In this episode, Mary Shea, a sales leader with over 25 years of experience, shares her journey and insights. She discusses the importance of embracing differences and being authentic in sales. Mary also emphasizes the need to invest in oneself and surround oneself with the right people. She highlights the significance of talent in leadership and the importance of communicating vision and leading with intention. Mary’s advice for success includes taking calculated risks and developing a strategic mindset.



00:00- Introduction and Background

01:17- Starting a Sales Career

04:35- Overcoming the Fear of Rejection

05:20- Being Authentic in Sales

07:04- Breaking Stereotypes in the Car Sales Industry

08:09- Embracing Differences and Being Authentic

09:31- Advice for Embracing Differences

11:23- Career Progression and Strategic Thinking

15:19- Investing in Yourself and Surrounding Yourself with the Right People

20:43- Taking Calculated Risks and Developing a Strategic Mindset

23:26- Transitioning to Managing Teams

24:47- Importance of Talent in Leadership

27:55- Communicating Vision and Leading with Intention

29:27- Lessons Learned in Leadership

30:06- Closing and Contact Information


Wesleyne (00:00.604)

Hello and welcome to another episode of the Transform Sales Podcast. Today I am so delighted to have a living legend with me today, Mary Shay. How are you?

Mary Shea (00:11.562)

I am so wonderful, Wesleyan, and it's amazing to be here. And I've been following you and your career for some time now, and I'm just thrilled to be on the show.

Wesleyne (00:26.93)

Okay, let me see you went out for a little bit. I don't know if it was me or you It went out for a bit. Okay, what you were talking. It's recording asynchronously and my podcast editor should be able to get that out So I'll just pick it up So now let me tell you guys a little bit about Mary She has over 25 years in business and she's held various roles such as CRO analyst evangelist

Mary Shea (00:29.194)

That didn't help, did it?

Mary Shea (00:39.018)

We'll be fine. We'll be fine. Yeah.

Wesleyne (00:51.474)

and most recently co -CEO. She's invigorated by working with smart collaborative professionals and has a passion for deep industry expertise in all things RevTech. In 2023, she joined MediaFly as a co -CEO and she was hired to raise capital, turn revenue around, increase brand equity and drive execution for the company's strategy across all functional areas.

So Mary, tell us how did you start your career and how did you become this evangelist, this person who comes in and shakes up organizations?

Mary Shea (01:26.762)

Yeah, thank you. I love doing that. And yeah, I have a pretty nonlinear career as I'm guessing some of your more successful guests have had. I actually started my career as a classical musician and I have a PhD in musicology and ethnomusicology. And I played in orchestras all over the world and made a living doing that in my early 20s. And to supplement my income while I was an artist, I actually sold cars.

Honda's and BMW's at a dealership in Boston. And I ended up selling a couple of cars to Forrester Research professionals. And they recruited me to come join the company. And I started my sales career out as an SDR, believe it or not, I guess, you know, over 25 years ago. So yeah, that's how I got started. And I think the rest is a little bit history, but happy to dig in more as it makes sense.

Wesleyne (02:26.994)

So tell me as a person who has a PhD, so I feel like I should call you Dr. Mary now because I understand how much work it takes to get that. Most people are like, no, no, no. So I'll be calling you Dr. Mary. So Dr. Mary. So tell me as someone who started in a very different industry, what skills, what things did you learn from your early career that has helped you in your sales career?

Mary Shea (02:33.418)


Mary Shea (02:40.298)

I'll graciously accept it.

Mary Shea (02:56.234)

Yeah, that's such a great question. And if you dig around a little bit, you find a lot of people sort of happened.

stance their way into the sales career and even into the business world, you're gonna find a lot of people who are musicians and PhDs and others. I think the biggest thing being a musician and also getting a PhD is just the discipline, the day in, day out discipline that you need in order to be successful. I think two to 3 % of people in America have these advanced degrees, so it's not easy, right? And...

day in, day out, doing the work, whether you feel like it or not, having that consistency, that structure, I think translates really well into the sales career specifically, especially because there's so much rejection, right? And I found in sales, what you put in, you will get out, generally, if you rep a good company and a good product and service. So it's about really kind of a little bit of the math and doing the hard work. I think the other thing I found being a musician is,

when I would go to interview or audition as we call it for an orchestra, there'd be a hundred other candidates trying out for that same position. And so, you know, there is a lot of rejection and you have to believe in yourself and overcome hardships and barriers and things that are preventing you from being successful and continue to find creative solutions to either work around or through some of those challenges and sales as we know has its challenges.

