24 hours a day; they’re more extensible, so you can put them in more places like in an app or in social channels.

And they’re also often less costly to manage in the sense that either agent can do more, so they can be more conversations at once or they’re just lower costs to deliver. And so, there’s a really a kind of a net, it’s like a win, win, win of the customer wins because it’s easier for them to use it, the agent wins because they’re more productive and efficient and the brand wins because it delivers a better experience.

And so, they’ve been in this space for a number of years. And he likes to say, “We drink our own champagne.” So, they have our own chatbots and experiences on their website and so Go To Meeting has a chatbot and Last Past has a chatbot and their Bold 360 project does. So, it’s also fun for his as a practitioner because he has his own little test beds where they can try different things and different experiences and test and learn and share those insights.

Me: So, you basically provide that integration for the companies that you serve as it relates to the different platforms that they maybe communicating with their customers on, so one central place where you can navigate on that customer experience.

Ryan agreed and shared that basically, all of those digital engagements are housed in one location. Once again, for you to get insights out of improve the content, improve the customer journey so you can think about it kind of as your one time investment to really accelerate your digital experience.

Me: So, we’ll definitely have the link for Bold360 in the show notes of this episode for any of our listeners who have businesses that want to take advantage of this wonderful software that exists. And I imagine you service customers not just in the United States.

Ryan stated that they have global customer base all over. So, all over North America, Europe, Asia, India. So, they certainly service customers, they support 50 languages natively with the chatbot in 88 languages more broadly. So this technology can work quite well in many, many applications.

Ryan shared that he mentioned earlier that he’s a people person, so he loves interacting with people, so that is a huge motivator for me. So just, inspiring those around him and bringing the best out of them and passing that energy back and forth. So that’s one.

And two, he really loves solving customer problems. So he gets very energized around thinking about their customers challenges and improving how they can solve them today and into the future. And then three, he really loves consuming and creating content. So, he also does his own podcast and he really enjoys listening to podcasts. So he finds that the creation and consumption of content really energizes him as well. His podcast is called CX Next.

They recently just changed it; they were doing a podcast for an AI and they were talking a lot about CX topics and then so about two months ago they changed it from AI IRL to CX Next. So the podcast is a little new, but they love it, he really enjoys it.

They also do a weekly video series also under the CX Next name, CX Next Live. But he finds like these kind of conversations are just once again, very energizing and interesting and you get great perspectives doing them very good. Ryan shared that the lives are housed across all but most of their engagements on LinkedIn. But they do also post them to YouTube and Facebook as well.

Ryan’s Tool He Can’t Live Without in His Business

When asked about an online resource that he cannot live without in his business, Ryan shared that he actually has two, ones older. Well, not old, but one that he used for a long time and one’s newer.

He loves a tool called Asana, he’s a big project manager in person. So his team loves and hates Asana because he’s always putting things in Asana, but he really loves it. It can be a little complicated at first. They may not like hear him saying that, but there is a little bit of a learning curve, but it’s a wonderful way to organize work across a team, especially a cross-functional team.

So that’s one. And then just recently and recently being in the last like two or three months, there’s a new tool called Roam Research. He was in a beta program and he thinks they just now started to offer a subscription, but it’s basically creating a knowledge graph of information. It’s a little bit hard to describe, but it uses like tagging and hashtags to start to better organize information.

And if you’re into research, he does a lot of primary research, it’s an amazing tool for organizing your work and your thoughts and you have a lot of ‘aha’ moments out of it side. He highly recommends if you’re into the world of research and doing research or even if you find you’re writing a lot and you’re trying to organize thoughts, Roam Research is wonderful.

Me: So, is it Roam Research is using tags and hashtags to kind of bring data that you are pulling from the web together? Or is it more so kind of putting your thoughts in order based on what you plop in the application?

Ryan agreed and shared that it’s more the latter. It’s more of a tagged based tool for organizing, disparate information. So, think about it more as like, how would you organize the thoughts into your head into a kind of a more structured mechanism.

But it’s very good in the sense of, so for example, they’ve been doing some primary research on different buying centers and value drivers for those buying centers and experience like customer journey mapping and some other things. And often they’ll do three or four different research projects. And sometimes the connection between research projects is hard in the sense of they may have different goals and the data in that may be a bit different.

So, Roam can sometimes help with taking those disparate pieces of work and better mapping them together. And they have these visualization tools like how is this project connected to this project and connected to this project….

And it starts to open up your eyes to connections, and going back to your point of sitting at your desk and having that ‘aha’ moment, Roam can sometimes be quite good at helping you think through some of those things.

Me: I actually was looking it up while you were speaking a while ago and the description that they use on their website is it’s a note taking tool for networked thought. So, I guess as you said, you put things down and then they’re able to kind of integrate and map and connect an easier flow so that it gives you a better, a bigger picture or a clearer picture of what it is that you’re trying to put together.

