Are you a solopreneur ready to grow your team?  Outsourcing some of the backend tasks of your business to an assistant or strategic partner will allow you to flow in your zone of genius and take your business to the next level.

But who should you hire first?  In this episode of the Advanced Freelancing Podcast, my guest Katelyn Hamilton shares the difference between an online business manager, virtual assistant, and project manager.  We discuss which you should hire first and at what stage of your business you should bring them onboard.

Here are some things we covered in this episode:

  • What is the difference between an OBM, a virtual assistant, and a project manager?
  • What does an OBM or VA actually do?
  • Should you hire an OBM or VA first?
  • At what stage of your business should you hire an OBM?
  • What you should expect from each type of service provider
  • An example of a typical contract and monthly retainer
  • The value of long term contracts

After listening to this episode, share your action steps and take-aways with our group:

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Katelyn began her career in marketing and public relations in Nashville, Tennessee. After working in the agency world for six years, she decided to pursue the entrepreneurship route to create more freedom and flexibility in her life. Now, Katelyn works as an Online Business Manager where she helps entrepreneurs organize, strategize and prioritize the backend of their business to go from overwhelmed to out-in-front. A Georgia grad, she bleeds red and black and is a diehard Georgia football fan, dog mom and outdoor enthusiast.

Website: www.katelynehamilton.com

Instagram: @katelynehamilton

Facebook: www.facebook.com/katelynehamilton

Read the Transcript:


Welcome to the advanced freelancing podcast. I’m so happy to have you here today. Would you like to go ahead and tell us a little bit more about you and how you got started owning your own business?


Yeah, absolutely. So, uh, thank you for having me on the show. My name is Katelyn Hamilton and I started in the corporate marketing and PR world. Uh, when I graduated from college, my goal was really to climb that corporate PR ladder. And I had, you know, the vision that you’re exposed to from an early age of, you know, you go to college, you get a job, you climb the corporate ladder, you retire. So that was really my focus and my goal. And it wasn’t until I got into that sort of world that, I kinda saw the corporate politics side of things. And, uh, I realized, you know, it just wasn’t as black and white as what I had thought it was going to be. So the long and short story is I did continue to advance through my career. Switched companies, worked myself up the ladder a bit, and then I ended up having an unfortunate sort of, encounter, I guess, with a previous boss.

And we just didn’t mesh very well. Eventually, I got laid off and that was something that really shook me to my core. I was never expecting that I had, Oh, I’ve always been a high achiever, go get her. So being like go was not in the plans. And during that time of looking for a new job, trying to figure out what I wanted to do, I started dabbling in freelancing and that’s where I realized, wow, this is an entirely new world. And it gives me that flexibility, that freedom that I really was looking for, and being a millennial, I love to travel. I love to do things on my own terms. I love to really just create and cultivate like that working environment that gave me the ability to travel and see friends work the hours I wanted to work and just live the life I wanted to live.

So as I was looking for a new job, I was trying to essentially fit a square peg in a round hole because I wanted all of these things, but that’s not what the traditional corporate structure gives you. So I ended up taking a new job and realizing that I hated that. So I launched my first business, which was really a full-service marketing agency. I’m on the side of working with my full-time job. My plan was to work that for a year or so, and then do that full time. Well, nothing ever happens according to plan. And about six weeks in, once I launched my website to that new job, my boss told me I had to take the website down or I couldn’t work there anymore. So I made the decision to leave, to walk out. I was like, you know what, this is exactly what I need to kind of go full time.

And that’s where that business was born. So, you know, you do what, you know, I worked with, uh, clients and found clients through the power of networking and past relationships and connections, and started building that business and worked in that sort of agency model, in the marketing space. And that led me to building the relationships in the online space as well because I again was kind of welcomed into this entrepreneurship world. And I saw the need for meshing my services of like marketing project management strategy in the online space with all these creative entrepreneurs. So you have all these people that have really amazing, brilliant ideas, and they’re so smart and they want to help so many people, but there’s a lack of organization, lack of strategy. There’s a lack of really just kind of having structure to that. They’re part of the bit their, their business, you know, in a way. So that’s what actually led me to transition into, uh, working as an online business manager and OBM. And so now I work with multiple six and seven-figure business owners in helping them to manage the backend of their businesses, to allow them to be really efficient, uh, organized and have a structure that will allow their business to thrive and give them the ability to focus on the stuff that they’re good at, which is coaching or serving their clients in the best capacity possible.


