EPISODE 497: Developing and Mastering Your Leadership Skills with Women in Sales Leaders Katherine Flesh and Margo Edris

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[EDITOR’S NOTE: This is a replay of the Women in Sales Fresh Voices virtual learning session sponsored by the Institute for Excellence in Sales on April 5, 2022. It featured an interview with Bentley Systems Sales Leader Katherine Flesh and Salesforce Sales Leader Margo Edris]

Find Katherine on LinkedIn. Find Margo on LinkedIn.

KATHERINE’S TIP: “Pay yourself first, invest in yourself first. Whether it’s through taking advantage of professional training and forums, like the Women in Sales Leadership Forum, whether it is making your world smaller by networking on LinkedIn to increase your village. That’s the micro step that everyone could take today is think, “Who have I wanted to connect with on LinkedIn? Who have I wanted to be in my circle and connect with them?” Be in charge of being your own PR, pay yourself first because your to-do list will always wait. Don’t make yourself be the one that waits.

MARGO’S TIP: “Be your authentic self, unapologetically you every single day. It may take time to build the confidence to be able to have your own voice and get to that level but know that it’s inside you and bring it out as often as you can in whatever form is the most natural when building these relationships to take you to the next level.”


Gina Stracuzzi: Both Katherine Flesh and Margo Edris have been through the Women in Sales Leadership Forum. They were just phenomenal in there and I’m so excited to have them back. They always added so much to the conversation. Welcome, both of you. I would like to start the conversation with you all telling us a little bit about yourself and your current role. Katherine, would you like to start us off?

Katherine Flesh: Absolutely. Thank you so much for having us. We’re thrilled to be here, and as an extension of the Women in Sales Leadership Forum, it’s an awesome opportunity. As Gina said, my name is Katherine Flesh. I’m out of San Diego, California, and I’m the Senior Director of Transportation Sales for Bentley System. We do infrastructure software and my team is dedicated to serving our nation’s DOTs and our rail and transit agencies. We’re working hard to help America rebuild their infrastructure. We’re spending a lot of time working with our customers on that. I co-chair our women’s diversity program at Bentley Systems and really the goal there is just to ensure that all colleagues, men, women, are able to achieve what they want to achieve at Bentley and in life. I’m just very passionate about transportation. I volunteer. I’m on WTS, our local chapter, Women in Transportation International, and attend a lot of events with AASHTO to engage our customers.

Gina Stracuzzi: Thank you, Katherine. Margo?

Margo Edris: Hi, Margo Edris. Thank you again for the opportunity today to be here. I serve as the Regional Vice President for the Rocky Mountain region at Salesforce. I also do a couple of things in my spare time in addition to the day job. I serve on the Salesforce women’s network, the Arizona chapter, I’m the president of that as well as Parent Force. It’s a group that supports parents all throughout their parenting journey at Salesforce. I act as the Growth Chair over the committee responsible for having new parents join. I’m also a mother of two little boys and a third little girl on the way. Very busy, but very blessed.

Gina Stracuzzi: I love hearing how both of you are involved in other aspects of elevating women and just elevating parents, and your passion for transportation, doing something outside of your given job to keep those things that are important to you alive. That is such a huge piece of how you get ahead. You don’t do it just for that reason, but the networking and the visibility that those things bring you is so crucial to a woman’s career. I really applaud you. Margo, let’s stick with you this time and tell us how you got into sales.

Margo Edris: Well, it’s a rather interesting story. I went to school at the University of Arizona in Tucson, and I actually thought I would be doing a career within public relations. I had an internship with MTV Networks in Santa Monica, California. It was a great experience for the summer before my senior year, but I really saw what it was going to take to be able to advance my career. Most people within that kind of PR, TV music industry, you really do have to start out as an intern, sometimes a coffee girl, really running errands, getting things for different executives for a lengthy period of time. Some people could be two years, some five, some 10 years. I had seen firsthand living in Santa Monica, I lived in Brentwood next to Santa Monica, but I was having to work three total jobs, because it was an unpaid internship, to be able maintain a base-level lifestyle in LA. I just thought, “That’s not really what I want to be doing career-wise for the long term.”

I had reconsidered. I was going into my senior year, I attended a career fair at my university. That’s when I started looking more into a career of sales, because you can make a high amount of income at a young age. There’s really no cap to the commission and the sky’s the limit in terms of career trajectory. That’s what really drew me in after having that internship experience of what I thought was my dream job. I ended up getting a sales role, it was really more of a sales development leadership opportunity where I had the ability to advance and become a professional at a company that hires people right out of school. It was a great experience that then led me to Salesforce years later.

