Transition from Corporate Exec to Empowered Entrepreneur & Transform Your Future with Erika Glenn | Ep. 184

9 Mar 2025 · 26 min

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Founder’s Story Podcast Episode Notes

Episode Title Transition from Corporate Exec to Empowered Entrepreneur & Transform Your Future with Erika Glenn | Ep. 184

Podcast Description The "Founder’s Story" podcast by IBH Media highlights extraordinary entrepreneurs, diving deep into the resilience and creativity that define true leadership. The show features insights from both well-known and undiscovered founders, creating a platform for raw conversations with real impact.

Guest Profile Erika Glenn

  • Award-winning C-suite growth and healthcare executive
  • Sought-after keynote speaker and business consultant
  • CEO and founder of Glenn Professional Services
  • Notable for a TEDx talk with over 500k views

Episode Overview In this episode, Erika shares her journey from a secure corporate role to becoming a successful entrepreneur. She discusses the importance of personal branding, strategic leadership, overcoming fear, and leveraging technology for business success.

Key Topics Covered

  • Transitioning from corporate leadership to entrepreneurship
  • Building and leveraging a personal brand
  • The fear of leaving a guaranteed paycheck
  • Strategies for scaling businesses
  • Mentorship and tailored go-to-market strategies
  • The role of technology and AI in operational efficiency

Key Takeaways

  • Invest in Your Personal Brand: A strong personal brand provides a competitive edge and acts as a safety net during career transitions.
  • Overcome Fear: Identifying and focusing on personal strengths is crucial for overcoming the fear of entrepreneurship.
  • Strategic Roadmap: Establishing a clear strategic plan, including mentorship and process optimization, is essential for sustainable growth.
  • Embrace Technology: Utilizing technology and AI can significantly enhance business efficiency and innovation.
  • Empower Your Team: Transforming from a hands-on operator to a visionary leader is vital for scaling a business.

Insights from Erika Glenn

  • Career Transition: Erika emphasizes the importance of preparing financially before transitioning from corporate to entrepreneurship. She advises saving ahead and investing in oneself even while employed.
  • Mentorship: Seeking mentors who provide authentic feedback can help navigate career challenges. Erika highlights how her mentors helped shape her strategic vision.
  • Sales Fundamentals: Erika points out that successful sales are built on repeatable processes and training, rather than one-off selling attempts.
  • Cultural Shift in Leadership: Erika transitioned from an authoritative leadership style to a more collaborative approach, focusing on team strengths and fostering a supportive environment.

Resources & Mentions

  • Glenn Professional Services: Erika’s business consulting firm offering growth strategies.
  • Personal Branding: Importance of crafting an authentic identity.
  • AI & Digital Tools: Discussed as crucial for enhancing operational efficiency.

Connect with Erika Glenn

  • Website: [erika-glenn.com](https://erika-glenn.com/)
  • Social Media: Active on LinkedIn and Instagram for further insights and updates.

Conclusion The episode encapsulates Erika's expertise and provides actionable advice for aspiring entrepreneurs on transitioning from corporate roles, building personal brands, and leveraging technology for business success.

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0:05Hey, everyone. Welcome back to Founder Story. Today, we have Erica Glenn. And Erica, you are an award-winning C-suite growth and healthcare executive, which I'm going to find really interesting to talk through corporate to business, because that is something I am a big proponent of and have experience as well. You're also a sought-after keynote speaker and business consultant, co-founder of Glenn Professional Services. Your recent TEDx on YouTube has over 500 ,000 views, which I've watched it a few times. It's amazing. But Erica, I'm excited to have you on. And I really think it's great to start off with your story and how you went from executive to business owner.

0:48Yeah, so really excited to be here, first of all. So thank you for the opportunity. But I've had a really interesting career with from a provider system and health care to a payer and PBM and then over to a digital health startup or health tech company. And so in the process of just learning about business and all the things that need to be done in order to make a business successful. You get to a point where you really just want to branch out on your own and apply those same principles and help others with different problems that they're trying to solve to make their business more successful.

