Summary:

In this client spotlight episode, Michelle interviews Jena Paulo, a ClickUp consultant. They discuss Jena's journey from offering various services to specializing in project management using ClickUp. They also talk about the transition from the retainer model to the VIP day model, the importance of maintaining relationships, and Jena's experience working with another coach before returning to work with Michelle. Jena shares her expertise in utilizing ClickUp as an operational hub and building a relationship with ClickUp corporate. They also provide tips for getting started with ClickUp and highlight the versatility and power of the tool.

Takeaways

• Transitioning from various services to specializing in project management can lead to more sustainable and fulfilling work.
• Maintaining relationships with clients and coaches, even during breaks or when working with others, can lead to future opportunities.
• ClickUp can be used as an operational hub for businesses, providing a centralized location for tasks, projects, team communication, and more.
• Building a relationship with a software company, such as ClickUp, can lead to recognition and partnership opportunities.
• Getting started with ClickUp involves understanding the basics of the tool, such as organizational hierarchy, task creation, and task viewing.

About Jena:

Jena is a seasoned ClickUp consultant and business efficiency strategist, Jena Paulo specializes in transforming chaotic workflows into streamlined processes. With over 15 years of experience and having empowered over 200 companies, she excels in customizing ClickUp solutions to enhance productivity and operational clarity. Her mission is to help businesses unlock their full potential through innovative, tailored systems and insightful training. Jena turns operational complexity into simplicity and success.

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Links:

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Chapters

00:00 Introduction and Purpose of Client Spotlights

02:00 Jena's Background and ClickUp Consulting

03:07 Transition from Various Services to Project Management

06:30 Transition from Retainer Model to VIP Day Model

09:26 Taking a Break and Working with Another Coach

10:56 Maintaining Relationships and Returning to Work with Michelle

12:21 Pushing Jena's Growth and Coaching Relationship

17:22 Working with Larger Companies and Scaling the Business

19:17 Utilizing ClickUp as an Operational Hub

21:08 Building a Relationship with ClickUp Corporate

23:23 Nicheing into ClickUp and Providing Value

26:00 Getting Started with ClickUp and the Basics

27:53 The Versatility and Power of ClickUp

29:06 Where to Find Jena and Additional Resources

Hey everybody, welcome back. We are joined today in the podcast studio for another client spotlight. We have the Jenna Paolo with us today. Jenna and I have been working together for, gosh, well, I think since 2020. There was a little bit of a break in there, which I definitely am going to, we'll talk about here in a little bit, but I want to give Jenna an opportunity to introduce herself. But again, one of the reasons why

I am doing these clients spotlight in case studies on the podcast. It is a couple of things. A couple of reasons I want to do it is because I really want everybody to understand the working relationship of what it looks like to work with a coach, mentor, strategist, whether that's me or with somebody else and just understand the journey, right? You will start to see a trend with the clients that are coming on and I'm doing spotlights with that.

this is not a short term relationship, right? That the relationships are long term and that's where the results come in. So we're definitely gonna talk a little bit about that, but also I want to spotlight and share my clients and their expertise. I work with some of the most amazing individuals and I love to see what they're doing and the impact they're making in the world and all of the growth that they've been.

seeing and I want to introduce them to you. Like part of being on this podcast and part of hosting this podcast is to introduce you to other people. That's my job is to be a power connector. So that's what we're doing here today. We're going to dive in. We're going to have a great conversation. You're going to learn a little bit about Jenna and then she's going to tell you all about how to use ClickUp. I deemed her the ClickUp queen. I gave her that title I think like three years ago. She

Halloween one year. So anyways, Jenna, tell them more about you and then we'll dive into the conversation.

I did.

Yeah. Hi everybody. Um, I'm Jenna Paulo. I'm a verified plus ClickUp consultant. Um, and I basically work with my clients to build out ClickUp workspaces that help their business grow, um, and scale. And so if you are a business owner, you should definitely be using ClickUp or some sort of project management tool.

Yeah, awesome. All right, so let's go backwards in time here a little bit. In 2019, again, we met in a Facebook group. So if you listen to the episode that we did with Britt, which was a couple of weeks ago, Britt and I also met in a Facebook group. So if for any of you that think Facebook groups don't work, let's just put the...

