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The Difference Between Hiring Help and Hiring Leadership (With Gillian Perkins)

34m 58s

The Difference Between Hiring Help and Hiring Leadership (With Gillian Perkins)

In this conversation, Gillian Perkins discusses her long-term experience hiring an OBM (Online Business Manager) named Courtney, who was trained by the interviewer. Gillian explains that she hired Courtney in late 2018 when her online business grew rapidly from zero to six figures. As a visionary entrepreneur, Gillian realized she needed a partner to handle the integrator role—managing systems, team members, and daily operations—because she got bored with details and struggled with consistency. Previous attempts to hire virtual assistants failed because they required too much oversight and only completed small tasks. In interviews, Courtney stood out for her assertiveness, clear plan, and ownership mindset, even though she was the most expensive candidate. They negotiated a trial period at a lower rate. Once hired, Courtney exceeded expectations by overhauling Gillian’s digital workspace and reporting her hours meticulously, demonstrating exceptional productivity. This built trust and led to Courtney’s pay increasing three to four times over the years. Gillian emphasizes that hiring an OBM is an investment that pays off when the person takes strategic leadership, not just task management. She highlights the importance of finding someone who can partner with the CEO, manage team hires, and free up the visionary to focus on growth.

Transcription

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Hey, I'm sitting down with Gillian Perkins, longtime online business owner and educator and the founder of Startup Society. And I wanted Gillian on for a specific reason. She is not just talking about what it's like to hire operational leadership. She has been living it. So Gillian has worked for years with an OBM that I trained, which means she can really speak to what happens after the honeymoon phase, after the first launch together, after you've really truly built trust and you have handed over real ownership. So this is a client perspective conversation about what great OBM support actually looks like over time, what changes when you stop being the person holding every moving piece and what you should expect from an OBM when you are scaling and what you should not expect and sort of how to know the difference between hiring help and hiring leaderships. (soft music) This is something that I'm totally excited to talk about because I love my OBM so much. - Yeah, so can we say her name, by the way? Well, we can't because you have YouTube videos where you've sort of featured your, like, day in the life with Courtney. And I trained her, I want to say like a decade ago, how long has she actually been on your team for? - She started working with me either at the end of 2018 or the beginning of 2019. - Yeah, I want to say it would probably be end of 2018. So it's been one, eight, going on eight years now. - Wow. - Which is crazy. That's so epic. - No, that's crazy, but then it doesn't sound crazy all at the same time. - The time has been blessed. - Yeah, the time just flies by. So what feels crazy about it? - The reason it sounds crazy because the time is gone so fast. Like we've had so much fun together, running my business has been so much more fun since hiring her. But I think also my business, like it grew really fast over those last eight years, especially, but in the couple of years prior to that too. And so it just, yeah, it just feels like time would really fast. So it's hard to believe that it did that. That's why it sounds crazy. - You know, I think Gillian, one of the things that I really want to talk about today, because I feel like you're like, you know, like a pioneer in, I think sort of just, I don't want to say taking chances because they're very curated. You know, like bringing on an OBM and hiring that level of team member is obviously something that a lot of thought goes into. But a lot of people weren't, let's say, hiring OBMs per se, you know, or so sure that that's what they needed in their business. So I would love it if you could sort of maybe share some indicators of when you knew you needed to hire an OBM, like what were you thinking? And also, yeah, I know that you grew very fast and you were scaling very fast. 'Cause there's growing very fast. And then there's scaling very fast. Growing very fast feels out of control to me. Well, I guess this is the other reason why I said eight years sounds crazy. Because when I think of eight years ago, my mind almost goes to like, that must have been a different time. Like, were OBMs popular? Yeah, like were people doing this? That's how it was like, it might have been before the common era, you know, where we are working with OBMs, but it didn't seem like it was. I didn't feel like I was doing something new and high in the air. And I felt like, I felt like I was jumping on a trend, but like lots of other people had OBMs. And I was a little bit behind the curve. I don't think I actually was, that I felt a little bit behind the curve in learning about how an OBM could be beneficial to my business. It seemed like it was already a thoroughly conversational organization. That makes sense. But it probably has become even more popular since. Yeah, let's talk a little bit about kind of what led me to hire an OBM and what made me think I was ready. But I think a lot of people's metrics, maybe even your Sarah, you might say that I wasn't right. You're a lot of people would have said, oh, you're not ready yet. Because my OBM hire was one of the first hires I made in my online business while it was growing very quickly. And we had perhaps hit some revenue markers that might indicate we were ready a few months before we had not been there at all. We had gone kind of from zero to 100,000 a year from sort of situation, zero to six, figure that year. Now, that was not the first year I started this business. And I had had other businesses prior. So this was not like my first foray into the business world. I've been running a local business for about 10 years at that point. And then I