She's That Founder: Business Strategy and Time Management for Impactful Female Leaders

065 | Building a Community-First Business: Strategy Tips for Female Founders with Jessy Grossman

• Dawn Andrews • Season 1 • Episode 65

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Do you feel like you're stuck in a cycle of transaction after transaction, struggling to build lasting connections in your business? Or maybe you're unsure how to identify the right opportunities to grow your company into something more aligned with your vision?

In today’s episode of My Good Woman, I sit down with Jessy Grossman, founder of Women in Influencer Marketing (WIM), who built a thriving agency from scratch by spotting untapped market opportunities. Jessy shares her journey of shifting from a transactional business model to creating a powerful, community-first organization, and the lessons she learned about listening to her audience, aligning with the right partners, and trusting her gut.

If you’re ready to stop chasing quick wins and start building a sustainable, fulfilling business that’s driven by authentic connections and smart strategies, this episode is packed with actionable insights that will help you get there.

Stay tuned as we explore the mindset shifts, strategies, and big wins that will empower you to take your business to the next level!


In this episode, you’ll learn …

  • How to build a community-driven business that fuels long-term growth.
  • How to trust your instincts to create a business aligned with your vision.
  • How to build resilience and adapt when facing unexpected business challenges.


This episode at a glance:

[2:45] – Jessy’s journey from commercial talent representation to influencer marketing

[12:10] – The birth of Women in Influencer Marketing (WIIM) and why community matters in business

[20:15] – The differences between an influencer talent agency and a networking organization

[55:33] – Jessy’s advice to female founders: Trust your gut and expand beyond your comfort zone


Resources and Links mentioned in this episode


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More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews.

Grab a seat at the table with me each week for candid conversations with culture-shifting, glass ceiling-busting, trailblazing women, who are leading enterprises that are making a change in the world. 

We discuss what makes them tick and how they get it all done. And we share actionable strategies to help you and your team get organized - so you can focus on your company’s growth, profit, and impact. 

Want to increase revenue and impact? Listen to “My Good Woman” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

My Good Woman
Ep. 65 |  Building a Community-First Business: Strategy Tips for Female Founders with Jessy Grossman


Dawn Andrews: Hey there, listeners! Before we dive into today's episode, I've got some exciting news. We're nearing the end of my good woman, as you know it. But don't worry, this is just the beginning of something even more epic we're transitioning into she's that founder where we'll take all the momentum we've built and supercharge it. 

I'm a Marvel super fan. So patriarchy be damned, I just love superhero movies and like in a Marvel movie, you've been with the heroes, through the origin story, learning their powers, facing the challenges. But now we're heading into the next phase where the stakes are higher, the action is bigger and the team comes together to conquer new challenges. 

This new phase will bring even more empowering stories, practical strategies, and bold moves to help you step into your full power as a founder and CEO. Here's the important part, we're going to take a short break. About six months before she's that founder officially kicks off. 

Six months, guys. 

But don't worry, I've got you covered. If you want to stay in the loop, be the first to hear about the launch, get a few sneak peaks and special bonuses along the way, make sure you join our mailing list. 

You'll get exclusive updates behind the scenes content and all the exciting news leading up to the show's return. To join the list, head over to dawnandrews.com/mailing list and follow us on social media for more insights and previews while we gear up for this next adventure. She's that founder is going to be packed with everything you need. To be the leader and business owner that you were born to be.  And I can't wait to share it with you. 

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Jessy Grossman: there are lots of things that I wish I knew getting into that situation, you know, luckily I feel like I navigated it fairly well. Luckily I landed with a business of my own now that I feel so much happier and more fulfilled in. But, the truth is it wasn't my choice to sell my own company and that's like a pretty insane statement to make. And that was my truth, you know?

Dawn Andrews: Welcome to the My Good Woman Podcast where we help female founders break past plateaus and get to the next level of business growth by refining their strategy building systems and streamlining operations. 

I'm Dawn Andrews, the founder and CEO of free range thinking business strategy consulting. Join me each week for candid conversations, with culture shifting, glass ceiling busting, trailblazing women who are leading impactful enterprises and grab their strategies to help your business reach extraordinary levels of growth.

In today's episode with Jesse Grossman, we're going to talk about how to spot opportunities and build something from scratch when you see a gap in the market, just like she did with her influencer agency. We're going to talk about why shifting from a transactional business model to a community first approach can lead to greater success and fulfillment, why listening to your audience and staying responsive to their needs can drive your business growth. You'll also learn about the complexities of business partnerships and what you need to consider when you're aligning long-term goals, especially when it comes to selling your company. Enjoy my conversation with Jesse Grossman.

 

Dawn Andrews: So welcome to the My Good Woman podcast, Jesse Grossman. I'm actually truly excited to re-meet you. We had like a little tiny chitchat before. But this is a whole area of marketing that obviously I'm familiar with on a general basis, but not in detail. So I'm totally excited to dig into your world today. Are you up for that?

