WOW your Clients and make them come back with Jena Paulo

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As the world of business evolves and competition increases, one thing is certain: your clients expect seamless experiences from you. That’s why it’s essential to have a reliable system in place to make that happen. Fortunately, it’s possible with the help of technology and project management tools like ClickUp – but how, exactly?

In this episode of Boss Your Business, Business Operations & fellow ClickUp Vetted Consultant, Jena Paulo, joined me to talk about the importance of building systems, processes, and workflows that allow seamless client experiences – from acquisition to onboarding, to project management to offboarding, and more. We also took a dive into some of the tools she personally uses to run her own business, so you can try them out and see if they work for you.

Boss Your Business - Providing Excellent Client Experience for Happy Clients with Jena Paulo-story

So if you’re looking for practical strategies you can use to wow your clients and compel them to keep coming back for more, then you’re in the right place. Because Jena has a ton of practical tips and advice to help you elevate your client experience and build systems that will have happy clients coming back for more. 

Ready to take your client experiences up a notch? 

Read the full transcript below and discover how you can build systems that allow seamless client experiences in your own business.

📄 Video Transcription:

Yvonne: Hey, hey everybody, and we are back with another episode of Boss Your Business, where we build businesses that support our lifestyle. And today I’m being joined by a fellow Vetted Consultant over at ClickUp. We might mention ClickUp once in a while today. I have a feeling, but we are gonna be talking about maybe just maybe a little bit on ClickUp. You know, ClickUp is gonna be talked about. Um, today, Jena Paulo is joining me and Jena helps entrepreneurs, agency owners, and large scale companies create scalable systems and processes that enable them to grow their businesses sustainably using ClickUp as their operational base. Now, you know, ClickUp is going to be a core piece of all of that, but Jenna, let’s start in the beginning.

What actually got you here? So you are a ClickUp Consultant. You help people in a group program as well as in one-on-one settings to run their business like you from the couch or chair, as we have seen on your Instagram, as well as being able to take care of your son when he is sick at home. So how, how did you get here?

I know you didn’t start like this.


Jena’s background

Jena: Yeah, absolutely. So I actually come from a background in educational operations and worked in educational operations for over 12 years, and when I was there quick. You know, over, over time it got burnt out and really looking for new and exciting and something that I could do from home.

Right? Because I said I have a son and you might even actually be hearing him in the background right now. Um, but yeah, you know, I was looking for something that I could do from home and mesh my skills as someone coming from this operations background, um, into something that I could do at home, right?

And work with a lot of different people and still have community and, and all of those things. So kind of what, what sparked, uh, the journey was my, my son and, and all of that. So, um, I gently came into the online space, right? And sort of eased my way in doing some, um, more administrative things. And, and then I quickly, you know, started working with entrepreneurs who really were lacking systems and organization and all of those things, right?

And so, you know, I was searching for ways that I could, um, that I could help them and help them really become super organized and scale their business and, and all of those things. So of course I needed a project management tool to help me do that, right? So I, I tried them all right? Trello, Asana, Monday, Basecamp, all of ’em, and finally landed in ClickUp and was like, okay, that’s it.

Never leaving. And uh, that’s where my business was born, basically.

Yvonne: So, yeah, so kind of like follow the yellow brick road. It seems like a lot of us are experiencing business like that, which I love because I have so many people in my audience that are like, oh my God, how do I figure out what I wanna do?

Who do I work with? Where do I take this? Just do you literally just do, yeah, you can play around with a couple of ideas of what are you good at, what’s that personality type that you wanna work with, but you are not going to get any feedback, figure it out, or get any quote data on what’s right for you if you don’t do it and just play around with it.

With that, I’m curious, Jenna, because I know you do builds for clients, so you are building ClickUp out for other people, but you are also doing your group coaching consulting training program. How, how did you get to that level of support of your clients? How did you find your way into those two offers?


Getting support from happy clients

Jena: Yeah, absolutely. So, you know, like you mentioned, I kind of started with the, uh, with the buildouts, right? So going in and really doing a customized buildouts from scratch, right? Either or they’ve created something in ClickUp and it needs like a total refresh or something like that, right? And so, as I’m navigating that offer, and you know, that offer of course has changed over the years, right?

And how I deliver it and, and all of that. Um, but you know, by, by, by doing that, by doing all of these builds, I’m really, every time I’m increasing my skill, right? I’m learning new things. I’m, I’m working with different types of businesses, any, anything from any type of business, from digital marketing agencies, to car dealerships, to e-commerce stores, to all of these different types of businesses.

Um, and what’s so interesting about that, although they’re totally different, the back end of their business is totally different from one another. It can fit mesh into a tool and it can be customized, right? So that it can support their business. And so as I’m doing this, in doing all of these customized build outs, there’s such a need, even after I’ve done these build outs for people to truly understand the inner workings of it, right?