started my online business and really struggled with it for the first couple of years. Like really struggled to get any tracks in to figure out when I was doing all of that. Then 2018 comes around. And I'm still basically at zero, even though I've been trying to do this thing for a year and a half. And then we go from zero to six figures that year. So a mid-year, like somewhat past the middle of the year, I decided to hire an OBM and do so. And it was a great decision for my business. There was absolutely no like, ooh, maybe I did this too early. And I'll maybe I should have waited. I never had any buyers remorse there. Leading up to the actual hire, I was kind of anticipating that there would be. That made my third share of bad hires in the past. Or maybe I overhired a little bit. And then I was, like payroll was too big, right? But honestly, it has been amazing since day one, probably partly to Courtney's amazing. I think it's partly probably in large part because Courtney's amazing. And so she really paid for herself really well. - Right, 'cause it's an investment. And I think that when I say that you had that, foresight, I completely forgot, 'cause I know I knew that you had managed a business prior to your endeavor into the online space. We were talking about how this particular person was a service professional before she hired her OBM. And we were just like talking about how you can really, not just commiserate, but really understand, as a business owner, that hiring a good person is an investment, whereas maybe if you're in sort of the startup phase of your business, you're not really that sure, or you don't have that experience because you were in the startup phase, but you had that experience so that you knew that it was gonna be an investment for you. And I think that is such a critical piece in this, because it really truly is an investment. And I think that if people looked at it more that way, of having someone on your team who can make the bigger decisions, who can take the bull by the horns and lead the truck with all of my analogy is kind of thing, but truly to kind of get things off of your plate. So when you hit the ground running with Courtney, what were some of the first things that you wanted to get off your plate as CEO and also bearing in mind that there's a lot, there's a lot that an OBM can do. So how did you make that decision to hand it off? - Yeah, so I've kind of like three thoughts, I think about this question of what did I want to get off my plate. First thought is I remember when I first heard of an online business manager, this was years before I hired an online business manager, and it wasn't even being used as like an all-in-official or I don't know, like a specific term of online business manager. It was more of just descriptive, if that makes sense, like from the need who was a business manager of mine said, like basically I hired this person to manage my online business. I was just like, "Yo, what?" - That's like, "Why don't you manage that business?" - "What you'll be managing your business?" That sounded really strange to me. Why would you hire someone to manage your business? So now like going back to your question of what was I trying to get off my plate. So what shifted in my mind to go from that makes no sense to I have something that I need to, you know, to shift off my plate. And we're talking about whether there are these two kinds of entrepreneurs. There are the visionaries and there are the, what's the word, integrators. - Which leader? - Yes. So basically the visionaries there are the entrepreneurs who have all the ideas and they're like charging forward with them and they're maybe kind of the visible leader of the company and then the integrators, they're more like the managerial side of thing is they're doing more of the admin to look very important leader in the business though. They're just maybe not kind of the base of the business. And so that really struck me and I saw in myself that I'm an amazing visionary, but at least that I am very done of handicapped when it comes to those integrator types of role. - I definitely think you are a visionary. Let's give it to ourselves. - I just feel that I get bored with those management side of things so easily that I'm not able to be consistent with them or be disciplined with being consistent with getting them done. And that was really holding me back when it came to building my business because I could have all the ideas in the world that I could actually be a very good action taker with, so I wasn't just dreaming. I was taking action, I was building things but then things were kind of crumbling behind me a little bit because I didn't have kind of that maintenance bone that I needed to have. - Good work. - And so I realized if I could have somebody come alongside me who could kind of fill those shoes and be my partner in a sense in running my business, then we could be a much stronger team. And I think that that's a big part of what's holding me back at this point. And when I say holding me back, I think I was foreseeing that because at that particular point in time, I was not being held back. My business was quickly growing, like I said, in 2018, zero to six figures, we were to the six figure point. So like we got zero to six figures, practically in the six months, huge amount of growth. But now like, am I gonna regret this all most? That's broke. - Right. - And so that was really what led me to hire an online business manager. And so when I hired the online business manager and when I was interviewing for, I remember what I thought I was looking for was somebody who would come and basically keep me accountable to the deadline almost of light. Okay, I'm say how I wanna do this project. I've strategized like here are basically like the some tasks that need to happen to get this bigger task done. And but then I know I'm gonna get distracted by a shining object over there. I need somebody who I'm checking in with on a very regular basis who's like, "Wake, we're working on this project. These are the things that you need to get done. These are their due date." And so accountability and also just kind of making sure that nothing slips through the cracks. Like