So I think those are two pretty good examples of how some of the hard skills translate.

Wesleyne (04:35.282)

Oh, that's good. I often tell people when, you know,

young people these days are like, what should I major in? What should I do? How should I do it? And I tell you, tell them, you know, college just teaches you how to think. It teaches you how to prepare. It teaches you how to study because so little, I'm a chemist by training, so little of what I learned in school. I actually apply today, but I know how to prepare for exams, right? So I know how to prepare for meetings. And I really liked the part that you talked about rejection. So when we think about salespeople having this very, um,

Mary Shea (04:53.61)


Mary Shea (05:00.426)


Wesleyne (05:09.714)

this soft touch in that they really fear rejection and they have this need for approval. Where do you think that really stems from? What's the root of that issue?

Mary Shea (05:20.17)

Well, I may not be the right kind of doctor to fully answer that question, Wesleyan, but I'll take a shot at it. I think it's, you know, a bit of that people pleasing, right? So I'm the first child out of five. I don't, do you have siblings or what?

Wesleyne (05:38.61)

I do. I'm the oldest of four.

Mary Shea (05:39.754)

And you are, oh, why am I not surprised? So, you know, I think a lot of it sort of stems back from sort of the cultural dynamics of how you were raised and in that sort of thing. You know, in my case, as a musician, I did like I was on stage a lot and preparing for being on stage. And it's not dissimilar from what we would do preparing for a really, really big pitch of like a seven figure deal.

Wesleyne (05:44.73)


Mary Shea (06:09.66)

for example, right? And you're working with not just yourself in sales, usually now that the buying groups are so large, depending on what kind of sale, selling motion you have, you could be marshaling a group of 10 to 15 folks on your end to support that pursuit. And so, you know, being on stage and being comfortable with communicating and being a little bit of the center of attention, I think, you know, helps too.

Wesleyne (06:41.074)

I love it, I love it. And you know, I really think that all of these diverse experiences we have, they really form us into the salespeople and the sales leaders that we eventually become. So tell me about, okay, so you were working as a car salesperson and I'm guessing when you were working as a car salesperson, there weren't that many women car salespeople? How was that experience for you?

Mary Shea (07:04.048)


It was a great experience because I think I was sort of the antithesis of what people expected when they came in to purchase a car and back in the day, and you're correct, it was quite a while ago, the only information you kind of had was the invoice and what the cost was and what the margin was that the dealer was trying to make. Today it's very simple. We know exactly what we can buy the car for and we go in, we do it. Sometimes we go to Carvana and we don't even do a test drive.

But yes, there were not a lot of women in the industry at the time, and there were not a lot of people like me. And so I really used that as my advantage because people were so excited to buy a car from someone that didn't fit some of the stereotypical ideas that they had. And I ended up being one of the most successful people in the dealership, and I worked only three days a week. So sometimes if you're a little bit different from what's expected, you can use that to your advantage, and I did.

Wesleyne (08:05.202)

I love telling people like, you know, your brilliant difference is really what sets you apart. And it seems like you really tapped into that. So if people are struggling with being different, you know, looking different, sounding different, having different ideas or beliefs, than those around them, what advice would you give them?

Mary Shea (08:09.546)


Mary Shea (08:24.394)

Yeah, I mean, I think that I just did really, which is lean into your differences and find out where those differences become an advantage. And I don't want to be Pollyanna -ish about it because certainly I've grown up with some privilege and things of that nature, and people do have hard roads ahead of them, as we all do, right? We all hit bumps in the road. But if you really can...

turn whatever differences you have into an advantage. I think that's something that's really, really great. And the other thing that I've always tried to do is kind of show up as my authentic self, you know, in the work environment. And I'm fortunate enough that that's worked out quite well. I know it's not easy for everyone.

Wesleyne (09:07.346)

Yeah, I was, it's not. And you know, I was speaking with somebody recently and I was telling them like, this is the person I am. I'm this person with my friends, with my kids, with my family, with my clients. Like everybody, if I got people in a room together, they'd be like, yeah, that's Wesleyne. That's how she is. And I think sometimes as women, we find that we want to kind of mesh in.

