Interview with Emily Reagan (How true operational leadership can help you scale)

Welcome back to the OBM show. So today's episode is extra special for me because I'm sitting down with a dear friend who has been in the online space for a long time. Emily Reagan. And also this is the first interview where I'm interviewing someone from outside our community as I do OBM community because I have you guys know up until now. I've been doing a lot of day in the life interviews with our accredited OBM. But I thought you know what? Emily runs a unicorn digital marketing assistant school and the digital marketers work group. She has an amazing podcast that I really recommend that we're going to talk more about today. And pulling back the curtain on what it actually looks like to scale as an entrepreneur. So when things start to get bigger, the teen grows and suddenly you realize you are spending way too much time living inside a sauna just trying to keep everything together and everything moving. And I want to talk a little bit. I really want to pull back the curtain today on what it looks like in a scaling business that is gearing up to hire an OBM. And that's why I really wanted to get Emily on. So we are also getting super clear on something founders confuse all the time. That's the difference between marketing and operations. And why expecting one person to do both can create chaos and how you know you are at the point where it's time to bring in somebody operationally you know and all that good stuff. So let's get into an Emily. Welcome to the show. Oh, I'm excited to be your first non-OBM guest. Ron OBM. I mean, I know you're still from the virtual world and we're worse than oftentimes you know, we marketing assistants and OBMs and marketing people. We all get sort of mixed up and put into the same bucket. So have I done a good job introducing you? Emily. I am mainly in the marketing department. Although sometimes my marketing assistants might help with like an inbox and you know help do some marketing project management within their scope, but they are definitely not overseeing the business part of it. So and it's really fun because my audience sometimes learns like actually love this and then go off in your directions become more of the online business manager. So it's like such a fun collaboration. You know, we were talking and and I think even in our last few conversations, you know, something has been becoming increasingly clear to me and that is that you are scaling your business, your business is growing, your school is growing, your students are growing and launches are becoming a little bit. I mean, I'm not to drop any iPhones or anything like that, but kind of a little bit of a shitshow which is which is very typical. So you know, for for I really like to kind of focus on what it looks like or how it feels when you're scaling to a point that is kind of over and beyond your team as it stands. And maybe you can give us a little bit of a glimpse of what things look like in your business. Yeah, and I'll be super transparent because I'm all about that, but I do not have an OVM in my business. It's something I know I need. I'm right around the 300 thousand dollar revenue mark. So I know I'm like kind of straddling that part. And so I've been having to DIY it a lot. And I have a couple different contractors on my team. I have about five specific roles, but I am lacking that middle tier. I almost think about it like a champagne fountain or like overflows and overflows. Like I am missing the middle tier. And so that's why this is going to be so it's me and catch all their champagne at the bottom flowing into my mouth. Oh, but at marketing. So I end up running a lot of it, but a lot of it gets stuck in my head. Do you know, I do want to be open and honest about it. But you were complaining about kind of the total 18. And I think, you know, in your defense, because you come from this marketing background, naturally, you're on the launch strategy on the marketing strategy. And then there's a very fine line between, you know, being a strategist and being the implementer or managing the implementation team for a strategist to now be off managing the team, managing all of the bits and pieces of the launch final. Now before we go on, what are those roles on your team? Like what does your team look like right now? Like what do some of them do? Okay, I have a dedicated podcast in YouTube editor. So she's like very much in her lane, but I do have ongoing weekly. She also military spouse, but it's just so like repeat like spit out the content send it to her. And I have an email tech who does a lot of all the email automations. She does, you know, the webinar sequences and nurture emails. She's very much in that lane. I do have a marketing assistant who augments my social media can help do what, just what I teach in the unicorn digital marketing assistant school like some of the blogs the SEO, the podcast support, and we augment social media together. And I have a community program manager. So I have a membership for marketers called the digital markers work group. I have my school. So I have someone kind of running that, which is some operations. It's a fulfillment and scheduling and following up with events and filling up Kajabi. And I do have somebody in my inbox who helps with that. And she also, we don't have like a fancy title, but like the inbox to me is such like a top of funnel, you know, situation. So somebody I trust to there who can make sure things are going the right spot. But she helps more with affiliate launches. And I have just hired somebody need to separate, like, so I have two program managers, one for the school, one for the community because it was so big. So I have five partner contractors, but you can see I'm missing the launch manager. I'm missing the OBM. It's just like then it's someone that's sort of straddling all the parties isn't being able to create some operational intelligence to that and just, you know, very sound because, you know, obviously launch is a little bit more beyond operations, but it's still very systematic. All of that. And I think that's where I find myself most frustrated day today in the business is I don't want to have all of those decisions on me, especially when they are not there's