180: {Interview} 5 Key Strategies to Simplify and Scale Your Online Business with Katelyn Hamilton

In this insightful interview, Caitlin Hamilton shares her journey from corporate marketing to becoming a successful business coach and entrepreneur. She discusses common challenges faced by high-achieving women in online business, the importance of simplifying systems, and strategies for scaling while maintaining work-life harmony. If you are an entrepreneur and know that you need to implement systems in your business to scale, this one is for you!  

Transcript

Caroline Pennington (00:01.422)
Welcome, Caitlin.

Katelyn Hamilton (00:03.114)
Hello, thanks for having me.

Caroline Pennington (00:05.744)
So you're a business coach and entrepreneur. You help high achieving women streamline their business with efficient systems and processes. Tell me your story and how did you do it?

Katelyn Hamilton (00:15.542)
Yes, so I came from the corporate world about seven, eight years ago now, nine years ago now, and I lost my full-time job and I kind of stumbled upon this online world and I've had quite the journey over the last like nine years really from starting my own PR and marketing firm. That's what I was, that's what my corporate job was in, was in marketing and PR and transitioned from that into becoming an online business manager and OBM. So I've done that for quite some time and

recently as the end of 2025 have kind of offloaded all of those clients. But that really is what led me to wanting to dive into business coaching, supporting other women. I learned so much by being in the back of these multi-six, seven-figure businesses and saw the inefficiencies and saw where people needed support and saw the consistent problems that these high-cheating women were facing and was able to support them in creating the solutions to help them get their time back, help them get their sanity back. And that's what led me to

wanting to provide those other solutions for people in the coaching space is, okay, here's what I'm noticing, here's the consistencies, here's how I can help you to streamline, refine your business, give you back those same things that I was doing in the day-to-day. The execution side of things that I wanted to pull back from and really lean into like the strategy and the support aspect that coaching provides.

Caroline Pennington (01:38.384)
What are some of the common problems that you would see with these high achieving women and their online businesses? And I'm sure none of them had unique problems. They all had similar problems, but everyone thinks their problem is unique when they have a problem, right?

Katelyn Hamilton (01:47.758)
You

Katelyn Hamilton (01:52.352)
Yes, yep. Yeah, I think the biggest thing is too many systems and too many things in their business to start, first of all. So they're trying to do too many things and have too many tools. And my answer is usually simplicity is best. So it's kind of pulling back the layers of like, does each tool actually do? How are you using this in your business? Is there one tool or things that we can combine in terms of steps even within the processes to simplify? Everybody seems to overcomplicate things.

And they think that more is better, but sometimes less is more, you know, that old adage, right? And I would say that's probably the biggest thing was just coming in and stop.

overcomplicating the business. The other thing was not having the right team support. I think that's a huge one is people have support or they have people in their business doing things, but it's not necessarily the right people in the right positions that are doing the things that are needed to move the needle forward or they're overpaying because they have, you know, lapse in or coverage in multiple different areas. So streamlining support is another method and finding the right people to do the right things.

And just really finding ways to help them become a better leader is probably the other the other part of that within that goes along with team, but that that kind of comes from not just having the right team, but also teaching people how to better manage the business as a whole. So when there's a whole bunch of different processes going on in the back end, so find those helps, then I would say also planning a lot of creatives. I would say most of the people I work with are really strong in like the creative side of things.

If you're familiar with human design, they're manifesting generators or manifestors, and they have no idea on how to be a projector, which is what I am. And so they need somebody with that brain to come in. So they're just kind of like, want this idea and I want to do it today. And they don't understand then how that impacts their team, how that impacts the back end of the business and actually how it impacts the client experience even too. So I found that those were three really big things that then I could come in on and be like, whoa, let's pump the brakes here.

Katelyn Hamilton (04:02.618)
it's slowing people down, simplifying proper prior planning to help them get the success that they want and have a streamlined business because of it.

Caroline Pennington (04:16.048)
I'm chuckling over here because I'm a manifesting generator.

Katelyn Hamilton (04:20.142)
So you probably face some of these same issues. You have all the creative ideas.

Caroline Pennington (04:23.748)
most definitely face some of these issues. So, okay, for someone who's listening to this, and most entrepreneurs that I talked to, they think their way is the best way of doing things, and they have a really hard time handing it over to someone else to do. So what kind of advice or what's the mindset shift that has to happen there?

Katelyn Hamilton (04:28.685)
Yeah.

Katelyn Hamilton (04:47.212)
Yeah, I mean.