That makes a lot of sense. And I think it’s a really common story for how a lot of people get into freelancing. One of the questions that I think we should kind of kick-off with is can you describe what makes an online business manager, the right fit for your business? Because a lot of people throw out these terms. They think maybe their first hire needs to be an OBM. A lot of times I find it needs to be a virtual assistant or some other type of contractor instead, is there a certain stage you need to be at to be ready to hire an OBM?

And this is definitely, this is a great question, and it’s definitely a complex question because to be honest with you, I could tell you, either way, it really depends on the goals ultimately of your business, how fast you want to speed up your business, how much support you feel like you want need and how much money you want to invest. So you’re either given the ability to have more time or more money. So if you feel like you want to invest and use that money to invest in hiring support, hiring a team, and you’re earlier in your business, you may hire an OBM, but if you are just getting started out for additionally, what I see and what I typically recommend to somebody is to hire a virtual assistant. So let me kind of break down what that difference in those roles looks like because I think there’s some confusion in that, in the space of like, what’s the difference between an OBM and a virtual assistant.


And the, I look at it is a virtual assistant is very task-oriented. So when you are working in your business and you need support with, scheduling your social content, uh, sending out an email newsletter, managing your calendar, or your inbox, they’re very specific tasks that are often repeatable that your virtual assistants can do it. Doesn’t take a ton of strategic thinking. Um, it doesn’t take a ton of strategy. You’re really just offloading those, those tasks and those things that, um, take extra time in your day or are monotonous, or, aren’t serving you in the capacity that you, you know, that you want to be doing, bookkeeping, invoices, things like that, the difference between that and what an online business manager does and think of an online business manager as your right hand, man, your strategic partner in the corporate world, you could think of it as like your operations officer.


So the person that will strategically sit there and think about your business and how you’re driving it forward. So, if you’re doing, if you’re, if you’re somebody that does launches maybe for courses or programs or anything like that, your OBM is going to be the one that’s kind of working on the timeline for that launch with you and figuring out the parts that need to go into that launch. So what needs to be included, you know, do we need to build a sales page? You know, we need to have emails, we need to have social content. We need to open up your calendar for sales calls. We need to have, you know, an education phase and excite phase of launch base. Like we’re kind of breaking that down with the business owner to make sure that they have all their bases covered. They’re not missing anything and allows them to, for example, uh, really be present energetically in their launch.


So they’re not worrying about any of those backend things. So the OBM really takes a little bit more of a strategy, side of things, as well as can be responsible for managing the VA’s or the team members. Cause sometimes some of my clients have like a team of 20 to 30 people and they don’t have time to manage all of those moving parts. So you could be managing as an OBM, like your graphic designer, your website person who runs your website, um, your tech team, your social team, etc. So it’s really the person that kind of is the glue that holds the business together on the back end. And, you know, does that more strategic business side of things. So again, that’s kind of why I go back to like being a right-hand woman or right-hand man, versus just somebody that you can outsource singular tasks to.


I liked that a lot. I think a lot of entrepreneurs are at the point where the very first person you hire is probably going to be that virtual assistant because you need to still outline the strategy and give them the tasks to complete it. So it’s very possible that you could end up with a virtual assistant who has more ability than just completing tasks, but a lot of times that’s how they start out. And so you shouldn’t expect someone that you’re paying entry-level virtual assistant rates to be helping you with strategy and project management and lots of more detailed things that would really call for an online business manager. We moved my executive assistant Melissa into the role of OBM pretty quickly, because it was clear to me that she was just doing a lot of those things already. She was already acting like an OBM without calling herself that, and it just felt like it was a better title to suit that.


