Meg Palazzolo When I use AI now, I have a second brain that I didn't know I could have. Save time, working smarter not harder.
Jen Weaver Welcome to Live Chat with Jen Weaver. I'm Jen, and today I'm joined by Meg Palazzolo, a customer success leader with 15 years of experience building and scaling customer-facing teams. Currently at a stealth-mode startup, Meg is leveraging AI to streamline processes and manage the many hats she wears at an early-stage company. She'll share how she used Claude to help create a user journey map, and why collaboration and community are vital for success. Let's dive in.
I'm super excited to have you on the podcast. We start every episode with a joke — do you have a joke queued up and at the ready for me?
Meg I do. Why do skeletons not like getting into fights?
Jen Why do skeletons not like getting into fights?
Meg Because they don't have guts.
Jen Okay. So we're here to talk about a process that you implemented recently and the tools you used to do that — really, everything somebody would need to know to do that themselves. So let's talk about AI. I think that is definitely a hot topic these days.
Meg It is. OpenAI just came out with a Pro version today that's $200 a user per month. I'm just like, wow, that's wild.
Jen I know.
Meg We're on this new path of using AI to help us be more productive in our day-to-day, help our customer experience get better, you name it. I've even seen marketing tools for AI. So it's touching every aspect of every business.
When I think about processes, and I think about where I'm at in my career journey, I'm back to building the zero-to-one all over again. There are lots of problems that pop up and there are lots of different hats to wear — hats that I may not be an expert in, or hats that I have never worn before. And building these processes from scratch, now I'm turning to AI on a daily basis versus Googling things.
A lot of times, having to Google stuff, you wouldn't always find the right information that you were looking for, or you would find bits and pieces. Now, using something like Claude or ChatGPT, having that in my back pocket and just pulling it up on a browser and asking it like I would ask a friend — "Can you help me work on XYZ?" or "Can you help me with a social media content strategy? I don't have any experience doing this, can you help me with this?"
Normally I would go about a process like researching on Google and finding a few different pages. But now I'm just having this conversation with this AI, and it's producing results for me, and I'm able to fine-tune those results over and over until we get to a spot where I'm just like, yes, this is what I can use, or this is what I need. And I am going to either send this to our CEO and have him provide some edits and feedback, or actually use it.
So it's everything from developing the strategy, to developing the actual content that we're using, to developing our content style guides. It's really touching multiple aspects of our whole overall strategy, which is really awesome. So to answer your question: when I use AI now, it's at multiple stages throughout the process, to overall just help me have a second brain that I didn't know I could have, and help me be more productive and save time. Working smarter, not harder.
Jen Yeah, that makes total sense. So you are in customer success — you oversee the customer journey for your team, and so that includes the marketing reaching out to them in the first place, even though that's not typically what a CSM would necessarily do. But as a small team you wear many hats, you have your hands in many different areas, and so AI is helping you to do things that you've never done before, essentially.
Meg Yep. And for earlier-stage startups, I think you bring on these generalists in the beginning, right? You might not need a head of marketing just yet, or a head of growth just yet. You build the foundation the best you can, you bring in some tools, and then you eventually pass it off once you start scaling. That's the phase that we're in right now.
I'm doing a lot of product stuff and product feedback that supports the overall customer experience — the holistic customer view, if you will. But eventually, as we start getting customers and I have less time on my hands, then we start bringing on more people who are subject matter experts in this space.
Jen I don't know about you, but that's what I enjoy most about working at small companies and startups. And you've done this before — you've worked at a startup before, right?
Meg Yes, this is my fifth one, believe it or not.
Jen So what's different now about startup life than in the past?
Meg I think what's different is I grew so much, both as a person individually and as a professional, in that short amount of time. I grew my overall understanding of what it looks like to scale at hyperspeed, how to hire the right people, and how to be more efficient in my day-to-day — what tools to lean on.
Last year was really when AI started to come out. We were using Ada's scripted version and it was an awful experience. But once generative AI came out, it was just a game changer for what customers experience, and for productivity internally, and just how teams can scale fast.
