About Hilary Swan: Hilary Swan is the Founder and Principal Consultant at Rebel Scout Consulting, which supports founders and CEOs without a sales leader during growth or transition as a fractional VP of sales/sales leader. Hilary has spent 14 years working for global sales organizations and has carried the bag, launched new products, led sales teams, and knows what good looks like and how to get you there. The wildly competitive culture of sales is where Hilary thrived, and this proved to be accurate as she hustled her way through the ranks and reached sales leadership, where she most recently led a $18M business over three divisions in one of the country’s most competitive industries and markets. Hilary has had a burning desire to feed her entrepreneurial spirit and coveted passion for developing people to win every step of the way. Still, she didn’t quite know how to share her wealth of knowledge and expertise until now. Check out the latest episode of our Conversational Selling podcast to learn more about Hilary.
In this episode, Nancy and Hilary discuss the following:
- Hilary’s background and motivation for starting Rebel Scout Consulting
- The concept of fractional sales leadership and how it supports startups and small businesses
- Supporting startups and small businesses in the absence of sales teams
- The importance of embracing sales as a positive force
- The positive nature of sales
Key Takeaways:
- I do not engage with any company for under three months, ideally six months.
- In the majority of startups and small businesses, all the sales are typically made by the founder or, in small business cases, the president or CEO of the company.
- I had always wanted to do something on my own.
- It’s interesting how you can be fueled by the sales piece and the environment in which you sell.
“I was in inside and outside sales, selling many different things. I was in sales leadership. I’d always wanted to do something on my own. I’m not surrounded by a ton of entrepreneurs or people who own their own businesses per se, but I was always so intrigued by it. So, I had been approached about a head of sales role with a startup, which was not right for me then. But it really got me researching what this all looks like in the startup world and where these people get the money. Do they make money? How many of these ideas are good? The failure rates are high. So, I had a, you know, cautionary risk. I researched, but I felt like I hit a crossroads. So, the company that I was working for at the time had been acquired, and I should have been very appreciative because I was going to be moving into a new leadership role, which was a bit of a promotion on paper. I was so not inspired by it. I just, the thought of having to continue to do this or do something in this role was just not, you know, lighting the fire. And so, I felt like this was the time. This is a clean cut to jump two feet in. For those who dabble in starting something while they have a full-time role, it doesn’t work for me personally. And so, I felt it was very clear that you have this job opportunity in front of you, and you should be so excited. It’s more money, more responsibility, a bigger role, and I couldn’t be less excited. I felt like that was my sign just to rip the bandaid off and do it. And so, I did it. And thankfully, it is working out very well. But yeah, it takes a lot to do that step.” – HILARY
“The fractional model is, I don’t want to say it’s not new, but it’s on the newer side and exactly what it sounds like. It’s a fraction, so you’re getting a fraction of the time of an executive or a leadership. So, what it really should feel like is for startups and small businesses, they’re getting what they need. So, this is across many different specialties. You’ll see operations HR. You’ll see the Chief of Staff. And so, what it is that you’re getting that team member for, to be honest, is also a fraction of the cost likely. And you need their expertise and their membership on your executive team. But having most of these roles filled costs a lot of money. So, what is not better than to tap somebody at a fractional? Engagement where you don’t have to bring them on as a W-2 or with the health benefits or 401k. It really is, and I know consulting is in the name of my business, but it’s not the consultant in the traditional sense of projects; they do all the stuff and then leave. You really, really should feel like you have a team member on your team with this fractional leader.” – HILARY
“We’re all in sales, and that is okay. That’s a great thing. So, the faster you can embrace that and feel comfortable with how to interact with people so that you can get across to them how you can help and serve them with whatever you’re selling or doing, the better it will be. So lean into it. It’s a positive thing.” – HILARY
Connect with Hilary Swan:
- LinkedIn: https://www.linkedin.com/in/hilarynswan/
- Rebel Scout Consulting: https://www.rebelscout.co/
Try Our Proven, 3-Step System, Guaranteeing Accountability and Transparency that Drives RESULTS by clicking on this link: https://oneofakindsales.com/call-center-in-a-box/
Connect with Nancy Calabrese:
- Twitter:https://twitter.com/oneofakindsales
- Facebook:https://www.facebook.com/One-Of-A-Kind-Sales-304978633264832/
- Website:https://oneofakindsales.com
- Phone: 908-879-2911
- LinkedIn: https://www.linkedin.com/in/ncalabrese/
- Email: leads@oneofakindsales.com
Voiceover: You’re listening to The Conversational Selling Podcast with Nancy Calabrese.
