Stepping up Your Business Operations with ClickUp and Jena Paulo

Jessica Rosario: 0:18

Hello and welcome to the Maximize Your Day podcast, a place for entrepreneurs who are building their business in pursuit of freedom and flexibility to do the things they love. I'm your host, jessica Rosario. I'm a New Yorker turn Floridian Who knows a thing or two on how to effectively manage your time while juggling multiple priorities. I'm an ex-corporate leader who walked away from my 9-5-ish to launch and grow my business. In this podcast, i share insights on mindset, business productivity, habits and strategies to help you take control of your to-do list and maximize your day, which will help you feel more confident and less overwhelmed and getting more done in less time.

Jessica Rosario: 0:57

I'm so excited you're here. Go ahead, listen in. Welcome back to the show. I am so excited to share with you today someone who is near and dear to my heart and I can't wait for you to hear her story and what she does, because she's been instrumental in my business as well. As you know getting things organized and you guys know this show is all about maximizing your day, So I definitely know you're in for a treat. I know I say that all the time in every episode, but you really are in for a treat. So excited for you to hear from Jenna Paolo. So go ahead, jenna, and introduce yourself. Tell us who you are and who you serve.

Jena Paulo: 1:43

Yes, thank you. First of all, thank you for having me, and I'm Jenna Paolo. I'm a business operations consultant as well as a verify click-up consultant, and essentially what I do is I help my clients maximize the way that they utilize a project management tool called ClickUp. I help them build out the tool. I consult on the tool, but essentially what I do is I want my clients to marry their processes with the tool so they can utilize ClickUp as their centralized business hub and have one place to go to manage their projects, their people, their processes, all of the things And mainly, who I serve, i would say. I mean, it's kind of varied. I work with a lot of different industries, but I do work with a lot of coaches. I work with a lot of digital marketing agencies, hr consultancies, people who are more service based typically is who I mostly serve, but my goal really, no matter who you are, is to really help you utilize ClickUp to maximize the way that your business runs and develop processes that just make sense for you. Awesome.

Jessica Rosario: 2:49

Awesome. I can't wait to hear what this episode is going to be about, because, even though I've been following you for a while, i purchased one of your courses about I want to say it was about a year ago and it just really changed everything in the back office of my business, and not only for my coaching business, but also I own a commercial cleaning business. For some of the people in my audience that knows that I'm a multi-passionate entrepreneur But the importance of utilizing this system in both ends of my business, it was just truly eye opening. So I'm super excited to have you here Now. Jenna. Tell us what inspired you to start your business.

Jena Paulo: 3:31

Yeah, so I actually come from a background in educational operations and I was managing large schools, large teams, doing trainings, doing all of those things. And when I kind of made the shift into the online space and one of my main reasons for really creating, making the shift is because I was kind of overwork in the nine to five, right Like I wanted to do my own thing. I wanted more flexibility in my schedule, i wanted to just have more time to do the things that I loved. And so, taking my experience in educational operations and kind of shifting that and utilizing that background, that knowledge in the online space, I was able to create a business that I love.

Jessica Rosario: 4:17

Awesome. Do you think that there was a big challenge when you shifted from doing schools versus moving into the online space?

Jena Paulo: 4:25

Yeah, i mean, there's always going to be a challenge when you're moving from something that you've been so used to doing, right?

Jena Paulo: 4:32

I was doing that for over 12 years And now I'm kind of shifting into this new world, right, that I'm not super familiar with, not super comfortable with yet. So, yeah, there are absolutely hurdles that I had to kind of step over, and I would say some of the big things that stood out was that I really had to. I was now managing myself, right, instead of being confined to these hours of work and like what I was supposed to be doing. And so, being someone who was really used to structure and having this structure kind of created for me, i then had to create that structure for myself, right, and really start to build a business. That one took into consideration what I wanted my life to look like, right, and two, how I could serve my clients in the most effective way. And so, yeah, there were challenges that definitely came with that, especially in the beginning stages, right, and I would say even with every stage of business, there's new challenges and new hurdles, right, but I would say just getting started in the beginning was one of the bigger hurdles.

Jessica Rosario: 5:42

Yeah, absolutely, and I'm so glad that you bring that up, because one of the struggles that I experienced when I left corporate in 2019 was that I kind of lost the structure of what my day looked like And in that moment I was the most organized person when I was in corporate and balancing all the things. But leaving that part of me, i kind of lost myself in that and trying to figure out. I was working all kinds of hours. I didn't have a real structure of a client called me on a Sunday.