Jen That's fantastic. The big heart of this podcast is representing processes that somebody could then replicate. So if you could walk me through, from the conception of your idea about the marketing strategy — or any other process that you want to talk about — how that landed on your desk, through how you decided to take next steps and which tools you used.
Meg Just going back to basics: one of the first things that you do as a leader in a customer-facing team is understand what the customer journey looks like, and visualize that both from an operational standpoint and understand cross-functionally how our other teams are going to be interacting with this as well.
So one of the things that I did on day one was build out a customer journey — knowing how our product would be functioning, and what were the tools that I would need to implement over the next month in order to make this experience streamlined and amazing from end to end, or as best as it could be for a V1.
I used AI knowing what tools I was already going to be thinking about using, to a certain degree. I gave the AI my word vomit of what the process should look like in words, and I asked — I was like, "Hey, I need you to create a visual customer journey map, breaking up the different tools that we'll be using. This is what the journey looks like, and this is how they'll be interacting with each different tool."
And it produced this image that was really good. It was a really good start. It would have taken me a lot longer than the 15 minutes that this whole conversation wrapped up in. So it produced this image, and it still needed some tweaks. So I went and I was like, "Okay, this is great, but it's missing X, Y, Z in the journey, and I forgot about this one touchpoint." And so it iterated on what I had produced before. Just going back and forth with the AI and producing this great journey that, again, would have taken me a few hours — much longer than the 15 minutes that I actually spent on it.
Jen So it didn't get it right the first time, though.
Meg Didn't get it right the first time. But I think what's important, as I go through and continue to get used to how AI thinks — if you will — or generates information: you have to be very descriptive. You have to talk to the AI like you would be instructing your 85-year-old grandmother how to use a computer without pointing. So you're using all these verbal cues of "okay, take your mouse and click on the Apple in the left-hand corner."
I worked at Apple for five years way back in the day, and we had to literally have our hands behind our back and instruct people how to do it. So I channel that moment in my career when I'm talking to the AI around what I'm needing it to produce. And when it doesn't produce what I want, I go back and see, okay, where did I miss, or what did I miss, and how can I reword this and be more specific?
Jen So after it generated that great-but-not-quite-right image, you went back in and said "change XYZ," and then it popped up another one?
Meg It would pop up another one, yep. Another version.
Jen So then you got to the point where you were happy with it, and then you — I'm assuming — were able to export it and use it in some way internally with your team.
Meg Yeah. So I am not an engineer, and I can't connect all the tools. Having this visual representation of what our customer journey looks like is really helpful for other teams involved in integrating those tools into our overall platform and ecosystem.
So I passed it over to our product team and said, "Hey, this is how I'm envisioning the operational, or customer support, or customer success tools to operate." Now they have a sense of what's happening. Passed it over to our engineering team: "Hey, I need you guys to so kindly connect these tools, please."
Now, instead of having them going back and forth — a lot of times in the past I would have engineers say, "Okay, this is great, but now what? What am I supposed to do? How do you want it to actually function?" You really have to spell things out for the engineers, because they don't like to interpret things, or there can be that misinterpretation. So now our engineering team is like, "Oh, this is perfect, I know exactly what to do," and they know exactly how to connect it. So it saves a lot of time all around.
Jen Was there anything in particular that you did to target this customer journey map to an engineering audience?
Meg I wouldn't say necessarily, no. It produces what a typical customer journey would look like, if you're showing that there are tools on the journey as well.
So I can walk folks through what it looked like. I had five different tools: I had Calendly, Intercom, the actual customer journey, HubSpot, and Notarize. I had those different tools in there and the customer journey, and you basically just weave it through each one. So when there's a different touchpoint, it's hitting the Intercom one, and then it goes down to HubSpot to hit another touchpoint.
Jen Okay. So you knew that this would be foundational to your work — you needed to know what the customer journey was and have it super clear. You also knew you needed to communicate it to engineering so they could set some things up. You worked with Claude to do that, and linked all your tools with where customers would interact with those in this map, which is amazing.