they're not priority, you know, because it takes your time away from the things that only you can do in your business. So I think when you're here, where how do I show them my business in order, what are the ways obviously teaching and coaching and doing those things like that, that's you and maybe you have a junior coach that eventually, but for now that is your main jam and then you need to bring on somebody that can do that 80% like if we're thinking of the pre-do principle, you know, you have like the 20% of the things that only you can do in your business and then, so I know me and you Emily, we like to play in that 80% because it's procrastination nation. Yeah, you're good at it. We know how to do it and it's very cathartic to be like, I think it's a control and you are your own OBM. It just, it can very quickly become overwhelming because you are at every team members that can call. You're doing meetings with all your team members. You are the one who is wielding all of the, you know, the bigger picture of the launch planning and the date and there's like nobody else in the kitchen for you and like you're making like 800 cakes and like shits on fire or a string. If we were in a restaurant, I would be the general manager, the food expediter. I would be the fixing the POS. Yeah, I'm the host, I'm the bartender. I feel like I'm doing a lot of that and I have some food runners, but nobody to manage them and I have not an operational person. I have all of my full-time jobs, which I was very lucky to get as military staff moving, but I was always a one-man band in charge of myself. So I also kind of lack the leadership and the delegation, right? So I'm learning that even though I also know better because of the date. Yeah, just because we know better doesn't mean that in practice, it's easier. Like, you know, advanced entrepreneur, I would say and running, you know, very structured programs. Like it's sort of natural to just kind of keep everything going and because we are part of service people and we have been, you know, providing services for years to clients. It's just a default. It's like default mode. Yeah. And manage all of these things. So what was your last launch like? Well, I think we have to talk about like the online market right now is changing the course launches. I did used to have six figure launches and the last two years I have not, but that just puts extra pressure on me to do it leaner because I don't know what's coming, but it's hard because I know marketing and I know all the things we should be doing. And so it's more of a capacity problem. And then also making sure we're focusing on the right things. I told you I'm like not an operational person and there's a problem if I'm in a sauna at midnight and I'm not fixing strategy or messaging or I'm fixing handoff problems. Right. Making sure the baton is getting to the right person and things are getting done. And I find that so draining even though I love the adrenaline of the launch. I love having a launch event in a webinar. It's just that I can't actually focus on the marketing when I am running the launch meetings too. Like I showed like a bubbling, bubbling idiot because my brain is so overtaxed with all these tabs. And I kind of kept telling myself, okay, well next time I'll get a launch manager just to be honest, but then it got kind of scary. And so yeah, so it's a capacity thing too to be able to change how we launch and shift into different types of like evergreen launches are ongoing. I mean, I think you you run like a monthly webinar. and like shifting to that type of model, but like I need, I still need the project management of all of that. It's just gonna look different. - Yeah, I think that's so, so true. And it really is a capacity. If your whole business runs on core sales and the core sale industry seems like it's changing, then do I hire that person? What does that look like? And, but the truth is too, you know, when it comes to hiring an OBM, you know, one of the things that we look at and one of the things I train my OBMs to really get clear around is like, Emily, what are the things that only you can focus on in your business? What is the existing team structure? And, you know, 'cause it sounds to me that it's not probably not just launched, but maybe there are other aspects of things that you can bring an OBM on to do and so that it doesn't feel like, oh, if the launch is going bad, then I need to like get rid of that launch person. You know, it has to more kind of holistic and somebody that can literally take the reins so that you, so what was last time you took like a solid holiday? - Oh, girl, just getting sick after Christmas count. (indistinct) I'm pretty good. Maybe that's my problem, Sarah, like putting my head in the sand a little bit and avoiding things. But yeah, no, I mean, I get a week here too, but it's never like the solid unplugged, like it's been a while. I think about hiring a launched manager and that's not what I actually need. I know now a launched manager is kind of like, they're executing one launch, one promotion. And I think the way things are changing, we're no longer putting all of our eggs in one launch basket. We need someone who can coordinate these contractors in these deadlines like on repeat. And so I see the role of an OBM getting stronger in 2026 because we're not doing these one-time launches. - Yeah, and it's like launch operation, you know? - No, no. So we have-- yes, we have-- in my business, we have the once-a-month Evergreen webinar that I run, that changes a little bit, and then we have the cohort more Evergreen quarterly. And we tweak things. Right, you need somebody looking at those key performance indicators and making those decisions on your Beaud-- that you're not feeling overwhelmed with that at the end of the day. Oh, I think that's one thing I'm really dropping the ball on. But I'm heavy on also reporting and tracking our marketing work. I find myself as the CEO, I'm kind of good at putting my head in the sand, default primary custody of four children. So I'm like drowning a little bit. So I really need people to step up with their lead, and not just report the numbers or go put them in a spreadsheet or collect a report, but actually look at them and smooth feed them to me, almost like