Today, host Lorie Jones sits down with Sheri Fitts, a vibrant leader whose journey from graphic designer to CEO, keynote speaker, and founder of Sway Live, embodies what it means to be resilient and purposeful in a male-dominated industry.
Sheri shares how she’s built a thriving career by serving others, following her curiosity, and embracing both innovation and emotional intelligence. From her early days creating 401(k) education materials to launching her own conference, Sheri’s path is a testament to the power of helping, mentorship, and being authentically yourself—no matter how winding the road may be.
Whether you’re navigating your own unconventional route or searching for inspiration to make bold career moves, Sheri’s story promises actionable wisdom, a dose of humor, and a reminder that your unique journey is worth celebrating.
Show Highlights:
- Sheri Fitts’ leap from corporate America to a new business at 50. [08:51]
- Insights on developing an AI–EQ intersection to keep financial services valuable. [12:36]
- The importance of embracing market flexibility and new tech. [15:35]
- How to be in the right rooms to grow a keynote speaker business. [16:48]
- Have only women’s numbers improved in financial services’ gender bias? [22:28]
- Learn a unique blended approach to sales as speed and marketing as strategy. [27:05]
- Uncover a rising sales role and why women can earn top sales dollars. [32:09]
- Explore Sheri Fitts’ nonlinear path to success without college. [33:54]
- Find out how to have a winning sales conversation. [36:54]
- Advice to young women on being of service and joining organizations. [42:56]
Connect with Sheri Fitts at https://www.linkedin.com/in/sherifitts/, and be sure to make a note of this episode of Fearless Females in your message. You can also reach Sheri by visiting https://sherifitts.com.
If you enjoyed this episode, please go to Apple Podcasts and leave a review!
For more information about Lorie Jones, go to https://fearlessfinancialadvisors.com/fearless-females.
00:02.16
Lorie Jones
Good morning, Fearless Females. Today, we are here with Sherry Fitz. She is CEO and founder of a firm that's been through many different iterations and is Fitz & Co.
00:14.34
Lorie Jones
She's a keynote speaker and a founder of Sway Live. And she's got a really interesting story. I was privileged to go ahead and and hear Sherry at one of the conferences that I attended. And I just really am excited to to let you hear what she has to say and hear her story. So thank you so much, Sherry, for joining us.
00:34.28
Sheri
Lori, it's wonderful, and congratulations on your podcast and your you know the new things that you're doing. I'm so excited to hang out with you today. Yeah.
00:44.42
Lorie Jones
Perfect. Well, I'm excited to get to know you a little bit better and hear a little bit more about your journey. And I always start with the same question because I love it. I'm a reader. i love any and all suggestions. What's your favorite book?
01:00.09
Sheri
Wow. Well, I've got to say that one of my favorite books is a book by Elizabeth Gilbert, and it's called Big Magic. And...
01:12.27
Sheri
It is really about the idea that creativity um and ideas, in fact, are almost like beings.
01:23.56
Sheri
And if you don't honor the idea, it might fly away and find somebody else. And I've always thought about that. I've always said to friends when they come up with that idea, I'm like, do it now or somebody else will do it.
01:31.17
Lorie Jones
Mm-hmm.
01:34.39
Lorie Jones
Mm-hmm.
01:35.73
Sheri
And so it's funny that she has that belief. But Elizabeth Gilbert, um I've been following her for a while. And in addition to that book that I love, she also, um you know, she was the Eat, Pray, Love author.
01:49.58
Lorie Jones
her
01:50.96
Sheri
um But she's got a new book coming out in September. And right now she has something that's a substack community called Letters from Love. And it's just a beautiful community um where she sends out a newsletter every Sunday about um writing yourself a letter from love every week.
02:14.00
Lorie Jones
Oh, I like that idea.
02:14.44
Sheri
It's just beautiful. Yeah, it's really sweet.
02:15.94
Lorie Jones
Yeah.
02:17.25
Sheri
Yeah.
02:17.46
Lorie Jones
I read Big Magic um and I loved it too. i The part that got me is the idea of fear. Fear can ride in the backseat, but fear doesn't get to drive.
02:28.85
Lorie Jones
And that really spoke to me. i think that i didn't i didn't love the Eat, Pray, Love um book, but I really, really liked the big magic.
02:41.75
Lorie Jones
So I think that would be interesting to see what she has. Letters letters from Love. Is that what they're called?
02:48.12
Sheri
Letters from love. Yes. Letters from love.
02:51.33
Lorie Jones
and We ah could all use just a little bit more love in our lives, don't you think?
02:51.49
Sheri
Yeah. It's beautiful. Heck yeah. Yeah. Indeed.
02:59.02
Lorie Jones
So tell me a little bit about your journey, Sherry. Where did you get started? um How did it kind of go? it a straight path or a loopy path? And where are you at today? Kind of what do you do? Just tell me a little bit about your background.
03:14.83
Sheri
Well, let's see. i won Paper Girl of the Year in 1976. So I've been in communications for forever. No, I've been in financial services actually for half my life.
03:27.72
Lorie Jones
Mm-hmm. huh
03:27.92
Sheri
So for more than 30 years now. So you guys can do the math.
03:30.28
Lorie Jones
isn
03:31.12
Sheri
I'm 63. And I started as a graphic designer. I started as a graphic designer when graphic design was moving from the standard kind of design to computer aided design. So that's how I got in was via my perspective of using technology.
03:51.12
Sheri
And in 1998, the materials that I was creating, so I was designing 401k education and communication materials. And in 1998, I actually started selling those materials to regional banks and record keepers.