Mary Shea (09:11.722)


Mary Shea (09:19.242)

Right, right.

Mary Shea (09:25.002)

Yes, right.

Wesleyne (09:31.602)

to the crowd and so we're scared to show that authentic self. And what I found in my career is that when you show up as who you are, one, you're more true to yourself. So it makes you feel better inside. You know, you're kind of at peace. And then on the other side, it's like people like that. They're attracted to, okay, you're not the status quo.

Mary Shea (09:43.018)

Feel better. Yeah. Yeah.

Mary Shea (09:52.074)

I think people are, you know, for the most part, really gravitate towards that in another individual. And we all crave human connections, right? And that's one of the reasons your podcast and the things that you do make you so successful. We want that connection. We want to learn from others. We want to hear about their experiences and we want to better ourselves. And, um,

You know, I think showing up as your authentic self, I would say, people would say the same thing about me too. And not everyone can take it, right? It's, you know, you may not be a fit in every place. And one friend and mentor I had gave me the most wonderful piece of advice is, you know, if you're at a job, you're at a work.

a place of work and it's not a great fit. She said, you know, if you don't like the channel, change it. And we as women are in very high demand now in terms of sales positions, sales leadership positions, and even that top job. You've got options, right? So if your authentic self isn't welcomed where you're at, or you don't feel that where you're at is a place where you can thrive and be super successful, you've got other options. So change it.

channel and I never forgot that she told me that.

Wesleyne (11:11.634)

I love that, change the channel. You have the powers in your hands. So after you became an SDR, what did your career look like? Did you make it? Did you go straight up? Did you kind of go sideways? What did that look like?

Mary Shea (11:23.978)

Yeah, I went straight up pretty quickly because, you know, sometimes timing is everything in addition to being a highly motivated individual and being able to grasp new concepts and new ways of working really quickly. But I was in the right place at the right time. So I went from an SDR to an account manager to an AE to taking over, you know, the Chicago and Midwest territory for Forrester. And then eventually they sent me out to Chicago to open up an office for the company. And that was the first satellite office.

outside of Cambridge, Massachusetts, I opened that and ended up staying in Chicago for 20 years. I subsequently moved on and took on more senior roles, but I went up the ladder pretty quickly and then wanted to get global experience and general management experience. And then of course, like many of your audience members, I wanted to get into the C -suite. And so I was aggressive about managing my career and finding opportunities that would give me the experience that I needed to gain to be

eventually a CEO.

Wesleyne (12:26.802)

So when you were really thinking about your career strategically, you had some great early success and then you started getting strategic about it. What was the thing that turned on for you that said, I need to be more strategic about what I want and here are the steps I'm gonna take to get there.

Mary Shea (12:43.338)

Such a great question. So I came to the party late. So we talked about my educational background. It took me 10 years to get a PhD. In the humanities, it's really hard. Maybe I wasn't quite the best student, but I was certainly determined in discipline. So it took me a while. And when I went into the business world, I think I was 35 as an SDR. So super humbling experience. Another learning really is sometimes you need to take a step backward to take five steps forward. And I've never been

afraid of doing that. What you will find is that...

female folks that identify as women can proceed very quickly in the early stages of their careers, right? And then you start to get to the director level, depending on the size of your company, it gets more complicated. You've got politics rears its ugly head. You start to make a lot more money and when more money is on the table, you're competing with others. And it starts to become, in some cases, and you have to remember this is 20 years ago, a little bit wonky for a woman wanting to make her way into the C -suite.

and you hit

I did, you know, these different ceilings, you're not strategic enough, you're not this, you're not that. You've heard this from all of the different conversations, all kinds of barriers that might not be the same barriers for others, right? And so I realized that I was coming into the business world late. I had to catch up quickly and I didn't have time for all kinds of different missteps and things of that nature. And I think the biggest game changer for me was I invested in executive coaching and I found a co -

Mary Shea (14:20.62)

and I became pretty intentional about what I wanted to do and...