Jessy Grossman: I'm so up for it and I'm super excited to be here. So thank you.

Dawn Andrews: Excellent. Well, why don't we start with a bit about your journey into the world of influencer marketing and then also what inspired you to found women in influencer marketing?

Jessy Grossman: Yeah. Okay. So I will give you the details, but not hour long, you know, backstory. So, everyone has a different route into getting into influencer marketing because it is like a fairly new industry. My path was in talent representation, before I represented influencers, I used to represent actors in commercials.

And so, you know, being here in New York, it's a big entertainment industry. I have like a BFA in theater, so I've always been in entertainment, but always sort of on the behind the scenes. When it comes to that world, it was a little, it was fun while it lasted, but I wanted something more modern.

I wanted something more fresh and new and exciting to get into. A friend of mine, an old colleague of mine actually was the one who tipped me off. She's like, you know, she ended up working in casting after talent representation. And she was like, Jess, you should really look into this influencer thing. She was like, we're casting campaigns and projects and commercials for influencers.

But like these people don't know the professional side of the business because they don't have an agent, they don't have a manager. They're just producing really incredible content online and we want to work with them, but they could probably really use that extra support. So. I ended up, starting this influencer department at the agency that I was at.

It was super fun. I love building things from scratch. It still exists to this day, so it's really exciting to build. I only left because I wanted, I got like the entrepreneurial bug and I really wanted to start my own agency. 

Dawn Andrews: Well, it sounds like you already had it, Jesse, because to start something like that on your own. Where, I mean, did the agency put people in time and attention on it? Or was it one of those things where they just said, we see something for you and if you want to do it, go for it. And so they just let you run with it. 

Jessy Grossman: I mean, transparently, like they supported the way that they could, meaning like they didn't understand it. You know, they had come from this very, very old school, traditional world of entertainment, but they saw that it was bringing in money. Like they saw that it was lucrative and that it had potential. I was the one that really drove it forward.

Dawn Andrews: Was able to package it and put it into a vertical business line for them. 

Jessy Grossman: Yeah, absolutely. Absolutely.

Dawn Andrews: Got it. Very cool. Well, and so that was before you left to start your own agency, which you then grew and built, correct? 

Jessy Grossman: So, then I left there only to start my own agency. We grew that to about 10 or 11 people before we decided to sell it. But that was an influencer specific talent agency and I don't know, again, like I'll probably repeat this a couple of times, but like, I really enjoy the building aspect. So I loved building it from, you know, from scratch, but also pulling from the experience that I just had at that other agency.

We had incredible clients. We were, you know, securing brand deals for them, commercials for them, endorsement deals. And just like very much navigating new waters though. I mean, it was very new to all of us and that was actually what led me to create what was at the time purely a passion project, which was called Women In Influencer Marketing or WIIM for short.

That's what I do with, you know, I'm full time today and that's what I decided to jump into after I sold that talent agency, but to be honest, like it just started because I was looking for more deals for my clients. I was looking to learn about this industry that like, I felt like I understood from an outsiders perspective.

Like I understood entertainment, I understood, negotiating contracts and deals and, networking, but there were so many nuances that were different. There were so many nuances that I wanted to wrap my head around and master. And the only way to do that, because it's actually wild nowadays, there are degrees in this and learning about influencer marketing, which I think is so fascinating, but it certainly did not exist back in the day.

Dawn Andrews: I know you're a trailblazer, girl.

Jessy Grossman: Well, I appreciate that, but I guess like what I want to, I'm always very honest about this. Like the reason it started was just because there was a need and I couldn't find the answer in other networking groups. I couldn't find what I needed elsewhere. And I was like, I'm going to build this.

I'm going to see, because I can't imagine that I'm the only one who wants to make these connections who are in this industry and have so many questions. So we built it and that's what I do today. It's the most incredible job. I'm so lucky. Cause I genuinely love what I do. I've always sort of wanted to help people.

And like, sure, I was making influencers money before a nd you can argue that that's helpful. But this is like, getting marketers jobs like this is, you know, seeing people get laid off and then being like, I don't know what to do next. And, educating them about, you can go out on your own and be a consultant, or if you want to dive into the job market, here's the best way to optimize your LinkedIn.

And let me connect you with all these people because they're actively hiring. You know, we have a mentorship program. That's incredible. We have events like it's just this incredible ecosystem on the internet, but also in person, that is WIIM. So it's a little bit about us.

Dawn Andrews: Let's back it up a little bit and give me the distinction for people who may not be familiar with what it looks like on the other side of the curtain. What's the distinction between the agency representing influencers that you had and what you're doing with influencers and women in influencer marketing. So what is the distinction between those two? 