I'm a proponent of outsourcing everything, but I also want it done my way, right? So I get that. I understand that. Document your process to start. So I tell my clients all the time, screen record everything that you're doing, everything you do, and then go back and watch that or put it in an AI tool to dissect it and pull out a transcript or build the SOP. There's a ton of different resources that you can use to do that for you and then review it, refine it. And honestly, you'll find things along the way that you're like, I didn't even

realize I was doing it that way. So I think that's that's the biggest biggest thing to start is record yourself doing everything because there are idiosyncrasies in how you do things that even if you put it into an SOP or you put it you know pen to paper so to speak it's not the same as like well I prefer this to be done this way when I'm doing this and that could be in regards to content it could be formatting I would say it's probably the biggest one that I found and experienced is people have a specific way they want their email newsletter

that are formatted, the way that their recordings go out, I don't know, everything was formatting, they want it done this particular way. So you're not going to get that by just writing out, here's how to do this. I would say video recordings come in so handy with that because then you really are walking people through it. And from there, I would say creating that video library or using your project management tool, if you're not doing that already, that's a huge thing, creating that and putting that into your project management

tool as you go, it gives them something to go off of. So even if they have questions that come up from that, they're able to point that out specifically in the video.

Caroline Pennington (06:30.072)
So why is putting the right systems in place a game changer?

Katelyn Hamilton (06:35.15)
You're going to get your time back, most importantly. I think that's the biggest thing is that if you don't realize where your time is leaking, that's costing you money. So getting your time back is going to one, reduce overwhelm and give you more clarity and then give you the ability to create that space to scale the business. So that's the most important piece of it. It also creates better harmony for your team, better understanding. Everybody's on the same page. They have the same thing to work off of or understand what is happening.

too I think for the biggest reasons. It's it's the foundation for what you're building your business on.

Caroline Pennington (07:11.674)
So what happens when you not only shift your actions, but your mindset from operator to CEO?

Katelyn Hamilton (07:18.616)
Putting your CEO hat on is so different than being the operator. The operator is kind of the executional piece and the CEO is the strategic thinker. So if you shift from that position out of like, how do I just make this happen? And you're kind of consuming and taking it in and then being reactive in a way from the CEO, you're thinking strategically, you're thinking big picture. So you're not thinking in like the nitty gritty day to day, get through this one thing and move forward. But you're really able to see how this one thing

affects not just the decision at hand or the project at hand, so to speak, but has a larger impact on the business itself and what other ripple effects that has. So I think that also goes back to that taking the time to pause, taking the time to process and think, because so many people are just reacting to things without really realizing that like what they're doing is maybe a band-aid solution that's not solving the problem at its core. And

it's gonna come up again.

Caroline Pennington (08:21.2)
All right, so let's talk tech stack. What do you like to use when it comes to like email marketing? Do you like Slack? Tell me about those things.

Katelyn Hamilton (08:29.666)
Yeah, so I have a very curated stack that said, I think it also depends on how you think and operate in the business. So for example, for me, I love Asana as a project management tool. It's simple, it's efficient. I'm a huge proponent of it, but a lot of other people like ClickUp. And I also will say though that it depends on the business. There's a client that I work with that has a PR agency and she uses ClickUp and it's amazing because we already have these pre-built out templates and we have automation set up within

business that

It works better for her tech. ClickUp is more techie, right? So if you are a tech minded person and you understand how that works, that's great for you. Granted, there's a lot of business owners that that overwhelms them and ClickUp is a huge turn off. And if you're not going to use that tool, then it's not going to be fruitful for you have in your business. So I kind of like dissect based on the client, I would say what I recommend. But that's one example. I do usually personally prefer ClickUp. Email marketing, I also think it just depends if you are newer

were in business or you have a more visually designed business, Flowdesk is incredible. I love Flowdesk. I love the pre-done templates that they have. It's simple, it's easy, it's one cost and it's awesome. That said, if you run a business with 10 to 20k, 30, 50, 100k on your email list, I think that there's better options out there. I love ActiveCampaign. They have incredible backend workflows. So lots of different points in which you can come into an automation. So if you need that, if you have people coming in,

at different spots that need to do different time-based triggers, I think that the tech side of Active Campaign is much better than Flowdesk. I've seen them come a long way. I've been a Flowdesk subscriber, like one of the founding Flowdesk subscribers for a while now, but it's not Active Campaign level, so that's kind of... Active Campaign is my go-to for somebody that has that larger list that wants to do those larger things. DubSado is a CRM platform that I absolutely love. It's complicated for a few people, but

Katelyn Hamilton (10:30.724)
I would always suggest finding the right person to build that out for you. But everything from proposals to contracts to automations with emails, lead forms.

managing clients in there. It's a great invoicing. It's obviously a great lead tool and great management, especially if you have one-on-one clients. ThriveCart is my preferred payment platform. I've also used SamCart. I've used a few others when it comes to the payment processor side of things. ThriveCart, though, is my go-to. When you get into course hubs, there's a variety that I would recommend. It just depends. Circle is one that's grown on me over the years. I really like that it has the

course platform in the community built in and it's seamless and really easy to use and they also have payment links in there as well. The data and analytics side of things isn't as great in that regard for pulling data from like say checkout conversions and things like that, but all in all you know you're gonna have your pluses and minuses for what you use, but those are probably some of my favorite and then I do use G Suite for kind of everything docs and

know, PowerPoint, things like that related as well.

