The Caroline Pennington Show
Heyyyyy & welcome to The Caroline Pennington Show!
I’m your host Caroline, former executive recruiter turned Digital Marketing Expert OBSESSED with helping entrepreneurs to start, grow and scale their personal brand & business online. I have a passion for empowering & supporting fellow entrepreneurs.
On this podcast, you’ll hear from fellow business owners sharing their stories and unpacking exactly how they did it in their business because we believe that as curious & ambitious human beings we can ALL learn from one another and to be inspired!
Every week you'll hear from entrepreneurs and workplace experts and no matter the size of your organization- you’ll gain insight and knowledge to help support you in your journey too!
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The Caroline Pennington Show
174: {Interview} Scaling Your Sales with Jillian Murphy
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Learn how to successfully transition from a corporate career to entrepreneurship with insights from sales expert Jillian Murphy. Discover actionable tips and key strategies for your journey.
In today’s fast-paced world, many professionals find themselves at a crossroads, especially after unexpected job losses. This episode explores how to navigate the transition from a stable corporate career to the uncertain yet rewarding landscape of entrepreneurship. In today's episode, we’ll delve into Jillian’s inspiring journey, the lessons she learned, and practical steps anyone can take to succeed in their entrepreneurial endeavors, especially when it comes to sales.
Connect further with Jillian on LinkedIn HERE on IG @thejillianmurphy
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ABOUT THE HOST:
Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara.
This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.
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Caroline Pennington (00:01.563)
Welcome, Jillian.
Jillian (00:03.214)
my gosh, I'm so happy to be here. I just had you on my podcast. Absolutely obsessed with you and everything you do. So super excited to pour into you and your audience today.
Caroline Pennington (00:11.879)
I was just like everything else. I had known you, known of you online and we finally got to meet. forget if it was at Powerhouse Woman or when we spoke at an event or what it was. Either way, I feel like I've known you for a long time.
Jillian (00:20.536)
Yeah.
I mean, I think that's like the beauty of social media, right? Like you think you know all these people and like you think they're your real life friends and then you meet them at an event and you're like, my gosh, I know everything about you, where you've been, your dog's name, your husband's and they're like, all right, but I also think that's like the beauty of social.
Caroline Pennington (00:38.489)
No, I'm with you. So you are a sales expert, a business mentor, a speaker and a top podcast host. So we can hear the backstory. How did you do it?
Jillian (00:42.392)
Thank you.
Jillian (00:49.262)
Yeah, so I love this story. It's very simple, you guys. I was in corporate sales for 23 years. I was a ride or die corporate person. I always joke if I could have like tattooed my company's name on my forehead, I would have. I had a great job, a cushy job, a job of just massive, massive security. I had no desire to ever be an entrepreneur. I didn't even really know what it was. I had some friends that were in the online space. They were always like talking on their phones. I thought it was like weird as shit. I'm like, I don't know what you guys do over there.
And then I lost my job a couple of weeks into the pandemic, which was really interesting timing because people think I lost my job because of the pandemic, but I actually lost my corporate career because our company was sold to investors. And that was, it just kind of happened at the same time. So I'm not like a COVID corporate, lose, lost my job girl just happened to be that right amount of time. And I remember going into the office and giving back my car keys.
giving back my laptop and basically giving back my entire identity of like who I had been for the last 20 some years. And my dad's a very successful businessman. I'm actually excited. had him on my podcast yesterday. And I remember calling him as I called an Uber to come pick me up from my corporate office. And I said, I don't know what I'm going to do. And he's like, take the day, be sad, go eat some ice cream, watch friends and tomorrow, like get your ass back in the game. And that's literally exactly what I did. And I moved to the online space almost immediately.
Caroline Pennington (02:13.597)
I love that story. And I didn't know the timeline was COVID. So that makes sense. And I'm glad that you explained that the investor piece too, because yeah, everyone could blame COVID for whatever fill in the blank, but actually that's even a bigger thing. That a lot of people when they have, when they work in corporate and their company gets bought out or whatever, they think like they're invaluable and like the company can't function without them. And that's just not the fricking truth. You're replaceable. So.