Jessy Grossman: For sure. Great question. So the agency that I had called Boldstreak, it was a talent agency. So we, our client was the influencer for all intents and purposes. And we would broker deals, mostly brand endorsement deals between them and the brand that they were endorsing. And we, you know, took a very hands on approach, but like, it was pretty much like a well oiled machine. Like that was what that business was.

Dawn Andrews: So you had like 11 to 12 clients and each day you'd be on the phones or out networking saying, Hey brand X, like, Hey Dev, I have this great person who would be a wonderful fit for your brand. Let's put you guys together. They'll create content. You'll pay them. That's the transaction of the influencer marketing agency that you had. Yeah?

Jessy Grossman: Definitely, Yeah. So we had about, oh, I'd say probably like 40 clients, 40 influencers that we represented. We had about 10 employees. Maybe that's the number that you're thinking. 

Dawn Andrews: Oh, got it. Got it. 

Jessy Grossman: And so we had about 40 influencers in different niches, like, most of our clients were, Instagram focused, but many of them were also on TikTok.

It was like when TikTok was just starting to be a thing. some of them were also on YouTube and, it was split into two basically, either, you know, we had relationships with tons of brands and agencies that represented those brands who were like, Hey, they'd come to us, I need someone who reaches this specific demographic.I need someone who reaches moms in the Midwest who might be interested in buying this type of product or using this type of service. Who do you have that fits that spec? And we would make suggestions of our clients, hopefully get a few of them on that campaign. And then once we, you know, landed on rate, landed on usage of the content.

Exclusivity requests, anything like that. We would, you know, negotiate the contract from start to finish and then manage the campaign flow from start to finish because there's rounds of approvals of the content. I mean, if you're getting paid to promote something, they want to make sure that you're covering your basis in terms of, you know, FTC requirements and, posting the applicable language that makes sense for what the brand is. Some of them are way more strict than others in terms of that back and forth approval process. We'd invoice and then, you know, move on to the next one. 

Dawn Andrews: Well, thanks for diving into that a little bit more because I was thinking about, at the higher level with larger brands that have bigger budgets and can cascade down from we're placing a major billboard buyer and ad spender, whatever, and then we're going to go more granular and find these influencers that have these pocket audiences.

I was thinking about smaller companies that using an influencer actually might be the most targeted way for them to be able to grow and to grow quickly. And many of them are not going, they're probably entrepreneurs, they're probably bootstrapped, so they wouldn't have been exposed to this influencer marketing world.

And I wanted to thank you for sharing it because I wanted to give them an idea of what's going on on the other side. You know, the other side of the transaction so that they get that it's not just that you want to reach that group of people. There's a whole world that's going on for that other person that's creating the content for you. And it sounds like that's what you're starting to do with WIIM a little bit. Like doing a little bit of global education for people. 

Jessy Grossman: So it's certainly educational. WIIM instead of being, you know, this transactional agency, it's not that. It's a community first and foremost. In a traditional sense we think of it as a networking group, right? And so we have, I think we're at about, just about 600 members predominantly in the US, but we certainly have some pockets overseas like London.

We have a lot of members Toronto we happen to have some people but mostly in the US and these members are mostly influencer marketers. So that means they work in house at a brand and they're hiring their influencers for that brand. Or they work at an agency that represents many brands and they're running all those influencer programs.

We have tons of talent managers, like what I was describing my company was before, but we also have lawyers who specialize in creator economy and accountants who niche down into working with creator economy folks. And, we have people who work in creator economy tech, like there are a lot of tech products that, help us find and search and discover for, the influencers that we're looking for for a campaign. 

There's tech that helps us manage the million of different, variables of what is, to run a campaign with a hundred influencers, let's say, and that's like, fairly standard for one campaign, giving the contract and tracking the approval process and tracking all the back and forth of, there's just so, you know, getting them the product and, the shipping, tracking information.

Like there's tech that has been created for the past 10 plus years to support that entire workflow. There are companies that are, working at those tech companies that are members of WIIM who just, you know, they're always looking to meet folks. They're always looking to continue to learn and be privy to, the latest and greatest of what everyone's experiencing because it is a new, pretty, you know, relatively new industry, like maybe 15, maybe max 20 years old at this point.

And then, you know, we've got in person and virtual events because, some people will have a question that they need answered ASAP, so they go into our Slack board. But for those who are looking to just generally, you know, have a girl's night out, because it is a women's focused group. And just like meet like minded women in the space who just get what they're going through on a day to day basis and want to have a fun night out though, we host community building events as well.

So we have a lot going on and transparently, it's part of the fun of running a community, part of the trouble. If you want to call it that is, keeping a pulse on what your members need from the organization and that changes all the time.

Dawn Andrews: How do you do that, Jessy? What methods do you use to stay in touch, especially, I was just thinking as you shared the kinds of people that are in women and influencer marketing in WIIM, I feel like I've dived into Atlantis, you know, there's just this whole world of people that you've brought together which is a beautiful thing because it sounds like you kind of have 360 representation of all the different parts of the industry, but that can be really challenging to be able to service the needs of the people that are in the community. So what do you do to be able to keep track of that? 