Yeah. I could build for you all day long. I could talk to you about ClickUp until you’re blue in the face, but until you actually know how it works, you know, and you start playing around with it, it’s not gonna work as well as you want it to work, right? Cause you have to have that understanding.

So that’s kind of where this group program was born. Where, you know, and, and the program first started as a completely live training program, um, and has now morphed more of a, um, kind of two, two things into recorded trainings and live, but you know, there was such a need for people to really understand the inner workings of the tool.

So that’s kind of where, where it stemmed from.

Yvonne: And I love how you brought up that the group program started as live. Um, that’s often a path a lot of us, um, group program people are going because simply it’s, you can’t, you can’t add to your time. You just can add to the amount of people you can take care of, which means one on one is limited to a specific point, and then we all know often enough, learning in a group setting is easier because people don’t know what they don’t know.

Now, if somebody in the group, in a Q and A call or in an office hour comes in and is like, Hey, how do I make this happen? Or, I’m running into this issue. Somebody else in the group might be, ooh, nice idea. I like where this is going. So the group, the group aspect in all of this has, has a high advantage to everybody joining.

Um, but also it allows you to be able to serve more people. So hearing how you have evolved from a live to a semi live setup simply because I know how you run your group program? Just a little bit because I’ve been stalking your Instagram. Um, it’s great to hear for the audience, I think, because it is a natural growth stage of going from just one on one to being able to scale your own business. Now, that comes a lot with managing a lot of people. You suddenly went from potentially, I don’t know, 3, 4, 5, 10, 15, 1 on one clients to potentially hundreds. I’m like, when you scale this thing. It’s there, there is no open end. So how, how do you manage your client experience, your client communication? How do you stay on track but also keep your clients and your, your group on task?


On providing seamless client experiences

Jena: Yeah. Yeah. Definitely. It’s, it’s a dance, right? Because you know, there’s a lot of back end technical pieces that have to happen in order for things to run smoothly for the client experience to run smoothly and all of that, right? So it really starts bef, you know, before I even get anyone inside of the program. A lot of it comes down to ensuring that I’ve got automation set up.

You know, when someone, let’s just use this as an example. When someone signs up, right, they, they go through Thrive Cart to pay, right? But I also need them to sign a contract, so then I have a Zap that allows them to sign a contract in Dubsado. I and many different pieces to it, but the technical aspects are really what ensure that the client experience is smooth and people are happy, right?

Because when someone purchases a program, if the, if the experience at the very, very beginning from that first touchpoint isn’t seamless, you’ve lost. So you have to ensure that all of the technical pieces are set up on the back end to ensure that it’s a smooth process, right? And then once they’re in the program, your program speaks for itself, right?

So, you know, you’ve ensured that your program is up to the standard that you have set that you’re delivering to them. Um, you know, even over, over deliver, right? That’s what we should be doing is really over delivering inside of the program. Um, but yes, the technical piece in the back end is like, where it’s at.

Yvonne: And it’s been, it’s interesting that you brought that up because as of late it’s, I work with a lot of 1099 team members for my YouTube channel, for writing stuff.

The whole, the whole supporting me in, in my content creation and all of the things. And it was interesting working with a new team member and he sent me a PDF invoice and I’m like, wait, no, whatever. Yeah. And I’m like, I’m at an age, I’m like, I’m sorry. I’m not gonna add Elle to, to the next how to pay you. Um, again, I like, I like him, it’s fine.

He is starting out in his journey of being an entrepreneur and making things easy, but it comes back to the point of it’s our job to make that experience, that client experience seamless and easy and in, in a year like 2022, it is so easy nowadays to send out an invoice that has a pay button on it or to have another way of easily being able to just make it seamless for your client.

Yeah, and skip the five emails of, I’m not gonna sign up Forze, how can I pay you?

Jena: Definitely where, and it makes it an e an easy yes for the client, right? If, if they’re able to pay and be able to just put in their card information, it’s such an easy yes for them.

Yvonne: And I think this, this is a big piece of where we are in general right now of we do have the technology.

When you are starting out a business and you might not have the technology knowledge, know that the technology is out there to make your life easy. Now, your job as the business owner, search or find people that are teaching it. There’s enough people out there that are teaching the basics of starting a business and the tools that are out there for you to learn how to make it easier.

But you are, um, it’s your job to say, hey, I need to put a little bit of work in to be able to really make that client experience seamless and enjoyable.

Jena: Yeah, absolutely. And you know, this is something that I work with my clients on all the time when we’re building out ClickUp workspaces, or even in my, in my group program where I’m teaching you how to manage client experience inside of the tool.

This is something we talk about all the time. How can we make this tool or these tools work for us and make it a seamless experience? Talk to me, user experience on the other side, like internally look great, but let’s test it and see how it looks on the other end on the user side, right, on the client side. So those are definitely important things that we should not overlook.