So you need to think about where you’re at in your business and what kind of person you want onboard. Virtual assistants tend to have potentially more clients than OBMs do a lot of OBMs will only work with maybe a handful of clients at a time because they are providing such high-level support. Now, a question that I see come up a lot, especially in Facebook groups of OBMs/OBM versus project manager, I feel like OBMs do a lot of project management type work, which is why it gets confusing for people. Would you make a distinction between project manager and OBM and if so, what, what is that difference?


That’s actually so funny that you bring that up. So yeah, I do think there’s a difference there because I work with one client in a project manager capacity because it’s just a unique situation, but she also has an OBM and, uh, she has both. So I think that there is a distinction, the project manager really is the person that’s keeping your projects, your tasks, your things, your can be your team to on track. So managing, you know, hours managing, um, specific clients and things like that, but doesn’t have the full necessarily overview of everything in the business. So to me, the OBM is like that overarching, um, support and yes, they do and can do project management. I do that for other clients as well. Um, but they, they may, they’re a little bit more big picture and your project manager is just over that one specific, you know, responsibility, I would say, you know, like they’re responsible for managing the team, making sure the projects are staying on track, making sure things aren’t getting lost in the shuffle and things are still moving.


And then you could have your OBM. That’s still responsible for that project manager and making sure those things are getting done. But again, it’s, it’s kind of taking your OBM out of the weeds a bit. So there is a difference. Could your OBM support both roles? Absolutely. Um, it really just, again, depends on kind of how your business is set up and where you feel like you need support. I mean, I feel like if you have a lot of projects and you, a lot of clients, it may make sense to have a project manager that can kind of be in the weeds every single day, managing those details and those people and those things versus if you just run a handful of different group programs or you have, you know, fewer clients, um, your, your OBM can kind of manage both of those things. Does that make sense?


Yeah, no, it does make sense. And I think a lot of times we hear project manager in the context of more traditional companies where they’re developing software or something like that. And it’s the project manager’s job to keep every single person in the company on track and report problems and identify, you know, breakdowns and workflow and things like that. So I think that’s a really important and helpful distinction to make. So as far as, is there a point, like in terms of the revenue that you generate in your business where you think business owners should be starting to think about hiring an OBM? I know it might depend on the industry, but I think that it’s really hard for people to tell when they’ve kind of maxed out their VA’s capability or when they’re asking more of their virtual assistant than they should. I mean, is there, do you see any common points that entrepreneurs hit where their business has grown past a certain point? And it’s like, it’s going to be a mess if they don’t have an OBM to help sort that out.


Yeah, that’s, that’s such a good question, but also hard to necessarily pinpoint. I think a lot of people bring me on board when they’re either close to or at the six-figure mark. Um, and again, I think it goes back to realizing, you know if you can maximize your time with your virtual assistant, your bringing in more of that income, right? If you have just a smaller team and then you get to a point where, you know, you feel like I can’t take on any more clients or I can’t do any additional work, um, it would really help me to have more of a strategic, you know, person in my business that, or a project manager or somebody that can kind of manage the team outside of just managing, you know, these one-off tasks that I’m asking somebody to do. Um, and then you can hire additional support.


I mean, I think I look at the business models differently too, because you can have a team of three VA’s before you even hire an OPM. Uh, you could have a generalist. So somebody that sort of works across your business and does a variety of things for you. And that’s usually what I recommend people start out with is hiring somebody that can just do a little bit of everything. And then as you grow, you may see a need to hire specific VA’s for individuals, specialties, or niches. So maybe you want to hire a graphic designer, somebody that specializes in just graphics and maybe you need to hire, um, something that really focuses more on text. So email marketing, website updates, um, things like that. And I think you can get sort of specialized in those roles, um, before you bring on the OBM to one, manage those roles and also help you manage other things in your, in your business, um, to help you to help you grow.