Jessica Rosario: 6:10

I picked up So, even if it was taken away from family time. so I didn't really have those boundaries set And I can see how, for some that are moving into something new, it just kind of knocks you off your feet just trying to figure out what that new process is going to look like.

Jena Paulo: 6:26

Yeah, yeah, absolutely. Because you come from having so much structure to no structure at all And you have to kind of build what you want that structure to look like because you don't want it to mirror that 9 to 5, right That you left. You want it to be a structure that makes sense for you and the life you want to live.

Jessica Rosario: 6:43

Yeah, for sure, For sure. So what would you say was the pivotal moment for you when you realized I want to incorporate a system and be specialized in this system? What was that aha moment for you?

Jena Paulo: 6:58

Yeah, absolutely So. When I started my business, i didn't go straight into ClickUp. Right, i didn't even know what ClickUp was when I first started. When I first started my business, i was working more on the back ends of my business, more as like an operations manager. Right, managing the back end pieces And quickly realizing that these clients needed a system in order to sustain the business. Right, because you know, we've got Google Docs here at Google Sheets, we've got notes in this thing and that thing, and you know it's kind of spread out all over the place. And so, quickly realizing that we needed some structure in the business, i went and did some research, right, so there's a slew of project management tools you can use.

Jena Paulo: 7:37

I dabbled in Trello, i dabbled in Asana, i dabbled in Monday and Basecamp, i dabbled in all of these other systems, and some of them would work for a while And then I quickly realized it has some things I like, but I need to do more. Right, I need more flexibility, i need more functionality here. And so finally I found ClickUp. And once I did, i literally never turned back. It was like this is the tool.

Jena Paulo: 8:04

And once I found the tool, i of course started implementing it for my clients, building out their workspaces and things like that, and really learned to just love the system and loved how I could incorporate my operational background into developing systems like this. And so it quickly evolved from doing some buildouts for clients but also offering other services to strictly offering ClickUp as a service right In the form of consulting, in the form of doing these very large buildouts and now doing things like coaching other ClickUp professionals right, and so it kind of evolved. But that was the pivotal point of utilizing these other systems, not really liking them, needing to find a better solution and then finally finding that solution and ClickUp.

Jessica Rosario: 8:53

Yeah, I completely agree. I will tell you, I dabbled with Trello also. I played with Asana for a hot minute, but Trello was my main one.

Jessica Rosario: 9:02

And I think at one point I was working with someone, a freelancer, that used ClickUp, so I kind of like moved over to that platform temporarily until I fully transitioned, and I think when I fully transitioned it was just a hot mess. So one of the things that led me to you was looking for experts in ClickUp, not necessarily to understand usage of the platform, because I could learn that on their ClickUp University, right.

Jessica Rosario: 9:30

But I think it was more so about the use case for our business, because I knew how to use it. For my coaching business It was okay. I was using it already with certain things, but when it came to our brick and mortar business we have a field service business We wanted it to talk to other systems. You know we use HubSpot. Hubspot now has an integration with ClickUp. We use Bamboo HR to manage our workforce and that has an integration with Inside of ClickUp. We needed something that can really help us, kind of like set up that back office infrastructure, and that's when I found you. So I'm sure that you hear a lot from clients that they're stressed out the user-friendliness of ClickUp. It's not easy to learn and all these things, because that was one of the things that I was telling myself until I found you.

Jessica Rosario: 10:22

So what would you say is the biggest hurdle that you've helped your clients overcome to be able to manage this platform?

Jena Paulo: 10:31

Yeah, definitely. So. I mean, many clients like yourself find that when they find the tool right, when they find ClickUp, they love the idea as the possibilities right, of what the tool can do and how the tool will perform. And so once they get started inside of the tool and start actually messing around with it, it kind of becomes a different story because there is so much robust functionality of the tool right, there are so many features that we can turn on and turn off and there is automation and there is dashboards and there is templates and there is all of these things right, which can start to become very, very overwhelming.

Jena Paulo: 11:08

And so when I work with my clients, what is really important is that we kind of just set the foundation.

Jena Paulo: 11:14

We really have to understand the business before we can marry it with the tool.

Jena Paulo: 11:20

And I kind of talk about that a lot, where we are marrying your business processes with the functionalities of the tool, right, because we don't want to change your business, we don't want to change the way that you function if it's working well, right, we want to marry those processes with the tool.