1:24I know it can be really scary going from getting a paycheck guaranteed every two weeks to no guarantee of a paycheck. And I personally also went from working in the corporate environment to then being a business owner. How did you overcome this? And what do you see with other people when they when they do this transition? Because I think it's a pretty big one. It's a pretty big jump. Certainly, if you if you have the opportunity, save ahead of time so that you you have a little bit of coverage there. Because it's going to take a little bit like you need to kind of sit with it and figure out what you're good at, what you can market and how you go to market to make sure that you're successful.

2:08It is a thought, I think, that sits in every entrepreneur's mind. But investing in yourself, you'll never lose. How do you see investing in yourself even when you are working for someone else? Because I think there's this thought that I see many times. People are like, okay, when I work for someone else, I don't build my personal brand. I wait till I'm on my own, which I think is a big mistake. And I don't know, not every employer is okay with it. Some are, some are not. But how do you see people throughout their career building up their personal brand and not necessarily waiting until they start a business to do so?

2:47Yeah, about three years ago, I started working with Heather Monahan, who was my executive coach. And I hired her because I wanted a neutral voice in the background. Certainly, you have plenty of coaches and mentors wherever you work, especially when you're an executive. but I wanted somebody that didn't have the bias or the agenda. And through her, she really pushed me to start with branding more broadly. I will tell you that there are employers that like it and there are employers that don't. I would even go further to say there are certain executives that like it versus the ones that don't. What I will say is even when they don't like it, your brand will come in handy.

3:26It'll help you negotiate differently, better. It helps you level up. people know you when you go out and you're able to help other people in the process. So it brings great candidates to you and it looks good for the business, whoever you work for, to have the bigger brand. You know, the reality is when you work for someone else, you could be fired, you could be, your position could be terminated, you know, things could happen that are totally out of your control. And so having that, building that up, at least you have something to fall back onto. Now, when it comes to pivoting and changing, it can be really hard for people to understand the timing of doing so.

4:11Even just making a change from one thing to the next, many times people, you know, they can't let go of something to do that when they need to, when they should. I know you've had a lot of pivotal moments in your life about when you had to change and adapt. Can you go through what makes people do this in a successful way? One of the best pieces of advice were the best piece of advice I received at about 23. I had a mentor that was a chief technology officer, and he asked me to tell him my five-year plan. And so, you know, I was an eager 23-year-old, I'm going to do all the things. I'm going to be a manager, and then a senior manager, and then a director, you know, just straight up the line.

4:51And he said, nope, that's not it. Try again. And I tried again. And he said, nope, that's not it. So after a couple of iterations, I finally looked at him and said, well, clearly, you know better than I do what I'm going to do. So why don't you tell me so that I can actually execute on it? And he kind of laughed and then just said, look, you have to be willing to take risk. You've got to be open to risk. And what I've done in my career has been exactly that. I was an IT person, turned to sales leader, turned into general manager of managing a$200 million plus P &L and close to a thousand people.

5:25The skills didn't necessarily translate, but it allowed for me to take risk while I was still in that corporate type of atmosphere. I would tell you that last year when I exited CVS and went to Redox, which is the startup, I was not ready to go on my own. I was, you know, some of the fear probably held me back. But going to a startup and seeing the differences and just really the change and how substantial the change is gave me a lot of confidence that I could go out on my own and do what I do best. I can relate. Five years ago, I was terminated or my position was terminated and the company asked me to reapply for a new position.

6:08And I thought this is the prime time for me to finally leave and 100 % go on my own. So I feel like sometimes we need to be like pushed or forced to do something because it is hard, right? When you're in that corporate environment, especially at an executive level to then leave in that fear. When it comes to the misconceptions around scaling and growing a company, or even if you're an employee and you're scaling and growing the company that you work for. What are some of those misconceptions? Yeah, I think the biggest is people can just go out and sell. Can I go out and sell to one person? Sure.

