She's Busy AF

EP 127 | How to Set Your Business Up for Successful Scaling With Optimized Systems and Processes with Caitlyn Wells

• Lauren Loreto

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In, or approaching, a scale phase in your business? In the growth mode of a business, chaos is almost welcomed. Chaos is where you figure A LOT of things out. But what about when you get to scale mode - when you're ready to take your proven product and 10x your abilities to offer it? In this episode of "She's Busy AF," host Lauren speaks with Caitlyn Wells, founder of Upwell Strategies, about the critical role of systems and processes in scaling a business. They discuss the challenges of scaling without proper systems, the benefits of project management tools, and the importance of clear communication platforms. 

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Timestamps: 

  • Caitlyn's background and passion (00:02:24) 
  • The role of systems in business growth (00:03:45) 
  • Challenges without effective systems (00:05:30) 
  • Impactful systems for scaling a business (00:06:19) C
  • Favorite project management systems (00:06:51) 
  • Balancing systems with creative flow (00:11:52) 
  • Continuous improvement of systems (00:15:20) 
  • Must-Have Tools for Scaling a Business (00:22:39) 
  • The Importance of Implementing Systems Early (00:24:33) 
Speaker 1:

Welcome back to another episode of she's Busy AF. We are a podcast that is focused on helping brands, entrepreneurs and creatives smash those barriers and scale their business. Today I'm very excited. I'm always excited because we have a guest on the podcast and her name is Caitlin Wells. Caitlin might go way back. She is the founder of Upwell Strategies and we've known each other for a couple of years now and it's been really fun to watch her business grow. Upwell Strategies is an agency designed to help you build an impactful and profitable business that aligns with your vision for your business and for your life. So Caitlin and her team and clients really care about making an impact on their communities just as much as they care about growing their businesses, and so her team has helped 55 plus diverse businesses gain immense clarity and grow sustainably through innovative and effective operations and business strategies. She's big on building sustainable business, and so are we here at she's Busy AF.

Speaker 1:

So are we here at Brand Good Time, and I wanted to have Caitlin on the podcast to really talk about strategic operations and systems and how to implement strategic operations and systems, especially if you are in the process of scaling your business. So can typically be a boring subject. I'm a creative, but I also really love the ops side of things, so I was super excited to have this conversation with Caitlin. I personally learned a lot about things that I may not have necessarily thought about. With systems and creating systems within the business, you may think you have it all, but it's always good to pick the brain of someone who's an expert, and so I think that's what you'll feel when you listen to this episode is that you're going to gain some insight on how you can improve and continuously improve your systems to keep up with the evolving growth and the evolving business needs that you have within your own business. So, without further ado, let's dive in. Hey, caitlin, welcome to the podcast. I'm so excited you're here.

Speaker 2:

Hey Lauren, I'm excited to be here.

Speaker 1:

We have connected a couple times, like over the years. It's crazy. I think we've worked together on strategy and it's just been really fun to see your business grow. I've loved referring people to you. So, yeah, it's like we've been with each other a couple years now. Yeah, two or three years. That's crazy. I remember we were both pregnant.

Speaker 2:

At the same time. We were like a week apart, yeah yeah, that's so funny.

Speaker 1:

There's a couple of people like that. I know from that time, that era, if you will, so well, okay, well enough about like me Background chat. How did you become passionate about business systems and operations? Let's start there.

Speaker 2:

Yeah, definitely. I have seen and been a part of a lot of businesses growing up because I come from a family of entrepreneurs and my husband also comes from a family of entrepreneurs and it's been incredible to see the way that if you balance technology and systems and processes well with your people power, just how much can be accomplished and how that can also create a better team culture as you grow.

Speaker 1:

Oh, team culture. I'm a big fan of that, yeah, okay, so what if we're talking about team culture and the growth and scalability of a business? What role does systems play in all of that?

Speaker 2:

Systems play a role. I would say they serve as kind of like the guiding light and the thing that can bring calm to the chaos. So as you grow and you're taking on more and more clients or growing your team, and so there's more and more people to manage, having really clear processes in place and systems in place to support that growth makes it where that increased capacity can be less overwhelming to you as a leader and to your team as they come on. Because if they come in and they don't know where to find things, they don't know how to do XYZ, then you have to do a lot of hand holding and a lot of like one-on-one live training, whereas if you have really clear, outlined processes, then someone can come in and feel empowered in their role very quickly.