picking up the pieces that I drop and meaning like, "Oh, don't forget about these things over here." I was also looking for somebody who would similarly kind of reorganize my file systems online because I felt like I was just making a mess. So those were the things that I knew I was looking for also helping me to manage other people like team which I didn't really have at the time. I had one other person who was working for me. The last thought was that I had already tried hiring some virtual assistants, a couple virtual assistants. One of them was truly virtual. I've been one of them I was hiring as a virtual assistant but she ended up being local, which was interesting. - Oh wow. - Yeah, which, but anyway, well, I had tried like putting things off my plate onto those virtual assistants and it really not worked. It really had not made me any less busy and hadn't helped us to get any more big things done. It had just helped us to get more little things done. But I didn't feel like it was having much of an impact and it was certainly taking more of my time to manage those virtual assistants. That's why I wasn't really trying to delegate like individual tasks when I hired a business manager and why I knew this needed to be very different if it was going to be productive for me. And also why one of the things I was looking for was help with management of a team so that we could hire a couple people and who'd get some more things done. - So when you got, so then you were like, let's keep these VA's and you brought on Courtney or there were no VA's in the building. - There were no VA in the building. So when Courtney came on, I had the second of the two VA's that I hired still with him and she was there. And then she ended up going through like a life transition herself, she basically, this is like a common problem we had especially in the early days of starting my business where I would inspire people to start their own business. And then you like, oh hi, I decided I'm really to be an online business manager or I'm decided I'm going to be a coach and it was like, well, I guess what I was saying was inspirational, I guess it worked. But now I have to hire her. - Yeah, I can do that. - And now turn over. - Yeah, we have to hire again. - But I happened with her. And because I had Courtney and because Courtney was now helping me steer this ship, she knew we needed some sort of virtual distance, right? - Right. - What was it like when she came on? She came on, I mean, I know, I hope I know what it was like, but it was like guns ablaze there. - Yes, that's all right. It was nice. - It was not on either. - What was it? - I love that you also, I have to highlight the fact that you use the term partner partnering with. I love that because that is exactly what it feels like when I partner with clients. You know what I'm standing alongside of them and I'm thinking, okay, I'm clear on the strategy. I know some of the goals and where the business is going. I know I'm confident in making the decisions for things. I'm confident in coming up with a plan. One of the first things that started to feel good for you or just started to feel like, yes, this was the right decision. I'm so happy that she is relieving me of the hiring. - But what are some of the new ones, smaller things that you hadn't expected? - Well, I really remember going through the interview process for hiring this online business manager and it was an easy pick when it came to Courtney. And the main thing was because she was, she sounded like she had a plan. She sounded assertive. She sounded like she was going to take ownership and lead. - And assertive and to have ownership. - I don't know if I would have said prior to the interviews that that is necessarily what I was looking for, but it just made me feel a lot more confident and a lot more comfortable that she was actually going to help and not take more of my time. - Right, and also I think somebody that's able to lead you as well, like someone who can be assertive in helping you or guiding you on the team members and then managing the team members on your behalf. Like it's an important piece to be able to take that fully off your plate is having those qualities where you can. Trust, I trust you because you're assertive because I know you're responsible because I see that you've made OBM in your thing. You want to have a few clients, you want to make this work for you. Like it feels good, feels really good. - I also remember that of the people who I interviewed, Courtney was the most expensive. So first few people who I interviewed, they really did not strike me as like very strong candidates. They just, they founded more like a VA at the end of the day, I would say. - And we know because Courtney invested in her certification with me, so it was very clear that she was very dead set on not just being an OBM and calling herself an OBM but actually having the skills and the credibility to like back that in addition to obviously the years of experience she had before that and how it all sort of conflates and compounds into these amazing dream OBS. Like even Courtney's personality stands out to me all of these years later, you know, and obviously we've been in charge and we've had our own communications back and forth and you know, I've been on your podcast to talk about her and OBMing as well. So we'll make sure we leave those in the show notes in the description below too. But I love that you're sort of highlighting some of these like more nuanced flavors that come in when you bring it in OBM and just, I mean, what else was there? Like what was it like when she started to like, I mean, hire on your behalf and then now have to interview, you didn't have to onboard, you know, that's, yeah. - Let me first say, finished just why I was gonna say about her pay rate and then I'll talk about that part. - Oh yes. - So second to last person I interviewed was more offensive than all the previous people. I really liked her. I would have gone ahead and hired her, but then I interviewed Courtney and I was like, she sounds like she's like really well organized and not just well organized but again, like assertive and like taking ownership, which I always