6:51Is it sustainable? Absolutely not. You also have a, you know, it could be one salesperson, it could be Ken. Nonetheless, you have to train them. And so it is really, really important that fundamental processes and systems, not, I'm not talking about IT systems, but systems are put in place to make sure that you can have repeatable sales over and over again. Otherwise, you're just really, it's a different sale every time you go out. So another is training. I think for your executives, anybody that's talking to people, your sales team, anybody messing with a client, there needs to be some sort of process letting them practice.

7:29You do not want them practicing on the client themselves. and that way you can also steer, hey, you did really great here, but try these three things. So it makes them better, but it also makes the presentation and being more buttoned up in a much better light as well. Wow. I mean, sales is the lifeblood, right? If you don't have sales and you don't have revenue coming in, you could do any, you could have the most amazing product, but it'll fade into history. When it comes to training and leadership, as you continue to, you know, lead more and more people into the thousands. Was there something that you had to change within yourself?

8:10Yes, a lot. And I will even tell you when I started the executive coaching, I thought, oh, I'm going to change all this stuff professionally. It ended up changing my life personally as well. And I think that happens in many cases. But one really transformative way that it changed me, I was caught more of kind of a steamrolling approach, like I'm the boss, like everybody follow me. I've had three mentors. It was one of those folks. And after that individual left the company and moved on, I realized all that was doing was putting a target on my back and I was making people angry. And so I had to learn a different way.

8:51And, you know, people talk about masculine and feminine energies. I kind of tuned up my feminine energy to make it more about the team and to focus on the strengths and weaknesses and being able to match those versus, hey, I'm the boss, do what I say. So I think just the change in that allows people to want to come work for me. And that's something I'm super thankful for. That is a great call out. And the fact that you can adapt and change and recognize, I don't know if everyone can look deep inside and recognize what they are or are not doing. I think many times, I don't want to use the word stubborn, but many people are stubborn where they just, you know, whatever they're doing is the right way and they don't change.

9:36And that might hold them back in their career. Sounds like you've had a lot of great mentors. You've had a lot of people to learn, good and bad people to learn from. If somebody is thinking to themselves, you know, I need a mentor or I need a coach. What are some of the things that you look for or how do you even approach somebody for that? So I remember the very first mentor I had, mentoring wasn't even a thing then. And so it was somebody I respected a lot. I worked with him on projects. He was an executive. And I went to him and I said, hey, I want you to be my mentor. He said, what is that?

10:09And I just said, well, you just teach me the business. You teach me, you know, all the things I need to know to run a successful business. And he said, I'm happy to teach you. But I get here at five o 'clock in the morning. This was two hours away from me. So for many months, I would get up to spend a couple days kind of in his presence before everybody came in, just learning from him. So it's really about finding somebody that you're working with that can give you feedback. You have to be open to taking that feedback to do something with it. But making sure that you're ready for that opportunity and willing to show up when it's presented is also important.

10:45If you're looking for an executive coach or somebody offline, again, that's where that brand shows up. You need to make sure that it's somebody that has been where you're going and also somebody that's compatible with you as a leader and generally so they can help you. Amazing. I'm totally a big proponent of mentorship or hiring a coach, finding someone that can really help up level yourself because it's very hard. Look, it's very hard to look within and see those things or to just guess what you think you need to do versus somebody who's already had the experience. when it comes to authenticity as well as personal experiences.

11:28How can people use these when it comes to building their brand and how that brand is perceived by the public? Yeah, I think if you have nothing else with your brand and trust me, whether you know it or not, you have a brand. It's really whether you want to control the narrative. But the best thing that you can do is when you do show up in social media or wherever else, you've got to be authentic. because if you're not, people can tell. If you're just repeating content, if you're just taking whatever from AI and posting it, people can tell. And typically when people meet me, they say, wow, you're so real.