Yvonne: Love the human aspect of all of that. I think with a lot of push out there of automating and, and hands off things, the human aspect has gotten a little bit lost. Happy to see it coming back with you and, and how you run your business. What are some of the processes and workflows that allow you to be like, hey, Yvi, I got, I got my son home today because he is sick, but I still need to take care of clients too.

And how, what, what are those, those common workflows and processes that have allowed you to run your business like you do?


Jena’s workflows and processes

Jena: Yeah. You know, it’s, it’s been a journey, right? Figuring out what that looks like for me. Mm-hmm. . Right? And, you know, you can think of all of the different situations in the world, but you’re never gonna all like, oh, what if this happens?

Right. So, you know, one, I think one that that comes to mind, especially when, you know, I’m talking with a potential client who’s a, who’s a new lead, maybe in my pipeline. I have workflows in place that to follow up with these people without actually having to do it myself. So, you know, I have that conversation with them.

We hop on a call. We talk about, you know, what, what service need and all of that sort of stuff. I send a proposal over through, I used Dubsado for this. And the workflows that I’ve developed in Dubsado take care of the rest for me. So it does my follow up for me. If they, if they, you know, accept my proposal, it automatically is gonna send them the invoice and the contract and the questionnaire and all of those different welcome emails and things like that, right? So I don’t have to touch it after I send that proposal. So that makes my life so much and so much more stress, stress free. Right? Because there was a time that I was doing them manually and do you know how much time that takes? Yes. It’s really nice to be able to automate those things.

Yvonne: Yeah. Fellow Dubsado fan over here too, where I’m like, it’s, it has, it has made life much easier on the side of when, when working with one on one clients. And just being able to, to set those automations while still have that, that human aspect, that personality with it.

I’m like, I always joke, um, when I work with one on one clients, I’m like, you’re gonna get a questionnaire and it’s gonna be a long one, but I’ll send you a coffee with it. So bringing, bringing some personality into those automations and just having fun with it.

Jena: Absolutely. You don’t wanna sound like a robot, right?

You want it to be friendly. You want it to be very, uh, like brand centered, right? You don’t wanna sound like you’re a robot. So I think that the personal touch is really important.

Yvonne: And with that, we already talk. We, we know ClickUp. We also know that you’re using Dubsado, kind of like, just like me. It’s like I feel like we have the same tech stack.

What are, what are some of the other tools that you use to make your life easier and your client experience better?

Jena: Yeah, so another tool I use is actually Voxer. So Voxer is like a walkie-talkie kind of app, right? So I use this and with uh, my team members, right? So although we’re using ClickUp for communication and all of those sort of things, there might be other things that warrant maybe longer conversations, voice notes, kind of back and forth, riffing back and forth or something that maybe needs like a really quick response, right? So that’s kind of where Voxer comes in and um, I’ve been using it since basically the inception of my business and I love that human element to it as well, where I can talk to you, right?

Something that I use when I do my build outs. Cause, um, when I am building your ClickUp workspace for a day, I do not expect you to be on Zoom with me for seven, eight hours, right? Like that would never be the expectation. So instead, we’re using Voxer to communicate throughout the day when I need a quick question answered or if I need to strategize with you a little bit throughout the day.

So that tool has been huge in my business.

Yvonne: In with the others, which is interesting. You mentioned Voxxer. Um, we’ve been internally starting to test vol because we know me, I got the German accent and I like to see people once in a while, so, we’ve been starting to test vol, which is similar to Voxer with asynchronous video messaging, audio messaging, as well as the text messaging, which which also gets transcribed.

So even if somebody sends me a little, little video or voice message, you have the transcription, which you have in Voxer tail. One of my big points was this whole, I can literally just send a quick little video message and the sweating capability in it, so it’s fun to hear that you are already in, in something like that too.

Where Voxer, easy communication, easy just jumping in. You don’t have to deal with an email or you don’t have to deal with Slack.

Jena: It’s like I tried email at all costs. I hate being on email .

Yvonne: The nice thing is the ClickUp integration of turning a email into it task, which is nice at some point. So ClickUp, can we get this in other messaging softwares too or something?

Um, but yeah, it’s like email is like the hell of stuff just getting buried deep.

Jena: That’s where things go to die.

Yvonne: And then I know you use, you use Thrive Cart. You use Dubsado. You obviously use ClickUp. Yep. I’m curious, and this is, this is a complete egotistical question for me because I’m playing with this idea.

Yeah. So with your group training, I know you have, I don’t even know how many videos in there. Anything. Do you also have some kind of support, accountability, potentially for your students in ClickUp?


Support and accountability

Jena: Yeah, so, so a piece of the program is we get live Q and A sessions and coaching sessions during, during the, the program.