Caroline Pennington (11:42.032)
Okay. Ooh, you really went off on that one. I like that.

Katelyn Hamilton (11:44.266)
Yeah, I have lots and lots of recommendations. I could probably tell you more if you have questions, reach out.

Caroline Pennington (11:51.822)
Okay, switching gears, what are you most proud of professionally and personally?

Katelyn Hamilton (11:56.471)
Hmm. Personally, I'll start just because that's easy. That one's easy. My kids, my kids are why I do this though. I have a 14 year old stepson who's huge into basketball. I grew up playing basketball. We are head down in tournament season right now. He's incredible. He's also just very kind and

giving kid like he is the heart of gold and same with my five-year-old son he is that way too an empath like I could just eat him up. I would have I've always said I will have one million fishers he is the best kid and then I have a three-year-old daughter who has taught me a thing or two about patience and she is going to be a CEO one day she's gonna run her own business or multiple businesses but yeah my kids are my greatest pride and joy.

and do everything for them. want to show them what's possible as a female and a mom and doing both is a huge part of what I quote and speak and preach, so to speak, is I believe you have this ability to be a mom and be a business owner and make a lot of money and be very present with your family. Professionally, I think the ability to continue to scale and grow and adapt and pivot and run businesses in multiple different formats. also own a brick and mortar. That's what

we launched in the last year and that's been a really fun, actually in the last six months, that's been a really, really fun project. And I've kind of applied all of the knowledge and expertise that I've learned for working for myself on the online space and taken that to Vitalis. And that's been, it's a wellness business where we offer saunas, cold plunges, salt therapy, red light therapy, and it's something that personally is a huge part about.

just me as a human. love the wellness space. So we co-own, co-opened that with two other couples and it's been probably my current biggest, proudest achievement is bringing that to life. But doing that alongside still running a coaching business, being a mom, it all is intertwined really in terms of like the success and what I'm proud of and just who I've become kind of throughout that journey as well.

Caroline Pennington (14:05.014)
I love that and I'm into all those things too, the red light therapy, the cold flinging, like all of it.

Katelyn Hamilton (14:10.506)
It makes you better at what you do, it you better mom, it serves so many purposes.

Caroline Pennington (14:14.83)
I know sometimes people are like, you're a dollar rabbit hole about that. But I'm always like, why not try something new? You know, like it's just going to cost.

Katelyn Hamilton (14:19.886)
Yeah, people are afraid of cold plunging. It's not as scary as I think it is, is it?

Caroline Pennington (14:25.464)
And it's so good for you. mean, the health benefits are like the list is endless. And yes, it's uncomfortable for a little while. And yes, it It's suck for a little while, but it's worth it. And you feel so much better afterwards.

Katelyn Hamilton (14:37.218)
Yeah, so much energy. It's like natural dopamine hit.

Caroline Pennington (14:40.282)
Yep. Okay. So what is lining up with some of the clients that you're working with right now?

Katelyn Hamilton (14:45.294)
So I have an incredible personal stylist. I love her. She is really focusing on kind of scaling her business. We've worked together now for a year. We're working into this next chapter for her. The first part, and this is really telling us to like what I do is, is helping people get their current business under control, so to speak. refining, auditing the systems and processes, refining that, and then giving you the ability to scale within what you're currently doing. So she's maxed out now her one-on-one support and we're figuring out, okay,

How do we get a little bit more off of your plate in order to create this secondary container for you where you can serve one to many right now that she has a waitlist now that she has people that are you know, she's in demand and so that's something that I'm currently working through with her is is continuing it's always a continuous refinement of the business and the operations and the team and the tasks and hiring the right support but getting to do that alongside growing into the next chapter and increasing her visibility and what that looks like so she's incredible. I also have a social media manager

Two social media managers actually a beauty owner who owns a brick and mortar.

and like I mentioned before, a PR firm and someone that actually is pivoting her business into kind of like, I would say, cancer concierge. So she's a virtual assistant for people that are going through cancer treatment and helping them to kind of take the burden off of everything else outside of the medical side of things. lots of incredible clients that are doing a variety of things, but the same goal is to build successful businesses while being present moms and business owners.

Caroline Pennington (16:18.412)
So how can our listeners find you?

Katelyn Hamilton (16:20.78)
I'm really big on Instagram, so I would love it if you sent me a DM. And I know you'll put my handle in the show notes, but it's just Kat at Caitlin E. Hamilton. And you can always go to my website. Same thing, Caitlin E. Hamilton dot com. But those are the best places to find me. I would just love I love a DM. Building relationships is huge for me. So just reach out. Let me know you listen to this podcast. And I just love to hear your story and how I could support you.

Caroline Pennington (16:45.85)
Thank you, Caitlin.

Katelyn Hamilton (16:46.84)
Thank you.