So now you'll need to probably store that somewhere. Will you also be able to go back to Claude and iterate on that if you need to make changes?
Meg Yeah. The great thing about having AI — or using something like Claude or ChatGPT — is that on the left-hand side you have all of your files. You can delete them if you want, or you can revisit them and iterate on them.
Here's actually a fun example. I use ChatGPT to create all of my workout plans. I've used it for the past eight, nine months, and it's the same thread. I'll be like, "Great, I need another eight-week program," and so it will program it. And there might be something that I don't like in there — I'll say I don't want to do burpees. Ever. Who does? But it can take it out.
So yes, to answer your question, you can go back and continue the conversation right where you picked off, even if it's several months down the road.
Jen That's great. I'm sure as you launch you'll have some thoughts about "oh, this is actually going to be different," or "we'll use this other tool," and so you'll be able to change that. And are there tools you're using internally to communicate this, or just store the information in your knowledge base?
Meg We're currently using Notion as our internal knowledge base. I just took a screenshot of it and then wrote up a little document in Notion around, "Hey, this is how we're thinking about our customer journey from the customer success side, and here's how this will impact other teams." And so we can actually use that to reference later down the road too.
Jen What just occurred to me as you were talking about that is that there was probably a step zero that you and I, as people who work in a startup, don't even really think about. That's the journey you took to absorb all this information from your founders and your executives and other people on the team. You came on and learned about this tool that doesn't exist yet. That's a whole skill set and a whole journey in itself.
Meg Yeah. The platform that we are creating — there haven't been any tools. I was the first hire, myself and our engineer. We were both brought on the same day, and we're literally building the car, if you will, and we're hand-selecting which tools to use for what.
I think there can be analysis paralysis when it comes to selecting tools. And when you have a tight deadline — we're launching literally in six weeks total, from start to finish — when you are going through that process and you're deciding what tools to pick, you just have to pick them at the end of the day.
I've used a lot of these tools in the past. When I was choosing a help desk, I was considering a few others, but Intercom is great. And talking about their AI, I know they're using Fin, which is built off of Anthropic, and it's really good. I've heard great things about it.
I have leveraged a few different communities. Support Driven — shout out to Support Driven. There's also Elevate, which is another great support community. Just super helpful, wonderful people. I leverage those two communities to ask folks, "Hey, what are your thoughts on this tool? What are your thoughts on that tool?" and just make the decision quickly once I gathered some information from other people, and use those tools to support the overall customer journey.
Jen That's fantastic. I have really enjoyed just learning from you person to person, and I really appreciate your time. Is there anything else you'd like to share about that process, or just anything?
Meg I would just encourage folks to not be afraid of really using it on a daily basis. I've talked to some former direct reports recently from my previous company and I was like, "Are you using any AI for this? This could really help you out."
It's a new way of being productive. I think we hear the term "working smarter, not harder," and there are so many AI tools out there — it can be overwhelming. But just start with ChatGPT. It's easy, it's free to use.
Jen Yeah, don't be scared to use them.
Meg And join a community, please. Join a community. Support Driven is free, Elevate is also free. And ask others how they're using AI as well.
Jen Well, thanks for tuning in to this episode of Live Chat with Jen Weaver. A big thank you to Meg Palazzolo for sharing her insights on leveraging AI and navigating the challenges of startup life.
Our goal with each and every episode is to empower you with a new process that you can duplicate in your own work, so I hope, like me, you now have a new AI assistant.
If you enjoyed this episode, don't forget to subscribe, rate, and leave a review — it really helps us reach more listeners like you. And as always, let's keep the conversation going. Maybe you recently did a thing and you want to share, or maybe you'd like me to find an expert for a puzzle that has you stuck. Connect with me, Jen Weaver, on LinkedIn to reach out.
And don't forget to connect with the amazing communities Meg mentioned, like Support Driven and Elevate — you'll find all those links in the show notes.
Until next time, keep creating exceptional experiences for your customers.