Speaker 1:

Yeah, that's a good point. I've definitely seen how that having systems and processes within our own business can do that and it's, it is definitely really powerful and you get that feedback too. I feel like, and you know, I mean we, we ask for feedback on onboarding.

Speaker 2:

How is your onboarding in the first seven days?

Speaker 1:

whatever. And I always, I always get something to the effect of like everything's really organized and like easy to find and navigate and whatever, and so it totally it's see the value and it makes a difference, because if your feedback was, I still really know what I'm supposed to be doing or where to go to get things.

Speaker 2:

I feel like I was thrown to the fire, like that's not the feedback you want to get.

Speaker 1:

No, gosh, and I can't tell you how many jobs I've worked where, like you just they even say like you know the best way to learn. We're just going to throw you in the fire and you're like great, not everyone can handle that.

Speaker 2:

A lot of people need structure.

Speaker 1:

Yeah, so what are some common challenges that brands face when they try and scale without effective systems in place?

Speaker 2:

When you're starting to grow your team and scale the level of revenue and sales and clients are handling things like that. I would say in this, common issues that come up is decreased client satisfaction because you're just dropping the ball because you're trying to keep up with too much with no organized system in place for it, and you'll start to see high employee turnover because they're going to feel burnt out, they're going to feel a lack of empowerment in their role or just general confusion, and so then they'll start looking for another job. That's kind of the too big like end results of a lack of systems as you grow. Yeah, that's kind of scary.

Speaker 1:

Yeah, yeah, it is. What are some specific examples of processes or systems that you've seen have a significant impact on scaling up business?

Speaker 2:

I would say a really clear file management system to make it easy for a team member to know where to find what. Having all of your SOPs in a clean, organized, searchable way and blending the SOPs with both written and either video or photo content, so it's visual. And then, I would say, having a clear, outlined, clean, semi-automated project management system.

Speaker 1:

What are your favorite project management systems?

Speaker 2:

I'd say ClickUp by far has been my favorite and I've worked in and tried all the different things. For some of the more creative minds they tend to enjoy places like Notion, but Notion is meant more for like a creative strategic brain dump kind of area. It has project management features but it doesn't have the same level of automation capacity that you can get in ClickUp. Asan is fine. I still think ClickUp's better, though Mondaycom is good Sometimes it has a little bit of a steep learning curve. I guess ClickUp can have a steep learning curve as well.

Speaker 1:

We use Monday, and I started using Monday on my own a long time ago.

Speaker 2:

Literally on my own.

Speaker 1:

I didn't have anyone else managing it. We're in there with me, which is kind of funny because it's really meant for teams. Clickup's probably a Notion or I feel like good places to start if you're just solo. But yeah, mondays become such a Bible for us. But I agree, when we're onboarding members who've never worked in project management systems, it's a little bit of a learning curve for sure.

Speaker 2:

Yeah, yeah, but it can be a powerful tool once it's set up well.

Speaker 1:

Okay, I want to dive a little bit deeper on the project management tool side of things. I used to work at an agency where we didn't even use a project management tool. This was back in 2016. I know that they existed. We had something called a hot sheet and it was just a Google doc that was color coded and had different department responsibilities on it. It was the focus for the week, the hot sheet for the week. I can't even remember how I kept track of my own tasks, but somehow things still got done. Whatever. What is the power of a project management tool?

Speaker 2:

I'd say the power of it is trackability and automations the ability to create templates so that when you're pulling in a new team member, a new client for XYZ project, you can easily duplicate that template and it auto assign out to whomever's responsibility is for each task.

Speaker 2:

From a leadership perspective, it's really helpful because you can go in and just about every project management spot there.

Speaker 2:

You can look at data around time spent on different tasks or a breakdown of where you're at in different projects, a breakdown of who's completing what, and you can do capacity planning in terms of wow, I'm giving way too much to Lauren. That's feasible within the scope of a full time job, but then Caitlin over here is only really if it's good enough being tasked out about the part-time job role. So let's like give some more of Lauren's stuff to Caitlin. So the PM tool just it really gives you a lot of that data and insights as you grow your team for you to be able to, from a high level, see what's happening and help with planning out the workload on your team. And you can get super detailed if you want. But you, especially for leadership, really enjoy it because they're not having to do that thing where you send messages to everyone, or you have 20 meetings a week trying to just figure out the minutia of if projects are on track or not.