04:04.62
Lorie Jones
Mm-hmm.
04:08.51
Sheri
Because at the time, in the 401k world, there wasn't this bundled approach with education and everything all in.
04:18.85
Sheri
so
04:19.21
Lorie Jones
OK.
04:19.81
Sheri
many of the bank and regional TPAs and whatnot, they didn't have their own education department. So those were my target clients. So US Bank and um Kansas City, United Missouri Bank, UMB Bank and Bank of California and Bank of Hawaii, those were clients of mine that used those 401k materials that I created.
04:27.81
Lorie Jones
Mm-hmm.
04:44.32
Lorie Jones
Okay.
04:44.43
Sheri
so You know, I was using technology to do design work. Then I got into sales. And that's how I ended up in marketing really is because I had a sales goal.
04:55.93
Sheri
I had a national reach with no marketing budget. And because my boss was the kind of guy, literally, that he cold called Phil Knight, you know.
05:07.11
Lorie Jones
um no
05:07.60
Sheri
so So he didn't believe in marketing.
05:10.85
Lorie Jones
okay
05:11.06
Sheri
And What i had to do then is just really get creative and scramble and hack things. So I was doing email marketing back in 1998, which wasn't a thing really.
05:22.24
Lorie Jones
Wow. Mm-hmm.
05:25.43
Sheri
So, um and I was doing thought leadership marketing back in 1998. So I was doing whatever I could to serve um my prospects and whatnot. And I started actually doing some speaking at conferences as well.
05:40.49
Sheri
And then in 2003, left that organization and I went to work for us Bank in a sales capacity, wholly sales capacity in their institutional trust and custody department.
05:56.43
Sheri
Big word for saying that ah predominantly I was selling um services and um solutions related to benefit plan four ah one k plans, 401k plans, et cetera.
05:57.86
Lorie Jones
Okay.
06:07.97
Lorie Jones
and okay
06:08.52
Sheri
And um right after
06:14.77
Sheri
standard, Standard Insurance, bought an organization called Investmart, again, way back in 2000 and I think, golly, four, maybe.
06:26.22
Sheri
Who knows? It all's a blur. I went to work and I ran the communication and marketing for Standard Insurance's retirement plan division. So, and then hopscotch to LPL Financial to run their marketing for their retirement plan division.
06:43.16
Sheri
And it was at that time that I got my little AARP card in the mail. So for those of you who don't know, when you turn 50, AARP knows somehow that you've turned 50 and they will send you a little, begin to kind of market to you as somebody who is one of their target clients.
06:49.45
Lorie Jones
Uh-huh.
07:02.54
Sheri
And I thought to myself, gee golly, um i guess I'm you know growing up now because I've been saying for the longest time, when I grow up, I wanna be a speaker and do my own thing.
07:15.19
Lorie Jones
yeah
07:15.30
Sheri
And when you get the AARP card, but the I just started to ask myself, what is it gonna take? When are you gonna do this?
07:24.79
Lorie Jones
when are you gonna be grown up huh oh wow
07:25.28
Sheri
So that's when I started my own business, yeah. That's when I left corporate America on purpose, golden handcuffs be damned and started my own firm.
07:36.08
Sheri
Yeah. yep Yeah.
07:39.02
Lorie Jones
That sounds scary. um And how long have you been running your own firm? And it's, it sounded like there's like different iterations of the way that your firm has gone. is that right?
07:51.01
Sheri
Yeah. When I first left corporate America, I had a creative services firm. So we did white papers and business cards and brochures and websites and ah yeah you know, LinkedIn posts and everything and anything related to financial services. So we kept it in a niche. And I had a team and, um you know, a cool office with brown walls and Japanese lanterns and the whole thing. And 2017, my sales plummeted.
08:19.01
Sheri
my my um sales plummeted I took my eye off the sales ball and I just had to, you know, shut my creative services firm down pretty rapidly to just be me.
08:25.38
Lorie Jones
Okay. Mm-hmm.
08:35.36
Sheri
And that's when I decided I was going to actually just be a speaker and focus on that. And um thankfully, I've got to say, firm snatched me up to be their chief marketing officer.
08:47.62
Sheri
So I kept my speaking. my foot in the speaking side. And then I was also a chief marketing officer for a firm out of Chicago.
08:55.66
Lorie Jones
Oh,
08:55.98
Sheri
Um, and then that contract ended in 2020.
09:00.68
Lorie Jones
ah wow.
09:00.74
Sheri
So I was like, okay, going go all in on the speaking thing in you know, March of 2020.
09:06.86
Lorie Jones
Yeah. Yeah.
09:07.25
Sheri
Um, yeah, that was kind of curious, but, um, So that's still the, you know, I've always had a speaking component for the past 12 years. I was just, I would say, Lori, I was kind of chicken to just lead with speaking. Like that wasn't enough, that I wasn't enough somehow.
09:24.75
Lorie Jones
yeah
09:25.38
Sheri
um And it took me a long time to see that there's value in the ideas that I can share and the inspiration that I can make happen.
09:34.08
Lorie Jones
Oh, yeah.
09:34.47
Sheri
Yeah.
09:34.71
Lorie Jones
And, and people do come away from those sessions with like ideas and, and ways that they can do better and just feeling filled up. And, and so that, it brings its own kind of I don't know, just growth and stuff like that. Like it is enough.
09:52.68
Lorie Jones
That's what I guess what I'm saying. It is enough. So.
09:55.84
Sheri
Well, I deeply desire, deeply desire to make sure that people walk away with one idea they can do and it doesn't have to be overwhelming.