Jillian (02:25.324)
Yeah. Yeah.
Jillian (02:36.066)
Yeah. Yeah. Yeah. Yeah. I want to like actually want to paint the picture for you guys really quick because I was that person. I was at my corporate career for over 20 years. I was the only female hired since 1963. I was the poster child in our sales organization. My picture was literally in the hallway when you entered our corporation. I had been to the owner's weddings. They had been to my daughter's birth. Like I had
never ever thought in a million years. And I remember the owner saying to me, when I now own 49 % of the company and investors own 51, unfortunately, like even I can't save you. And it's really interesting because I worked for a family owned company. There was a mom, a dad and five brothers and only one brother is left to this day. So even the family members of the company are all gone to this day.
Caroline Pennington (03:27.133)
It is crazy and I'm glad you added some more color to that picture because I feel like, I mean, and I'm even guilty of it when I worked in corporate. I was like, I'm the best at my job. Like they can't replace me, but like as I've gone through more things and now myself, it's like you're replaceable. So figure it out, get a side hustle going or something else for insurance for yourself.
Jillian (03:45.55)
100 % I think that in today's market I think everyone should have whether that's a network marketing like I'm a big believer in like network marketing or affiliate sales or just something else that you're doing because You you never know what's going to happen
Caroline Pennington (03:59.302)
Okay, switching gears, what is the difference between marketing and sales?
Jillian (04:04.142)
Oh my gosh, such a great question. think me and my girl Shelby could riff on this all day long. I'm also sporting her hat today. Shout out to Shelby. Marketing is what gets people to you. Sales is what gets the sale closed. So I'll give you an example. I'll use Target for an example. An ad gets you into the store. But what happens when you're in the store and you take that shirt that you saw in the Target ad to the register, that's the sale.
So again, a lot of you guys are really good at sales. Let's be honest, most of you guys are not. Most of you guys are not really good at marketing either. And you're wondering like where the disconnect is. So they also work hand in hand. think like marketing and sales go so much hand in hand, but they don't do each other's job. And I've been really fortunate because my dad owned a sales and marketing agency for, my dad was in sales and marketing for 57 years, but he owned his own firm for almost 40 of them.
So I also saw what that looked like to bring brands in and then have the sales rep sell it because it's two very different things.
Caroline Pennington (05:08.315)
You made a great analogy with that target example because yeah, marketing and sales are two different ballgames and I've been, I've worked in sales as a business development rep. I've done marketing too. So I understand like the marketing is the awareness and then the sales is the hard close. So.
Jillian (05:10.606)
Thank you.
Jillian (05:21.846)
Yeah. Yeah. I, and I also think like touching on like the Target ad really quick. I talk a lot about Target. You guys imagine if Target did everything that it's currently doing, but their ad next week went to 50,000 men who loved fishing. We would instantly think like, Target's not working anymore. Or we have to change it. We have to do it. No. Most of you guys have also the wrong people consuming your marketing. So you have to make sure that the right people
your ideal avatar, ideal client, whatever you're calling it, is then reading or into your marketing and then from there it's selling because so often we try to fix the sales and the marketing but really it's a lot of times just the leads coming in.
Caroline Pennington (06:05.021)
What's the biggest mistake you see business owners and or coaches making when it comes to increasing sales? Let's say maybe they're at a $100,000 business or $500,000. What do they need to be doing in the sales department to push through those thresholds?
Jillian (06:18.914)
I'm always like, how long is this podcast? But no, you guys, this is the thing. I think that I talked about this yesterday on another podcast. Not that I've ever been a heroin addict in my life. So let's make sure that does not get put out there. But I almost feel like it's like being a heroin junkie and you come to the online space and like you instantly want like a hundred thousand dollar a year. And then you're like, I need a $200,000 a year. I need a $500,000 a year. I need to do funnels. And there's like this constant like adrenaline that you get. And then you sit back and you're like, why am I even chasing this?