Nancy Calabrese: Hi, it’s Nancy Calabrese, and it’s time again for Conversational selling – the podcast where sales leaders and business experts share what’s going on in sales and marketing today and it always starts with a human conversation. Today we’re speaking with Hilary Swan, the founder of Rebel Scout Consulting, a provider of fractional sales leadership services to startups and small businesses. From founder-led sales support, sales team buildouts, growth strategy, and fractional head, Rebel Scout Consulting customizes every engagement to meet the founder and CEO where they are in their growth journey. The wildly competitive culture of sales is where Hillary thrives, and this proved to be true as she hustled her way through the ranks and reach sales leadership where she most recently led an $18 million business with over three divisions in one of the most competitive industries and markets in the country. Awesome job. Welcome to the show, Hillary. I love anything that has to do with sales.
Hilary Swan: Thank you for having me, Nancy. [1:23]
Nancy Calabrese: So, I’m always interested in where people come from, what got you into sales and what made you start your own company.
Hilary Swan: Yeah, good question. So, I had a job, all my internships in college happened to be in the entertainment industry. So, I came out of college with a job with MTV Viacom, which would be most college grads dream jobs. And it was, I thought. But in approaching graduation, I was realizing that this is a job, not a career and I was going to have to live at home and a lot of things didn’t feel right about it. So, I figured I had a little bit of time. This was the March before graduation. I’m going to look for a job. And if not, I have one, great. So, there was a job there at my university and a little company that some may know called Medtronic, which happens to be a global medical device company, had just acquired a small a company out in California that sold diabetes insulin pumps and they were building at an inside sales division. So, I met with the head of sales, interviewed, fast forward, I accepted my first job out of school with an inside sales team out in California. So, from there, that’s where I got my start and worked my way up in sales. [2:56]
Nancy Calabrese: Wow. And what motivated you to start your own company?
Hilary Swan: So yeah, it’s a big jump into it. So I was in inside sales, outside sales, sold a ton of different things. I was in sales leadership. I’d always wanted to do something on my own. I’m not surrounded by a ton of entrepreneurs or people who own their own businesses per se, but I was always so intrigued by it. And so, I had been approached about a head of sales role with a startup, which at the time was not right for me. But it really got me doing some research into what this all looks like in the startup world and where do these people get the money? Do they make money? How many of these ideas are good? The failure rates are high. So, I had a, you know, cautionary risk, did some research, but I really felt like I hit a crossroad. So, the company that I was working for at the time had been acquired and really, I should have been very appreciative because I was going to be moving into a new leadership role, which really on paper was a bit of a promotion. I was so not inspired by it. I just, the thought of having to continue to do this or do something in this role was just not, you know, lighting the fire. [4:25]
Nancy Calabrese: Right.
Hilary Swan: And so, I felt like, you know, this is the time. This is a clean cut to jump two feet in. Those who dabble in starting something while they have a full-time role, you know, it doesn’t, personally, it didn’t work for me. And so, I felt like it was a very clear, you have this job opportunity in front of you, you should be so excited. It’s more money, it’s more responsibility, it’s a bigger role, and I couldn’t be less excited. [4:52]
Nancy Calabrese: Right.
Hilary Swan: So, I felt like that was my sign to just rip the bandaid off and do it. And so, I did it. And thankfully it is working out very well. But yeah, it takes a lot to do that step.
Nancy Calabrese: Wow. Bravo! Well, you know, as I said before we started, it takes a lot of courage to go out on your own, right? And the early days when I started my own business, I had a tick on my face because, you know, it was all up to me to make business happen. Yeah. So, what is fractional sales leadership?
Hilary Swan: So, the model of fractional is really, I don’t want to say it’s not new, but it’s on the newer side, and it’s exactly what it sounds like. It’s a fraction, so you’re getting a fraction of the time of an executive or a leadership. So, what it really should feel like is for startups and small businesses, they’re getting what they need. So, this is across many different specialties. You’ll see operations, HR. You’ll see Chief of Staff. And so, what it is that you’re getting that team member for, to be honest, also a fraction of the cost likely. And you need their expertise, and you need their membership on your executive team. But it costs a lot of money to have most of these roles filled. So, what not better than to tap somebody at a fractional? engagement where you don’t have to bring them on as a W-2 or with the health benefits or 401k. It really is and I know consulting is in the name of my business, but it’s not the consultant in the traditional sense of projects and they do all the stuff and then they leave. You really, really should feel like you have a team member on your team with this fractional leader. [6:54]
Nancy Calabrese: Wow. Right. So how many companies can you work with at one time?
