Marketing Happy Hour - Inside the Evolving World of Influencer Marketing with WIIM’s Jessy Grossman

Episode Date: September 4, 2025

This week on Marketing Happy Hour, we’re joined by Jessy Grossman, Founder of Women in Influencer Marketing (WIIM). From building one of the fastest-growing influencer talent agencies in under two years to creating a global community that empowers women in the influencer marketing space, Jessy has been at the forefront of industry innovation. In this conversation, she shares her career journey, the inspiration behind WIIM, and her perspective on the challenges women face in business today. You’ll also hear her take on where influencer marketing is headed in the next 3–5 years — and why community-driven spaces like WIIM are more important than ever.Key Takeaways:// How Jessy built one of the fastest-growing influencer talent agencies in under two years.// The biggest challenges women face in influencer marketing — and strategies to overcome them.// What it takes to keep a professional community valuable and relevant in a fast-changing industry.// Predictions for where influencer marketing is heading in the next 3–5 years.// A reminder of why connection and community are critical for long-term career success.Connect with Jessy: Instagram | LinkedIn____Say hi! DM me on Instagram and let us know what content you want to hear on the show - I can't wait to hear from you! Please also consider rating the show and leaving a review, as that helps us tremendously as we move forward in this Marketing Happy Hour journey and create more content for all of you. ⁠Join our FREE Open Jobs group on LinkedIn: ⁠Join now⁠Get the latest from MHH, straight to your inbox: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Join our email list!⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow MHH on Social: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

I think that people are playing it very safe because of things like cancel culture, which I just hate because it like prevents people from, you know, creating some really interesting work. So my hope is that people feel comfortable enough to be able to experiment and create really beautiful work and have the space to be able to fail and have it be okay to do that and learn from it. We need to create a world where people can live. learn. Welcome to Marketing Happy Hour. I'm Cassie, consultant, podcaster, and your host. Every Thursday, you'll hear episodes packed with insights from brand leaders on an array of topics, from crafting effective marketing strategies and hitting career goals, to building leadership skills and launching your own business. Inspired by those unfiltered Happy Hour combos with peers, this show is all about practical, empowering chats to support your professional journey. So grab your favorite drink

and let's get to the episode. Today we are joined by Jesse Grossman, founder of Women and Influencer Marketing. This is a brand that I have personally followed for a long time. Allie has also been engaged with Jesse over the years as well. And so, Jesse, welcome to the show. We're just super excited to have you today. Thank you so much for having me. I've been looking forward to this conversation all day, seriously.

So I'm really excited to be here. Yeah. And Jesse, our paths, you know, crossed while I was at Upwork, particularly when we were looking to activate influencers, really to help bring the platform to the next level. I'm, I'm so grateful that, you know, our relationship led us here to having you on the show today. So thank you so much. Thank you. It's like what I, I, my experience all the time, it's why I have a networking group. It's like you just see things come full circle in terms of like professional relationships. And it's like such a, it's such a cool experience, you know? Absolutely. Well, we have to. kick off with one of our favorite starter questions here on the show. Jesse, what's been in your glass lately? A lot of juices, whatever puts together a mocktail because I am a very new mom of a little eight-month-old little boy. So maybe not the exciting drinks that I used to have, It's just yummy. I never really had mocktails before. I was like pregnant. People were like, you don't have to just not drink, like get a mocktail. And I was like, oh, I didn't think of that. It's just like a cup. So there we go. We love it. And it's, it's just fun. I love that that's

non-alc is becoming more of this thing and that we don't have to have alcohol in order to indulge. So it's just kind of a fun reminder there. But love that. So can you tell us too, Jesse, you know, what led you to starting women in? influencer marketing and just tell us a little bit about your career journey as well if you don't mind yeah i mean when i started whim it was like back in 2017 uh things were really different i don't want to be that person who's like back in the day when influence are started because i hate when people do that when i hear them say that so i just i started it because i were there was a need at the time for me just very personally and candidly um i was representing uh influencers and i wanted

to get them brand deals. And at the time, like, influencer marketing wasn't as pervasive. Being in New York, there was never any shortage of, like, networking groups and people to meet, but also people looked at me. Like, I have five heads when I would tell them, like, I worked in influencer marketing. I had a lot that I wanted to learn because it was really new to me. I used to represent actors, not influencers. And that world is so regulated and unionized. And it's so different from influencer. So I had a lot to learn. And I wanted to. And I wanted to to meet a bunch people, nothing like that existed. And so I don't know, I enjoy building stuff. It's fun for me. So I built it and for selfish reasons, honestly, right? And then it ended up

being like one of the most selfless jobs that I could ever have imagined because now I just get to help a bunch of people, you know, make their own connections, which is amazing. Yeah. And so fast forward to today. You've been quoted in the New York Times, featured in Forbes, named in the influencer top 50. So just overall in the last several years, you know, the neon sign behind you says 2017. So in those past few years, you know, what has been one of your proudest career moments? I mean, I think I had an inkling that I always wanted to have a job that helped people. And I feel like it to a certain extent when I was a talent manager, you know, I'm like helping people be able to afford college for their kids, you know. But it was