feel like that's more important than just being well organized because somebody could be, have like the mindset of, I, I, the boss still need to tell them everything to do, even if they're well organized, but Courtney, like I said, she sounded like she had a plan. She was the most expensive. I negotiated to sign you a bit. I was like, okay, so I'd lend to hire you, but you are significantly more offensive than this other person who I'm also considering. Could, would you possibly open to at least for like a trial period doing a somewhat lower rate or somewhat smaller pack? Courtney said yes to that, but I have to say, today I pay her three or four times what our first original agreement was because she turned out to be so amazing and so helpful and you know, if she was able to help me grow the business further. So it worked out really well. - She came in guns blazing, that was a perfect part of the phrase. - Yeah, I'm not sure. - I was like, whoa, what's happening to my business? So she was like going over and above what I was expecting. I remember two things, particularly vividly. One was that she just like, overhauled my vote, like the online workspace of my whole business. - The digital owner. - That's the Ricky Smith digital office. - Yeah, it was awesome. I didn't know I needed or wanted that. So I was a little bit like, I don't know if we need an answer and she was like, you need this. I was like, okay, you say, I'll trust you. That's decision ever. And yeah, 'cause the foundation, not everything else grows for us. - Yes, and she just, if she wouldn't weigh like above and beyond there. And then I although remember to this day, I should probably ask her, 'cause I don't know like how true this was if you will, but she would like report to me each month, like how many hours she had done, even though I was paying her a tanger, not hourly. But she had, you know, a certain number of hours in her itinerary. And the amount of work she would get done, compared to the number of hours, I was like, you were the most projective person I have ever tried to hire. - Right. - I still don't know exactly what it was. She's continued to be a very productive person. I kind of think what it was was that she was only having what she was like, physically like doing something. So all the time when I was doing a task, but kind of not daydreaming, you know, the train figure how to do it, he would not count that time. She would only count the time when she was like, physically doing something, which I'm not thinking you need to do that way. But it very much impressed me as a client, but it made it feel like it was very well worth the amount I was paying her because she was getting so much done. So it definitely kind of cemented her into my fist forever. - Forever in your. - And led to her getting paid all the long more down the road. - Yeah, and at least I think it's you a much bigger role in your business. You know, as you know, the responsibility, it's the ROI, it's the time she's there. It's just grows and grows and grows and grows and grows. I mean, never eight years, but at least five or six years. And it really is a partnership and it starts off as, you know, yes, you have to be assertive. Yes, you have to be able, you know, talk a lot on the podcast and on the YouTube channel about how you do have to really lead the client and the client, even though they may not be, they need you to sort of take you by the hand and tell you what to do because they're busy with their vision. They don't, you know, like even her saying, like, you know, that's it. We're gonna, we're fixing up the digital office. We're gonna clean it up so that we can continue to scale, continue to bring on good VA's and people who can get the work done. That means we need a project management tool. We need to have, you know, something for real-time team communication and getting all of those pieces in place is such a wonderful thing for an OBM when, you know, so she went to the client and said, "Well, I don't know." And then you do it. And I think it's part of what was so impressive about Courtney doing what she did was that I wasn't the client was like, "Well, I don't know. I was the client who was like, I want to do this." And Courtney was like, "Actually, I think we should do that." Which was incredible. Yeah. I love that. I feel like I just have to sit on that for a second because, you know, it really is so important. Not enough OBMs realize the beauty of, you know, I thought I'd tell you so many what to do is about being assertive about what you feel. Speak that strategic part of what you already talked. And you know, when we were talking about visionaries and integrators, when it comes to visionaries, would you very much are? You can be sort of up in the clouds and you need somebody that can bring you back down again and it's just such a beautiful relationship when you acknowledge that you need both to kind of have these, I think businesses that really do move and shake and grow very quickly and scale very quickly. Like startup society has, like your podcast has like a lot of the things that you've built. Are there things for your wife? Courtney, is my work wife? But I think a probably a better term to use for this would be probably my work mom. Like she is the person of my business who's basically like you need to your metaphor. You know, you're a curvy. Yes, work mom. I mean, I feel like we need to like make that into a shirt or something like that because I, I think exactly what it is, that's what it feels like. You know, it's like, it's eight o'clock, you got to wake up, you know? I don't know. It's not good for you. Yeah, that's so funny. I just have to sit on that for a second, like cracks me up because it really does feel like that. Sometimes, you know, you have to be the bearer of bad news and like say things and sometimes you're afraid of your client because they're like that that angsy teenager, you know, who's like, no, let's do. Click up. Wait, no, I like a song. Wait, no, let's just grab something else and like, no, and let's not do that because remember, you said you wanted to do X, Y, and Z and we had this goal set for the year. So it's that to you know, for visionary entrepreneurs