So the first thing I would have anyone do that wants to grow their business, get really clear on why. Why do you want to grow that business? Is it a business that you want? Is it a business that you see Caroline having? Is it a business that you see me having? Or is it like what you actually want? So I think that's like first and foremost, like we have to get into like, and I'm not like a feels girly, but also like, why do you, why do you actually want this? Right? Then from there, strategically looking at what is working and what is not.
So many people try to pay attention to like, what's not working, what's not working, but like, what is working? And how can you pour more gasoline or fire onto that and take what's already working? And then I'm a really big believer. That's just my own personal opinion. I love a scrappy business because I don't care how much money you make in your business. It's about what you take to the bank. So also making sure that you have the right people in there that can actually build it and support you to get it up to the next place.
I'll give you a quick example of this. I'm a visionary and I'm a creative, but I'm also strategy, but I'm not like a tech person. Okay. So recently I wanted to create this new offer in our business. I wanted to generate some more income, generate some more leads. So I had the idea as the visionary and the creative of like what I want this to be. I went out, I sold it. 39 people joined the first week. Now I have to make sure I have the right people in place to build it out on the app, send the emails.
Onboard everybody, make sure we have contracts or agreements, payment plans set up. So it's like making sure that you're building your business with the support that you need in the backend. Otherwise it's just going to be a terrible customer service experience.
Caroline Pennington (08:24.999)
for entrepreneurs that are so guilty of, it's not going to be perfect unless I do it. And that's such a terrible and wrong mentality. Like you have to outsource things and you have to delegate.
Jillian (08:34.624)
Yeah, I've read this thing one time. I'm not sure if it was in a Dan Martell book or 10 X is easier than two X, but basically it's like a quadrant and it's like, what are you good at? What do you love? What are you bad at? And what do you hate? And you guys, we should absolutely be delegating bartering trading services with anything in the things that we are not good at or we do not enjoy because usually the things that you're good at and you enjoy are like the income producing activities. You know, I could be right now on Canva.
trying to make something and missing out on talking to this podcast and probably hundreds of thousands of you right now versus having someone do it for me for a couple bucks and I can be in my zone of genius. So really write that out. If you guys stop the podcast right now and like do that exercise, it's really powerful.
Caroline Pennington (09:20.541)
Okay, I love that and rewind that to those listening because that was some freaking gold right there. Okay, so I've heard you talk about this and I feel like you're really passionate about it and I love it and I wanted you to share with all the listeners and you, I saw you speak at Shelby's event last fall and you really laid into the power of the follow-up and I think that people get scared about that because they're like, I have once or twice or whatever and that's not enough a lot of times, most of the time. So I want you to pop off about the power of the follow-up.
Jillian (09:25.986)
Yeah.
Jillian (09:46.286)
Yeah.
Yeah, so this is the thing, and I say this with so much love, you are not that important to people that are following you. They are not paying attention. Like, they're not, right? Like, they're watching your Instagram stories, like, maybe while they're going to the bathroom, maybe when they're in their kids' pickup line. Like, maybe they, maybe, I how many times I've, like, watched somebody's stories and I put it down and, like, I realized, like, an hour later, I've been watching stories all day. You guys, people are not paying that much attention to you.
So it is absolutely, you're like J-O-B to follow up with people. Now, I'm not here to teach you to be like salesy, slimy, weird, cringe, any of those things, but if someone has come into your world, right, let's use my friend Shelby. Let's say my friend Shelby comes into my world and she's like, hey, I really wanna get better at my content. This is not Shelby, she's a content machine. But let's just say she's like, I wanna get better at content. She has told me that she has a problem. So why would I not?
give her solutions and stay there until I actually do it. You know, like that's the thing I think so many people miss. And I just read an article recently, clearly I'm like a reading nerd, but I just read this article recently in Business Insider. And this is a really good stat for you guys to pay attention to. If you sell something a dollar to $5,000, your audience needs 50 meaningful touches before they pull out their credit card. Okay, great.