Gina Stracuzzi: Not many of us get to see the reality of what we think we want before we’re mired in it, and then backing out isn’t always so easy. Good for you that you got that taste and you did something about it. Katherine?

Katherine Flesh: Well, I feel like I come by my love of sales, honestly, through my genes, if you will. I’m from a family of entrepreneurs and from a very young age, whether I was selling girl scout cookies or butter toffee peanuts to earn my way to Y-Camp, I really had examples in my family of how interacting with people and selling, even in that very small level, was something that I was pretty good at. In fact, in high school, my high school job that took me all the way through school, I cut my teeth in sales telemarketing, and I was telemarketing timeshares. That’s what I did. I would call those people during dinner time, cold call, cold call. That develops a lot of skills that served me now today, resilience, tenacity. You certainly do develop a thick skin when you’re calling people during dinner time telemarketing for a timeshare.

When that job wound up, I did that actually for about five or six years. Through there I went into selling office supplies back in the day. You might remember printer ribbons and typewriter cartridges and things like that. I was selling subscriptions. Those were the very early days. That’s how I spin it, those were very early days of technology subscriptions. You’re selling to those firms. Then I went into high tech. I have loved my career in sales. I think what that taught me, the early experience of just having those cold call experiences, was my love for people, how much I really enjoyed connecting with people and connecting with a team to get to a goal. Even though that was a different start, Margo, than you had, I definitely am happy for my start.

Gina Stracuzzi: Well, I love both those stories because how we get into sales really tells a lot about who we are as people and what really drives us. Lots of people were afraid of sales or it had a bad reputation for a while. The truth is so far from that. For women, it is, as you said, Margo, not just rewarding like it’s been for you, Katherine, but also lucrative. If you’re making your numbers, and you have kids, and you want to cut off and go to their soccer game, you can. That’s everything to a parent. I’m glad you both found it and were able to make it work for you and build these lifelong careers.

Let’s turn the conversation to the here and now. There are so many things happening, not just for women in sales, but sales organizations across the board. One of the biggest ones is the shortage of qualified people for every role. While this is a sales podcast and we will talk about what the impact is on sales organizations, what you’re doing and what you’re finding, I’d like to know how it’s impacted your own career as you’ve moved up in the ranks. and what you’ve learned for yourself. Let’s really open this can and pull it apart a little bit. Katherine, do you want to start us?

Katherine Flesh: I guess we’ll start with today. Today, I think we’re all challenged with the remote work environment of COVID and we’ve come through that. I think we’ve learned a lot. We’ve learned that there’s different ways that we can connect with our customers and with our teams and wherever they are, we’re able to connect. I think that getting back post pandemic or almost post pandemic, if I could be optimistic, is that we are getting that experience to go then rejoin our customers and rejoin our teams.

That said, the job market’s hot right now. We are experiencing a challenge where candidates have a lot of opportunities. There’s a lot of new technology. IIJA has opened up and flooded the market with companies who are looking to get their bite of that apple and move into that market space for transportation specifically. We’re really finding a challenge attracting that talent. One of the things that we do here in my team is I always say that I will hire for attitude and aptitude and train for skill and industry acumen. That’s one of the things that we’re doing to help with the work shortage. How about you, Margo?

Margo Edris: I would say Salesforce is an amazing company for women, or really any diverse community, to join. I feel super grateful to have that type of support. But it’s one thing getting in the door with an amazing company, and it’s another thing taking the opportunity ahead of you. I think back to when I first started building some of my early on relationships, there was someone that led a sales programs team, and we had built a relationship really just through social media interactions, her posts on LinkedIn. I got to know her more and she had nominated me to be a part of this Women in Sales Leadership Forum, that I didn’t even know existed. Having her see that potential in me had then transpired to me going through this program and explaining how the content is impacting me professionally and personally.

I used the experience to then build a relationship with an executive in my company at the very highest levels within public sector. I would meet with him every other month with a tailored agenda based on what I learned in the forum and how I think it’s impacting our company. Really trying to push forward that agenda, but really in a relationship building type of way. From there, we had a really great monthly cadence all centered around women in sales leadership, and how things were progressing within our organization.

