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Podcast

Igniting Next Gen: Building Relationships - Skills for Successful Career Growth

By Alliant / January 16, 2025

Karen Caterino, Alliant Public Entity, welcomes Myshell Gresham, Ascot Group, to discuss her unconventional career path and advice essential for career growth in insurance, or any relationship-based industry. Myshell shares the internal and external challenges she has faced that have helped her learn the importance of investing in yourself, constant learning, maintaining curiosity and being an effective communicator. Defining herself as a relationship maverick, Myshell emphasizes the value in developing your personal brand and leveraging social media as a networking tool.

Intro (00:00):
You are listening to a special episode of In The Public Eye Podcast, Igniting NextGen for Careers and Risk Management, where we explore all the exciting career opportunities and possibilities within the insurance industry. Here is your host, Karen Caterino.

Karen Caterino (00:18):
Hello, welcome to Alliant's Igniting NextGen podcast. I'm your host, Karen Caterino, and our guest today is Myshell Gresham, Senior Vice President of Partnership Engagement with Ascot Group. Welcome to the show, Myshell.

Myshell Gresham (00:32):
Thank you. Hi, Karen. Thank you for having me. It's an honor.

Karen Caterino (00:36):
A pleasure, a pleasure. We certainly like to start with hearing about your background and talk a little bit about your career path in insurance and marketing. How did you get started?

Myshell Gresham (00:45):
It is a long story, but I'll keep it very short. I started my career as a cosmetologist when I was about 13. Went on to college, built a successful cosmetology business, owned a salon, and I originally went to college because I wanted my own hair care line. I was a chemistry major for a couple years, and I quickly changed disciplines when I realized that working as a hairstylist in college and studying as a chemistry student was not going to work, didn't have enough time for both, and I was very passionate about my cosmetology career. I'm a creative at heart, and so I changed my major to finance where I said in my head, I can finance the haircare line.

As you know, that did not happen. I continued as a cosmetologist after leaving college. I went on to banking, doing healthcare media lending. There was consolidation in the late 90s, early 2000s, which led me to seek out new opportunities because I didn't want to be displaced from the merger. The company I worked for was being purchased, so I interviewed. I interviewed with many banks, but only one non-bank, and that company I spent about 19 and a half years in many different roles. Yes, 19 and a half years. Actually, I didn't know it was going to be emotional when I left, but it was. Great career. I had an opportunity to be in many different disciplines. Most of the career was in credit risk. I did underwriting, worked in surety, and then I had a conversation with a mentor who was quite amazing. The group reported up through that structure. He took the time to hear what everybody wanted to do next, and I said, I want to get closer to the customer. Folks may say, what gave me that drive? I've always been a relationship builder. Building a business, you have to know how to form relationships. You have to know how to establish what a client needs. At the time, I didn't think about the transferable skills, but I just knew I wanted to do something different, and I said, hey, I want to do marketing.

Many people within the organization had set up opportunities for me to talk to leaders within those roles. It's called distribution. So when I was at the carrier one day, a mentor, this mentor came to me. He's no longer at that company, so hopefully I can say his name because I think it's really critical to give people their recognition for supporting and taking chances on folks. Gregg Piltch was my mentor and still is a mentor to this day. I just saw him last week in New York. And called me up and said, hey, I got you a job. And I was like, where is it at because you're on the West Coast and I'm in New York, and it ended up being a role in San Francisco, and I said, I can't leave yet. My daughter is about to graduate in six months. And he said, I'll hold the role for you. I was floored and stunned, but really grateful because that was the first lesson. The way you show up is what people will remember, and he remembered that. And he took a chance on something I had no clue about doing anything, and it's called distribution at carrier. So I moved out west in 2016 and did a job that I had no clue of how to do it, but I crafted it in the way that I know how, and I brought what I knew about building relationships to the role. That was my first experience at being in a marketing role. From there, it really blossomed into other things.