Yeah.

Put that spotlight there is like they do work and you know, maybe not in the same way. I don't know that they work in the same way that they did back, you know, a couple of years ago, but there's still, it's all about building relationships. So, but when Jenna came to me, Jenna was actually making great money. She was doing incredible, but you were doing something different for every single client. So she introduced herself as the verified plus clickup consultant. When Jenna and I first started, that's not at all what you were doing.

Mm-hmm.

Right. Yeah, not at all. Not even close to what I was doing. Um, I, when we first talked back then, I was spread thin. I was working with a lot of different clients. I think at one point I had 14 clients that I was working with on a consistent basis every single month and I was dying. I was burnt out and I needed someone to come in and.

talk some sense into me and figure out like what's actually going to be sustainable for me and my business and That's where you came in

Yeah. And actually one of the things I remember very clearly was that every single client was doing something different. Right. And so I think in general, um, again, I want to give some key takeaways and some action tips here for everybody listening is that in the beginning, it's okay to start and do all the things. I am a huge fan of that. And I actually encourage it to try everything, right? Do everything because it's going to give you data, right? And that's basically what Jenna was doing is when she came to me, we had

Totally.

all of this data that said, you know, she was doing VA work, she was doing project management work, she was doing OVM style work, you were doing website updates when you were doing graph, I mean, you were doing like everything for everybody. And one of the first things that I think we worked on was like, what do you like doing out of all of this work? What do you actually like doing? And that's really when you started getting more into the project management side, right?

Mm-hmm.

Mm hmm. Yeah, definitely. You're right. I was doing anything under the sun that they wanted me to do. Right? It's like I could be I was trying to be someone that could fit into all of these different boxes, when a lot of those boxes, I actually hate it. And I didn't like doing them. And I didn't even like the model in which I was serving those people right on like the monthly retainer and

And all of that. And when you, I remember when you asked me that question, it's like, well, what do you even like to do out of all of those things, what do you like to do? And the project management is what kind of surfaced and working inside of ClickUp specifically and building that out. Cause I've, I had been working in the tool for a little bit of time, building it out here and there for, um, business owners that I was working with. Um, obviously not in the capacity that I'm doing it now, but I was dabbling in it.

And that was what I liked to do, but I was still doing all of the other things to, you know, to ensure that my business was still standing. Right. So yeah, that's kind of where I was at in the beginning.

Yeah, I want to talk a little bit too about the business model. So if any, you guys listen to my podcast all the time for the most part, and you know, I'm a huge fan of monthly reoccurring revenue. I almost always try to convince, not convince, it's not a convince, but I, I really encourage every one of my clients to have some level of reoccurring revenue, um, stream, right? Something Jenna is the exception.

I'm sorry.

to that rule. And this is, I think it's so important to talk about this because that was like such a pivotal pivot. I never say that word right. Pivotal, pivotal moment in our working relationship. When I finally said you hate having clients on retainer. And that's when we started looking into the VIP day model, which is how you scale your business because the VIP day model worked very well for

Yeah.

Mm-hmm.

you and how you like to serve and everything else. And so that, if you're listening and you're thinking like, God, I hate this, like it's okay. It's okay to hate it. And it's okay to admit that you hate it. Right. Because some people just don't enjoy, Jenna does not enjoy having clients on retainer. She likes to get in and get out. Now this is not to say we don't like repeat clients. There is a difference, difference between repeat clients

Okay.

and retainer clients. And so that's a topic or an episode for another day. But talk about that. Talk about how you really came to that. What is it about that with the retainer and why does that not work for you?

Yeah, definitely. So retainer clients, that's what I was doing before. I was always working on retainer for, you know, three month period, six month periods, whatever. And I just, I didn't enjoy being inside of someone's business every single day, working on things kind of spread out across a period of time. That to me didn't feel efficient.

When I moved in and kind of transformed the business into more of a VIP day project based model, that to me felt more efficient, right? Where I can, can have a strategy call with someone. I can jump into their ClickUp workspace and build out this system in one day. Um, as opposed to spreading out that project over the course of a few weeks or a month or however long I can sit down and just be head down in one person's project.

for that dedicated time and then I don't have to think about it again. Right? So there was a lot of appeal in that for me where it was like just getting in and out and then having time to do other things besides work inside of my clients' businesses every single day and spreading my time thin that way.