those like level 10 meetings. Like I know I'm missing that kind of old-ergid-up. Yeah, you need an OBS. You guys are listening and you're like, oh my god, I feel like Emily, I get it. I'm a successful entrepreneur. I hold my own. I mean, we are also different. We have different strengths and different weaknesses. But if you are listening right now and you're thinking, I need an OBM, head on over to obmschool.com/matchmaking and check out our directory for accredited OBMs. And also, I personally match clients and OBM and Emily. I'm happy to do that for you as well, because we've got an incredible community. But alas, yes, I mean, it's really important to sort of recognize. I find that even in my own business, and even after OBMing for a million years, I can still very easily lie to myself and make myself like things look a very different way. Is it like, when you're honest like, why not? How do I even think they've got team member was, you know, sort of taking that responsibility? Because I hear what you're saying around, you know, you want people to not just stay in their lane, but like own their lane and all the reporting in their lane. But the truth is, is that when an OBM has that big picture vision and they know what the goals are, and they know what their vision is, like your client care person doesn't necessarily know what Emily's grand vision and goals are. I mean, it's not part of her job description to be like, oh, I'm very clear on what's happening. I can make decisions on behalf of the business. Or if I see this really shady KPI coming, I'm going to sort of be able to approach Emily and be like, Henry, red flag, this isn't working. Or hey, red flag, I noticed that this KPI was really low, so I went ahead and I audited the funnel. And I, oh, I love it. We're broken, right? And I love that. Save me an entire day of having to pull my own hair out, try to now, you know, so I mean, it is the wonderful thing about any team member, but I think in OBM especially, is it really is an investment in your own state and your ability to sort of stay in the Emily lane, which is where you can really double down and, you know, sell more people into your membership or, you know, really make an impact on more marketing assistance and all that good stuff. Yeah, because I need to focus on sales in 2026. Like it, I had a lower income, I lower revenue last year, and I know like, all right, now I need to double down on this and I really have to make some trade-offs and hand-offs. And one of the hiring mistakes I made because I'm not an operational person, I'm actually more hands-off. - You know, background, yeah. - Yeah, yeah. - But I made a hiring mistake 'cause I'm almost two hands-off sometimes. And I'm like, oh, I expect you to be self-managed, be self-directed. I tell you, like, this is my goal, I want this done, and then I kind of step away. And I feel like if I have to come in to remind you of deadlines and check on stuff, I'm getting depleted. And I'm already doing that with my teenagers all the time. I'm like, I don't want to manage you. And so I made a hiring mistake thinking somebody was going to kind of step into that role and I admit, I'm like, I don't want to be in the nitty-gritty details of how you got it done. But I felt like I'm explaining the outcomes. Like I feel like I'm coming in as a good client. And then that backfired with a hire last year. And it took me a couple of months to make the moves. I was going through divorce. So there's like personal stuff going on. And I delayed it. And when I finally got in there and looked at it, like under the hood, it was bad. She wasn't meeting the deadlines. When I did fire her, she threw it all back on me. And it was just like an ugly situation. And so what I learned from that is probably, maybe like overseeing the project plan or like asking her to submit it. Like I probably should have done that instead of trusting. But I also, if I was not blown away with her in the first 30 days, I should have let her go right away. Because that's when you see the most excellent work in people on it. But like I find myself being like nice because I know it takes time. I'm a client work. And I was almost too nice. I was also very distracted. And I'm embarrassed to see that. But like I did learn some good lessons. That's good. You know, that's business, right? Everything is in the problems. But yeah, I do. And one thing that OBMs do when they hire is we always do a test project. Now obviously, I know that it's really hard sometimes to see if people are strategic or we'll go above and beyond something. So I mean, yeah, even a test project can't necessarily help. I think they can do it. But if you don't see it, and I'm like, wait, there's a problem. If I'm more operational minded than this person, like there's a problem. And I should expect someone to really come in there. Another part that I kind of struggle with, I think there's like really good VOC here and this podcast for all the OBMs listening. When they're like, what are the pain points? My person is it, you know, experience. It's like, yeah, the launch being stuck and click up in a sauna. But I think we really struggle. And I do with like the baton passing, right? And who does what next? And it's not just during a launch. Like even this week, I got an email from my teammate. She's like, all right, someone so completed the training. And I'm like, yeah, but what comes next? Like who's over being having that like system mindedness and being able to pass it to the next person? Like that's the part that's missing this. So critical and creating all these like leaky buckets and we're losing money when that happens. And it affects your bottom line. It affects your customer retention. It affects your reputation. - Do you or do team kick the ice? - No, I don't. - I mean, we're on top. And sometimes part, like what exactly is your cable? But when it comes to things like, let's say the follow up for someone completing the program. And then I guess they move into the ongoing membership. - Yeah. - Whatever that dial is, right? Like that's where the maybe what frames the KBI. So if, you know, if 20 people are completing the program, you know, you expect that like 19 out of the 20 move on to the next space. So if they're not moving on, then there's something