09:55.89
Lorie Jones
Yeah.
10:05.27
Lorie Jones
Yeah.
10:05.88
Sheri
So I really work on that when I speak.
10:05.99
Lorie Jones
yeah
10:08.09
Sheri
Yeah.
10:08.34
Lorie Jones
but Well, good. That actually ah happened. I did come away with one idea and and a few more, actually. So that's good. but But what um what did you what were you speaking about? Was it was it all the marketing piece? or Or talk to me a little bit about that.
10:27.85
Lorie Jones
Like when you when you gave up all of the the corporate stuff, what were you what were you trying to
10:34.86
Sheri
Well, you know, when I started out, so I've, I've been teaching the financial services industry since 2006, how to use LinkedIn. So I, you know, i did speak a lot about LinkedIn and interestingly, I still do because people still don't get it, which is just amazes me because it's been around for 20 years now, but, um,
10:48.91
Lorie Jones
you
10:52.82
Lorie Jones
Yeah.
10:54.81
Sheri
And what i what I really think is hilarious is when I go speak at universities, all the college kids or all the college folks are like connecting with me on LinkedIn now. They think it's the coolest thing. I'm just like ah loving it.
11:07.79
Sheri
um So, you know, I would do that and I would talk about marketing, kind of very, very strategic kind of things.
11:12.53
Lorie Jones
Mm-hmm.
11:16.91
Sheri
um
11:16.95
Lorie Jones
Mm-hmm.
11:17.54
Sheri
And my message has evolved over the, you know, many years, I think.
11:24.29
Lorie Jones
Mm-hmm. Mm-hmm.
11:25.06
Sheri
you You probably you know know this from just doing podcasting. You get more and more comfortable with your own voice and your own ideas. It's like a muscle. And so for me, I started to ah constantly look out to the following year and think, what are the trends that I'm seeing?
11:44.41
Sheri
How do I stay viable and valuable? And more importantly, how can I help the financial services industry stay viable and valuable? and And so um really lately, I've been doing predominantly two key kinds of presentations. One that's really heavy on emotional intelligence and the other one that's really heavy on artificial intelligence.
12:09.31
Lorie Jones
Oh, yeah, that makes sense.
12:09.61
Sheri
So I've been doing, you know, and what I've also been doing is the intersection of those two together. So how can you use ai to get better um at emotional intelligence like EQ?
12:25.52
Sheri
So I've been doing a lot of that.
12:25.84
Lorie Jones
Mm-hmm.
12:26.92
Sheri
I just, you know, i um I'm curious. I've always leaned into digital. And so I just, you know, I follow my little rabbit trails and who knows what I'll come up with.
12:39.09
Lorie Jones
ah I like that. that That's a really, ah i am financial services and I need 10-year plan, 20-year plan, like triplicate sort of spreadsheets around. So this this idea of like, you know, looking to next year and seeing what's relevant makes me like hyperventilate and panic. But I love...
13:02.96
Lorie Jones
i I love that you you're doing that, that you're like taking it as it's coming, because because we wouldn't have known really that AI was going to be the next big thing until it started being the next big thing.
13:08.08
Sheri
you
13:16.08
Lorie Jones
And then, you know, and everyone jumped on that bandwagon. But but but kind of. Knowing how to how to take the pulse of the market so that the people that you're trying to help are getting fresh and interesting ideas. i think that's really important and and staying flexible enough to do that.
13:36.86
Sheri
Well, and I follow my curiosity, Lori. So like, as an example, when it comes to AI, I was experimenting with AI about a year and a half before chat GPT came out. I was using a platform called Jarvis and now it's called Jasper.
13:46.78
Lorie Jones
Mm-hmm.
13:50.82
Sheri
And I was, you know, I've got to create content, right? And so I was using it to optimize my headlines and yeah maybe streamlined bullet points or whatever.
13:59.53
Lorie Jones
Yeah.
14:01.26
Sheri
And I was still feeling really uneasy about using it. And the minute that GPT came out, I was teaching people how to use it because I'd already been using ai for a year and a half.
14:10.57
Lorie Jones
yeah
14:14.25
Sheri
So, um you know, that was definitely a smart move on my part. Yeah.
14:21.89
Lorie Jones
Well, yeah, and and remaining relevant and kind of seeing what's coming down. um it's It's a talent, too. It's, you know, you can't you can't always predict, well, you can't ever predict the future, but but a lot of times you can kind of see it coming and and you know where to maybe turn.
14:40.74
Lorie Jones
um Tell Sherry, what's the best investment you've made in yourself? Is there an investment or something that you've done that you're like, oh my gosh, I'm so glad I did that.
14:51.03
Lorie Jones
I just don't think I would be where I'm at today if I didn't.
14:57.92
Sheri
I would say probably there's two. one um back 2003, when I was at U.S. Bank, I started to go to the National Speakers Association meetings here in Portland.
15:14.69
Lorie Jones
Mm-hmm. Mm-hmm.
15:15.59
Sheri
I didn't even know that there was such a thing as a professional speaker. And then I think it was 2008, two thousand and five maybe, I'm not sure, that I decided to take their speaker um accelerator class where you learn from um some some wiser speakers about running the business of speaking.
15:48.75
Sheri
What are the things that you need in order to pitch a speech, that kind of thing. yeah That was certainly...
15:58.36
Sheri
from what I, you know, I always, when my friends talk to me about wanting to be a speaker, I always send them to the National Speakers Association because that's um the percolator for the business of running a speaking business.