Then there happened to be an opening for a Regional Vice President, and that executive let me know that there was that opening and asked me if I was having those career conversations with the middle layer leaders in between him and where I was at the time. I had said no, and he encouraged me to start those conversations. Then I had the executive level sponsor, my immediate boss had great faith in my potential as well. We had from the top down and the bottom up advocating on my behalf, to then allow me the opportunity to be a Regional Vice President, which is really what I had worked for for over 10 years to get to. It just had to be the right people and the right pieces coming together, because I was with my past company for almost eight years. I did have some opportunities, but some doors were closed. It was also a learning lesson to really stay the course, keep doing what I know I was meant to do, and then aligning it with the right people when the right opportunity came about.

Gina Stracuzzi: Tamara Greenspan from Oracle, who leads the session in the forum on mentors and sponsors and how critical they are to women’s career growth will be so pleased to hear this story. She’ll know that she’s done the right thing. Katherine, tell us a little bit about the opportunities that you’ve had along the way as well, and your advice along those same lines of what you do to help yourself and what other women might do. DOD is a man’s world anyway, slowly turning. I can only imagine the transportation aspect of it is even more so. Kudos to you that you have made it so far and you’re such a strong voice. Tell us about your journey in that and what you’ve learned along the way, and maybe some advice you have.

Katherine Flesh: Piggybacking on what Margo had to say, I think it’s really, really important to leverage a workforce with you, get your PR team. It’s one thing to do the time, do the work, put in those hours, and hope that you’re going to get to achieve your goal within the company, but really finding and seeking those sponsors who are going to help you, who are going to speak when you’re not there, who are going to help you get that seat at the table, I think is really important.

Equally important, and one of the things I’m really passionate about is growing leaders on my team. I believe absolutely that the best way for you to be successful is to have the people who are working for you, their success reflect back on you. We spend a lot of time in my sales organization grooming talent, retaining them, so that we can have that consistent career growth experience for them. I believe that that strongly reflects in my success and it’s been able to help me make my way through Bentley.

I’ve been at Bentley for a very long time. I came through acquisition. I believe RAM Structural Systems was acquired in 2005, and I’ve had many, many opportunities to work in different departments in Bentley. That has to do with people realizing the work that I’m doing with solid and innovative and getting an executive sponsor to help you navigate that ladder. That ladder might look different at any company, no matter where you are, if you’re at Salesforce, or if you’re at Bentley, there’s opportunities in just leveraging your resources to help you get there.

Speaking about transportation though, you’re right. I’ve seen over the years the line at the restroom, let’s just measure it that way, during the breaks and the conferences. That’s the one place you can do at an AASHTO Conference where the women can just sail into that restroom and the men’s line is down the hall. I’m starting to see that change, if I can measure by that simple way, but I think it’s a great time to be a woman in transportation. I think transportation is changing. We’re innovative in the way that we are delivering projects, infrastructure that we so badly need to rebuild for America.

I think, Margo, you’re probably also seeing from your vantage point at Salesforce that organizations are wanting to modernize their workflows and all of their business to solve a lot of their business problems. By bringing that diversity that women bring to the table, I think we’re seeking to solve new problems. Because we have that influx of diverse thought, we’re solving them in different ways. For me, that’s really what’s exciting and the change that I see with women in transportation.

Gina Stracuzzi: I love the analogy of the line in the men’s room. I think most women would just love to see a long line of men waiting to use the restroom, because Lord knows how many years we’ve all stood in line collectively [laughs]. I love too the optimism. I will be honest, I don’t know a great deal about the transportation sector within these large organizations. I can imagine that, especially with the Build Back Better campaign, that there’s so many opportunities. I’m sure companies are moving, even if they didn’t have a big transportation sector previously, are probably moving in that direction. I think you’re right, Katherine, there’s probably going to be multiple new opportunities for women who, like you, have a real passion for that. Good for you, and Bentley sounds like a great company. I applaud you both in that respect.

Let’s talk a little bit about what you think women in sales could be doing within your company and your sector, what you know knowledge-wise, not necessarily just the women within your companies. Where you see opportunities for growth that women may or may not be taking advantage of. How do you mentor your peers or maybe women that work for you? What would you tell them in this particular time that we have, where there is such a shortage and there are opportunities for growth? Where would you lead them? Margo?

Margo Edris: I would say oftentimes you don’t believe it until you see it. That’s really been my main objective getting into this role, is paving that path for other women that are about to come after me and want to see if it’s possible. I feel like sometimes there’s still those old school mindsets around women and their place in the home, and what they can do career-wise. But really within sales and sales leadership, you can do it all as long as you have a village, a support system, you make your goals known.