Jessy Grossman: I mean, I think from the outside it sounds like this incredibly niche community, right? It's not just any type of marketing. It's like influencer marketing and it's, women focused. So it sounds so niche. But in fact, it's such a huge industry that that's actually like a fairly large amount of people.

And each of those people, some of those like subgroups that I sort of described earlier, they all have very different needs. Right. And so for us, I think it's always about trying to connect the dots. Like who is best to be in next to and in company with who, like who, who should we pair together? 

So for example, we have, a casting portal basically where, brands will say We're looking for these types of influencers who fit this, type of spec and who, fit this type of budget that we have. Who do you have? Who do you know? Who's right for us? And then our entire talent management community will then pour into that and say, we represent this person, that person. So we're always trying to connect the pieces together. It's an interesting place to be that we've always had a community forum.

It's changed locations a couple of times and I'm really happy with where we are now, which is on Slack, it used to be a Facebook group for context. But having all that chatter, I'll tell you, I'll be honest, like, whether it's specifically in WIIM or it's just business in general, I've had my biggest successes professionally because I'm a great listener.

And so it's not necessarily that I'm like the ideas person sometimes, but rarely, most of the time it's like, you know, oh, interesting. This conversations like really getting some engagement, some traction, like what's in that? Like, obviously this is a problem for people, or this is an issue, or this is something that needs to be solved.

Or, you know, we need to have more conversation about it. So it's truthfully, it's just listening to the chatter that's happening organically within our community, but of course, like proactively asking certain stakeholders that you think could really have a pulse on it. 

We have a couple groups of folks that are like, extra involved. Our mentors, for example, they're like more senior level folks who've raised their hand to say, I want to mentor the next generation of influencer marketers. Right. So I'll use them to pick their brains sometimes. And then, we have a group of ambassadors who are planning and orchestrating like these in person community building events for us and all these different pockets in the U.S and so for them sometimes I'll tap them for certain things.

Right? We're a small, nimble team when it comes to who we actually employ and the contractors that we work with, but I have 600 other people that I can ask about their opinions and insight and what they really need and it also makes them feel like valued at the same time. It's so mutually beneficial because, you know, if, I can ask them what they'd like more from the organization and what they're struggling with, we can be nimble enough to create an event around that. And then we give that to them and it's so mutually beneficial and helpful for everybody. I think. 

Dawn Andrews: What's popping for me as you share this is my brand in particular, I don't reach out to influencer marketing. So some of my listeners, they may be devouring every word that you're saying because it's such an exciting possibility for them. And then for other listeners, what's popping for me and what you shared, first of all, was your listening and leveraging the power of your community to tell you what's next.

Because what I think can sometimes happen from an entrepreneurial perspective, your founder, you think you know what's best and you may or may not be fully connected to the people who are using your service, your product, et cetera, and really understand what they're telling you is next and your life can be so much easier if you just leverage your community of 600 and talk to them and see what starts to gather steam.

And the second thing that popped for me and what you shared around sort of being your own personal influencer, like being the influencer related to your brand and sharing on social, et cetera. I realized that sometimes I get very precious about what I choose to post or I try to think about what the right thing to post is.

If I just start sharing and then see what the community says. Then that'll start to direct me and make the process easier. And I don't have to work so hard at trying to get it all right before I put it out there. You've freed me up just in sharing how you're working with your community. So thank you for doing that.  

Jessy Grossman: You're welcome. And about that in particular, that last point I can share that like, that's been a personal struggle that I've been trying to sort through for the last like couple years in particular is like post pandemic when WIIM was In like V2, like the version that it is today, closest to that.

A lot of people were telling me like, you as a founder should be sharing more. You should be sharing your story. You should be more connected. It shouldn't just be everybody else. You're the face of the company. Like I shared with you, like, I've always been entertainment, but I've been like behind the scenes.

I've always been like way more comfortable in that role. And like you were describing, so I'm like, okay, so I've been, I'm being told that I should do this. I should share like on LinkedIn, for example, which is an incredible, I mean, you can have a whole conversation about the power of LinkedIn, you know, and, or sharing within the community.

And I'm being told that I should do this, but I would overthink it. Because I wasn't comfortable with it. I'm like, I don't like really necessarily being on camera. So like when people were doing all these live streams and creating all this content, I'm like, that's just not me. That's not how I would want to share my thoughts, but trial and error and figuring out like, well, I do love writing and being very candid about certain things and being sort of like, you know, whether it's calling people out or just like really pushing boundaries and what's being said.

And, also just cultivating, a safe space where people can talk, like speak back and to say like, well, here's what I think, here's what I think, or just like be the epicenter of like some really interesting conversations. That started to resonate with me personally. And so when I started finally discovering what felt more natural for me and fun and certainly comfortable. Then I leaned into that and everything. It didn't, it wasn't a chore anymore. It wasn't this scary, like, oh god, I got to do this thing this week. Cause I'm being told that I should do this. 