16:11.41
Sheri
So that was probably a really good investment for sure.
16:11.57
Lorie Jones
Mm-hmm.
16:15.48
Sheri
And then the other one was that I decided to launch my conference and
16:15.56
Lorie Jones
Mm-hmm.
16:21.59
Sheri
who launches a conference? i mean, um and, and year, and I, and I gave myself five years, right? And the reason I did that was because I do lean into innovation as a skillset regularly.
16:38.52
Lorie Jones
who
16:41.18
Sheri
And I often am ahead of the financial services industry. And so my challenge is, i feel like as an example with LinkedIn, I had a LinkedIn course in 2015 about social selling.
16:55.20
Sheri
I was too early and I thought I was too late.
16:58.99
Lorie Jones
Oh, yeah.
16:59.58
Sheri
So I gave myself a five-year window for Sway Live to become what I had, the vision I had for it. And the first year we had 25 people.
17:14.13
Sheri
Last year we had 75 people. And this year we're going to have 150. Or should say, I'm going to cap it at 150. Yeah, that's pretty, know.
17:22.46
Lorie Jones
Oh, that's great.
17:22.95
Sheri
And so that investment... you know and so that investment
17:30.48
Sheri
You know, I deeply desire to create a place for um people to come to to, you know, to dive into expressing who they truly are
17:43.16
Lorie Jones
Mm-hmm.
17:43.86
Sheri
And so I'm not a big fan of, like, personal branding being all tied up and, you know, wear the right color and that kind of thing. I'm very much in the camp of it's, you know...
17:50.97
Lorie Jones
Mm-hmm.
17:54.57
Sheri
um live a purpose-filled life um within you know with a heart of service, and that's your personal brand.
18:04.99
Sheri
And so um it's been great to see the community grow, and that was a really good investment too.
18:12.17
Lorie Jones
Yeah, I love that idea. If you build it, they will come is basically what you're saying, right? Like, first, you build an authentic, real you and, and people will come to that.
18:25.62
Sheri
Yeah. And I think the other thing of it is, is a lot of times as entrepreneurs, we have great ideas and then we go, here's a great idea. Here's a great idea. Here's a great idea. And, um, sometimes we just need to slow our role and let people have a chance to kind of catch up to us and understand what the idea is.
18:45.06
Sheri
And a conference, you know, a new conference on the, and you know, docket, that's a challenging, thing to ask for somebody's time for three days.
18:57.04
Sheri
So, yeah.
18:57.17
Lorie Jones
Yeah. Yeah. I like that. I like that you've been so successful at it too. And that's, um, I, what did you think that first year you put it on and 25 people came? Did you think, oh, great.
19:09.02
Lorie Jones
Perfect. This is wonderful. Or did you think, gosh, maybe not so many.
19:15.13
Sheri
I wanted, um,
19:18.52
Sheri
I was by set my goals for 50 people and I was disappointed.
19:21.65
Lorie Jones
Yeah.
19:23.28
Sheri
um But from the minute it started, I wasn't disappointed at all because it was absolutely perfect. It was perfect. And then last year I wanted 120 and holy criminy, you know, I'm learning as I'm going along what it means to sign a contract and all of those things.
19:43.27
Sheri
And goodness help us if we had 120 there because
19:43.30
Lorie Jones
yeah
19:47.57
Sheri
yeah we wouldn't have fit in the room that they said we would fit in.
19:51.17
Lorie Jones
ah huh
19:53.02
Sheri
So um I'm really, you know, getting better at what my requirements are. Like we don't have any more than four people at each table because we want we want to allow for intimacy and conversation and not having eight people at a table yelling at each other, you know, because you can't hear.
20:04.52
Lorie Jones
yeah
20:11.97
Lorie Jones
Oh yeah, that makes sense. Yeah.
20:14.25
Sheri
So when there's four, you can lean over or you can lean this way. And it's super easy to have a conversation even with four people, right?
20:20.22
Lorie Jones
Conversation.
20:21.67
Sheri
You can all put your heads in and you've got your own little space. So um that's why we're having 150 people there this year. And that's all because I have to have it in a spot that is big enough for 300 people, right?
20:37.00
Sheri
Because if I have four, usually there's eight people at a table or six people at a table.
20:37.52
Lorie Jones
ah huh
20:41.27
Sheri
There's only four at each table. So I've got... A lot more tables.
20:45.95
Lorie Jones
Yeah, yeah, yeah.
20:48.49
Sheri
Yeah.
20:50.17
Lorie Jones
What is the worst advice someone gave you, Sherry? Did you ever get some really bad advice and did you take it or did you not take it Did you learn from it?
21:06.33
Sheri
Well, okay. So I've been in financial services for 30 years and I've been in a sales and outwardly facing role many times.
21:10.23
Lorie Jones
Mm-hmm.
21:14.75
Sheri
And I've worked in, you know, very male dominated arena. Um, and
21:30.59
Sheri
would come home from work and I'd be overwhelmed and full of rage because I got passed over for something because ah guy had a family. And so other guys decided that that was better to take care of him.
21:51.88
Sheri
I had a family.
21:53.02
Lorie Jones
Mm-hmm.
21:53.33
Sheri
i was a single mom, but you know, that wasn't viewed in the same light. And I would come home and I would just be filled with just sorrow and rage. And, um,
22:14.25
Sheri
My sweetie pie i thought it was all my fault.
22:22.15
Sheri
You know what mean? And it wasn't.
22:25.82
Lorie Jones
Mm-hmm.