I actually sell something over $5,000. So for me, it's a hundred meaningful touches. Mind blown when I read that. It used to be like 10 to 12 touches where all somebody needed, but we're getting inundated with things on Instagram or social media, LinkedIn, whatever platform you're on. also are in like, people are calling it a trust recession, whatever you want to call it, but people don't believe anything that they're reading. They don't even believe that like you're a real thing. So the more that you follow up,
Jillian (11:37.263)
It's so, so, so important. I want to tell you guys a quick story. I love stories when I like have things that I feel like it really like edifies it. When I was in corporate, there was this account that I wanted. It was called Mike's Pizzeria and it was at the corner of my street and it used to make me crazy that they got all of their products from somebody else when I literally drove past it every day. I was in food service distribution. So think anything that a restaurant or bar uses came off of like our truck. I called on Mike's Pizzeria 81 Tuesdays in a row at 4 p.m.
every week. And Mike used to be like, you're not going away, are you? And I'm like, no, I'm going to grab a cup of coffee. I'm going to sit here and order a piece of pizza because guess what? Someday your other distributor is going to make a mistake. And I'm going to be right out here at the bar on my computer working. And guess what? On the 82nd week, it actually happened. In no way, or form was I annoying. Mike just saw that I was there. And for so many of you guys, your people need to see that you're going to be there, whether they're paying or not.
Caroline Pennington (12:37.029)
Okay, I love that story. back in the day when I was in business development, I called on this manager, I was in staffing and recruiting at the time, and I called on this man for seven years with three different firms that I worked for. And on the seventh year, he finally called me back and he said, I know you've been calling me for seven years and it took seven years you guys for the competitor agency to completely fuck up.
Jillian (12:38.232)
Thank you.
Jillian (12:49.463)
less.
Jillian (13:05.708)
That's exactly what it is. Yep, that's exactly what it is. just had a girl recently in my own world in the coaching space. She reached out to me about a year ago and she actually ended up hiring one of my clients. And I was like, hey, no worries. And I was like, eventually it will go south. I'm just gonna sit back here, eat my popcorn and wait. And when she's ready, like I'm here. And guess what? It did. So you guys remember, it's not even always about what you're doing. It's about when someone else drops.
Caroline Pennington (13:06.694)
Yeah.
Caroline Pennington (13:33.437)
One thing I've heard you talk about a lot and I want to hear more of this from you and our listeners too. A lot of people think you have to do the marketing, do the sales, jump on the sales call, close a transaction. And you talk a lot about that, that you don't have to do that. You don't have to sit around 18 Zoom calls trying to sell people all day. So talk about that method that you've learned and perfected and you teach and share all the things.
Jillian (13:55.821)
Yeah. Yeah. So this is definitely probably one of the main things that people hire me for because you guys, people don't want sales calls. Like I hate to break it to you. Nobody wants to get on your clarity call. Nobody wants to get on your discovery call and have you like pick their business or their health or their sex life or their parenting apart. Like they don't want to do it. Right. So I basically, what happened was I started selling in the DMs. This is like kind of how, again, like I think a backstory is important. I started selling in the DMs and people were like,
how you just sold me, I wanna learn. And I was like, oh, I don't really have like a framework or a script. And then I was like, no, I actually do. It's like what I'm doing. And what I realized the number one thing was, was that in every single conversation that I closed in the DMs, and just to give you guys context, I have offers anywhere from $5,000 up to $56,000. Okay, so I'm not selling like a $97 ebook in the DMs. These are like high ticket coaching programs, high ticket consulting. I realized,
that every single conversation began with me asking things about them. It began with me building a relationship on something that had nothing to do with business, hair extensions, clothes, being at the beach, their kids, right? Whatever it was. And then through that, the relationship was built in the DMs, like a genuine connection, a genuine friendship. But then, because I'm like a content machine, content monster, whatever you want to call me, my content was being served to them.