I also find that it really depends on the personality of the business owner. So for me, I’m very type A, a very organized, very masculine sort of energy because I’m very structured. Um, but a lot of the clients I work with are the total opposite of me, very free-flowing, very creative, have no organization or structure, and they don’t always work well necessarily in that. So that’s what they need an OBM for is to bring them in and keep them organized, keep them on track, give them sort of that structure of the plan so that then they can flow, you know, in their launch or in their business. Um, but they have that structure. So to me, it’s partially personality and how you work, if you need additional support and structure and somebody to give you that, you’re not always going to get that from the VA. Cause again, they’re very task-oriented and they’re doing what you tell them to do. Whereas an OBM can kind of see those blocks, see what you’re missing, fill those holes, bring certain things to your attention that you don’t always think about because you think about them in a different way. So I think more importantly than income, it’s how you function and as a business owner and how you run your business.


I liked that a lot. I think that it’s so easy to get hung up on, you know, knowing that you need to outsource, but not being sure exactly which person that you need to outsource it to. And so it’s, it’s very customed to you, right. And as you were saying that, I was just thinking about how often people ask me, well, who are the team members that you have on your team? And the answer is, well, one, it changes a little bit from time to time, you know, we’re heading into a book launch. So I have extra people and extra expenses as a result of that, that not all of those people will stay on and consistently work with me after the fact. But there’s also people that have been on my team for five and six years that just work with me on retainer on a regular basis. And so I think the answer is you have to figure out where the holes are in your business.


If there’s things that you shouldn’t be doing, things you don’t like doing things that take you a lot of time to do, you definitely need help, but that doesn’t always mean you need to go directly to an OBM because I think you can also frustrate an OBM by saying, oh yeah, this is an OBM position, but I’m also going to need you to be scheduling social media posts and reviewing my calendar. Like if the bulk of the activities are really something that a virtual assistant can do, it doesn’t make sense for you or the OBM to be paying that person more. Now, can you talk a little bit about the way that you structure your contracts and packages with your clients? Do you have them sign a minimum monthly package? Is it on retainer? I’m just sort of curious because it’s all over the board with VA’s for sure. So I’m curious about OBMs.


Yeah. It really, and it really is, I think, in this world as well, I think, um, so, so I personally structure my business on an hourly early rate with a minimum set of hours every month. So my minimum is 15 hours a month. Um, it used to be 10. And you know, when I was first starting out that, you know, I had more clients, what I’ve realized over, you know, of course, if my business is kind of like what you said earlier, having less clients with more hours is going to not only serve me but serve my clients better as well. Um, because I’m able to give them more attention versus switching from client to client so frequently. So that’s why I have a minimum of 15 hours a month. Um, could that increase again in the new year? It could, um, it could be 20.


It really just depends, um, on kind of the business and where I want to take my business at that time. But right now it’s 15 hours a month of a minimum and I require a three-month minimum commitment. And the reason that I do that is what I used to do was just require, um, one month and then we would reevaluate and see how that month, you know, make sure we were in an energetic match and then the contract would roll month to month. But really when you’re hiring an OBM, you’re hiring somebody for, to me the longterm of your business. It’s not just a short, um, support decision and onboarding a new client takes a lot of time and it takes a lot of investment on my end because I want to know the ins and outs of their entire business. And it takes a full month in my opinion, to really dive in and do that, to understand how they work, how their programs work, what systems they have set up, where their lack is and where we need to create efficiencies in their business.


Um, what team members they have are they serving them in the best capacity? Is there a better way to structure and organize their business? Um, so again, doing that deep dive can truly take time to integrate. And if you know, a month or two months in, they decide they don’t want to work with you anymore. That’s so much that you’ve now invested that you have to go and do again in terms of not only from a business development standpoint, finding a new client, but reinvesting that time and energy into somebody new because how I run my business is I’m, you know, the OBM, but then I have a team of five actually under me and that team supports me. So I, I do outsource some of those VA tasks that my clients give me that can be repeated, you know, repeated, such as social engagement, scheduling content, um, doing even just some research on podcast to pitch or things like that.