and OBM that can bring you back to that point and say, hey, just reflect the mirror. This is what you told me. I'm holding you accountable to these three goals we set for Q3. And if you go and you changed from Asana to click up, you're going to completely derail that entire plan. Yeah, I totally agree. But giving your like qualified or your experience recommendation, your confident recommendation, that's not going to come across as like bossy, but it is so helpful and also gives me as the client so much more trust in your ability to help and to lead and to go the way that you are recommending, you know, when you give that very confident recommendation. Yeah, trust is something that I think is so important. And that's why, you know, when we train OBMs in OBM school, we make sure that they're very clear and what that onboarding process needs to look like. With that 90 day strategic plan, it needs to look like an even just in hiring, you know, Courtney and hiring other people over the years and just having other people in your business. What are some things that you feel really helped in still that trust in you? I mean, having that confident plan, he is huge. And then the other thing mostly is just about follow through, you know, do you say, do you do what you say you're going to do and when you say you're going to do it, right? And I think it also showed, you know, that she wasn't just taking orders and I see this with you, the lots of other people who are on our team today, where they don't just take orders, they aren't just like doing what I said in the past, they should do, but they are actually being proactive. They clearly care about the business. They're looking for issues that need to be solved and for opportunities, right? And they are taking action on them or at least bringing them to the table early. So, you know, we've talked a little bit about trust. We've talked a little bit about what, you know, what it sort of, what it looks like to kind of bring an OBM on your team. You mentioned earlier on in this interview that you feel like perhaps you hired an OBM prematurely, but you knew that you were scaling. You had hit that revenue mark. You know, if someone's listening right now and they're thinking, am I in that in the space right now? Do I need like, is it time for me to bring on an OBM? Like, what are some, what is like one thing that you would say to that person who is contemplating hiring an OBM right now? Yeah, I would not tell them that they need to wait for their team to be a certain size or even necessarily who's certain revenue number, but what I do think is so important is that hiring an OBM is in some ways just like anything in your business that you might try to automate or outsource in that when you automate or outsource anything, you tend to get more of the same results that you are already getting. It might also help you improve your results, but tends to just be like more of those same results. And so getting zero, like, it's not bringing in any sales, well, switching to an email marketing software that enables you to automate all of your emails, yes, it will stay few time, but it's not going to make you get better result with your email marketing. Okay. And so that's how I feel about hiring as well. You're bringing someone into your business and I am totally made this mistake. Like I hired somebody to manage Facebook ads for me. Okay. I did this a couple of times actually and one time I was not running Facebook ads and I brought someone in to like set them up properly and get us going. Another time, I was running them myself and I brought someone in because I wanted to get it off my plate and hopefully get better results. But really both times because it wasn't something that was already working well in our business, we really struggled to turn it into a profitable aspect of the business. Yeah. The revenue, if you're not already on track to get to the revenue number that is going to pay for that OBM, that wouldn't hire the OBM. They might help, hopefully they do help you grow way beyond that energy like they huge things, right? And do so in a way that is more sustainable and you know, that supports you really well. But if you're not already on track to achieve something, or you haven't already achieved something, they're not going to like pick you up from the gutter, you know, and the kind of rhymes to riches or if that makes sense. Yeah. Yeah. And you have to already have kind of like made yourself a little bit and have a business. And then they can come in and they can help your business take you way less time to run and run way more efficiently and effectively and enable you to then like stair step on top of that and get you bigger and better goals beyond. And very much focus on your lane too and the things that only you can do in your business. Do more that. But they're not going to like pick you up by the shirt colors or whatever it is, right? And like turn you into something if you're not something already. So, you know, if you are feeling like you are scaling in the right direction and you have things that you could automate slash delegate in order. And I think that's such an important point you're making. Like it's really about being able to continue growing. So if you are, you know, you need to be picked up out of the gutter as you said, Gillian, which made me crack me up. You know, maybe higher, you know, B.M. isn't going to save. It's not going to save you, right? It's just enhances. And I love that you had made, you know, so lovingly mentioned how important it is to recognize that, you know, it's really about doubling down some of the things that are working, right? Like with automation, you automate email campaigns. You can automate many things in your business. You can delegate many things in your business, but you have to be really delegating the right things that help you focus on the things that only you can do in your business. So if it's like recording your podcast, coaching your students, doing live events, whatever that looks like in your business to that person, considering hiring, you know, B.M. you need to know what falls into that. That's a view of 20% of what are already working well for you