It was more like, okay, like this feels natural. Like this feels good. And I saw that it was absolutely serving the business as well and felt right. I would also just say like for people who are being told, you know, you should be more vocal or public or like whatever that is. And if it doesn't feel natural for you, there probably is a version of it that does. And I just think it takes a little bit of time to figure out what that looks like. 

Dawn Andrews: So what did it finally look like for you? Getting like nuts and boltsy for a minute. So what has been recommended to me is, across multiple platforms, right? So I'm not going to go into every single platform, but like posting five times a week, getting at least two reels done, turning me basically into a content creator and I'm like, girl, I'll talk for that.

So what does it look like now that you've found something that really resonates and is a little more in alignment for you personally, what are you doing these days to promote the brand, but also share yourself? 

Jessy Grossman: Yeah, I mean I would say like for me I  focus on like a couple different mediums in particular. I'll distribute content in other places but I really have a couple focuses.  So for me, I mentioned LinkedIn, it's been a really powerful place for me. I've met other people like I'm part of the LinkedIn creator  program. It's my social network, you know, where it actually is a social platform, but it's with a business mindset first and foremost. 

So it feels so different from like an Instagram or, you know, a Tik Tok. And so for me it makes sense. It's one of the only social platforms where the text of your content is always first. Even if you post a picture with a caption, it's the only social platform where the text is actually always above any sort of imagery or video or anything like that. I think that says a lot about what LinkedIn is. It's all about thought leadership and, discussion and ideas that's always just resonated with me. 

Dawn Andrews: You just made me fall in love with LinkedIn, seriously. That's my primary platform as well, it's one of those things where you're like, I feel like there's something there. We've gone on a few dates, but I'm really not sure. Like, is this a thing or not? And so now I'm like, oh, okay, you just totally like pop that bubble for me. I'm all excited about it now.

Jessy Grossman: And then you start to find your group of people too, who, you know, will engage in those conversations with you somewhat regularly on LinkedIn and it's similar, I'm sure, to what people experience when they have a following on any platform. But again, it's like dating apps, like the people that are attracted to each one are like slightly different. It's like, are you a Tinder person or a Bumble person? 

Are you a LinkedIn person or an Instagram person, you know? And so I love LinkedIn, I use it all the time on a regular basis. And then I'm also a podcaster, you know, I think I see a through line and similarities between the two. But I, just love sort of being in conversation with people and, getting everyone's thoughts and ideas out there. 

Dawn Andrews: I share that with you. I think we're, I mean, do you consider, not that this is meaningful of anything, but do you consider yourself more introverted or extroverted?

Jessy Grossman: I'm definitely more of an introvert naturally, but I can be extroverted, you know, like I can host an event. We host events all the time I do a lot of panels and speaking engagements and moderating and you know, it's interesting I'm like professionally trained to be on stage. I've had a theater education for middle school, high school and college. So like, while I can do it and I feel really confident in that, the end of the speaking engagement or the end of the event, I'm physically and emotionally exhausted. 

Dawn Andrews: Girl, oh, man, I feel you. 

Jessy Grossman: And what I've learned, I don't know how familiar you are with like disc profiling, for example. So I've learned-

Dawn Andrews: Yes, we, I use the disc profiles in my work. Yeah. 

Jessy Grossman: Yes, I'm, I loved it. I like, when I learned about it, I was like, Oh, this is so fascinating. So when I learned, about disc profiling, so like I'm a D and a C, I'm certainly not an I at all whatsoever.

And so, again, like while I might be able to do do these things. It's not my like natural style. And so I finished doing it and I could, I need like a two day recuperation period. All the things. So yes, a little more naturally introverted. You too. Are you more naturally introverted than extroverted?

Dawn Andrews: I am. Yeah. Well, I mean, we share similar love LinkedIn, love my podcast, tend to, you know, my greatest joy in my work is being in conversation with my clients. And I do so much. I'm, I don't know if I had taken measurements of my ears when I first started my company to now, but I do truly do feel like they have grown because they are the muscle that I use the most like that in my brain.

So I do share that with you. I have the big chair in my office. That's me in a book most of the time. And it's just a happy place, but same also a theater geek. Also college trained and I do love to be on stage when it's, a great audience and, content that you're excited to get out when you know that you can make a difference for people. But I also have to have the sleepy time.

Jessy Grossman: And it's so interesting too, because I, feel you, like, some of it sounds conflicting, some of it's like, well, how do you do that? But also you consider yourself an introvert or you just like alone time and like, I don't know necessarily even how to describe it, but think the best way I guess it's just I can do it and there are certain elements of it that I do enjoy, but it's just not like my natural way is being I love alone time. I thrive, like I need some alone, like every week I recharge when I have alone time, but, and I so prefer being with like one on one with people versus me and like a small group even. 