22:26.26
Sheri
It wasn't. It took him a while to kind of understand it. Like, oh, wow, you do work with all men. Yeah, I do.
22:33.72
Lorie Jones
Mm-hmm.
22:35.27
Sheri
Oftentimes the only one at the table. um... um
22:41.79
Sheri
Certainly, i am responsible for how I process things and what I choose to do with that information for sure. But
22:55.43
Sheri
I wasn't not performing, wasn't it? It was I was a woman.
23:01.04
Lorie Jones
Yeah.
23:02.75
Sheri
Yeah.
23:03.11
Lorie Jones
It wasn't, yeah, it wasn't, it wasn't your fault that, that these opportunities kept going. Did you, did you see that you've been in financial services for 30 years now? Did you see that dynamic change or not?
23:23.90
Lorie Jones
No, huh?
23:24.59
Sheri
um I don't
23:32.80
Sheri
i don't know, really. I you know i think that,
23:34.39
Lorie Jones
Okay.
23:37.34
Sheri
um
23:40.07
Sheri
you know, sadly, the conversations about diversity, equity, and inclusion are like a bad thing to talk about these days. But I think that my experience has been um when there are different voices at the table,
23:53.67
Sheri
um There's different kinds of creativity and different kinds of talents. And, you know, that can only um lead us to being able to serve different kinds of people.
24:05.84
Sheri
And there are so many people that need to be served by financial services. So
24:09.67
Lorie Jones
you
24:10.45
Sheri
um I think um I was very excited when I spoke at a University of Florida event recently, and there were about one third of the students in the room were women.
24:21.83
Sheri
So I was excited about that.
24:22.00
Lorie Jones
yeah
24:23.96
Sheri
Yeah.
24:24.31
Lorie Jones
there There are a few more female faces and i I've um been in financial services now for 15, 16, 17 years. So about half the amount of time that you were.
24:35.68
Lorie Jones
And I know that when I started showing up, I and i was one of two. So I wasn't the only one, but I was usually one of two. But now I see that I'm one of three or one of four. And so we are getting, you know, bigger representation. but um But I have certainly had conversations with when you're the only woman in the room, the only one there. And I never really thought about how um ah a male dominated industry did things like promotions and raises and, and you didn't have the network that a lot of the men had and you didn't have the opportunities to have a lot of the network that the men had.
25:19.16
Sheri
Yeah. And I got to say the other part of it is is that I had many men who were my mentors and supporters, and they lifted me up at every opportunity. So, um you know, I stand on their shoulders.
25:29.57
Lorie Jones
Yeah. Yeah.
25:33.25
Lorie Jones
Yeah, I found that as well, that there are men out there, many of them that want their wives, their daughters, their, their, you know, aunties, their sisters, they want them to do well and show up in this space.
25:33.50
Sheri
And yeah. Yeah.
25:46.18
Lorie Jones
Like, I've talked to a lot of different financial services firms where they're like, we'd hire woman, show us where one is.
25:46.27
Sheri
Yep. Yep.
25:54.06
Lorie Jones
Yeah.
25:55.32
Sheri
Mm-hmm.
25:59.56
Lorie Jones
So what about, Sherry, is there some situation that you can kind of look back on?
26:00.72
Sheri
Yep.
26:05.82
Lorie Jones
and And I'm not going to say regret, but that you would do differently. If you knew what you know now, back then, would you have changed the way you'd handled something? And how would you have changed it
26:18.18
Sheri
Well, um you know, I don't i can't think of the specific time, but I will tell you that um I think that um i i it came to me last year. And I'm doing some marketing work for an organization as a contract.
26:35.03
Sheri
And um I've always loved being part of the sales um team. I love being part of the sales team.
26:45.92
Sheri
Like when I took that job as a CMO, I went in there and the first thing I said was, okay, where when's the next time you have an opportunity to sell something? I want to help you do that first. You know, sometimes chief marketing officers come in and go, we need to rebrand and we need to do this. And I'm like, no, we need to sell.
27:01.98
Lorie Jones
yeah
27:02.42
Sheri
And I think, you know, that's one of the things I'm a little bit different. And I think that's kind of irritates marketing sometimes is that I'm more sales leaning than I am marketing leaning. And what occurred to me was that marketing is built for strategy.
27:17.97
Sheri
Sales is built for speed. So there are two different mindsets. Like marketing is working on, oh yeah, if you get a brochure in three months, it'll be perfect.
27:30.21
Sheri
And that sales is sales is like, I need that brochure tomorrow because I've got that conversation tomorrow.
27:36.37
Lorie Jones
Mm-hmm.
27:36.41
Sheri
And I think that's where the disconnect is.
27:36.53
Lorie Jones
Uh-huh.
27:39.29
Lorie Jones
ah
27:39.47
Sheri
And if I would have known that a little bit earlier in my world, um
27:51.35
Sheri
I might have not locked horns in as many, you know, because I, you know, like I'm a redhead. You can't tell. keeps getting darker. But, you know, um i I think I would have not been so put my head down and turn forward. I would have, I could have managed that differently. Yeah.
28:12.30
Lorie Jones
Yeah, that's, that's interesting. And it's interesting, too, that you, you gravitated so towards that sales role, um because you traditionally don't find a lot of, you know, women in the sales role, that's, that's probably how come there's not as many advisors that are women.
28:31.63
Lorie Jones
that you find them more in the supportive and the back office roles. So tell me how you got, like, do you just show up one day and you're like, oh, sales is where I'm meant to be or I loved it?
28:44.28
Lorie Jones
tell me about that.