Hilary Swan: Great question. So, it does vary. And I say that because every engagement is different. So, there are some startups that I’m currently supporting and simply an advisory role. So, we meet once or twice a week for an hour or two, and we just stay laser focused on pipeline review, deal flow, upcoming meetings, objectives that they’re really running into. And that’s, you know, a little bit of a light version. You know, we don’t. They either can’t afford or don’t need somebody, but equally they need somebody to bounce off from a sales and growth perspective. Am I doing something wrong? Is this right? Can I be doing more? All the way up to there are startups that I support where the sales team reports to me and I report to the CEO. So, it does vary. I tell people it’s anywhere from three to eight clients at a time. And I know that does sound like a range, but you can see how based on the engagement and support that it can vary. [8:00]
Nancy Calabrese: And how long are most of the assignments for?
Hilary Swan: So, I do not engage with any company for less than three months, ideally six months. But what tends to happen is we do that six months and then we re-engage for another six months. So, on average, it’s six to 12 months. And then truly as the company grows, which is the goal, you do need somebody full, full time. And that’s where we take that final step and I help the CEO or founder to really hire the right head of sales to be, you know, 150%. [8:40]
Nancy Calabrese: Yeah. I mean, do you target certain industries?
Hilary Swan: So the only industry I currently do not support is B2C. So given my background, I do have the ability to support a lot of different industries and you know, SaaS, tech, FinTech, MedTech. So that’s really the only area, the B2C piece, where I say, you know what, I’m not your gal. You know, I’m not, it’s not my area of expertise. And to be honest, and Nancy, probably know this, you know, that B2C really is typically very marketing heavy. And so, it’s just not the, not what I support. [9:23]
Nancy Calabrese: Right. Yeah, I mean, we play in the B2B space. Very rarely will we do B2C. And in a case like that, the client has to provide us with the leads because then you’ve got to play around with the do not call lists and get them scrubbed. Yeah. So, talk a little bit about what you do and how it supports startups and small businesses.
Hilary Swan: Yeah, so the majority of startups and small businesses, all the sales typically is being done by the founder or the, in small businesses case, president or CEO of the company. They don’t have sales teams and maybe they tap somebody like you, Nancy, to help with that, but they really are taking the top of funnel opportunities and working them through. And the very fact of the matter is, statistically, they do not have any sales experience. So how do you possibly grow something if you have no tactical, strategical sales experience? And then on top of it, they don’t have, again, statistically, there’s an exception to every rule, but really that growth strategy. It sounds good in theory. You’ve obviously felt compelled enough to jump two feet in to start your own startup as you, you know, we had talked about before. So, you really feel passionate about what you’re doing, but guess what? Not everybody’s going to feel passionate about it. So how do you truly sell? So that’s where I hop in because so many of these founders, despite their idea of being good or bad, are just really throwing spaghetti at the wall. There’s not a lot of strategy. They don’t understand the sales process. Um, so what I do is again, starting. [11:17]
Nancy Calabrese: Right.
Hilary Swan: You know, given that I’m engaged early on, helping that founder. What is the discovery question? Why does it matter? What should we be asking? That whole stakeholder management piece, who should I be talking to? Who should I be targeting? Why? What are the problems that we solve by stakeholder? So really getting into the weeds, and the reason that this is also important is because often. They are on to something. They have a good idea. They’ve sold it likely to investors because even if you’re pre-seed, somebody’s giving you a little bit of money. So how do we help scale this? Because you’re on to something. So let me kind of reverse engineer and get everything pen to paper. Because in time, if we’re hiring out salespeople and I’m helping them to build a true process, I must understand how their brain works. So, it’s really hopping in and kind of being their wing person and getting them where they can truly sell and handle objections. So like when somebody, you know, you think you have it and then we talk and they go, yeah, and they’re not getting back to me. Well, how did you leave it? So, all the way up to like I shared, you know, there’s a sales team or a few salespeople and their coaching and helping them grow and build their pipeline and move those opportunities through and close. So, it’s a range, but you can see where those plug in. [12:50]
Nancy Calabrese: Yeah, you know, your company name jumps out to me. How did you come up with the company name?