I'm just like, too much. It's like the energy of it is like a little overwhelming sometimes, certainly with like big groups of people. And these are important things, I think, to just like ultimately have a self awareness about. Because I think it really can help you if you're, you know, running your own business and you run into these obstacles where you're like, Oh, I, can't seem to do this task because I'm putting it off so much. And then you figure out it's like, well, cause it's something that's just not.

Dawn Andrews: It's out of alignment for you. 

Jessy Grossman: Yeah. And the only way to problem solve that is the, I mean, the first step is just being honest about it and having the self awareness to be like, okay, like this isn't me. So now I can problem solve it. I can outsource it. There's a ton of ways that you can work through it, but I find that, yeah, when I'm coming into some sort of like, turbulence within my business. I'm like, all right, I got to take a beat and figure out what's going on here. You know? 

Dawn Andrews: Speaking of that, so you've built and sold a six figure influencer management company, what's your personal philosophy on leadership and leading and being an entrepreneur and how has that evolved as your career has progressed? 

Jessy Grossman: So it's a very complex answer. You know, so when I had my business, I also had two business partners. I think that's important to bring up because, even selling the company, the way that the company was run, it wasn't my sole decision. And in fact, it wasn't even just me and one other person.

There were three of us in the mix that had, ownership of the company, right? So that's a very different thing than when you're 100 percent owner of a company, which is what I have with WIIM now. So when it came to leadership, like, I sort of spearheaded, things that I felt most passionate about, I felt most knowledgeable about. And then I would sort of, Divvy out, the other things for other folks who were co owners of the company. 

Dawn Andrews: What did you hang on to, Jessy, and then what did you pass off to them? 

Jessy Grossman: Yeah so for me, I felt like I was mostly wanting to be the client facing person. So in influencer marketing, when you're managing influencers, it is the most relationship based business. From the outside perspective, it should be transactional, it should be professional, but you know, these people on social, when they're successful influencers, most of the time they're posting about very personal things.

And so, if they're posting about, challenges with their children, let's just say, I represented like a lot of family influencers, they could be approached by, a company like, I don't know, we have, so many sensitive topics like, therapy companies, there's so many out there that are working with influencers or, financial companies, or we're talking about with somebody the other day, like health issues, that they're products, medications, things like that, that are like looking to help those people. 

And when it comes to influencer marketing, one of the most successful ways that influencers build their brand and their entire business is because they're incredible storytellers. And so I'll circle back to just say like, it ends up being very personal, the relationships that you have with these creators and I took all of the relationships that I had at my previous agency and brought those clients to this new company that I built.

So I felt, extra indebted to them. They took a chance on me, they left this well known huge agency to work with me at this, fledgling company that we were just building. And so I really leaned into the client facing part of that and make sure to constantly check in with them to manage their expectations. It's a huge thing and to just feel like we're all on track for what each of us is looking for from the other in our relationship together.

Dawn Andrews: As you came closer to the sale of the company, your leadership perspective was handling, you're managing those relationships. How did that work with your partners in terms of the continuity of the company and the next steps that you were taking as you guys are looking to let the company go to its next owner? 

Jessy Grossman: Yeah. I mean, transparently we were in very different pages when it came to even the sale of the company in the first place. I could have had that company for a lot longer, I didn't want to sell, transparently. They went into the business always wanting to sell it, but didn't necessarily communicate that in a way that they, they should have early on.

And so we sort of got to this, like this friction point where it just made the most sense at that point to let it go. But yeah, it was a very interesting experience in a lot of ways. I sort of had this business to a certain extent for two to three years prior under a different company, right?

And so with that agency that I worked with, then when I went off and did it on my own, well, with them, they were like, so here's what we can bring to the table. You know, we can bring this expertise, that expertise, this, that, and the other. And so they sort of came to the table telling me that they would elevate the business in certain ways. And so I think that that was like an interesting scenario to be in and that like those expectations were sort of set early on.

Dawn Andrews: Yeah. it's fascinating to hear about, I mean, we could have a whole conversation just about the process of selling the company. What I find when you're in a partnership or in your case, a trio, there's so much that needs to be worked out before you even get the business started.

And then there's so much you realize you didn't work out when you're trying to sell it. Things that you thought were clear things that, and I don't know how much of this is true for you, but just speaking in general about getting to the place of selling when you're in some sort of partnership and, things that you thought were clear expectations.

Where each of the founders are and what their needs are at that moment when you're getting close to sale, as opposed to what they were when you started. it's a huge moment for everybody. So how did you continue to lead during that time? How did you manage yourself to get through the sales process? Was it a quick sale? Once you guys decided, did it turn around pretty quickly or is it protracted? 