I ended up leaving that company in 2019, going over to the broker side, which that marketing background in managing a client portfolio, understanding products across the board, and growing a client from, let's say a hundred thousand to multi-million, was something that was quite valuable once I went to the broker side. Spent a couple years there and another friend reached out and said, hey, I know someone looking for a leader for the west for their partnership engagement. Actually, they didn't have a name for it when I was approached, and I was like, sure, I'll chat. We were in the heart of the pandemic, connected us via text, started the conversation, and it went from there. Second lesson, it's about how other people speak about you and recommend you. I must have left an impression on this person, still a really good friend of mine in industry and a confidant, and I was deeply grateful that I was thought of in that way, that this was something that I could do and really quite honored. I think in that moment it taught me something about how I should continue to speak about myself and show up so that others can also advocate when I'm not in the room. That's how I got started. A little bit about how I got started.

Karen Caterino (05:51):
Myshell, it's so interesting, the background. First of all, your hair always looks amazing.

Myshell Gresham (05:55):
Thank you.

Karen Caterino (05:57):
Clearly some of that skillset still comes into play, but I think what's so intriguing about your story is the fact that you didn't start on a typical career path in this industry. But what the skills, the relationships, the I want to get closer to the customer, leveraging mentors and being mentored were so critical to your success and where you've landed today. I think it's a great story for students, particularly early career professionals, just starting out that you never know the path or where you may go. However, invariably the beauty of insurance and banking and credit risk and all the things that you've done, is there are so many things that you can do. I think that's probably what you like about your job, and maybe speak to that a little bit. What do you like about your current role and everything that led you to where you are today?

Myshell Gresham (06:48):
The people. I'm naturally curious, and I get an opportunity to meet incredible people every day. I was thinking the other day, it's like having a lot of first dates. Sometimes you don't know the people, you've only corresponded via email or something. Then when you get a chance to sit and chat with them, it's like this blossoming of worlds that come together and you learn something very unique about them. They learn something very unique about you. I rarely start with business first. It's always what is that grounding or that common thing that you can find that really creates that connection? I think that is what I've been told and now I'm saying it out loud about myself, is a superpower in being able to connect with anyone and just have a conversation. We hear it all the time that we're so much more alike than we are different. It's absolutely true. I discover that daily in my role. It's actually quite fascinating. I love, I call it scanning people. When I don't know them, and I'm trying to prospect on business or meet new brokers. I will scan LinkedIn, find out who the leaders are of certain products, reach out to them and make a cold intro. It always goes to a warm one. I haven't had anyone who hasn't responded.

I will tell you, just recently it's been one of those things where the person hadn't responded and what I know because I've gone through sales coaching, I put myself through sales coaching because you got to invest in your own skills. One of the things I remember Tim saying is that it's generally the average of eight tries before you get a response. Most of the times, I never get to eight, but I've gotten to eight recently with someone. I share the story with them, and the person started laughing and was like, I'm really busy. What I know is my priority isn't someone else's priority. That creates some grounding for me and patience because this person doesn't know me. I have to be creative enough to get them to say yes, and I find a way to do it at times. It’s quite exciting. Let's see how long it's going to take for someone to actually bite. And when they do, they never go back.

Karen Caterino (09:07):
Yes, great advice, Myshell. What would you say are some of the challenges that you've experienced throughout your career?

Myshell Gresham (09:13):
Where do I start, Karen? I've been in industry for 25 plus years, and so there's been many things, but I think the challenge is what builds our keratin business. There's been times when I haven't been taken seriously. I could make a statement and it's second guessed and it's, look, I need to check on that. I have verified information. My decisions being challenged, being in the outgroup, my education questioned. That one was particularly interesting. I was fresh out of school, and I was in credit risk. It was something about EBITDA, if you know anything about credit or financials, it's understanding valuations in EBITDA and how you look at multiples with EBITDA. I'm fresh out of college. I knew the concept of EBITDA, but I'm learning how we value transactions. This is part of my learning. I was at a different office, and I like to tell this story because it is something that really stuck with me. It's a lot of things that I don't remember, but I remember those very impactful things. We had two different offices. I was in the Princeton office, and then we had an office in another town in Central Jersey.