Speaker 1:

Yeah, yeah, it's definitely been powerful for us for that, for the automation part, for the capacity planning part. I feel like PM tools still have a long way to go when it comes to capacity planning, like actual, but it's so nuanced, but still you can at least have a view of like here's everybody's tasks for the one week, Yep yeah and see like very quickly on a task basis, who's got more, who's got less. So I agree, I agree. Yeah, when you are working with a client to implement or improve existing systems, how do you make sure that that won't limit creative flow or disrupt existing workflow?

Speaker 2:

Yeah, whenever I work with a client, I spend the first few weeks of our project together strictly just kind of getting a data dump, learning how they currently work, the working styles of them and their team members, the current tech they use and kind of figuring out just how the business operates as a whole. And then, as we start to implement new tools and systems or optimized current ones, we're very clear on communication, like, hey, we're doing X Y, Z next week and this is how it impacts your work, and we're really intentional about making it a very collaborative process to make sure that as we're doing things, it doesn't stifle any sort of current thing they have going on and that they're well-informed and so it's kind of created and they're trained on whatever those changes are as they're being implemented, instead of like building the whole ship and then saying this is how it works.

Speaker 1:

Yeah. I love that I know that something that you've mentioned before is like how a lot of business owners and brands can think that going this route of really prioritizing systems and processes can hinder the ability to think big. What are your thoughts on all of that?

Speaker 2:

I think that it comes from a place of maybe fear that if they have these detailed processes in place, that it means that they're forced to follow this specific step-by-step procedure and it can hinder creativity or like innovative thinking and things like that.

Speaker 2:

But processes are outlined in a way where it's specific enough to make sure that there's consistency and ease within creating whatever that outcome is.

Speaker 2:

You know, the process is to get something from point A to point B, whatever it may be, and once you get that in place, you'll find that as team members work through them, they'll still find, like probably a faster way to do it, and so then you just update what your SOP is for it.

Speaker 2:

Or, once you have things more streamlined through systems, automations, processes, you now find that you have freed up time and just freed up mental capacity to think larger within your vision for your business. Once, when you're in an overwhelmed state because of how much your brain is just having to keep up with, like if you don't have a project management tool and so you're trying to keep up with this like ongoing mental list in the back of your head of all the things that need to make sure they get done that week, it can make it, where you're kind of in like a survival mode and that creative part of your brain is blocked. So once you're able to kind of offload that off your mind into a PM tool, into other systems to allow certain things to be more streamlined and run kind of on their own, it really opens up that mental capacity for you to think more creatively with how you can continue to grow your business.

Speaker 1:

That's so true. That's so true and I want to speak to that because we have a client strategy manager on our team whose job is like she's not a project manager or an account manager. For a reason she's a client strategy manager because half her role is dedicated to project management. The other half is dedicated, well, project management. Let's say, like half her role is project management and SOPs and making sure things are like working smoothly within our project management system, and the other half is operational support, where she's interfacing with clients and also helping improve client experience. You know team capacity, like all of that.

Speaker 1:

And it's really crazy, like you're right when I talk to her and she's like in the thick of project management or updating SOPs or creating processes, she's like gets into a silo there but then she gets so much reprieve and creative reign when she can get step out of that and go into the other tasks she has, and like it's wild how she'll excel in those things when she has processes in place and doesn't have to be so in the weeds with, you know, updating the processes or creating processes because there aren't any.

Speaker 1:

Yeah, yeah, exactly, it's really cool. So kind of on that note, systems and processes are not set and forget. I definitely went into the kickoff of creating SOPs for my business as when this is done we're going to be in such a good place. But then the next thing you know we're in a meeting and we identify we should really update that SOP because this is a new line item and there's clearly confusion with the team, so it needs to be documented and that can also just feel daunting. So how do you suggest continuously improving those systems to keep up with the evolving business needs?

Speaker 2:

Yeah, a lot of times SOPs are created and then they kind of sit in their folder and it's like there is a resource but not ever updated or really used and then they become an outdated resource.

Speaker 2:

And so it's really important to have a dedicated team member who's in charge of essentially kind of scrolling through all the SOPs and making sure they're still up to date. And that can be a singular dedicated team member, kind of like the one your team member you mentioned, who will go in and make sure there's SOPs for things, or it can be kind of a duty that split up among different people who have ownership related to those processes. So if you have, like a client success specialist, then any SOP related to, like, client experience and things like that they're in charge of reviewing on a monthly or quarterly basis to make sure it's still up to date and also making it where. It just becomes part of the team culture that if you're going through a process in your day and you find that there's a better way to do it, or maybe there's been a huge update on this specific software that you're using, so the way that you would complete that task is different now that they know that they are expected to then go into that documented SOP and update it.