I had someone to work on those blind spots with me because we all have them. And so that, you know, that was a real game changer. And I think oftentimes you think, well, HR's gotta provide, you know, coaching or, you know, skill set, or my company's gonna do this, or this is gonna do this. If you're ambitious, invest in yourself, invest in your career, you know, join some of the many communities that are out there like yours, have mentorship, peer mentorship, like do everything you possibly can.

can to get the advantage because between director and VP and then VP and C -suite is very difficult and you see women super successful earlier but then they win or off as we get higher and higher up the value chain and so get the support. I think that's the biggest thing that helped me.

Wesleyne (15:19.122)

Yeah, I really like that invest in yourself. I find that a lot of people do as you kind of said, it's like, well, the company will do this and the company will do that. But the company isn't invested in you going up. They're invested in you staying just like you are because you're doing a good job. And so they don't have a problem with you, right? And stuff.

Mary Shea (15:34.666)

Yeah, yeah. No, right. It can keep you in your little, your swim lane and extract as much value that they can from you and tell you nice things. But at the end of the day, you're responsible for you.

Wesleyne (15:47.73)

Absolutely, absolutely. I work with some organizations and I'm like, I don't even know the nice way to say it, but I'm the last step before they're at the door because they've gotten looked over for many promotions and they're not hitting their numbers and they're having lots of challenges. But the company at that point is saying, hey, we will invest in you because we see something in you. But before it gets there, invest in yourself, right? Like carve some money out your budget. And then the thing that you said is right is,

Mary Shea (15:58.314)



Mary Shea (16:13.704)


Wesleyne (16:17.266)

Who do you surround yourself with? I like to surround myself with people who are smarter, who have had diverse experiences, who can help me when I'm stuck in my own head and stuck in my own way, get out of my current slot.

Mary Shea (16:30.058)

Yeah, I think that's a real game changer for all of us, for many of us. I have something that I call a personal board and that's a collection of women mostly in tech, some academics and we do have diverse backgrounds and so on. But we support each other behind the scenes and we have people to talk to, to celebrate with when things are going great and people to give advice and lift us up when they're not. And I find that,

the higher you go as you elevate within an organization, the closer to the sun you fly, the more often you might get burnt. And so it's important to have the support system to succeed at this level.

Wesleyne (17:18.226)

Absolutely. The thing that you mentioned is something that I hear often from women and also men when they're trying to get to that next level and they're not strategic enough. So you've been on both sides of this aisle, right? You've been on the side of I want to become more strategic and then you're on the side like this person isn't strategic. So what are, so share with us what, one, what does it mean to really be strategic and two, how do you develop that strategic mindset?

Mary Shea (17:29.672)


Mary Shea (17:38.216)

Yes, I remember.

Mary Shea (17:48.458)

Yeah, I mean, I think there's, in some ways it could be a bit of a dog whistle that, you know, it's just for whatever reason, we don't see this person as someone who can elevate and those reasons may be legitimate and they may not be. But I think underrepresented folks will encounter that or do sometimes encounter that because it's kind of a nebulous way of saying, we don't want you in that club, that club that makes the decisions, that makes all the money, that drives the company and gets recognition.

So knowing that you could face that and then accepting it and then finding ways around it. So I think the biggest thing is trying to not just stay in that swim lane, you know, do your job, right? You have to meet and exceed your expectations and you have to do a wonderful job at your job. But put yourself out there for other assignments. You know, maybe there's a really difficult sales territory that no one can crack. That was my case when I took on the Midwest for Forrester at that time. No one knew who Forrester was.

we literally would high five each other when we got off the phone and someone knew who the company was at that point in time. But no one knew who the company was. We couldn't beat Gartner that had a very strong competitor that had a very strong foothold there. And I took it on and built a business to about 20 million and they told me, now go run an office, open up an office and go run it. And so I think looking outside of your direct purview, because it's not just about delivering great results in your role, it's about

showcasing how you can continue to grow into different roles that may be bigger than what you currently have. So take on a new project.

Go do some international business. Do something in addition to your day job to help the company be more successful. Another example, I was a founding member of Forrester's Diversity, Equity, and Inclusion Council. It took a lot of my time. I didn't get paid for it. I oftentimes was doing that piece of the work on the weekends and nights. But I met.

Mary Shea (19:52.432)

C -suite executives when I wasn't one. So put yourself in these situations where you're seen and you're contributing and I think that will help overcome some of the barriers that typically we face at different junctures.