Jessy Grossman: So it was a very quick sale, for sure. A lot of people hear that, you know, oh, she sold a company or, oh, like anybody sells a company and it sounds like it's like the pinnacle of achievement for anybody in business.

And I thought that too before I had sold one. And then I sold a company and you just learn a lot of the realities of what's behind the scenes and doing that. And then I of course met many other people who have sold their companies after I did. And a lot of people have stories where it's like, it is not this romanticized story that we hear in Forbes and we, look up to and admire all these people, the realities can be very, very different.

It was the right move for me. And like I mentioned earlier, it wasn't my choice to sell my own company. And that's a pretty tough pill to swallow. And having business partners is something that I would not see myself doing in the near future, because it was a very tough thing to navigate. 

And, you know, so yeah, you, there are lots of things that I wish I knew getting into that situation. Luckily I feel like I navigated it fairly well. Luckily I landed with a business of my own now that I feel so much happier and more fulfilled in. But, the truth is it wasn't my choice to sell my own company and that's like a pretty insane statement to make. And that was my truth, you know?

Dawn Andrews: Yeah. Well, I'm curious, going back to the top of our conversation, you were saying that you really love to build things and you've sold the company, you've built WIIM, what's next? What's the next goal? Is it going deeper into the world that you've created with WIIM? Is it a next new company that you kind of have in mind? Like, what's your goal? 

Jessy Grossman: Yeah. So I appreciate that question. I think like with WIIM, it's having a community is really enjoyable for me because it is constantly evolving and changing and I enjoy that out, like that element of it so much. So I feel like, you know, it's, we're in like a really exciting growth phase right now. We're leaning so heavily into in person events right now. We're producing in person events in like 12 different markets every single quarter. So it's like 40 plus events like in a year where last year we held these, you know, we held like five tent pole, like a hundred plus person events, but we're trying to really explore something different.

And it's going so well, but it's like, it's a learning process. I think that's part of what I learned. I appreciate the most about this business is that I can be nimble. I'm in a position where we're the size of the company that we're at. I love being nimble. I love being efficient. I'm like obsessed with automations and operational stuff. I'm like such a nerd when it comes to that. So like, I love seeing how much can we build with the fewest resources possible, but still create like a really quality product for people. That's been fun.

Dawn Andrews: Be nerdy with me for just a second. Like, what's your favorite automation at the moment? And I get that it may not be the same tomorrow, but what do you dig in today? 

Jessy Grossman: Yeah, I mean, I'm obsessed with Zapier. So I was just in there earlier, like we got a new sales person for example. And so I'm trying to share with her when job postings are posted to our site. How do I get her the information best when people say, I'd also, I'm also interested in being sent, you know, these couple other additional pieces of information. So I was like, Oh, let me tweak this. So we have probably hundreds of, you know, they refer to them as Zaps and Zapier.

I love Zapier. I'm obsessed. We also have a very custom website built on WordPress. So some of the stuff in there will automate, you know, we've got funnels when it comes to our email marketing, which I love MailerLite.

Not everybody knows about them and I think they're one of the best email marketing programs there are. So I love MailerLite. I've been using, well, we're in, there's a really cool, uh, new, I don't think that it's that new, but this cool app that I've found, it's a website, I guess, called Common Room.

That's been really exciting to automate some of our messaging in Slack. So when, for example, when a new member joins, they automatically get sent a welcome message in there. And then if they're inactive for X amount of time, they get another follow up message that says, you know, Hey, just wanted to check in, blah, blah, blah.

We are sponsored by companies, that want to get in front of our members. And so when it comes to those, sometimes we'll also use common room to just send people messages, in an automated way to say, Hey, you should check out this product, blah, blah, blah. Or, what are your thoughts on this topic? So we use it in a number of different ways, but I think people from the outside who don't necessarily realize that I'm like this operational nerd or like, how are you that like communicative with hundreds or thousands of people. And you know, I do think it's important to take automations to a certain extent.

I'm obsessed with like AI automations, all that stuff, but I do think that you should take it. It's like it saves you like the first 10 percent of your workload, right? And then when the person responds, then I respond as me, but it's like best opener. It's the best way to get people more engaged, a reminder to check in, stuff like that. I can go on and on because I use this stuff in so many aspects of my business. 

Dawn Andrews: Oh, I'm so appreciative of it. Yeah. I'm I also, most tech, least effort always.

Jessy Grossman: Yes. A hundred percent. And it saves, it saves time and there's just nothing more valuable to any business owner than your time. And so if you can save some of that by automating things, like it's such a, game changer, you know?

Dawn Andrews: For sure. Okay. I got a couple more questions before we wrap up, but what I'm wondering next, because you are, you are a young woman who has accomplished a lot. And I am very curious, looking back even from this point, what advice would you give to your younger self when you first started out. Especially knowing the hurdles that female founders face, especially being in this influencer marketing space that is a newly developed industry. What advice would you give yourself?