Speaker 1:

And I like putting the onus on the team because I feel like not everyone has the luxury of having a project manager or an account manager. In my corporate background experience, you are responsible for your own SOPs and I remember anytime I would leave a job. Part of your off-boarding is going in and making processes and procedures for everything you've done.

Speaker 2:

Yeah, and the reason that I really emphasize that it's checked and or updated, if needed, every month or quarter is because you never know when a team member might leave or when some unfortunate event happens and someone might not be able to work for a few months or things like that, and so you kind of want to prepare for potential worst case scenario and just making sure that everything is always up to date so that, should a team member leave or something happened where they're unable to continue working with you, then whoever you bring in to take over their role can very easily just kind of slide right in and understand how to do everything within that responsibility list.

Speaker 1:

Totally totally so I'm going to take a little bit of a hard left here. Okay, as a service provider. So Brand Good Time is a marketing agency. We often work with clients who we're marketing support right. So we often work with clients who have marketing team members, or we might be working with the founder and their ops people and we find these are established businesses but they don't have any systems or processes in place for marketing and that can make our onboarding challenging. That can make, I mean, they are maybe not even just marketing. It's like they don't have documentation of the things that we need down to, like how they run a service or their products itself to market. So you know, adjacent to this conversation of looking within your own business for businesses who are service providers, how can we be successful in those partnerships with our own systems?

Speaker 2:

Yeah, I guess kind of two directions for that answer. So when you're bringing on a client and they're not really having things documented that you need, like how they would deliver service, for you to be able to aid them in the marketing of that, I would say it's then kind of a educational slash, maybe collaborative process of you kind of educating them on the importance of having that outlined somewhere, and then maybe you extend your project timeline by a couple of weeks and those first two weeks are you asking them to take the time to document that for you. It's just like how if you were to hire if I were to hire you for web design and I had my branding done by someone else the year or two ago, you can't design my website unless you have my brand guidelines and my color palette and my logos and things like that, because you need those assets to be able to do the website. And so if those weren't created then you would probably extend the project start to give me time to get those together for you. So that would be my answer to the side of like they don't have the information or assets. You need to kind of do the best job you could do.

Speaker 2:

But then, in terms of when they don't really have their own systems and processes in place, I would say when we onboard clients, we kind of have. So we use ClickUp for our project management, for all internal things and development and stuff like that. But we have a different tool that we use called coordinate. That is our strictly just like client facing kind of hub for projects and so we bring the client into our own system for making sure that the project runs smoothly. And so in coordinate we have the templates built out for the different projects we do and we invite the client and any of their team members who need access to that and invisibility on that project into it and they can very clearly and easily see what we're doing for their project, what they need to do, what they need to provide to us. And so if there's a lack of systems from the client side, then we just make sure we're fully bringing them into the system we have in place to ensure that that project succeeds.

Speaker 1:

That is really interesting. I've never heard of that tool before. Does it integrate with project management systems?

Speaker 2:

It can integrate via Zapier pretty well with different things. The reason we chose to go that route because it is like a PM tool as well is because trying to bring a client into your ClickUp, even as a guest, to only their project list was sometimes overwhelming for the client. Coordinate is a very simplified view to create that client portal for them to easily see okay, caitlin needs me to send X Y Z to them by Friday. Then that leads to then Caitlin being able to do this, or Caitlin's team member or whatnot. We've decided to use that for all of the client project hubs for them to have line of sight with what we're doing for them.

Speaker 1:

That's really cool. I love that, yeah, because I feel like most of the time at least in our business. We have agendas for the client and they have their Google Drive and we use Slack to communicate with them. We give them private channels with to-do lists in there, but that doesn't get updated that often and it's not very succinct. So that's really awesome. I love that perspective on the client operational side.

Speaker 2:

Yeah we were trying to make it as simple as possible for the client, because the more complex it gets, the more room there is for things to get missed, and so the reason we're using CoordNate is they only have one thing to click on, one link to go to, and in there it has the links to all the other things, but all they have to bookmark and remember is their link to their CoordNate portal.

Speaker 1:

That's awesome. Well, I'm definitely going to be checking out that software and, kind of on that note, what are some must-have tools or software for the scaling process of a business, like if you could just riff on all of the software you love. What is all that software and what does each thing do?