wrong with that team member because she's assuring everybody into the next iteration. - And instead of going Emily here. And then like, no, it needs to go this person. - It ain't her line, meaning her mind. She's like, yeah, seven finish. I'm gonna tell Emily's to she like, it'll be. And you're like, Kim, how be it? Like facting you to be really on top of the delivery and the client experience so that we can ensure that we have a high, you know, just retention of our students. - Well, and that would be a good communication tactic is like, don't just like bog down your, I'm like, I, okay, Sarah, I've worked in so many businesses. A lot of hot mess clients, no one's super organized. I used to get mad at my clients for slowing my work down. And now that I am the client, I see it. Like I have so much going on and I probably do too much visibility. but I'm not over here like scrolling TikTok and like, oh, I kind of feel bad for some of the thoughts I had about my clients. I'm like, they are busy. So how can you be clear, concise, and show off that you got them covered? And so that email instead of like, hey, you know, Sarah completed, you know, the self-study, like, go ahead and like, slip in what you're doing next and like, wow, my socks and remind me that you got it instead of leaving me with a question mark, because I'm wondering. And I mean, we do have a system. It's not that we don't have a system. It's just now I'm questioning, is it kicking off, you know? Is the system clear of my expectations are? And that's the wonderful thing about having an OBN because they are your mouthpiece, standards. They know the vision. They know the goals and the big picture. So if that team member is like, hey, this person's finished, they're like, okay, a goal, KPI. You know, did you usher them into the next step? It x, y, nz happen. And like, more and less thing for you to worry about because we're seeing, you know, piece of bits and pieces of the business. We need OBMs in our life to like, take that noise and strip it down and just take care of us. Yeah. It's hard to find, you know, your clients are not pit-spot-slinging and free Facebook groups. They are frustrated because they can't stay on the ball as much as they were when things were smaller, when things were less intense. And then there's also this, you know, the growing pains, right? Like, you have all of these, you know, one team member, two team members, five team members, like it's also five weekly meetings or monthly meetings. It's also five people to which have you birthday to and Mary Christmas and like, did you care of like, it's a lot of the team management also becomes very taxing as well on top of the expectations on their performance. Yeah, even when I had an agency, that was the part I know my weakness. Yeah. I would much rather get in and do the work, do the brain work, the innovative, the, the, the visionary, the creative. And so it's always been for me the people management. And I know that's right. It's why I closed my agency. I was like, I didn't enjoy all the people management of it. But I just want anyone listening to realize like, if you have that strength, like you are needed. I think people like me, we're not out there telling you our hot mess expressed over here. We're not like telling you that we're in funny spots where we're in that's gross stage of business. Profit margins are lower, but we're never going to get out of it until we can increase our capacity and help us go out and make more money. So it's a heart spot. I think I always remind my students that we your clients have to know their best use of energy. So if you are giving them back five or 10 hours in their week, because they're not having a duty meeting, they're not having a manager to launch, what are they doing with that newfound freedom? Or are they focused on writing the book, getting on more podcasts, attending conferences, the things that only they can do in their business. So I think an important thing for anybody considering hiring an OBN has to know their 20%. They have to know what it falls into their realm of getting shit done. That only they can do in their business and how to amplify that as well. Because when you have a clear vision for that, feel it to me. It would feel less scary to bring an OBM on the team, because you know you're very clear in your value and where you need to be. Yeah, and bring that conversation into your discovery call and get that business owner to admit with the value of getting their time back would be in love with you with that. And I mean, that's how you sell your service. Not as many people. Some people just aren't ready for it, but like get that client to name it. We've got tons of podcasts episode on the client. They, but they need to be making money. They need to know their value and know where their best use of energy is in their business. And also like where, because the OBM is unique in everybody's business. Like, but what are all the other things that you, you don't want to be doing and being very clear and maybe auditing your time and since you know, keeping kind of a document going of like, what are we spending all of my time on? Like launching that can be best utilized in other ways like, you know, doing other things and not even necessarily just working. Oh, yeah. And kids, you have your kids, I mean, no, we talked about this on your podcast, but like, you know, the kids take out so much of our time, carpooling and I say carpooling. It's show foring. Oh my god, my son slept in this morning and I'm like, I had that hour carved out to add it in this lesson because my audio messed up yesterday. And so I just, I'm, I just lose time with children. Children. Where does it go? So I mean, but also understanding that that's also as entrepreneurs and as business owners, such as being part of what you do. Yeah. And I think going into its 2026 is so critical that you said something that really like popped out was the time to write a book. Right. You know, what is that dream aspirational, that revenue stream that that client cannot pursue because they are stuck in the weeds. And I think it's so critical in 2026. So I think it's a really critical thing to do. And I think that's what I think is really important. And I think that's really important. Thanks.