That’s really been my main objective, is women that are in their 20s, maybe late 20s, early 30s. Maybe they’re about to get married, maybe they’re recently married, maybe they’re starting to have children, or they have children. They’re curious about if they can progress forward within their career or need to step back for a little while. I strongly believe that you can have it all. It’s all about prioritization. It’s all about the calendar. It’s all about building meaningful relationships with every single person that you interact with. When you’re on customer meetings, you get to know the janitor, the security guard who’s checking you in. You know the executives. You know the people on the elevators. You have this tribe of people that are also interested in your success, both professionally and personally, and helping you throughout their life experience. I think it’s all possible, you just have to believe it in order to achieve it.

Gina Stracuzzi: One thing in particular really is, and you know from being in the forum that it’s like something that I preach almost, and that is make your goals and your desires for career growth known. People can’t read your mind, you cannot assume that someone’s going to tap you on the shoulder and say, “It’s your turn.” If you’re doing a great job and you just keep doing a great job, people aren’t really necessarily going to want to move you. Why would they? You’re doing a great job and you’re keeping us going in that area, so if you don’t make noise, nothing will happen. I love that you’re coaching women on that.

Katherine, I know from your time in the forum as well, your dedication to building the person and helping them find their thing that they are super good at and making sure they get opportunities to leverage that at every opportunity, which I just really applaud. Because it’s when we try to push people into roles that they aren’t interested in, or they’re really not that great at, we’re going to get mediocracy. I have always been a fan of your approach, a very personal, “What is it you are good at? What is it you want?” How do you translate that to women that you deal with and you’re coaching or mentoring, or even young men, in the transportation field?

Katherine Flesh: To your point, it could be men or women, whatever the talent that I have on my team, and I have a lot of talent on my team. I encourage them to say yes. We spend a lot of time choosing what not to do in life and what boundaries we said about saying no as women, which I think is really important. But I think the power to say yes, yes to new opportunities. What I believe I’m really good at with my team is dialing in and figuring out what each of my colleagues is passionate about, what makes them feel good. They might be driven by money, they might be driven by recognition, they might be driven by moving up in the organization, or giving back.

Finding what that thing is that drives their passion and helping them direct it within the organization, and the opportunity to really leverage that and get into a position might not be on my team. To my peril, I’m helping people to grow, which helps Bentley, of course, which is all good as a corporate citizen. But in a nutshell, yes, just encouraging them to say yes to those new opportunities that will align with their strengths and their goals and I help them make their goals be known.

Gina Stracuzzi: You gals are absolutely the quintessential leaders, really. You take the personal aspect and you figure out how to make it work for you and for your teams. That is really such a crucial piece. We like to leave our audience with one final tip that you would advise to advance their careers, something they can maybe put into motion today. Katherine, we just had you, why don’t you take us home on this piece and then I’ll go over to you, Margo?

Katherine Flesh: Quickly I’ll pass along the advice that my mom always used to say, pay yourself first, invest in yourself first. Whether it’s through taking advantage of professional training and forums, like the Women in Sales Leadership, whether it is making your world smaller by networking on LinkedIn to increase your village, as Margo says. I think that’s the micro step that everyone could take today is think, “Who have I wanted to connect with on LinkedIn? Who have I wanted to be in my circle and connect with them?” Be in charge of being your own PR, pay yourself first because your to-do list will always wait. Don’t make yourself be the one that waits.

Gina Stracuzzi: That is great advice. Margo?

Margo Edris: Just be your authentic self, unapologetically you every single day. It may take time to build the confidence to be able to have your own voice and get to that level, but know that it’s inside you and bring it out as often as you can in whatever form is the most natural when building these relationships to take you to the next level.

Gina Stracuzzi: Also great advice. Well, I cannot thank you enough. I have missed your beautiful faces since the forum. I look forward to seeing you at the conference, Katherine, Margo, I don’t know where you are along the line and when you’ll have your baby, but if you can make it…

Margo Edris: Exactly, no travel. We got the baby girl. I won’t bring her out for the show, so she’s right there. No travel.

Gina Stracuzzi: [Laughs] Well, the next time then. All right, ladies. Thank you very much. Thank you everyone who’s listening. We’ll see you next Tuesday.

Transcribed by Mariana Badillo

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