Jena Paulo: 11:34

And so in working with my clients, that's a really big thing is first understanding how the business functions, what your processes look like when it comes to client experience, what the processes look like when it comes to marketing your services. you know what I mean. So just really diving into what the processes look like and then developing structural higher key inside of the system. And if you know about ClickUp or have heard people talk about ClickUp, we talk about the hierarchy a lot inside of the tool And that basically just means how you organize yourself right, your spaces, your folders, your lists, and so really teaching the fundamentals to my clients is a really big piece of them then understanding the broader aspects of the tool and how to apply those things to the business. So it's the processes and then it's really understanding just the foundational things of the tool.

Jessica Rosario: 12:27

I love that. So would you say that the traditional business owner, whether it's an online space or brick and mortar, doesn't matter? Would you say that every business should have a project management tool? It doesn't have to be ClickUp right, But they should have a project management tool.

Jena Paulo: 12:46

A thousand percent, yes, they need something to really keep all of the pieces of the business in one place, right, because things get lost. You forget things. You have team members who you want to communicate with and you're sending messages in Slack or you're sending it via email. The communication can get lost very easily, especially when you're working with multiple people inside of a business. But even if you're a solopreneur, you need ways of keeping track of your projects. You don't want client tasks to fall through the cracks, right? You don't want to lose leads. You don't want to not manage your email campaigns in the right way, right, whatever that looks like for you. So, absolutely, no matter what the tool is, you need a tool.

Jessica Rosario: 13:26

Awesome. So I'm going to ask you a couple of questions. I just need you to tell me if it can be done in ClickUp. Okay SOPs.

Jena Paulo: 13:38

Oh hell, yeah, Absolutely Right. Yes, so you need to create a SOP database inside of your workspace so that you don't have to go looking for the document somewhere else, so that you have an actual documented process that you can connect to a task, right? So if you, let's say, you bring in a social media manager to help you manage your Instagram posts, they know exactly how to do it from start to finish, with this SOP that is connected to their tasks or inside of a database in some way inside of the tool about.

Jessica Rosario: 14:09

You already hit it, but marketing.

Jena Paulo: 14:13

Yes, absolutely. You wanna manage the creation process there right, from taking that idea, that post idea from start to finish or a real from start to finish right, and so being able to manage those things, your marketing through workflows, tracking, dates, tracking, assignees, tracking, kind of where it's on the process. It absolutely can do that. Goal setting Yes, there's actually a goal setting feature inside of ClickUp And so you're able to manage your goals in there utilizing that feature. But then there's also other creative ways that you can utilize the tool to manage your goals, your KPIs, all of that sort of stuff.

Jessica Rosario: 14:50

Awesome, awesome. I mean the list can keep going right. But when you think about, even when I think about the way I use my ClickUp on one business and the other, i mean there's my marketing, there's my headquarters, information of how I manage my business, there's my speaking engagement, there's my podcast. I was so proud of myself when I reached out to the Jenna Paolo to let me know hey, do you want to be on my podcast so you could test my workflow while you're at it, and it was so cool to be able to kind of see the things.

Jena Paulo: 15:21

So that was all.

Jessica Rosario: 15:21

by the way, I learned all of that through Jenna, So I thought that was awesome. How about personal?

Jena Paulo: 15:27

things? Yeah, you definitely can, and so I know a lot of people that I've worked with. They have a personal space inside of their bigger ClickUp workspace right, just to help them manage those day-to-day things groceries, or to do things for the kids. Whatever that looks like in your personal life. You can absolutely manage those things. They actually just created something really robust for myself and my husband. I'm like you're going to utilize ClickUp. We're going to manage all of the household things inside of ClickUp, and it's been great.

Jessica Rosario: 15:58

That's awesome. that's awesome. I did see a couple of weeks ago, you posted something on your stories I think it was an Instagram on how you guys delegate some of your household tasks, so I thought that was really neat. Haven't been able to get Alex there yet. Maybe one day, but I haven't been able to get him there yet. So, jenna, tell me now, on the other side of systems and operations and all these things aside from your brain which I'm thinking is similar to mine, where I'm always thinking systems, processes, goals. I need to plan, i need to know things in advance, how do you keep yourself motivated when things don't go your way?

Jena Paulo: 16:37

How do I keep myself motivated? That's a really great question. I think that a lot of it kind of comes from knowing that it's worked before right, because I've gone through waves each business goes through waves right, where some months are really great and then you kind of fall off a little bit and go back up right. So keeping yourself motivated is really important And I think the best way that I do that, just personally, is knowing that I have proven strategies that have worked and that I can always go back to those strategies right, because if I'm trying something new and maybe I'm offering a new service, whatever it may be, maybe I'm trying a new way of marketing myself utilizing LinkedIn, let's say, which I don't do, right, maybe I wanted to go and try that. I know that, although I can venture off and try these new things, that I have kind of a home base of what I know works well for myself and for my business, and so just giving myself the flexibility to try new things but also continue to utilize those proven strategies if I need to.