than bringing an online business manager or someone else into your business to take some things off your plate. So that you can do more of those things that are working. I think that can be really smart because they're working well. Then giving somebody some of a thing is that are like even if you're super busy, but there's nothing is that are working well. Right. Getting more time is not going to be your fix, right? Like you need a strategy that's working first before getting more time will be helpful at all. And I just want to also say, you know, when I was saying like pick you up out of the gutter, I say that with all the love and speaking to my former self, you know, I'm talking about what I hired my O.B.M. a little bit prematurely, but it was the right time for me. But six months prior would have been a way prematurely. Six months prior, there were some things that were starting to work, but there was nothing that was working very well. And like I had said before, like I a bit at that point working on my online business for a year, a year and a half, and it like a struggle for that year, a year and a half. And I tried hiring a couple of BAs, they'd hang maybe, you know, I just made some help here. And it had not helped at all. It had only been an expense. Because I didn't have anything that was working well, so getting some of my time back didn't enable me to Be more effective. It just enabled me to waste more time. It's that makes sense Like I needed to find the one thing that if I even only had five hours a week I could have been doing that one thing and been seeing some success with it But instead I had 20 years a week. I was not accomplishing anything in 20 years a week I was at the end of the day like bottom line. I wasn't accomplishing anything So getting me five, ten hours back a week. It just enabled me to do 20 more hours of wasting my time And I think like I think sometimes at first when you onboard that VA as your first hire and you're not you know maybe With all the time in the world to focus energy and time on that team member and set up that virtual office and be the OBN That's going to lead that team member and have those ongoing meetings. It actually over time starts to really sort of strain and actually take a lot of your time away and what maybe gave you back five hours is now taking five hours Because now you need to make sure that this person can find the Google Drive document and there's no project management tool So they're like half hazardly reporting things you and maybe it wasn't like that in your business But this is you know my experience of seeing what this typically looks like and if you truly are a visionary and maybe you're not that Integrator entrepreneur, you know if you truly are that visionary it's going to be difficult for you to find maybe Time but also like the effort to put forth to train and onboard and hire because it's just not your jam and like let's be honest We cannot be good at everything like it just doesn't work like that you can't you can you know Compensate and you can work hard, but over time it will erode and it ends up feeling you know quite taxing and Exhausting but we'll definitely make sure that we link that Courtney and some of our interviews that we've had in the past about OBM and hiring and You know, I know that a lot of the people listening to our podcast are in the startup phases of their business I'd love to hear a little bit about what you guys have cooking inside of startup society and perhaps how that could help Springboard Someone's career someone's business. Yeah, so start a society. It's one of a few programs we run But it is our membership program. I started started a society because I wanted to provide like an affordable Online business training to people when I was in that first year and a half or two with my online business I was struggling so I joined figure out just like how do you quote make money online? I could not figure it out And so I just wanted to give people the training that I wish I had had and it was like I don't think this needs to cost thousands of dollars You know to learn the basics how to start an online business So it's an affordable membership that teaches people like all the roads and have started an online business start making money with it It's also just an amazing community a lot of people come for the training But they stay for the community because we have like co-working and so you know running an online business Obviously can be a rather lonely endeavor when we are sitting in maybe a bedroom in our house on our laptop Working day in day out and you don't have co-workers You aren't in an office space all those sorts of things right and so It can be so life-giving and make Growing your business building your business be so much more sustainable long-term when you have business friends Ed people who you are checking in-weighs on at least a weekly basis But we also have like an amazing flat group where the conversation happens every single day So anyway, that's our society opens for enrollment just about twice a year And I think you said we're going to be releasing this probably in the summer and for the curling schedule very soon So but you can just go to sort of society.com you can see when that next enrollment period will be coming if you're interested in joining us We would love that Thank you Gillian for pulling back the curtain and sharing what it really looks like to work with an OBM long term If anyone listening is interested in getting matched with one of our accredited OBMs We do offer matchmaking services inside of Serenoke.com inside of our agency. So if you go to serenoke.com for slash services You can learn more about getting matched with your ideal accredited OBM so you too can experience the freedom that Gillian has expressed today And the changes of what actually happens when you let someone else own the operational heartbeat of the business Now we're going to leave all of Gillian's details below including startup society And I hope that you enjoyed this episode you can learn more about our certification program over at obiam accreditation.com Thank you Gillian for being on our podcast. Sure. Thank you so much for having me