28:44.63
Sheri
Well, what's interesting is is um I was um at that investment consulting firm back in 1994 when I started as the graphic designer for the education and communication thing.
28:45.04
Lorie Jones
Mm-hmm.
28:56.29
Sheri
In 1998, our salesperson left. And so I was de facto head of a department without anybody selling anything. And that was very concerning because then, you know, you don't have nobody selling your product. You're not going to survive.
29:11.51
Sheri
And I was out there hunting for a salesperson, dadada and two people who I worked with who were on the consulting side of the thing, the advisor side of the thing, sat me down and said, Sherry, why are you hiring a salesperson? Why don't you be the salesperson?
29:26.27
Sheri
it never occurred to me that I would be the salesperson.
29:28.31
Lorie Jones
Mm-hmm.
29:31.07
Sheri
But I went along on a couple of sales calls just to learn what you're supposed to do, right? And then I was off to the races. And that, um with me in the sales, lead sales for that division, as well as running the top line and then the bottom line, running the operations or overseeing the operations, that um division was profitable for the first time.
29:59.53
Sheri
in its existence.
30:01.91
Lorie Jones
ah
30:01.97
Sheri
So, you know, the first thing I did when I took over was raise prices. And then when I started selling, I did not sell individually.
30:06.62
Lorie Jones
Wow.
30:09.86
Sheri
I started looking for, um you know, selling multiple subscriptions, not just one subscription as an example. So, you know, the newsletter, i think it was at 20,000 printed versions and I changed it to 750,000.
30:19.71
Lorie Jones
yeah
30:28.34
Lorie Jones
wow
30:28.59
Sheri
So I was able to do a couple of different things, sell, and then also manage the print production because I had that skill set so that we could have even more timely newsletters that we could get out to the market. So it was very fun. It was really a really great time of learning and growing for sure.
30:51.28
Lorie Jones
Yeah, I like that.
30:51.67
Sheri
And now people send me their sons and daughters who are in marketing, and i always immediately tell them, Get into a sales role. If
31:03.63
Lorie Jones
Well, and that kind of ah well and of goes back to your idea of like, if you
31:03.99
Sheri
you want to have credibility in marketing, right?
31:10.72
Lorie Jones
had maybe had a little bit more understanding of ah sales and marketing and how they work together, you could have you could have helped a little bit earlier. you know So I wonder if if that's, you know like like there is a divide there in the sales and marketing teams. If if you can bridge that gap, the sky's the limit, really.
31:36.35
Sheri
Well, there's a new role that's starting to happen, which is um sales enablement, which is taking the stuff that marketing does and making it work for sales.
31:48.15
Lorie Jones
Yeah.
31:49.37
Sheri
Sales enablement, which is a perfect role for sure. um And i'm you know I'm glad that that exists for sure.
32:00.68
Lorie Jones
um
32:01.47
Sheri
Yeah.
32:01.65
Lorie Jones
Yeah. That's kind of, it's really interesting and it kind of does fit a lot of traditionally women are communicators and collaborators. And, and so that idea of like communicating and collaborating between these two,
32:16.11
Lorie Jones
um maybe differing ideas is is a really interesting place to be. and and I didn't realize that they were coming up with a sales collaborator or sales helper.
32:30.35
Lorie Jones
But I think that's a really great idea.
32:31.03
Sheri
Yeah.
32:33.84
Sheri
Well, you know, here's the one thing also that when you're thinking about salary, okay, when you're thinking about salary, um when you go into a sales environment, a sales dollar is a sales dollar is a sales dollar. There's no moving around it. You've got the compensation structure. Everybody has the same compensation structure. You sold 25,000 XYZ.
32:57.94
Sheri
Somebody else sold 20,000 XYZ. You're going to make more than them because of the how the sales commission structure works. So, um you know, therere um i would love to see more women in sales capacity in our industry for sure.
33:14.86
Lorie Jones
Yeah, me too. What, if you go back and talk to yourself at the beginning of your journey, 20, 21, 22, 18, somewhere around there,
33:26.90
Lorie Jones
what would you tell her
33:43.66
Sheri
Well, I didn't go to college. Well, shouldn't say that. I didn't finish college.
33:49.35
Lorie Jones
Mm-hmm.
33:49.99
Sheri
And um I remember for like my 10-year high school reunion, I wrote an essay about everything um that I learned. I learned after, you know, I left high school and it had nothing to do with college and everything to do with you know, me having a son, in fact. So um
34:21.98
Sheri
i think I think I would probably letter let her know that, you know, not everything has to be tied up in a bow and perfect, like, you know, what you see in the movies.
34:39.08
Sheri
That's probably what I would.
34:43.32
Sheri
but that she's enough even without school.
34:43.57
Lorie Jones
That life can be beautiful.
34:46.27
Sheri
Yeah.
34:46.34
Lorie Jones
Yeah. Yeah. I like that. I think that's neat. um And there are a lot of paths to success. I i think that i was just talking to somebody else about this, how like the young people nowadays are like, you do this and then you do that and then you do that.
35:01.92
Lorie Jones
And it keeps you from seeing some of maybe some of the more beautiful pieces of your life if you If you follow a prescriptive path, um sometimes you miss out on things.
35:15.17
Sheri
You know, did you, have you seen that movie, Everything Everywhere All at Once?
35:19.68
Lorie Jones
Uh-uh.
35:21.03
Sheri
Oh, okay. Well, in it, she's she's she's she's fighting with some bad guys and they flash back to her, um like spinning one of those, you know, mattress signs.