Wesleyne (20:05.796)

That's good. It's get out of your comfort zone do something a little bit different and you have to learn to take calculator risk as a Executive that's what you do every single day you take calculator risk sometimes you win sometimes you lose But you have to demonstrate that you're willing to do that

Mary Shea (20:19.208)


Mary Shea (20:23.274)

I completely agree and when I look at the areas of my career where I've received the biggest satisfaction, it's because I took that calculated risk. But you you're right, you don't win all the time and you have to accept that, but that's the way that you really get yourself a couple of levels up pretty quickly.

Wesleyne (20:43.73)

So recently I have encountered many people who are, you know, middle career, so 30s, 40s, and they're considering switching into sales. And it seems a little bit scary to them because they're taking a pay cut. They may be going from leading a team in one area to being an individual contributor. What advice would you give your younger self when you first stepped into your role as an SDR?

Mary Shea (20:51.848)


Mary Shea (21:08.744)


The SDR role was actually not difficult for me. I mean, I was lucky that I was surrounded by really great sales talent and they invested in me and mentored in me. And so, I'll give you a little bit of advice there, which is, it's really the people that you work with are the ones that are gonna help elevate you and help you be successful at that point in your career. And so I had four to five really great people and...

When I set meetings up for them, I was contributing to the food that they were putting on their table. And so you've got a great symbiotic relationship. So I would say for SDRs, a lot of it is just, it's hard, right? You're using the tech, you're a micro marketer, it's a lot of outbound, there's a lot of rejection. I would say invest in the relationships of the folks that you're setting meetings for. Learn from them, ask them to, if you can sit in on the next stage of calls so that you can continue to evolve beyond that role.


Um, so I wouldn't necessarily have done anything differently when I was in SDR. I think it happened naturally where I ran into trouble is when I became a manager and, um, the biggest piece of advice I would give myself is don't expect everyone to be as committed, dedicated, driven, smart, whatever it is, fill in the blank as you are, because people are, are, are doing your job for different reasons, right? Some people may love sales and want a tremendous career. Some people.

Mary Shea (22:40.65)

maybe going back to work after raising a family and there's different levels of priorities and some people, you know.

may have different motivations. And I had a really hard time in the sense that when I first started, I was so used to being successful that I wanted to drive the people who work for me to that same level of drive that I had. And I mean, that's just not reasonable, respectful, and you're not gonna get results. So I learned over time to really dial back my expectations and really dig deep into what the personal motivators of my different team members were and to help.

you know, focus on those. But it was a rough two to three years when I first became a manager, I won't lie. You may hear that story from others that you talk with and work with as well.

Wesleyne (23:26.194)

What's that?

Wesleyne (23:30.866)

Yeah, that is, it's always a huge transition. It's, I equivocated from to having, going from one child to having two kids, cause it's like, oh, I have this one baby that I can do all these things with. And then you're like, okay, now I have two humans and there are different stages of life. And that's just what it's like when you're leading a team. It's like, I'm managing me, so I'm managing all these people and personalities and like, how do I even do this?

Mary Shea (23:39.018)

There you go. Yep. Yeah.


Mary Shea (23:49.77)

Right. Yeah.

And forecasts, and it's easy when you forecast for yourself, and then when you have to forecast for seven, it's a little bit different, you know? So I love that analogy. My span of control was seven, so I hope you don't have seven kids, but I love the analogy.

Wesleyne (24:09.88)

It is so true. I mean, going from managing one to managing more than one, it's like, it's a whole party. And then you have three, four, five kids and it's like, oh, this is easy. I got this, right?

Mary Shea (24:19.498)

Yeah, I mean, yeah, I think, yeah, yeah, I think that is really true.

Wesleyne (24:23.698)

So as you talked about really stepping into that leadership role and managing your first team and getting your feet wet, as you continue to move up the ladder and you no longer were managing individuals, but you were managing managers essentially and having to manage by influence and impact, what are some things that you learned as you continue to move up the corporate ladder?