And so it gives me the ability to outsource, you know, some of that’s my team too, but I don’t do that when I first started working with my clients, make that investment in them and their business. And it’s just me in our business until I can get my head wrapped around what it is that they strategically need and what we need to do and implement to help them be successful and continue to be even more successful than they already are. So again, that’s why I required that three-month minimum commitment because usually what I see is my clients stay with me for the long haul and for the longterm, but I was attracting in the wrong clients with just requiring, you know, that month to month retainer because I don’t think people were necessarily taking it as seriously. They liked the idea of having an OBM, but they didn’t totally understand.


I think the role in detail to know that it’s really your strategic partner, you know, so that’s, that’s how I set up my business currently. Um, and I think that it’s, it’s worked, it’s worked so far and I don’t have a ton of, capacity to take on new clients in the continuous OBM role. I’m actually, uh, looking to bring onboard a new one to two new clients over this next month that I’ve already had calls with people and I have a waitlist. So that’s how I run my business now. But what I do is I offer other services. So, you know, I have intensives that people can book with me to just get their business sort of straightened out on the backend. And then it gives them the ability to continue to run with their business. That’s a little bit more, um, efficient or organized, so to speak, uh, working on creating, you know, courses for the future.


So again, I think that you really have to find what works for you and the types of clients that you want to work with. Um, versus just there’s, you know, there’s not a one way to necessarily do it. Um, I know other people take less hours and then I know other people that have a flat fee and they only take on say three clients at a time, but it’s at a premium price point, um, to manage, you know, just those three clients and that way, you know, their time, they don’t track their hours necessarily. So again, I don’t think that there’s a one size fits all model. It’s just what you want your business to look like. And a little bit, so, you know, some trial and error too.


Those are all really good points. And I like the idea of doing an intensive too, because not everyone is going to be ready necessarily to hire an OBM on an ongoing basis in their business, or they really don’t understand what it looks like. And so this is a good guy trial situation to see, you know, does this work for me? And Oh, now that things are organized, wouldn’t it just be easier if I hired this person to implement on all the things we strategize. So I think that’s an important note that if you’re hiring an OBM or thinking about becoming an OBM, there’s all types of different things out there, and you can determine the policies that you want to have in your own business-specific to you. Well, this has been super helpful just for me to learn information about it, and I’m sure my audience as well. Where can people go to learn a little bit more about you and the kinds of services you offer?


Yeah. So I think my website’s probably the best place and that’s www.katelynehamilton.com. Or you can find me on Instagram, I’m always sharing, just tip little tips and tricks that I’m seeing in my client’s businesses or my own business to help increase efficiencies. Um, so my Instagram handle is @katelynehamilton. Um, and then I am going to offer just your audience a discount of my course. So I have a course called automate everything and it focuses on Dubsado. Dubsado is one of the platforms that I use in all of my client’s businesses that has been the number one tool and just creating overall efficiencies. It’s, you know, you can use it as a CRM to manage contracts, invoices, onboarding clients, and it’s sort of smoothing out in automating that process as a whole. Um, and it’s just an amazing thing tool. So I’m going to get 50% off that course as well. And that is on my website, that all that information for automate everything and just use the code FREELANCE to get 50% off.


Awesome. Well, thanks so much for coming on the show.


Of course, thanks for having me.

Meet Laura:

Laura Briggs is empowering the freelance generation. Through her public speaking, coaching, and writing, she helps freelancers build the business of their dreams without sacrificing all their time, family, or sanity. Laura burned out as an inner-city middle school teacher before becoming an accidental freelancer with a Google search for “how to become a freelance writer.” Since then, she’s become a contributor to Entrepreneur, Business Insider, and Writer’s Weekly. She worked for more than 300 clients around the world including Microsoft, Truecar, and the Mobile Marketing Association. She’s delivered two TEDx talks on the power of the freelance economy for enabling freedom and flexibility and how it’s being used to address the technical skills gap in the U.S. Laura is the host of the Advanced Freelancing podcast, a sought-after public speaker on the gig and digital freelance economy, and a freelance coach focused on aspiring six-figure freelancers. Laura’s books, courses, and coaching have reached over 10,000 people.

As a military spouse, Laura is passionate about serving her community and founded Operation Freelance, a nonprofit organization that teaches veterans and military spouses how to become freelancers and start their own business.