I can't think of the name of it right now. Cranford, that's what it was, Cranford. Apparently, there was this deal going, and I got a chance to be on probably one of the largest deals that I ever worked on. The owner of these radio stations was a black woman and is very famous, so you can look it up. She talked about sleeping in her office with her son, and she eventually became one of the largest owners of radio station. That was the media part of what I did in these deals. I was really excited to work on this deal. She's an African American woman. I'm doing this bank book, and generally when you finish the bank book, it's about 25 plus pages long. I didn't know a concept, and I was asking questions around something, but apparently it was a conversation in the Cranford office. Somehow this woman called me, did not know her. She worked at the bank, and she said, listen, you're being questioned. Your education is being questioned. I thought she graduated top of our class. She graduated top of our credit risk class. By the way, I was in top five of our credit risk class of that year because you had to go through credit risk training when you got to the bank for six months. If you didn't pass, you didn't have a job. So, this chatter was going, she's really smart, but she can't get this concept. The woman tells me, you need to make sure you cross your T's and dot your I's. You're being questioned. I said, okay.

I think I probably for the next few months didn't go to bed before 3:00 AM, but that was par for the course in banking. But I studied and I reread and I studied. There would never be a question about my ability or my ability to learn. I will say that probably wasn't the best way to go about it. What it did for me was I constantly tried to dispel any negative view of me. I put an undue pressure on myself. That's just one example. Later I realized that my biggest challenge was myself. There’s a theory suggesting that the more success you have, the greater the imposter syndrome you may experience. It never leaves us. But I had to figure out a way to talk through the doubt. I put on hype songs anytime I doubt myself. I got a couple hype songs, one being gospel, I love gospel. I grew up Bible Belt South. I have a couple hype rap or soft metal songs where I get in my head and I pump myself up. Once I began to focus less on the external obstacles, I found that I lessened myself as the biggest barrier. It’s all about our mindset, how we see ourselves and how we take in messaging. While I've had challenges throughout my career, I had to develop routines to help me conquer those and not internalize them, if that makes sense.

Karen Caterino (13:26):
It does. I think it leads into the question I have about when you consider entry level opportunities for students, what are some particular skills that they should look to develop, that they should have working in this industry and things that they can certainly work on? You've touched on some of those, but what would be your suggestions?

Myshell Gresham (13:45):
Read. Reading is a lost art.

Karen Caterino (13:49):
It is and being a consummate student too, right?

Myshell Gresham (13:53):
Yes, it absolutely is. Being willing to always learn. Like we're constant students, like you just said. I never stop learning. I'm right now reading three different books, and most times I'm listening to them just to get them in because I don't have enough time. But I try to dedicate and put aside time for reading, staying abreast of what's industry news, being inquisitive, asking questions. What I realize is, even to this day, a lot of times I will ask a question, inevitably someone will email me that was really good. I was thinking the same thing. But I think we're afraid to say we don't know. We are afraid to ask for the things that we want, especially women, because a lot of times we've been brought up to be very demure. Hold your place, don't ruffle feathers, don't go against the grain. Keep it easy. Keep it smooth. That has not served us, but we have come a long way in business. What I would say to anyone, man or woman, is that ask for what you need, be curious, read. When I say read, not the social media headline, actually get books. I always like to ask when I'm talking with people that I meet, what are you reading? That way I'm getting a collection, a very diverse collection of books that I probably wouldn't have come across had I not asked someone what they're reading. Karen, what are you reading right now?

Karen Caterino (15:21):
That’s a funny question you asked because I use reading to decompress, so I am usually reading thrillers, psychopaths, just to turn my mind off.

Myshell Gresham (15:31):
No, I love that too.

Karen Caterino (15:32):
I do try and read two at a time, so I'll have that. One of my favorites that I still go back to is "First Break All the Rules." It's understanding people and psychology and teams. Instead of focusing on people's challenges or weaknesses and trying to correct them, focus on their strengths and let them run. Always good to come back to, I think self-help books for sure.

Myshell Gresham (15:56):
I love that. One of my favorites is "Positive Intelligence" by Shirzad Chamine. I went through his program, and it talks about how do we focus on our, what they call sages versus our saboteurs. I highly recommend it for anyone at any level.

Karen Caterino (16:15):
Yes, that's a great question, Myshell. Thank you. What would you say is your best advice for students considering a career working in the industry and even with your firm, Ascot?