Jessica Rosario: 17:44

Love that, love that. Can you speak to the importance of being able to kind of disconnect yourself from the day to day to be able to just maximize your energy?

Jena Paulo: 17:58

Yes, yes, for sure, because I've been on both sides, right, i've been on the side where business consumed me and I Want, first of all, i love doing what I do, so I always wanted to be doing it right and I wanted to be, you know, utilizing new things and trying new things and all of this stuff. And so at one point in my business I was basically consumed with that and I would work really late hours and you know I would stay up all hours at the night, wake up early to record and like do all of these things right and That's a quick way to burn out right, that is a quick, very quick and easy way to burn out. And so once I realized like I need to like take a step back right, like let's take a step back, let's prioritize. How can I better serve my clients? How can I better serve myself without having to Like kill myself by working all of these hours and trying to do all of the things right?

Jena Paulo: 18:53

and so one of the ways of doing that was really kind of looking at My ideal day and my ideal schedule and what I wanted that to look like. Right, because I want to have time To spend with my son. I want to have time to spend with my husband and do fun things and, again, i didn't leave a nine to five to work those types of hours. I wanted flexibility in my day right, where if I wanted to go to the park at nine in the morning, i could go to park at nine in the morning, right.

Jena Paulo: 19:22

And so really the first step for me was kind of looking at my schedule on my ideal day, like what did I want that to look like? how many calls did I want to take every day? where there days I didn't want to take calls, right? So kind of looking at that and then kind of puzzle, piecing it together, right, and really creating the ideal day, the ideal week, the ideal month. What does that look like and what do I need to do? What action do I need to take in order to hit my goals right? what are the actual things that That are gonna make me money that I need to prioritize over things that might not bring in any money right Or serve my clients in any way? so that was kind of how I approached it.

Jessica Rosario: 20:03

Awesome, awesome and and you are. You seem to be somewhat of a nature girl, right, so so you like the outdoors, so is there something specifically that you love to do when you're, when people can't find you, behind a click of dashboard?

Jena Paulo: 20:19

Yeah, for sure. We're always out camping and in the wilderness like not. We're not really like Campground kind of people or people that take our off-roading Jeep and off-road into the mountains and Literally have no service. So that's what. That's where you'd find me.

Jessica Rosario: 20:36

Yeah, that's kind of terrifying.

Jena Paulo: 20:37

You won't find me there but that's awesome, awesome, i love that.

Jessica Rosario: 20:42

So now I want to spotlight a little bit about you and how you can support Your clients. So for the woman that's just starting out and obviously there's some guys out there So if there's a guy listening to the podcast, kudos to you. But but say there's someone out there that's starting a business and They don't you know project management or this type of platform. It didn't even cross their mind. Is this something that you can recommend from the startup?

Jena Paulo: 21:13

What I would first recommend if you're starting to look for a project management tool for you that works specifically for you. You want to be able to go into the tool and utilize it just functionally, just very basic. Be able to create a task, set a due date, assign it to yourself. You want to be able to do those easy, functional things. When you're thinking about utilizing any kind of tool, the easier and most simple it is the better, because you're more likely to use it.

Jena Paulo: 21:48

If you start to dabble and click up and find that click up has the simple functionalities that you can follow and you're comfortable with that, click up is going to be the one that's going to grow with your business. You want something that's going to grow. If you go into Trello but you plan on being a million dollar company in 10 years, that's not the tool for you. Really thinking about long-term when you're thinking about a project management system, but being able to just utilize it in its most foundational way so that you get comfortable. You don't want to dive in and start trying to utilize all of these more advanced features. You want you to ease in slowly.

Jessica Rosario: 22:33

I love that. Personally, i wish I would have started from day one, but also knowing where I was mindset-wise from day one probably would not have been the right time. I love that you're sharing that, jenna. how do you help businesses identify areas of inefficiency rather and areas of opportunity in their operations?