And I utilize pick up forms for them to submit those questions, videos, images, things like that. Um, so they can get support and submit those things that way. Um, and then, yeah, so that would be like the, the ClickUp element of it. There’s another piece inside of the portal where the training lives, um, where they, they’re, they have the ability to comment, add comments and things like that.

And I can provide support within, within that as well, where everyone can see it and, and all of that good stuff. But the ClickUp element is the form that they get to fill out. And then I go through those submissions and all of that live inside of the live training.

Yvonne: Yeah, which makes it really, really simple.

And I pretty much, I pretty much guess that you have something like that. Um, because it makes it really easy to jump into an office call, um, having the questions ready. It’s, it’s pretty much the setup that I’ve been talking about too, that you can also use just for client, um, ticket management, where it’s like, hey, I need this fixed.

Hey, this needs to change. And you have an easy checklist rolling list to go off of rather than like, so what did you wanna talk about today?

Jena: Exactly. And you know, this was something I was talking on my Instagram Stories about yesterday. When I do my build outs, you know, I have a, a list inside of ClickUp where my client is adding any changes or revisement or questions or anything like that. The goal with that is to, first and foremost to get them used to working inside of the tool with someone else, communicating and doing all of that. But the second piece of that is , I guess, to keep me sane because I don’t want a million emails, right?

So all of those things are gonna go into ClickUp and you know, and then we take care of ’em, right? It makes it really easy to take care of those things.

Yvonne: It’s interesting to mention the, the sanity piece of it. I made a mistake in, in a one-on-one client that I’m working with. Um, part of adjusting their process and workflow is also that team communication, that simplicity, because everything for them is happening in Slack right now.

And I started getting them out of it and getting them into the habit of task communication happening in ClickUp. But last week, I caught myself getting into the same habit of having those communications and having those, you need to do this in Slack. Like we had our call on Tuesday and I’m like, I’m guilty of it.

I followed your lead rather than being the consultant. We need to pull this back again because Slack is just as much a black hole of tasks as emails is.

And it, it doesn’t really matter which tool everybody chooses to make it happen, but you need one simple single sort of truth and that usually is your task management tool.

Jena: Yeah, I mean, you’re speaking my language. That’s exactly what I tell my clients, right? I mean, so many of my clients are utilizing Slack and I would say out of all of the other tools that, you know, my clients use, it’s the hardest to pull people outta Slack. It’s the hardest to do. Right. But you’re right, it’s a, it’s a black hole.

And, uh, you know, streamlining that communication inside of a tool like ClickUp makes life so much easier.

Yvonne: And especially for for the long haul. I’m like, when in your example of working with a one on one client and a build out, you have your list of, hey, we wanna fix this. Hey, we wanna optimize that. Hey, we wanna streamline that.

Hey, you have the list. But then you also have the, the wishlist items and the communication that happens in that specific task. Where you can go back, you can chunk down on that specific issue, and you can go back into the comment history of, what have they tried before? What has worked for them? What hasn’t worked for them?

Yeah, and and even if you bring in your new team member, you now can build up on that communication for specific SOPs or for guidelines or anything. It’s just so much easier.

Jena: It’s so much easier.

Right. And you know, yeah, you’ve got the communication back and forth between you and the team members, but then there’s also kind of that unspoken communication that ClickUp is doing right with Click Bot inside of that section as well.

So you can see the history from the inception of Pass card, right? That just makes a huge difference, which Slack cannot give you.

Yvonne: No. Yeah. There’s a reason why it’s a black hole. Like it’s a nice water cooler conversation. It’s a nice brainstorming that can happen over in Slack, but everything else just needs to happen in ClickUp.

But there comes the human aspect again. It’s like guilty here. Where I suddenly join the habit of, and their strategies of how they’re doing things right now when I’m jumping into Slack. It’s, it’s a continuous, just adjusting your habits and strategies. Yeah, it’s, it’s an ongoing effort.

Jena: It is. Yeah. Oh, I mean, over the course of your business, it’s, you’re always evolving, you’re always, you know, changing processes and, and optimizing things, right? So it’s going to always be something continually you’re working on.

Yvonne: And I think that is a perfect end to our live show today, because we started with follow the yellow brick road.

Well do the thing, get the data, adjust, and then pivot. The world and the data is gonna tell you what you need to do. I am so happy you got to join me. Guys, as always, in the show description, go follow Jena, and she has the funniest but also the most educational Instagram Reels, so make sure you check her out over there.

It’s like every, every time she posts on her Reel, I’m like, okay, what is she doing this time?

Jena: Thank you and thank you so much for having me.

Yvonne: She even goes as ClickUp for Halloween. So go follow her over there. We have all of Jena’s links, um, right in the description. Go stalk her. I’ve been stalking her long enough.

Thanks so much for joining me, Jena.

Jena: Thank you for having me.

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