Mary Shea (24:47.178)

Yeah, I think this is really important in sales and it's really important in leadership and you need when you move up the ladder, it's really all about talent in people, right? So it's so crucial to surround yourself with the right talent and to quickly assess the talent you have. Maybe you have folks that are great for the company, but they might not be in the right role. So you help them get to the right spot. Maybe you have folks that could be doing much more.

or if you opened up the playing field for them. I've had that experience happen so many times where someone who is at the VP level or director level is being kind of squashed by their direct manager. And so, you know, finding those ways to let folks shine who maybe haven't shined before is really important. And then going out and hiring the best possible talent you could do. So as a leader, as a CEO, CRO, I was constantly interviewing and I was very focused on talent because...

you know, you're not going to do it yourself. It's the people you surround yourself with. And then of course you have to enable them with the right technology, the right processes, the right training and up -skilling. But you've got to start with a really great base of talent. If you don't have it, make some moves and get it. And so I think that's really important.

Wesleyne (26:07.762)

Yeah, it's so much easier to find someone who has what you need them to have, whether it's core, raw talent, whether it's experience, whatever the thing is, and then you develop them and you cultivate them into what you want them to be than having somebody who's mediocre and trying to upskill them every single day, right? And so really starting with that strong foundation. I find that that is, as you said, it's one of the most important things. Our people are our biggest assets.

Mary Shea (26:26.762)

Yeah, it's just, you can't, yeah.

Wesleyne (26:36.87)

Some leaders are focused on the numbers and the technology and the products and the services, but our people are our number one assets. And if we don't invest in our people and spend time, and I often tell leaders the same thing as you, I don't care if you have an open job, always be interviewing, always be looking. You should always have your ear open, have your eyes open.

Mary Shea (26:52.458)

Yeah, I completely agree. Yeah. At the very least, you're going to learn a lot from those conversations, right? So I think the talent is really crucial. And it's a really important message to amplify now, especially as we see how quickly generative AI is maturing and the impact of automation and all of these different texts that are going to make us more efficient and effective.

At the end of the day, it is about people, right? There may be a smaller cadre of people that we have on teams now because we're so amplified and augmented with tech, but get the best people you possibly can and once you have them, make them really, really happy so they want to stay or follow you to the next adventure.

Wesleyne (27:39.73)

Absolutely. So you have shared a lot of amazing experiences and insight. I was wondering, is there one experience personally or professionally that has impacted the way that you lead?

Mary Shea (27:55.338)

Wow, you know, it's hard, you know, there's lots of little experiences that sort of add up over time. But what I will say is in thinking about sort of my recent adventure,

as a co -CEO and I'm a little bit introverted, but I know I'm an extroverted introvert. So at work, I'm very much out there as an evangelist, right? But my personal vent is a little bit more inward. And so...

When people know me one to one, they really know, you know, sort of what's the vision for the company? What's my vision for them? Where are we going? Why should they follow me? How can they be loyal? I think I've done a great job of that one to one. But being more intentional and thoughtful about communicating and getting the message out there as you get higher up in the organization around who you are as a person, why they should follow you, why you're going to lead, where you're going to go, and why this is going to be great for.

or the company, its employees, the stakeholders, shareholders, customers. And so be more intentional about that communications. And so I think as I take lessons learned from my last role, that's something that I'll take with maybe intentional about communication and make people understand why they should follow you because it's not a given, right? You have to earn that.

Wesleyne (29:27.89)

Oh, that's so good. That's so good. Just this warning I was actually thinking about, and I got this insight from somebody I spoke to recently, and he was saying, oh, so you teach people all about sales, whether it's selling themselves, it's selling their products, selling themselves internally or externally. And that's the part we often forget. It's the best thing we can ever sell is ourselves, right? And we are an asset. We are saying we have to think about ourselves when we're trying to...

you know, grow community. We're trying to go up the ladder and really sell whatever it is we think we want, we believe. I love that.

So if people wanna reach out to you, what is the one best way if they wanna find you?

Mary Shea (30:10.762)

Yeah, I think LinkedIn DM is really great. Also, my email and phone is available on LinkedIn. And I'm super accessible. I'm posting all the time. And I love the discourse. So I'm not hard to find.

Wesleyne (30:27.986)

Awesome, well thank you so much for your time, your talent, and your expertise. It's been a fantastic conversation.

Mary Shea (30:33.162)

Thank you, I loved it as well.

Wesleyne (30:36.764)

That was another episode of the Transform Sales Podcast. Remember, in all that you do, transform your sales. Until next time.

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