Ryan also shared that they give you a daily page and he actually find that’s one of the best things they do for a number of reasons. One is, you have a page every day that appears and then for him, he’s like, what are the three things he must get done today? And he wants to get more than three things done, but what are the three things he knows he’s going to get done?

And then also you can then map forward and back of, “Here’s what I want to get done tomorrow”or “Here’s what I thought I was doing three days ago and why didn’t I do it?” So he can start to create a really nice cadence of like giving you a little more discipline in your days and then your programs and in your research. He really enjoys it, it takes some getting used to also, but it’s been very powerful.

Books that Have Had the Greatest Impact on Ryan

When asked about books that have had the biggest impact, Ryan shared that two books that are very different, but both had a big impact on him.

So, one is a book called Made to Stick: Why Some Ideas Survive and Others Die by Chip Heath and Dan Heath. And it’s really about how do you think about products and it extended to more human experiences that are very sticky. So things that people remember, they want to come back to, they really kind of love. And so, he thinks it’s a great book. Often times we get caught up in a single wow moment like the monument versus the thing that drives people to come back.

And so to him, it’s like the journey through the Super Bowl ad, which is one time and memorable versus that experience, that people will just crave, they always want to come back for more. And so, he really feel like Made to Stick is a great way to think about the world of building product solutions, experiences that are very sticky and drive your customers to want to come back.

And at the end of the day, even if you’re in customer service and your goal is to reduce inbound, reduce costs, you still want to make it a great experience so someone remembers it and wants to come back again the next time.

And the second one is, it’s actually an older book, it’s more of a psychology but Ogilvy on Advertising by David Ogilvy. So, he wasn’t trained as a marketer, but now he spends a lot of his time in the world of marketing. He loves these older books that survived really well and a lot of it’s around psychology of how people think, why they make decisions. But why he likes Ogilvy on Advertising, if you read a psychology book, oftentimes they’re hard. It’s not an easy thing to process but Ogilvy on Advertising, it’s the world of advertising and we all can relate to advertising because every day we’re giving ads.

So, it’s a really nice book that kind of talks about the science behind it and why people make decisions they make and the psychology behind decision making. So it’s a classic that he thinks is definitely worth reading, because he thinks it also very much applies to the world of customer experience where it’s how do people think about decisions? How do they weigh factors? What’s the psychology around decision making? Because we often get caught in the tactics, the journey map, the average handle time, there’s always metrics we are caught up in.

But at the end of the day, people make decisions oftentimes based more on themselves and their psychology than they do around the journey map we’ve defined for them. So, he thinks that’s a great book and good perspective.

What Ryan is Working on Now that He’s Really Excited About!

When asked what is one thing that he’s working on right now to develop himself or people, Ryan shared that with everything going in the world right now, it’s a timely question. Their specific team is working a lot on how do they help to bring more diversity into the world of tech and specifically into LogMeIn. There’s a lot going on right now in the U.S. specifically related around violence with the police, especially toward minorities or people of colour.

So he’s spending some time trying to get more involved. There are great organizations in Boston like Hack Diversity and others. They have a black employee’s organization at LogMeIn. So, they recently did a really challenging but really impactful discussion around being a black employee and being someone of colour.

So, they’re spending time at LogMeIn, certainly the U.S. has made some strides, but there’s still a lot of work to be done on helping to improve diversity, improve access and improve people’s lives where they don’t have to fear about going out their home and being killed. So, that’s a really recent one and he thinks is really important.

And then outside of that, he has two small kids, so he’s always thinking about the broader world in education and everything else. “And as you can hear, one of my interns is yelling. I think she has an important thing for me to work on.” he says jokingly about his daughter.

Where Can You Find Ryan Online?

  • Ryan shared listeners can find him at –


LinkedIn – Ryan J. Lester – Mister Lester


Ryan’s Quote or Saying That Keeps Him Energized

When asked about a quote or saying that helps him to refocus, Ryan shared that there’s a short version and there’s a long version. So, the long version, there’s a Mario Andretti was a very famous race car driver of Formula One race car driver in the U.S. and he has a great quote that says….

“If you feel like you’re under control, you’re not going fast enough.” 

Mario Andretti

And he always feel like that for him is very much a case of like if you feel like everything’s fine and calm, especially in the world of technology, you’re not probably not moving fast enough.

And so the short form version of that with his team is always, he would say, “Ship it.” And so for him, it’s like if they say should we do this? He’s like always there on the side of shipping it, get it out there, let the market tell you if it works or doesn’t work. You obviously want to have some quality control, but often times better air on the side of let’s get in front of the customer and see what they think versus trying to make it perfect before we get it out the door.

So those are his words of advice to the team of if you feel like you’re completely under control, you’re not going quick enough, so let’s go ship it out the door.

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