So I never needed to tell someone, I help you with this. I help you with this. My content was feeding them. Most people in the online space, again, I say this with love, but I'm here to be honest. Your content is garbage and you're trying too fast to sell them in the DMs. So like you're coming off salesy in the DMs and then they have like no idea what you even do. So that's like the myth. So I teach relationship building human to human sales. I don't use any many chats, no bots.
No chats, no VAs. There is literally no one in my DMs. I don't even think my director of operations knows how to get into my Instagram. And then my content is also all done by me because these are going back to the things that you're good at and the things that you love. This is how I sell. So why would I ever give this to somebody else when this is like my income? They can do everything else around.
Caroline Pennington (16:10.375)
That is so good. And I am with you 1 million percent on that and the DMS, especially on LinkedIn and on Instagram too. It's me, you're going to get me. I will not outsource that. And that's where all my magic's happened for everything. Every transaction, every speaking opportunity, every podcast, guest opportunity. And so, my gosh, that was so good.
Jillian (16:11.864)
Thank you.
Jillian (16:23.854)
Yeah.
Jillian (16:27.585)
Yeah.
Yeah, and if you think about it, like think about who your ideal client is, right? If you're listening to this podcast right now, I know you're a high achiever. I know that you're trying to call in someone that has a great business. If they have a great business, guess what? They're on their own calls all day, right? So again, I just booked a photo shoot this morning. The first thing she said to me was, hey, let's get on a Zoom call and talk through the next steps. I can get you on a Zoom call on my calendar in about 30 days from now. By then the photo shoot's over. But it's like, hey, can we just like riff it out here when I'm on a walk?
later or I'm in the bathtub later or I'm like making my lunch, you guys, your clients don't want to get on calls. And quite frankly, they also don't have time if you're calling in the right people. If someone could get on your calendar today in an hour, they're not that busy. They're probably not making any money in their business.
Caroline Pennington (17:15.995)
So good, busy people, successful people, they don't have the time. And so you have to keep that in mind and you have to get on their level. And that is a voice memo or a DM or something like that. So get creative, okay? Okay, we are in a quote trust recession in 2026. What are your top three to five sales strategies that are working right
Jillian (17:30.028)
Yeah. Yeah.
Jillian (17:40.449)
Yeah, so I also think that like there's two camps right now and I think that you can sit back and this and you can say like, we're in a trust recession. No one's really buying. It's a lot harder, which it is right. Or you can be in the camp of like there are people still winning and go figure it out. And I'm going tell you, that's exactly what happened to me. I had been with the same mentor for five years and I was in a room where people were like, this is a trust recession. Nobody's buying. It's a little bit slower. And then I saw up here in that mastermind,
basically take her entire business model and flip it on a Ted. And I was like, okay, just worked for her. So I'm going to go hire her and figure it out. You guys, this is why I just created my first ever low ticket offer, which I'll tell you about in a minute, which is like why I created this. But the reason why I created a low ticket offer is because people right now have more discernment than ever. They're waiting longer. They're asking more questions. It's not even that they don't trust you. They don't trust themselves.
because they've made a bad investment, because they listened to someone on the interwebs, or they didn't do their homework, whatever it is, right? So they almost need like the Costco effect of where it's like, I'm just gonna go in and I'm gonna try this popcorn first. And maybe they come back a couple of Saturdays in a row. So number one, I think that everyone, even if you've only ever sold high ticket, I think that you all should have something right now that is low ticket, that it works as a bridge from your low ticket to your high ticket. So this is what we did. And I'm like, I love to share like BTS.
I did not have anything in my world under $5,000, nothing. And this has been working like gold for me for years. And I would say mid December, which I first said was like just the holidays. And then in January, I was actually down $127,000 in January. And that's when I said something else has to change because guess what? The offer didn't change. The messaging didn't change. The content didn't change. All of sudden, like it was like, it just dried up. So we now have this bridge offer.
which allows people to come into my world, test me out, and then I have my own conversion event inside of there every month that then brings them up to the buffer offer, which is the next offer up. So I did this as a trial. I launched it last week. We have 39 people in in one week. It's not about the 39 people that joined at $500. Yeah, that was a great cash injection. But now what this is is 39 new leads that I know have my problem that I now get to nurture almost like in this fishbowl.