35:32.89
Sheri
Like she's using it to bash, you know, the bad guys or or she's doing something and she's rolling them up in a, but you know, like a, like,
35:36.54
Lorie Jones
Uh-huh.
35:41.74
Sheri
a rug like a burrito and it flashes back and she's making a burrito at the Taco Bell. I mean, it's so hilarious, but, but it, it, it flashes back to her learning some random skill in her past and how it's still serving her in the present.
35:48.19
Lorie Jones
Thank you.
35:55.90
Sheri
And I, for, for me, that is the thing that's been so much fun is I still continue to design. I still continue to do print production stuff, you know, and I, um,
36:09.80
Sheri
You know, I just designed a full page ad for Sway Live last week. I mean, I just so um i love the fact that. All of the parts, you know, parse parts and pieces of who I am continue to kind of show up and and I'm i'm grateful for it every day. I'm grateful.
36:30.48
Lorie Jones
Yeah.
36:30.58
Sheri
Yeah.
36:31.73
Lorie Jones
Like the path may not have been straight and prescribed and perfect and spreadsheeted, but it was exactly the path you needed to be on.
36:40.77
Sheri
Yeah. Yeah.
36:43.38
Lorie Jones
Sherry, what scared you the most when you started your career? And does it still scare you today or did you learn how to combat that?
36:52.99
Sheri
Hmm.
36:59.05
Sheri
Well, I, you know, I didn't, um,
37:05.32
Sheri
you know, the the biggest thing when I started the sales part was just even knowing how to have a sales conversation and, and never having like feeling like I never had any formal sales training.
37:20.22
Sheri
And it's hilarious, you know, that U S bank then put me through sales training and, and, and, um, that's all out the door, but
37:35.55
Sheri
Sales conversations.
37:44.20
Sheri
i think i I think I'm done being afraid of them. i think, you know, and I think that this came up just even with my son a couple weeks ago because he started a new role in a sales environment.
37:48.22
Lorie Jones
Mm-hmm. Mm-hmm.
37:56.76
Sheri
And I said, babe, don't worry about selling anybody anything. Worry about helping them you know, get their message out because he works for they the ABC affiliate here.
38:06.36
Lorie Jones
um you
38:10.69
Sheri
Help them find a way to get their message out. That's what you're doing. You're not selling advertising. You're helping them get their message out. And if you come from that place, um you're going to get your fair share, right?
38:24.02
Sheri
And so for me,
38:31.35
Sheri
having those sales conversations I'm still getting better at it. I wrote a blog post about it the other day. I've decided instead of calling it a call to action, I'm calling it an invitation.
38:42.39
Lorie Jones
Ah, I like that.
38:44.55
Sheri
Yeah.
38:44.67
Lorie Jones
Yeah.
38:45.46
Sheri
Yeah.
38:46.34
Lorie Jones
Yeah. Doesn't sound so much like you have to do this as much as, hey, let's just get together.
38:51.41
Sheri
Yeah. Like come along. This is fun. If it doesn't work for you, that's totally cool. You can ah RSVP. Yes or no?
38:57.61
Lorie Jones
Yeah. I like that. That's cute. I think that's a really neat idea.
39:00.27
Sheri
Yeah.
39:02.04
Lorie Jones
Because you do have those, um you know, sales is hard. um And it's... it, I, I tend to not actually want to say that I'm in sales. I don't actually think I am. I i feel more like I'm educating, helping problem solving.
39:21.88
Lorie Jones
So I like the idea of like, how can I help? Like, what can I do to help you out? Um, and that is a much more authentic and happy place for me to be than, um, can you buy now?
39:35.19
Lorie Jones
You know, that sort of thing.
39:37.46
Sheri
Yeah, yeah, it feels better, right?
39:40.01
Lorie Jones
Mm hmm.
39:40.29
Sheri
It feels better, for sure. Yeah.
39:44.26
Lorie Jones
Then I'm helpful. Right. What? um
39:47.97
Sheri
Yeah, and it just feels like service. Service is a good thing to be.
39:52.46
Lorie Jones
Yeah, yeah, exactly. And yeah, and that's what, you know, we spend our whole lives doing is just helping and serving and being there for others.
40:03.04
Lorie Jones
So what about um any unique challenges because you were a woman?
40:15.05
Sheri
Walking around a conference in high heel shoes. Damn.
40:19.79
Lorie Jones
I know. Those conferences are like 20 miles long. And if you get a pair of high heels that is getting blister on your feet.
40:24.03
Sheri
I love that there's a... Right?
40:30.78
Sheri
Like you think you have to. i got rid of all my high heels when I left corporate America. Now I just have cowboy boots. Yeah.
40:39.42
Lorie Jones
oh
40:39.86
Sheri
Yeah.
40:40.25
Lorie Jones
I'm a little bit jealous. I'm not even going to lie. I'm a little bit jealous. So...
40:46.65
Lorie Jones
so
40:46.95
Sheri
Yeah, I got rid of all of my suits that look like I you know was trying to look like a football player, right, with shoulder pads and dress up like a man and be what we think is.
40:53.11
Lorie Jones
yeah
40:55.41
Sheri
It was so cute when I was at University of Florida. And um all that all the students, they they were all dressed in the same attire that we would ascribe to financial services.
41:09.05
Sheri
A dark suit, dark jacket, you know, blue shirt, button-up shirt underneath.
41:09.89
Lorie Jones
Mm-hmm.
41:12.83
Lorie Jones
Mm-hmm.
41:15.67
Sheri
The guys were wearing, you know, regular shoes, loafers and women were wearing high heels. It was just like, oh my gosh, they just have this, you know?