12:03And it always surprises me and catches me off guard because I'm like, well, isn't everybody real? But they're not. So I will tell you that a lot of the attention from social media or for me to speak has come from people being attracted to that quality of being really real and honest. So the interesting thing, and I'm glad you bring that up, I would say you do seem very real, whereas some people don't. And I'd have to find why some people don't seem real. But when it comes to this piece of authenticity and showing up, I think many people in the corporate environment, they're not necessarily encouraged or they don't see this as something they need to do.

12:49where when you're like a founder, entrepreneur, you pretty much have to, right? Like if you're gonna get business, you've gotta show up. So how did you get over the fears of showing up? So I think everybody still has fears. I don't care how big you are. And if anybody tells you different, they're probably lying. But you have to take a step at a time, right? Like if it's scary, do one thing and then follow it up with the second. And before you know it, you'll be able to crawl, walk, run, as we say, and kind of show up. I do agree with you that in a corporate setting, it is not pushed to have a brand.

13:26But I will tell you in negotiations for exits and things like that, it's also very important that you have a brand because people don't want you out there talking negatively. And you can negotiate on a much different level and much different terms to help you be ready to go start your own business. So now you're putting yourself out there. You're getting over the fears. Now you just did the TEDx, which it looked amazing. You're speaking all around the world. So what's next for Erica? So this week I'm headed to Paris to speak on International Women's Day. And then next week I'm headed to Boca Raton to speak with an incredible lineup of speakers just around it being Women's Month.

14:09So really excited about both of those engagements. And I have a couple podcasts coming up as well as some interviews. So one of the most important things I feel like is having a good strategy when you are starting, when you're starting something new, when you're entering a new product, entering a new market. I know you have a lot of experience with go-to-market strategies and the things that you've built into the hundreds of millions in a P &L. So when somebody is starting out with that, they have a great idea, product, service, and they're ready to go. What's a good strategy or what have you done where you're like, okay, this is what I always have people do?

14:49From my career, the favorite or my favorite way of doing this, we had a diabetes product or service that we brought to life. And we were we had brought in that company to actually sell to our customers. They exited the company. We had to build something. And so not only were we building something new, we were also selling against the people that had we had literally like walked into to sit down with the clients. So in that case, I literally took a week away from the business and I sat and kind of gathered all the evidence. I looked at market intel, understood the pricing, looked at the products, did comparisons, looked at, you know, what are, what is the competition saying about us?

15:32And how do we go ahead and put that in the sales pitch so that when it's time for it to come out, there's no question to be asked. You've already answered the question. So I essentially spent a week just going through, looking at the product. I came back with a list of 10 things and I said, you've got to change the product in these 10 ways in order for us to be as successful as we need to be. In addition, I came back with a new pitch. So I worked really closely with marketing. I had said, this is not going to work. Like you're going to have to give me something different. We started from scratch, rewrote it.

16:03And then just as I talked about earlier, I pitched against some of the biggest and best sellers that I knew over and over again until we could truly get the story where it needed to be. And once they were good, we saw massive success. We went 300 percent from a sales perspective that year and were able to really triple the business. So it was it was such a great experience. The sellers really took hold of it because I sold with them that year. So I was able to teach them, but I was also in the field with them because there was just, quite frankly, so much to do. So I think there's a couple things in there, really understanding the product fit, understanding how to actually scale it and how to get it to the in the hands of the sellers, as well as get feedback back from the environment.

16:49having a great and responsive marketing team to help you with that, and then practicing and making sure that things are tight and exactly the way they need to be for you to compete effectively. I think it can be tough to find a good sales manager, sales executive, building a great sales team. For many founders and business owners, what I've seen is that is a big struggle for them. So when you're hiring this person, what is it that you are looking for or what is it something that you would look for when it comes to, I would say, not the like sales reps, but a really, really good either sales executive or sales manager?