Jillian (20:04.088)
So I think that's the first thing that's working really well. The second thing that's working really well is to go against the grain. So what I mean is like go against Manichat, go against chat GPT, go against carousel posts, grab your phones and just talk because people want to hear from you and they don't believe anything. I just did a podcast with my friend Allie the other day. We're both talking about this girl we were like obsessed with on Instagram comes to find out she's actually like an AI robot.
We both had like a massive like girl crush on this girl. We were buying her stuff. We were buying her jewelry. She was a jewelry influencer. You guys, she was not even a real human. That's how good it is right now. So the more that you can grab your phone and just talk the better. So those would be probably like the, like two of the biggest things. And then also knowing it's going to take longer. You know, people are not just like setting into your DMS day one and buying like you need to have a longer runway. I used to be able to do a master class in like
put it up on my stories and in like a week get like 100 people to sign up. I have a five week runway now for a free training because you're competing with everyone not in their business but for eyeballs and attention.
Caroline Pennington (21:13.757)
I love that and that was pure gold because I hear you the same thing of my clients. They all want the Amazon effect They want to blow up they want to go viral. They want the numbers They want the whatever fill the blank the clients the vanity metrics the bookings all of it and it takes time and no one wants to hear that but That's the reality these days
Jillian (21:30.798)
Yeah, it really is you guys you have to embrace like delayed gratification right now You absolutely need to something that I tell myself every day and again You guys can steal this write it on a postcard write it on a post it Whatever you need to do is I tell myself every day there are people that are gonna buy from me that I don't even know yet I've never even hit their algorithm yet. They don't even know me I've never met them because so many of you guys are so focused on like who right now are you talking to? Just go out keep doing what you're doing right like today
on this podcast. There's people that have never heard of me, have no idea who I am, right? But now they're in my world, awareness. So the more that you can do to build awareness is going to be key right now in this like a little bit of a quiet time.
Caroline Pennington (22:12.989)
All right, so last question before I get to how they can find you. What is lighting up with some of the clients that you're working with right now?
Jillian (22:14.391)
Sure.
Jillian (22:18.774)
Yeah. So what is light lighting me up right now with the clients that I'm doing is people that have been in all the things, but hasn't really had someone in their business helping them. So this is kind of like my secret sauce, which means like they've been to the masterminds, they've been to the groups, they've been to the trainings and they come to me and they have 87 notebooks, flip notes, and like they're all over the place. So what works really well in our world is I get like in their business and I kind of start to see it. And then I start to see them really light up.
because they've been lost in all these things. So that's the first thing. Number two is my clients get hella good results. So I love showing other people that like, it's actually not really a trust recession right now when you change the game, right? My coach always says like, we've all been playing checkers and now we just got to play chess. That's the only difference, right? So it's like being able to take what I'm doing and then integrate it and then show them and then have them work it as well has been really, really good. And I'm actually kind of excited about this new offer, even though it's like super low ticket.
because it's just getting new people and new energy into my world and it's going to be a great resource for the next level for people.
Caroline Pennington (23:22.855)
How can a listener find you?
Jillian (23:24.526)
Yeah, so I have a podcast called the Jillian Murphy show. Go over and listen to Caroline's episode as well. It'll be dropping soon. We drop two to three episodes a week, short, tangible, right to the point. And then of course on Instagram at the Jillian Murphy. And if you're listening to this podcast today and you need help with DMs, I have a totally free offer. It's called dmstarters.com. Go grab it. It's 20 quick DM starter conversations that will not make you feel ick, that'll not make you feel gross. And it'll start the conversation with your people.
Caroline Pennington (23:52.615)
Thanks, Jillian.
Jillian (23:53.461)
Thank you so much for having me.