Yeah, and I think too, so having that awareness of just being able to know exactly how you work best and quite honestly, even still, so that was what four years ago, three years ago, you scaled that and you scale that very, very significantly too. But there's a key point here too, in the fact that you worked your ass off on that to scale it and you were working what 20? I mean, eight.

Mm-hmm.

Yeah.

to 10 VIP days a month, I mean, trying to figure this out. And so if you're listening, like listen to that number, like anywhere from, well, I would say six to 10 VIP days a month, like on a project basis, that's a lot of lead generation. It's a lot of marketing, it's a lot of time, it's a lot of connection calls, it's a lot of strategy calls, right? And so it definitely led you a little bit to a place of burnout.

Mm-hmm.

Would you say?

Mm hmm. Yeah, definitely. And I think because you have to constantly be searching for those clients having conversations with people and putting in an effort to bring in new clients, right, because on the on the retainer model, you have these consistent clients over a period of time and you're not having to search for new ones. So yeah, definitely. I mean, and then and then eventually you get to a point where

referrals start coming in and all of that, but the buildup to that, right? That definitely took a lot of, a lot of effort for sure.

Yeah. Okay. And now I want to also talk to the audience. I'm big on transparency. So I would, I think it was at the end of 2021, you came to me and said, I think I'm, I'm ready to take my business in a different direction and I'm ready to work with another coach. Like I'm ready to go in a different direction. And we took an entire year off. And so like, this happens, right. And

Mm-hmm.

Yeah.

you know, when that happened, like I was really sad. Like I was telling my mom, I remember like telling my mom and my husband, I was like, man, like this one hurts. Like I love working with Jenna, but like, I get it, you know, and you got to do your own thing and you made that choice. And so I would love to hear, you know, like what led you to that. But also the other thing too is obviously here, Jenna is, is here now. Right. And so this

Thank you.

It happens in business, right? Like people feel like, Hey, I think I need to take a break. I think it's, but maintaining that relationship all while she was working with somebody else, you know what I mean? She was working with another coach. I continued to follow her on Instagram. And I'll be honest, I think this is one of the biggest mistakes I see people make is that when somebody decides to go work with somebody else, they completely eliminate them, they ghost them. They're like dead to them. They leave that, you know, and.

Thank you.

you are missing out on so much opportunity because Jenna obviously came back and she just agreed and we're getting ready to sign another 12-month contract with a different, you know what I mean? So take notice of that. Obviously I want Jenna to share her story and like how that came, you know, what went on. But I'm sharing from my side of the story is like, you've got to learn to continue to maintain relationships even when it hurts, right? Because

It does hurt, but this is growth, right? So can you do mind sharing a little bit about that, Donald?

Yeah, yeah, for sure. So when the time came to renew our contracts together, this was two years ago, something like that. Yeah, yeah, something like that. I was at a place where I was like, okay, well, where am I at in my business? Where am I at in my life? What do I want? Do I need new perspective? So I think from my side, it was like,

I think it was 2021, at the end of 2021, yeah.

maybe I need a fresh perspective to get a fresh perspective on my business, right? Is kind of where I was coming from. Um, and so I decided that I was going to work with another coach and I did for, for a whole year. Um, and I got some valuable insight, I think, from that relationship, but I think inevitably what led me back here was that the way that you coach the way that you

offer your advice and how we strategize together and just vibe together. I felt like that was what was missing that entire year, right? That I had moved on and worked with somebody else. I felt like that was missing and I'm so happy that I've come back into this relationship and we're here now. But, um, yeah, it was, it was, I think just getting, trying to get a new perspective and a new.

Just new set of eyes, I guess, also on the business. Yeah.

Yeah. And I think, you know, we, sometimes we need to do that to realize that like, we don't necessarily need new. We just need to continue doing what we are. You know, and I think for a lot of us as business owners and entrepreneurs, we do chase new, we do think, Oh, maybe, maybe if I get, if I go this direction or maybe if I try this, I'll get something, you know, that'll be what's going to change it. And you know, in a lot of ways, it didn't really.

Mm-hmm.