Speaker 2:

Yeah, I'm a big advocate of Slack for team communications. I think it's a lot better than losing things in email threads. So I'd say, as a team grows, slack is pretty integral. You need some sort of project management tool whatever works best for kind of your team style and project management whether it's Mondaycom, clickup, something like that but it needs to be a project management tool that can handle growth Like I don't really recommend things like Trello and stuff like that because I think as you grow into bigger teams it's not as efficient as some of the other ones and you want your PM tool to be able to pull you really good insights and data as you kind of grow into more of a hierarchy with a leadership team and down.

Speaker 2:

I would say I tend to recommend the G Suite over the Microsoft Suite, but it kind of depends on the clients you go for. But you need one of them, something where you can have email for outbound communication that's not within your Slack with your team. Some sort of file management storage solution, things like calendar management, things like that, and then, as you grow, building out marketing automations, so having some sort of email marketing software, tech software, if that makes sense for your business, things like that. But I would say like the core base ones are the project management, the CRM team, communications and then something like a G Suite or an Outlook Microsoft Suite.

Speaker 1:

I love G Suite. It's like Mac versus PC, right, yeah, yeah, yeah, like. How can you?

Speaker 2:

I don't know. It's so much easier to integrate things with the different G Suite applications than it is with Outlook. I just think it makes it a lot easier to help your different softwares communicate with each other.

Speaker 1:

Totally 100%. I agree. Awesome. Do you have any final tips?

Speaker 2:

when it comes to everything we've just discussed systems, processes, scaling operations I would say, a lot of times people are in the mindset of I'm not big enough yet to need systems in my business, and I would say that that's not a good mindset to have. I think that the sooner you can begin to implement different tools, systems, documenting processes, the better, because then whenever that moment of growth sparks because it's you know, there is the slow growth moments, but there seems to always be random peaks that happen in businesses and you need things in place to help support you when you do hit those peaks.

Speaker 1:

Totally, totally. I love that. Well, this has been a really, really great episode. Thank you so much for coming on and providing all of your insight. Where can people find you and how can people work with you?

Speaker 2:

Yeah, we are mainly active on Instagram and LinkedIn. So on Instagram it's at of Well Strategies, and on Instagram we have the Apple Strategies company page or just Caitlyn Wells personal page, and then, if people are interested in working with us, they can check out our website and fill out our inquiry form, and we would love to chat with them about auditing and analyzing their current systems and helping them get ones in place that can support them as they grow, yeah.

Speaker 1:

so what does an engagement look like with your company?

Speaker 2:

Yeah, so we're at a point where we've kind of refined our processes in a way where we know it drives the best results, and so any clients coming in are required to go through what we call the audit and analysis first.

Speaker 2:

And so it's a one month project where we dive deep into how the company as a whole operates and we work collaboratively with the founder founders to figure out what their goal is, their long-term vision, and then from there we map out their operation strategy that we know can support growth towards that long-term vision, and then a three to six month recommended action plan to get them in the right direction.

Speaker 2:

Once we finish that audit and analysis and strategy project, that's when we then propose like hey, these are the ways we can support you in building out this ops strategy, or here's a detailed overview of how your team can take it and run with it. And the reason we started doing that is because it was hard to provide a really accurate estimate of what you truly needed in your business from a 30 minute sales call, and so instead we found that it was really helpful to give people this in-depth analysis and strategy report and then they could kind of pick and choose. Okay, we really want your expertise on implementing this part but, like these, people on my team can handle these types of optimizations on their own.

Speaker 1:

I love that that's really cool. Do you see success in that too? Where, like if they do pick and choose, do they actually follow through with?

Speaker 2:

Yeah, yeah, we do so. The clients that choose to not engage with any part of implementation from us, afterwards they tend to move along a little bit slower on implementing it. But the clients who choose either for us to do the full implementation or even a part of it, or do some sort of consulting to kind of guide their team through the implementation, they see really good success with it. Even the ones when maybe we're only implementing a third of what we recommended and their team does the rest, since we're still kind of in the picture and kind of helping to hold them accountable as we do our parts of the implementation plan, they tend to see really good success from that.

Speaker 1:

That's awesome. Well, thank you, Caitlin, so much for coming on the she's Busy AF Podcast today. It was a pleasure.

Speaker 2:

Thank you so much for having me.

Speaker 1:

All right, and, with that being said, we will see you on the next episode of she's Busy AF. Upbeat music playing.