Jessy Grossman: I'll tell you what I wouldn't tell myself. I wouldn't do anything differently. I'm just a very firm believer that even if I struggled back then, or even if it wasn't perfect by any stretch of the imagination and I felt all this angst and whatever. It also like completely led me to where I am today.

So, I wouldn't necessarily change anything. If I were to give myself some advice, I don't know. I would expand beyond my comfort zone more, you know. I feel like I did that , but I wish I had done that more. 

You know, like living in New York, for example, you have access to so many different things. And I feel like now as, a 37 year old, I'm exploring new networking groups, like I'm part of, EO entrepreneurs organization now, and I'm part of all, some other communities where I'm like, I just wanted to like, get out of my circle, like the people that I know and just be introduced to different things, new things, and it's all been additive. 

It's all really helped me see things better, more clearly, certainly differently. And I, I wish I had done more of that when I was younger, earlier on in my career. And I guess one other thing that comes to mind too, is like, I had a lot of people, and I think this applies a lot to women in particular, I speak very personally. I had a lot of people who, not a lot, I had a handful of people who were not my cheerleaders. 

In fact, they were the complete opposite and they would make me doubt myself. They would say, you know, this isn't your area of expertise. Like, let me handle this. Or, basically make me feel as if I didn't know what I was talking about and in my heart of hearts, I knew that I did. But if you hear something enough that's critical, at the very least, you start to question yourself. 

And you then in a lot of instances, I would start to believe it because I just heard it so much. And I know that it affected me in so many different ways. And I just wish that I stood my ground more and that I, you know, eliminated those people in my life that weren't additive in any way because it's just a waste of energy and it's okay to be open to feedback, in fact, we should be.

But if you hear something and you just in your gut, you're like, this isn't true or this isn't accurate. This isn't me. Then I think it's also okay and important to just say like, I'm setting a boundary here. Like this is not serving me and this isn't what I want my life right now. So some advice that I would probably give my younger self. 

Dawn Andrews: It's so perfect. Before I ask you the last question, I would love to have you back and dive into the conversation around community and the technical aspects of managing a community, the social and, caring aspects and helping people develop and transform inside a community. Would you be open to that? 

Jessy Grossman: Oh my gosh. Yes. And I love that topic so much. So of course. 

Dawn Andrews: Yay. Okay, good. Cause I like, as we're talking, I have like another question and another question and they're, they're just like, the list is getting longer. So I'm like, okay, second time. Well, I'll be back.

Okay, so last question for you. Imagine yourself in Times Square, surrounded by all the sparkly billboards. You get the biggest one, you get the biggest board to share a message with women entrepreneurs. What message would you like to share?

Jessy Grossman: I think it's just trust your gut. I think that it's like, that's just that simple. For me, it's a matter of, always been open minded, open to hearing other things, other perspectives. And I think that that's incredibly valuable, but you also have to trust your gut when it comes to your judgment, your morals, what's going to fill you up.

Like just nobody knows your path more than you anyway. And some of us seek outside validation because, you know, they're like, Oh, well, other people must know more. They have more experience or, I don't know, a variety of different reasons and that we, we look externally, but I can share that like, whenever I've had a really important decision to make and I've, looked within, it's been so much more beneficial than looking outside. So that would be my advice. 

Dawn Andrews: Trust your gut. I love it. Jessy, where can everybody find you and where can they find WIIM? 

Jessy Grossman: Yeah, so I mean our website is iamwiim.com. That's I-A-M-W-I-I M.com. we've got a website of the same name, Women in Influencer Marketing. I'm super active on LinkedIn, like I mentioned, and it's Jessy with a Y. So those few places are probably best. 

Dawn Andrews: Perfect. Well, thank you so much for joining me today. It's been really wonderful having you. All kinds of good things popped. Just your sharing has made me feel, first of all, very excited. I'll see you over on LinkedIn. And I think that there are some really wonderful, I've appreciated your, candid sharing about your process of going through the sale of your business. It was really helpful. And I think we'll help founders that are listening, feel a little more confident in their process. 

Jessy Grossman: I hope so. So thank you for having me. I really appreciate it. It's been fun chatting with you. And, uh, yeah, I hope we can help people and hope it was fun. 

Dawn Andrews: It was super great.

And that's a wrap on today's episode my fabulous female leaders. I hope you're just as excited as I am about what's coming next with she's that founder. The journey we've been on together has been incredible. And I know the next phase is going to take things to a whole new level. Remember this break is just a pause, not a goodbye while we gear up for she's that founder don't forget to join the mailing list at  dawnandrews.com/mailing list forward slash. So you'll be the first to know when we're back. 

You'll get all the exclusive sneak peeks bonuses and behind the scenes magic along the way. Thank you so much for being with me on this journey and trust me when I say. She's that founder will be worth the wait until then keep building, keep leading, keep the momentum going. And I'll see you on the other side, ready to conquer those next level challenges together. See you soon.