Thank you.

Mm-hmm.

it kind of set you backwards a little bit. Would you say that? Is that a fair statement? Like that's a pretty bold statement on my opinion. For like me to say that, but I was like, it did kind of take you a little bit backwards. Wouldn't you say?

Hehehehehehe

I would say, that's definitely a bold statement. I would say it kept me, I don't, I would say it didn't move me forward. I would say it kept me pretty like stagnant. Yeah.

It didn't, yeah. Yeah. Just a different strategy, for sure. There was another, something else you said I wanted to really, I'll have to come back to it. You made a statement. Oh, one of the things that you said about was the working, our working relationship was.

Yeah.

the Voxer or like that, we don't use Voxer because I hate Voxer, but Facebook Messenger, like just being able to like send a message in the moment, right? Like, and I feel like, you know, if you, anybody's listening, you know, I love the rapid fire coaching model, but from a client perspective, isn't that one of the things that you value the most in the coaching is the Voxer?

Yeah.

Yeah, for sure. That's the greatest. Yes. That's the greatest piece of it all because For me, I am someone who has ideas and as soon as I have this idea I want to take action on it, you know that and so having the ability to be like, okay, I've got this idea I'm gonna send it to Michelle see what she thinks before I do anything and know that You're gonna respond back to me within, you know a short very short period of time

is really valuable to me because, you know, in the, in the other relationship, um, with the other coach, I had to wait an entire month until I had another call. Yeah, she'd answer emails and things like that, but it's not, it's not the same. It's definitely not the same.

Yeah. And that's, I think, you know, if you're on the fence about the rapid fire coaching or boxer coaching, or you're seeing it like, and you're seeing it gain popularity, it's gaining popularity for a reason. Like it is so, so powerful. I say it all the time, like it's powerful on so many different levels, both on the client side and on the coaching side. Like I love that being able to just

you know, stop people in their tracks when they're getting distracted. Like you were doing yesterday, even with like she was getting ready to send a proposal out and I was like, wait, time out, time out, wait. Like this is not what we are trying to do. And so anyway, I think it's been, I, I obviously I love and appreciate all of what you do. I think we have now also hit a level where I am really starting to push back on you a little bit. And I think too,

Mm-hmm.

This is, this is growth. And one of the best things I see when you work with somebody longterm and what I love on the coach side is being able to say like, okay, no, we've been doing this. Now it's time for me to say, like, I, if you want me to push you, I've got to push. And, um, I would say probably in the past three months, I've been pushing you a little bit harder than I've, than I've ever really pushed you on that. But I feel like at this point, that's what you're paying me to do. Right. And I think that's where.

Yeah.

Mm-hmm.

that growth comes in is being able to say like, nope, it's time to push and say, even yesterday, I think with that proposal, I was like, all right, where did this even come from? Like, explain it, like, come up with it. Like, it's time to think differently. And that's such a testament to your growth. You started out in doing everything, you know, being everything to everybody. Then we went to VIP days, you raised up your, you know, you increased your prices slowly. And now you're doing like...

Right.

massive, massive build outs, which is a great segue into talking about like what exactly you're doing, who do you love to support, how are you doing that, but you're working with a pretty big company right now.

Yeah. So, you know, back in the day, I was working with very small businesses and it's, it's gradually grown over time, right? With the sizes of businesses, the types of businesses that I'm working with and really getting to understand and know what I like, who, who I like working with us, like what industries and things like that. So, so yeah, now I'm working with some much larger companies, which is fantastic. And this

piece of, I think, my journey too is there's a lot of growth here in this stage, right? Because now I'm shifting from these like done in a day models into much more large scale projects. So yeah, so definitely, definitely growing in that way.

Yeah, I mean, and so talk a little bit, tell the audience, like, what is it about ClickUp? How do you love to utilize it? Because I think, you know, for a lot of us, we view, like, ClickUp, project management, but like the things that you're able to do in project management, like in this tool, like always continue to blow my mind. Like, oh my God, how can you do that? But like, what are your favorite features? Like, what draws you to ClickUp more than anything else?

Mm-hmm.