Podcast Summary

Key Points:

  1. Gillian Perkins hired an OBM (Online Business Manager) named Courtney, who was trained by the interviewer, and they have worked together for nearly eight years.
  2. Gillian realized she needed an OBM because she is a visionary entrepreneur who struggles with the integrator role—managing details, maintaining systems, and staying consistent.
  3. Her business grew rapidly from zero to six figures in 2018, but she anticipated that growth would become unmanageable without operational support.
  4. Previous attempts to hire virtual assistants failed because they required too much management and only handled small tasks, not strategic leadership.
  5. Courtney stood out in interviews for being assertive, having a clear plan, and taking ownership, even though she was the most expensive candidate; she negotiated a trial period at a lower rate.
  6. Early on, Courtney overhauled Gillian’s digital workspace and reported hours meticulously, showing high productivity and value, which led to significant pay increases over time.

Summary:

In this conversation, Gillian Perkins discusses her long-term experience hiring an OBM (Online Business Manager) named Courtney, who was trained by the interviewer. Gillian explains that she hired Courtney in late 2018 when her online business grew rapidly from zero to six figures. As a visionary entrepreneur, Gillian realized she needed a partner to handle the integrator role—managing systems, team members, and daily operations—because she got bored with details and struggled with consistency.

Previous attempts to hire virtual assistants failed because they required too much oversight and only completed small tasks. In interviews, Courtney stood out for her assertiveness, clear plan, and ownership mindset, even though she was the most expensive candidate. They negotiated a trial period at a lower rate.

Once hired, Courtney exceeded expectations by overhauling Gillian’s digital workspace and reporting her hours meticulously, demonstrating exceptional productivity. This built trust and led to Courtney’s pay increasing three to four times over the years. Gillian emphasizes that hiring an OBM is an investment that pays off when the person takes strategic leadership, not just task management.

She highlights the importance of finding someone who can partner with the CEO, manage team hires, and free up the visionary to focus on growth.

FAQs

An OBM is a professional who manages the day-to-day operations of an online business, taking on leadership and integrator roles to support the visionary business owner.

Gillian realized she was a strong visionary but weak at integrator tasks like management and consistency, causing her business to crumble behind her growth. She needed a partner to handle operations and accountability.

Gillian felt immediate relief when her OBM, Courtney, took ownership, overhauled her digital workspace, and reported high productivity with detailed hours, making the investment feel worthwhile.

Look for someone who is assertive, takes ownership, has a clear plan, and is more than just organized—they should be able to lead and make decisions without constant direction.

A VA handles individual tasks, while an OBM takes on leadership, manages teams, and oversees strategy, freeing the business owner from operational burdens.

Yes, Gillian found that her OBM paid for herself quickly by driving growth and efficiency, even though she was the most expensive candidate initially.

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