Hilary Swan: So I’m glad it jumps out at you. That was my hope. So, as I’m sure you get sometimes with sales, it can be super cringy. People hear, nobody wants to be sold to, and they hear sales, and it’s just, they come a little guarded. But guess what? The fact of the matter is anybody who owns a business must be focused on sales and growth. It’s just what it is. So, I wanted something that was approachable. I wanted them to truly feel like engaging with a business that would be fractional head of sales that, you know, I’m a guide or as my sales team growth, as my leadership team grows out in sales, we are guides and that it’s, um, it’s not a cringy, you know, used car salesman type piece that so the rebel piece is the point of, you know, it takes a lot to do this. You know, you got to break the rules and a lot of people doing their own thing or doing a startup or have a small business, they’re swimming upstream. It’s the majority of us that are doing this. And the Scout piece really, really leaning into, I’ve done it, I continue to do it and continue to grow and learn and let me guide you through this. So, I was hoping that it would resonate for people when it came to that. [14:21]
Nancy Calabrese: Right. Wow. Well, it definitely, the rebel, you know, when I saw rebel, I mean, you don’t seem like a rebel, but I guess you are, Hillary. Ha ha ha!
Hilary Swan: Yeah. I think for the good and the bad, I think yeah. I think I have, and equally it is kind of a hat tip to my CEO and founders that I work with.
Nancy Calabrese: I think that’s really great. Is there a story that the audience would find interesting?
Hilary Swan: Specifically, about myself or about the company?
Nancy Calabrese: Anything. Sales, yourself.
Hilary Swan: Hmm, that’s a good question. Let’s see. I will say a couple of things that are a little bit unique that I think bring maybe the rebel a little bit full circle. So, I grew up in New Jersey and I went to school in Ohio, and I moved to California as I shared after adulthood. I love to travel. I love new things. I love interacting with people. I mean that it feeds me. So that’s where I really think that the sales piece has just continued to be the right journey for myself. From a career perspective with the sales, I mean it’s so interesting the types of places that I’ve sold into. I’ve sold into a lot of my background is specifically in healthcare. [15:49]
Nancy Calabrese: Right.
Hilary Swan: And it’s just wild, the types of people and the things that you experience. I mean, one of the hospitals that I supported, and my team has previously supported is LA County, which is the busiest ED in the entire country. I mean, there’s documentaries about it. So, I just, it’s, it’s interesting how you can be fueled, not only in the sales piece, but the environment in which you sell into. And so, some people, as you asked about, how did you get here? I think you had shared before, but I think that’s being flexible and genuinely enjoying the interacting with all different types of people and that sales piece, figuring out how you plug in to help them. It’s really my favorite part of it all. [16:40]
Nancy Calabrese: Listen, sales is my drug. I can’t get enough of it. Right. I can’t get enough of it. Um, we, uh, we believe in ongoing training here. Everyone in my company is involved. I believe everybody is in sales, whether they like to admit it or not. Right. Yep. Totally. Um, I, you know, we’re almost up with time. What is the one takeaway you want to leave the audience with?
Hilary Swan: Yeah, totally. Yeah. Well, you know what, Nancy, you just kind of said it and I love it. We’re all in sales and that is okay. That’s a great thing. So, the faster that you can embrace that and feel comfortable with how to interact with people so that you can get across to them how you can help and serve them with whatever you’re selling or doing, it’s just going to be better. So just lean into it. It’s a positive thing. [17:34]
Nancy Calabrese: Yep. It’s a positive. You hear that? It’s not only coming from me, but also from Hillary. It is. How can my people find you, Hillary?
Hilary Swan: Yeah, it is a positive, it truly is. So, you can visit my website at www.RebelScout.co. You can also find me on LinkedIn at Hillarywith1L and my last name is Swan, like the bird. [18:02]
Nancy Calabrese: Okay. Love it. Love it. Folks, this is an amazing lady. And if nothing else, my takeaway in listening to Hillary is she’s the person to go to. She’s got passion about selling. She’s got experience about selling. If you could, you know, you led that $18 million business, one of the most competitive industries markets in the country, you know what you’re doing. So, folks reach out to Hillary. And Hillary, I hope this is the beginning of future conversations for sure. And, uh, I hope you’ll come back.
Hilary Swan: Yes, thank you so much for having me, Nancy.
Nancy Calabrese: Thank you for sharing your expertise and everyone make it a great sales day.