Yeah, my goal in building out ClickUp workspaces for businesses is really to make it your operational hub. This should be the place that you go to start your day every day. It has all of your tasks, your projects, your team, your communication, client projects, everything that encompasses your business should basically live inside of this tool. So what I do is I create an ecosystem for the business inside of ClickUp.

And yes, there are several other project management tools like Asana, monday.com, Basecamp, right? The list goes on and on, there's tons of them. But I choose ClickUp because of its functionality and the continued growth in the tool itself. They're continuously creating additional features, enhancing features, and building a system and a tool that can really work for a

for anyone, a wide variety of different businesses. So I've built this tool out for, I work with a lot of digital marketing agencies, but I've worked with a lot of realtors. I've worked with a lot of travel agents. I've worked with a lot of other bookkeepers and other interior designers. So this tool is very functional in the way that it can be customized to really any business need.

interior designers. Yeah.

It's just my job is to then really get to understand and know how the business functions in order to build the tool out for them. So it's functional for them.

Yeah, and don't you even use it like to manage your house?

I do. Yeah, I use it to manage our household. I use it to manage. I've got other businesses that I manage utilizing ClickUp as well. So it's very helpful in all areas of life.

Yeah, definitely. Talk about a little bit about your relationship with ClickUp corporate and how you managed to get in, not get in, but you know, just how you've built that relationship with ClickUp. You've helped them develop this verified program, the Verified Plus. Like you're one of the, how many, there's not very many Verified Plus consultants out there. So yeah, just talk about like your journey with them and getting to know them and all of that.

I'm gonna go to bed.

Mm-mm.

Yeah, definitely. So when I first started utilizing ClickUp, I was just talking about the tool, right? In, in posts and things like that and tagging, tagging ClickUp corporate and, and in my reels and in my videos and posts and all of that sort of stuff. So I gradually grew inside of like the, they have a Facebook group, right? So providing tips and tricks and things like that. So getting noticed by them in that way. Um, and then ended up

meeting one of the co-founders of the tool at an event. And then from there, he accepted me into the verified program and all of that. And so there's two different levels of verified. So there's verified consultants, which ClickUp gives badges for these so you can be recognized as a verified consultant. But now they've also introduced a new level to this, which is verified.

Plus. And so I was one of maybe six or eight people inside of the beta program for Verified Plus, and they just recently launched it more broadly. But yeah, so I'm working directly with ClickUp in several different capacities, like creating content for them, doing a lot of internal work with their Facebook group.

and all of that sort of stuff. So it's more of a partnership now where it's mutually beneficial to both parties. Yeah.

Yeah.

Yeah, and how long has that been going on? Like three years? Two years, three years?

Yeah, it's been, yeah, yeah. So I've been a verified consultant for some time. It's just until recently, we started the Verify Plus program.

Yeah, so if you're listening and you're thinking like, maybe you have a really great relationship or you love to work inside of Dubsado or you love to work inside of, Moxie is a new one that a lot of people are using or Trello or Asana or any of these things and you're wondering like, man, how do I get there? Like, how do I get them to notice me, right? Like, how do I niche into this so deeply?

find the groups and give value. Like that is 90% of how Jenna really started her, you know, entire like niching into ClickUp was just living in that Facebook group. I mean, for a lot of times she was like in that Facebook group, continuing to provide value, answering questions, learning about it, sharing about it. She created her own Facebook group where she was also sharing. I mean, it really is just about giving value.

Mm-hmm.

a ton of value and then getting recognized and companies and corporations will start to recognize you. If that's something that's important to you and you really want that and you want to build those relationships, number one, they don't happen over time, like overnight, you know, it takes time. And number two is you got to give them a reason. Give them a reason to notice you, you know, give them a reason to go, man, this girl, like

she dressed up as freaking click up for Halloween. Like she's kind of obsessed, right? Like give them, I'm not saying everybody needs to go and like dress up for Halloween or whatever, but like give them a reason to notice you and build that relationship. And that's not just because, you know, you're in a sea of many, we're all in a sea of many. Jenna is not the only person talking about click up. Jenna is not the only verified plus consultant, but she gave them a reason to notice her.

Yeah.

and it's paid off and it's done her business very, very well. So if you're in that space and you really want to niche into, you know, a software, give them a reason. Give them a reason to notice you.