17:30So the first thing is, in order for you to sell, your sellers have to stay like this. And the thing with sellers is they're either up here or they're down here. So you have got to have somebody that has a lot of emotional intelligence that can, you know, when you need to go toe to toe, you go toe to toe. If they just need somebody to listen, you listen. It's really about understanding where that seller is. And you've got to find a leader that has that unique ability and talent because that is so important. I also enjoy more of a team selling approach. Certainly I hold people accountable for, I'll go ahead and put that to the side.

18:05But as long as the sellers compliment each other, or even the sales leader is able to compliment some of the other sellers, if they work together as a team, you're able to accomplish three times as much. So when you're working on those incentive plans, make sure that the sales leader's awarded financially for that and also make sure the sellers are awarded to sell that way. So that would be the first thing. The other thing, you know, people love to look for contacts. The reality is that people will go into interviews and say, I have a ton of contacts and they're just on LinkedIn. So what I have seen recently, and I've even got some affiliate marketing partners that are doing this, they've hired me to make introductions for them and to go in with them to see if I'm a good fit to try to help them.

18:49And so having an arrangement to try and then buy a few if you're interested and they're interested, it works for both parties. It's probably the best thing that you can actually do because you'll actually get to try them out and see how good they truly are. That's a very unique approach. I like that. It's almost like affiliate marketing just kind of flipped with a unique spin. And yes, I've heard people say I have, you know, 40 ,000 people in my network, but it legitimately is LinkedIn. And I don't know if they really know those people. So you have to be, you know, you have to be cautious. And I appreciate you bringing it.

19:27Anyone's going to bring their A game to an interview. Like you're going to say whatever you have at an interview, but can you can you execute is always, you know, it's always an issue. So what are some of the things to, as you were building up in this company, you're building something brand new. You had to have this new vision. You had to have this new mission. You had to get everyone, you know, rowing the same direction. What did you do in order to really rile everyone up with something that was brand new? It was uncertain. You didn't know if you were going to succeed. You had a lot, you know, things stacked against you.

20:02Like you said, you were competing with the company that you were also working with. So it sounds like there's a lot of complexities. But how did you motivate everyone and continue that, getting everyone on that even keel? So I'll give you an example. We built a weight management program when I was the general manager and vice president. And I was given eight months to build. So I got put and dropped in the position, literally had one of the top sales leaders come to me and say, I need this program in eight months. and I literally was like, do you know where we work? Things don't happen that fast.

20:38Luckily, we had been building different pieces of other products that we were able to leverage as well as kind of a network of physicians. And so it worked out really well. We were able to complete that. Keeping everybody motivated is not an easy thing. So it's really like, what are you going to do in addition to helping them? So are you ready to dive in? Can you keep everybody aligned. I would have governance calls, and I know it sounds super corporate-y, but truly it works, where you would especially get sales and product on calls to make sure they truly agreed and everybody was being heard.

21:13So I think a lot of it was the product teams were super excited to see the sales team selling. And so across the board, even in operations, everybody wanted to see it successful. So we celebrated every win as they started coming in the door to get everybody in a good place and comfortable with moving forward. I think there's so much that translates from a corporate job to business. I think people always find a way to separate those two. But you can take so much of what, from what I'm hearing from you, you could take so much of the learnings that you had and the experiences and then put them into a business, which I know you talk about with other people as well.

21:55So something that nobody wants to go in, nobody wants to experience, but we all do is failure in business. I don't think anyone is going to be in business. And I mean, if you've never failed in business or you're not failing in your business currently, I mean, you have not lived in my experience. It's not a road that's like paved in gold and it's so amazing and everything is great. And that can be very, very scary, like super duper scary. I've been through it myself. you feel like your world is collapsing. But what do you look at when people bring you in to turn a company around or if they're at that point and they're just not sure what to do?

22:35Yeah. So, you know, always go to the numbers first, right? You look at the financials to see what's going on. What does the cash situation look like as well as sales? And then you start digging in the pipeline to understand top of funnel conversion rates. So really getting into all the numbers. If there's an operations piece to the business, how are you, are you efficient and effective at operating? If not, what are some of those efficiencies that could also apply to sales? So again, all of this is process and systems and making sure you have the foundation to be really efficient and effective and move quickly.