41:23.42
Lorie Jones
Yeah. yeah yeah
41:25.82
Sheri
Yeah. So I'm so glad I gave up high heels. Woo.
41:28.52
Lorie Jones
Yeah. Yeah. ah i I do tend to once you reach a certain age, I think I've decided that I don't have to wear high heels and i can wear a little bit of color every once in a while.
41:43.52
Lorie Jones
So I i think that comes with being more comfortable troubleable with yourself, but I've heard that
41:45.28
Sheri
Yep.
41:50.22
Lorie Jones
so many times. And I felt it like personally felt it in financial services where I had to show up, I had to be wearing the black or the dark colors or the, you know, and, and I, I couldn't put a hint of, of motherhood or children into my speech or dress or mannerisms. And um it, it feels sometimes like you're bringing only half yourself to work.
42:15.42
Sheri
Exactly. Exactly.
42:19.88
Lorie Jones
What is the thing you're most proud of, Sherry?
42:30.57
Sheri
Well, my son. But all I did was, you know, decide to have him at 23. um He's just an amazing man.
42:44.81
Sheri
and a beautiful father. And, you know, it's been a really, um it's been a tough time for him. you know if he had had ah You know, he had his own little hero's journey and into the, you know, veil of darkness. But um I love my relationship with him and i get to go and hang out with my granddaughter now. And um so I'm most proud of him. Yeah.
43:15.19
Lorie Jones
ah It's, it's quite inspiring what they, what these children turn out to be and who they turn out to be.
43:25.84
Sheri
Yeah, yeah, he's a good man. Yeah.
43:30.42
Sheri
yeah
43:30.42
Lorie Jones
Any advice for a young lady who's just starting down the path you're successful at? Like if someone was starting today, what would you tell her to help her be successful like you?
43:43.10
Sheri
um I would say, you know, um one of the biggest things you can do and certainly what um was helpful for me was I was part of two very large communities. So when I was in Portland, um I was part of the Portland female executives community and that allowed me to test my leadership wings a lot. And that was phenomenal.
44:03.90
Sheri
And then, um In 2008, 2009, I got together with 12 other women and we started an organization called WIPN, Women in Pensions Network.
44:15.12
Sheri
Now it's We Promote, something, inspire, something, I can't remember, but WIPN.
44:18.83
Lorie Jones
Mm-hmm.
44:20.23
Sheri
So WIPN.org. And that community, um by you know giving of myself to that community, um i have dear friends that are now all over the United States. So My, you know, my thing really is for anyone just getting started, find a place where you can go help.
44:44.25
Sheri
Find a place where you can go help because there are so many places that need help. And in doing that, you'll be rubbing shoulders with people that might be lifelong friends or mentors or whatever, you know?
44:56.32
Sheri
So, um, find a place, be of service for sure. Yeah.
45:03.79
Lorie Jones
I like that. the i i do I love the WIPN organization and I think they do great things and they've got really good research and it's grown huge. We just had some sort of a ah birthday party and it was, yeah, it was like, yeah, great.
45:17.33
Sheri
Yep. 15 years, 15 years. Yeah.
45:21.23
Lorie Jones
Yeah.
45:21.29
Sheri
We started with 12 women. Our first event, we had 85 women. I remember sitting outside in Arizona with the 12 women who started the ah first event and we were sitting there celebrating and talking about what was going to be next after it. And a guy walked by and went, where's the men in pensions?
45:39.87
Sheri
And we're like, look around, dude. So yeah, Whippen has been, you know, watching Whippen,
45:42.20
Lorie Jones
Yeah.
45:46.09
Sheri
um I just, you know, i still there's I still have dear friends who are all over still involved and i still dip my toe in um on the regular.
45:57.75
Sheri
Yeah.
45:58.08
Lorie Jones
yeah
45:58.59
Sheri
I'm glad you find it resourceful too.
46:01.18
Lorie Jones
And I do think that it's it's an important idea to to kind of find your tribe, find where you belong, find the people that are going to help you get there. Like, you know, if you if you look and act like the the people closest to you, find people that are that have your same mindset, growth and, and um you know, positivity and helpful and giving back, like find those people.
46:19.92
Sheri
Yep. Yep.
46:26.80
Lorie Jones
And then you really can do one person. can do really amazing things in this life. So thank you so much, Sherry, for your time today and for sharing your story.
46:34.38
Sheri
yeah
46:39.00
Lorie Jones
I've really appreciated it. If I have a young lady who wants to get in touch with you and ask some questions, how does she reach you?
46:46.50
Sheri
You can find me on LinkedIn. So just, ship you know, we but we'll say it and then Siri will want to get involved again, but it's just linkedin.com slash in slash Sherry Fitz.
46:57.96
Sheri
You can find me there.
46:58.00
Lorie Jones
Okay.
46:59.13
Sheri
Just make sure you put a little note in that you are listening to Lori's podcast. So, because I get... um Some people that invite me and I have no idea who they are and I'm, I always want to make sure I protect my network.
47:11.35
Sheri
So I'm discerning on my LinkedIn invitations, but you can also find me at sherryfitts.com.
47:12.15
Lorie Jones
Yeah.
47:17.81
Sheri
Yeah.
47:17.88
Lorie Jones
Perfect. Sherry, thank you so much for your time today and for sharing your story.
47:19.41
Sheri
Yeah.
47:22.07
Lorie Jones
I've appreciated it
47:24.38
Sheri
Thank you, Miss Fearless Female yourself.