Yeah, that was a huge piece of my strategy, right? Was being very, very active inside of their Facebook group and providing, just providing value. I wasn't promoting, I wasn't doing anything like that. It was purely value that I was bringing to that group. And then I was able to create my own Facebook group, which now is almost at 4,000 people inside of this group. So just over a few years, it's grown pretty quickly.

Mm-hmm.

Amazing.

Yeah, absolutely. So if somebody wants to get started with ClickUp, I know primarily you're doing a lot more with Teams now. They have Teams, but you have a lot of just resources and different things, but what would you say is most important when starting with a project management tool for people? Like, what do they need to have in order to really benefit or gain the most from ClickUp?

Mm-hmm.

Yeah, I mean, really what it comes down to is just understanding the functionality at its most basic level. So with ClickUp, I talk a lot about building out the hierarchy in ClickUp. And basically what that means is just building your organization, your organizational structure in the tool. So understanding some of the basic lingo, right, of the tool, because that might be different from any other tools that you've been using previously. And then just how to create.

basic tasks in the tool and how to view your tasks. Those are gonna be the most basic things to get started with. And then of course, there's tons and tons and tons of other functionality. But if we can just get the basics down with your organizational hierarchy, the way that you use and interact with tasks and the way that you view your tasks, that's a good foundation for setting up for success.

Yeah, and you've got some templates and master classes on like how to manage your leads. Um, so if any of you have purchased, um, the lead gen done different or the coffee chats, the client's bundle, you'll see there's like a click of lead generation, but, uh, template in there that obviously was, um, with the help of Jenna creating that and using all those custom fields. So like, there's so much power in it and you know, you can.

Mm-hmm.

You can make it what you want it to be. I think that's what I love about ClickUp. I use it literally just to track my leads and nothing else. I probably should do more with it, but I haven't taken the time to do it. I'm still pen and paper task person, but.

Mm-hmm.

Yeah.

you can use it, you literally can make it your own, right? And you can just keep adding onto it. And I think that's where, and that's where you get a lot of repeat business. So earlier in the conversation, we were talking about reoccurring, but you get a lot of repeat business in the sense of people just getting them into the tool. And then it's like, oh wait, I can do this, wait, I can do this. You just did that with a big company. You started with one department, now they're adding on three other departments. So that's the beautiful thing

Yeah.

Mm-hmm.

Yeah.

a tool like that and also working with a consultant like yourself is that once you've got it figured out, you can just keep adding onto it. Right? I mean, isn't that one of the most versatile parts of ClickUp is the ability to just add on.

Yeah, for sure. You know, as, as your business grows and scales, you need to make adjustments and changes and, and additions, right? So ClickUp allows you to do that with the functionality of the software. Makes it easy.

Yeah, absolutely. Awesome. All right, well, where can people find you, Jenna? And if they want to get started, where can they find some resources? Obviously you mentioned your Facebook group. We'll make sure we link that in the show notes, but where's your favorite place to hang out these days?

Yep, definitely the Facebook group. And also when you enter into the Facebook group, if you leave your email, you'll get a free mini training. It's called ClickUp Simplified. So that's a really good place to start learning about ClickUp. And I also hang out on Instagram, so at the Jenna Apollo.

Awesome. And is Level Up still available?

Level Up is still available. Level Up with ClickUp, that is my training course. And so if you want a full training course on how to utilize ClickUp, that is definitely helpful and super beneficial. I was actually just told today by someone who went through the program that it's even more helpful than ClickUp University, which is ClickUp's actual training site that teaches people how to use ClickUp. So, so there's that. Yeah.

Yeah. So that's amazing. So definitely I would, especially as you're in the new year, hopefully we're at time of recording. And by the time you're listening to this, it's December, it's year end. You know, if you're really looking to up your organizational game, get a project management tool in place, like grab level up with ClickUp. It's really robust. I know that for a fact. I'm speaking from experience. I know exactly what it looks like on the backend when it is very, very robust. So definitely if it's something that you're interested in.

Go check that out. Check out her website, find her on Instagram. And if you just want somebody to do it for you, Jenna's your queen. All right, awesome, Jenna. Thanks so much for being here. I appreciate it. Take care, bye.

That's right. Thanks, Michelle.

Yeah, thank you. You too, bye.