23:11Well, thank you, Erica, for this. I know we talked earlier before about you had a mentor, you hired a coach. I have done the same. I think it's huge to be able to bring an outside perspective. And I don't know if you heard the Jahari window. You know, we can only see so much, right? We need someone that can come and see things from a different perspective and watch us to see what we are doing right or what we can work on. So if people come to you and they want to know about how that they can hire you as a business coach, what are some things you would tell them? Typically, and I was not planning to coach, but I've had quite a few individuals come and say, hey, we coach.

23:53And so I typically have an introduction call to see what's going on with them. What kind of role are they in? What are they experiencing? Where do they need help? Because everybody is different. So whereas I may have somebody that's been laid off and really low, needs to be picked up and helped, I may have somebody else that is really out there in the job market that just needs the right connections and needs the right type of networking. So I try to look at a very customized approach to understand truly what that individual needs and add K-LOR basically a program to that. And the cost is associated with what's also needed.

24:30So I think one of the things that I have seen missing in the coaching environment is not having deliverables, literally just saying, hey, I'm going to coach you. I try to put a lot of rigor behind it to make sure you can actually see the value and not just you as a person growing because sometimes that's really hard to see but also deliverables that you've been able to achieve as i've been able to help you but yeah i know so that that is great about having those deliverables i think it really makes people feel more comfortable uh when they are getting coaching and stuff because everyone is i know so many people that say they're a coach but i i always question um what is even their experience or or how can they really help me uh and so why would i hire them but this is great if you want to get in touch with the erica they want to find out more information, they want to see where you're at, how can they do so?

25:16Yeah, sir. I am at erica-glynn.com or you can find me on most of the socials. Definitely big in LinkedIn and Instagram. But yeah, those are the best ways to get a hold of me. Well, thank you so much for all the information today, the tips, strategies, all the things you're doing. I know there's a lot of people that were in your shoes before or in your shoes right now and they want to know what they should do next, where they're at. Everyone wants to obviously scale their business. We want to grow as entrepreneurs, which I think is great. And that's what we're all about is impacting more people in business.

25:52But thank you so much for joining us today on Founder's Story. Thank you for having me.

From the publisher

We sit down with Erika Glenn, an award-winning C-suite growth and healthcare executive, sought-after keynote speaker, and business consultant who is also the CEO and founder of Glenn Professional Services. Erika shares her journey, transitioning from a secure corporate role to building a scalable business, with her TEDx talk at over 500k views. Her insights on personal branding, strategic leadership, and embracing technology are invaluable for any entrepreneur seeking to transform their career and reclaim their life.

Topics We Cover:

• Transitioning from corporate leadership to entrepreneurship

• The inspiration behind building a powerful personal brand

• Overcoming the fear of leaving a guaranteed paycheck for entrepreneurship

• Practical strategies for scaling a business with a clear vision and empowered team

• The importance of mentorship, communication, and tailored go-to-market strategies

• How technology and AI drive operational efficiency and innovation

• Lessons learned from decades of experience in diverse industries

Key Takeaways:

💡 Investing in your personal brand provides a competitive edge and a safety net during transitions.

💡 Overcoming fear is essential—focus on your strengths and learn from your mistakes.

💡 A clear strategic roadmap, including effective mentorship and process optimization, is crucial for sustainable growth.

💡 Technology and AI are transformative tools that boost efficiency, creativity, and overall business success.

💡 Empowering your team and evolving from a hands-on operator to a visionary leader is key to scaling.

Resources & Mentions:

• Glenn Professional Services – Expert business consulting and growth strategies

• Personal Branding – The importance of building an authentic, differentiating identity

• Strategic Mentorship – Leveraging guidance to avoid common pitfalls

• AI & Digital Tools – Enhancing business efficiency and innovation

Connect with Erika Glenn:

📢 Website: https://erika-glenn.com/



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