Myshell Gresham (16:24):
If there's young professionals that's listening to this, we generally start our recruiting in the fall. Right now we have internship opportunities available. I've seen a ton of postings from various business units promoting the roles that they have within their groups. We have cyber, legal, all the business lines have something. We even are getting a marketing intern this year. I would say utilize your career centers at your schools if you can. I would also recommend that sophomore year, if it's not something super formal, getting some type of exposure in business, whether it's an informal or formal internship that you can do. Again, asking questions, shadowing professionals. If you don't have parents that are in the professional roles that you want, seek out their friends. I have a lot of my friends' kids now are in school and I say, hey, send me all the résumés so that we can get them to apply for these positions. You have to seek it out. People aren't going to come to you. Be inquisitive. Be curious about what people are doing and get outside your box. I think being well-rounded in a world that is very diverse will lend to your ability to talk to anybody.

Karen Caterino (17:52):
Couldn't agree with you more. Tell us a little bit about how you've developed your personal brand and how you've leveraged LinkedIn, which I think is an important resource for students to know and understand on how they can stand out as they're pursuing jobs in insurance.

Myshell Gresham (18:05):
Social media is still a daily challenge for me. I think I've talked about not liking to talk about myself. Social media is an extension of promoting yourself. One of the things that I have done is listen to feedback that people have given me. One of the things that folks have said a lot, you are a great connector, you're very generous with your network. I don't think I'm necessarily generous with my network. I think that that's what you do as a professional, where you know folks and you understand what they want and what they're looking for, and you think about who's in my network that can support them. I'm always offering myself, hey, let me know how I can support you, let me know how I can help you. In doing that, one day I said, how do I stand out? How do I get your labels to stand out?

I came across the word maverick, and I absolutely love the word maverick. It means doing something unconventional. Because I had gotten this feedback about how great I am with connecting people and developing relationships, I coined the phrase as a relationship maverick versus just saying a relationship manager. I'm a relationship maverick. I do it differently. I do it really good. Hence why I have my role, and I leaned into what people kept saying about me.

Karen Caterino (19:25):
How did that look on your LinkedIn profile? What did you do there?

Myshell Gresham (19:29):
I put it as, you know how you give these little short descriptors? I put Chief Member Relationship Maverick. I think I have something like Connector or something like that to give a little splash, different words that you don't see all the time. If it's something that you do really well, find something splashy to put towards it. There's this woman in business that she calls herself the Beyoncé of Insurance, and I'm sure that always prompts someone to ask. It's almost like an opener, an icebreaker. Tell me why you're Beyoncé in the industry. Like wearing a jacket with some signature pins. I like to do that too when I'm at networking events. Actually this is a great tip that I learned from, what's the woman that was Secretary of State? Was it Madeleine Albright? She talks about her broaches, if you know that Madeleine Albright used to always wear these broaches, and it became her signature.

I saw her speak at this carriers event at the company I used to work for, and she spoke and she gave the story about these broaches. I picked that up. Find something unique that helps you stand out in a room because I will tell you, when I talked about being in the ingroup and the outgroup, a lot of times I have to break through the ice. People won't always naturally talk to me at networking events. I have to have something that will grab them. I generally try to find something that can be an icebreaker, like a nice broach or something interesting, a bright color. It always leads people.

Karen Caterino (21:05):
So probably important to develop your personal brand.

Myshell Gresham (21:10):
Yes, developing that personal brand that people look for.

Karen Caterino (21:13):
Makes sense. It's been a pleasure talking with you, and thank you so much for taking the time to be on our show and share your experience.

Myshell Gresham (21:19):
Absolutely. Thank you, Karen.

Intro (21:22):
Thank you for listening.

Alliant note and disclaimer: This document is designed to provide general information and guidance. Please note that prior to implementation your legal counsel should review all details or policy information. Alliant Insurance Services does not provide legal advice or legal opinions. If a legal opinion is needed, please seek the services of your own legal advisor or ask Alliant Insurance Services for a referral. This document is provided on an “as is” basis without any warranty of any kind. Alliant Insurance Services disclaims any liability for any loss or damage from reliance on this document.