Jena Paulo: 22:56

Yeah, typically what that looks like is we hop onto a call and I really dive into your business, whether you're already utilizing a project management tool or not. I want to see the inside of your business and I want to pick your brain. I want to pull things out of your brain that maybe you didn't even think were important or didn't even know you had a process for. This is really high-level auditing and consulting for creating a plan, because I need to first understand how your business works, what your business is, in order to give you suggestions on how to build out a tool that's going to support you. That's always the best. First step is really doing an audit type consultation. We can understand the business and then give you the action items on how you can start to apply a tool like ClickUp.

Jessica Rosario: 23:49

Awesome. How can someone work with you? What are your current offerings?

Jena Paulo: 23:55

Yeah, i have a handful of offerings. One is a consulting hour. You can purchase consulting hours just one off, or in bulk Again. This is where I would come into your system, audit your system, do that kind of stuff. But if you've already been utilizing ClickUp, let's say, and you're wanting to continue to improve it, you utilize a session for that type of thing as well. Then I also do larger buildouts. Let's say that you're the person who knows you need a project management tool, but just either don't have the time or don't have the capacity or the knowledge to build it out yourself and you want an expert doing that for you. That's always an option as well. This is more like a partnership. We're really partnering together to create a system that works for you. It's very customized. Then, if you are a ClickUp professional, i also offer coaching and mentorship programs for those types of entrepreneurs as well. Then I have a course, which you are a part of, level up with ClickUp, which teaches you how to build it from start to finish.

Jessica Rosario: 24:59

I love this course. I mean it was so good and you can tell that you have a background in education Because it was so good that I don't think there's any reason why anybody would take this course and say I just didn't get it, i just didn't know how to use it. Because you're so patient and you're so thorough in your explanations and even in the visuals, and being able to build it exactly the way you have it, it was just an incredible process. I really loved it. I still refer to it.

Jena Paulo: 25:26

I love hearing that Great. I love that With ClickUp 3.0 coming out, there will be some updates to level up eventually. I just got access to 3.0, which is very exciting. I love that.

Jessica Rosario: 25:40

You know that's funny. It didn't even cross my mind, but, yes, i love that. That's so exciting, awesome. Yeah, they did a massive update and I'm hearing great things about it, so definitely for those that are listening and that are looking for a platform that can grow with them. Zero regrets We will never leave ClickUp. I mean ClickUp better. Never leave us either, right.

Jena Paulo: 26:01

Yeah, I don't think they plan to.

Jessica Rosario: 26:03

That's a great platform And it's just really helped us in scaling our business, growing our business and just keeping things organized. I think the most important thing has been team communication, too to be able to communicate with our team and see where certain tasks are and what's pending and whatnot. So that's been really great. So, jenna, how can people find you.

Jena Paulo: 26:22

Yeah, so if you are interested in learning more about ClickUp, you can join me inside of my Facebook group. It's called ClickUp for Entrepreneurs And I offer tons and tons of tips and tricks inside of that group, as well as free trainings and inside looks and all of that fun stuff inside of the group. So I'll pass that Facebook group link along to you And then also you can find me on Instagram at the Jenna Apollo.

Jessica Rosario: 26:49

Awesome, awesome. I love that. For those of you that are driving, those links will be listed on the show notes, So feel free to check them out there and feel free to connect with her directly Now. Jenna, as we wrap up our episode here today, tell me how do you maximize your day?

Jena Paulo: 27:08

Yeah, love that. So I maximize my day by doing a few things. First, i utilize ClickUp to prioritize my tasks, and the second thing I do is I ensure that my day is structured the way that it's going to be most productive for me. So I would say that I'm not super, super productive early in the morning I'm more of a night person or later in the afternoon. So all of my priorities and tasks that might be more difficult or more challenging, i utilize the time where I'm most focused to accomplish those things. So the morning's not for me, but later in the day is, and so that's kind of how I prioritize and maximize my day.

Jessica Rosario: 27:52

Awesome, awesome. I love that. Well, you guys, there you have it. I mean, we had the Jenna Apollo on our show. I'm so excited to be able to air this episode And if it impacts or helps one person, then we've done our job on who we've been called on the surf to serve. So excited to be able to share this time with you and get to know a little bit more about you And just look forward to continue watching your growth and continue to work with you as we move forward.

Jena Paulo: 28:21

Yes, thank you, and thank you so much for having me.

Jessica Rosario: 28:24

As always. thank you so much for listening in. Don't forget to subscribe to the show to be notified the second a new episode is released and share with your friends who you believe could benefit from listening. Contact me at justrosariocom forward slash podcast to share your feedback, ask question, make topic suggestions or even be a guest on my show. You never know if your topic will be next until next time. Maximize your day and own it.