was like it was all like very money focused and uh you know and then when i had my own agency was about you know building the agency so that we could you know pay the people that we had hired it was just it was it was very i didn't get to feel the feels the feel good feels of helping people as much in that capacity so my my favorite part is like when i get to talk to people and they tell me like I got a job like my dream job because I joined your organization and met someone or like I met my best friend you know like from whim or you know I just like love going to the events that you guys how like I don't know just the personal stories that I hear from people and how it's like really truly made a difference in people's lives um that's been like unbelievable uh like and it's and it's

just been fun to sort of create something that there's really been, at least in my life, like no precedent for. Like, it's fun experimenting. Like, what can this be? I don't really, I don't know anybody else who has a networking group and a community and stuff like that. So the fact that there's like no rules, so we get to sort of, you know, experiment and see what works and what does it. Like, that's really fun and rewarding for me. Yeah, absolutely. And I think a couple more deep dive questions when it comes to whim, I'm curious. So as you built sort of the talent agency in general, what were the things that you did to kind of increase speed to market in that first kind of like early days of the agency? Yeah. So the agency, which we sold a couple

a few years ago at this point, you know, that was my whole upbringing in the creator economy. Like everyone has a different entry rate rate into it. Mine happened to be in talent management. So when I started this agency, I had a couple of business partners. Like, it certainly wasn't just me. We ended up getting like a great team together. And in growing it, you know, our like our, it's certainly not a secret. But like our formula, secret formula for success was really just like, how do we make.

It sounds so cheesy and cliche, but like how do we make our client's dreams come true? I always thought it was really important to think of each individual client as its own separate business. So, like, I don't have a roster of creators that just lumps them all in together and makes them sound as if they all have the same career goals. Of course they don't. They're all individual unique businesses. They have different LLC names. You know, they're different businesses. And so I think it's important to treat them as such.

And so it was, like, constantly having conversations to both educate them about what is possible. to create in their business because, you know, we're all sort of creating it together and discovering it together. And then, you know, being realistic with them about like what's possible and managing expectations in terms of time frames, but essentially just having these types of conversations with them to continue to grow and their businesses, their individual businesses, and sort of approaching it in that way and thinking big picture, thinking long-term. I think really helped grow the business as fast as it grew because it's not like we were just like taking a $500 brand deal left and right or, you know, anything that came our way. I'll give my former clients a lot of credit.

Like they gave me a lot of negotiating power as a talent manager because they were okay turning things down. And there's not a lot of creators that necessarily feel comfortable with that. I mean, we're in a crazy economy right now, for example, where people would be. a little nervous to turn things down and it was a different time then. So, you know, things have changed. I have to acknowledge that. But they certainly helped me as the one negotiating their deals. What I could just say, like, no hard feelings, nothing personal. Like, it's just, it's not a fit for X, Y, Z reason. Because they gave me a lot of leverage to be able to work with, which was nice. That's great. And I'm sure that having that autonomy really made you feel like an owner in that

sense in terms of the relationship as well, which is always just such a really good feeling to have from a relationship standpoint. I'm curious if there's one thing, particularly with running an influencer talent agency that most people on the outside wouldn't expect. Oh, my God. I feel like it should be a reality show, like, because there are so many things. I feel there was, there used to be one about like, I mean, you've seen them about like models and actors. Like they're like, mark my words right now, there's going to be a reality show about like influencer talent management someday. Maybe this is the impetus to us, like, starting. Yeah, right.

So, but as a little preview of what that future show is going to be, I mean, a little behind the scenes is, it's so personal. It's way more personal than I ever thought it would be. Again, like, I used to work with actors, and I felt like I had a nice relationship with them, but I knew my creators on so much of a more personal level than I ever did the actors that I used to represent. present because, you know, they're constantly putting their personal lives on display. They're constantly telling stories that are just like, you know, they're not playing a character. It is themselves and the more vulnerable and raw and real that they are. Usually their engagements better and they're get more followers and there's a reward system to that.

And so just being sort of inundated in that world, you inevitably become part of that, those really like personal conversations and you become what it feels like family to these people. So I, it was surprising to me at first, I'll just be very honest. Like I wasn't necessarily comfortable with that. Like I just, I kind of, I was like, this is my job. I like my personal and professional lives were very separate when I kind of like first, you know, actually had like my real jobs, you know. And, and now I, I feel much more comfortable with that. And I think, that was probably an opportunity to practice getting more comfortable with it and, you know, how to still have certain boundaries and please. I do think that's important regardless of how

close you are to the business. But it was really interesting how personal and how close we became, you know, it wasn't just business by any stretch. So you've talked about this a little bit already but just in starting whim and building whim what gap in the industry were you trying to fill back then and even now how has that evolved and what are you looking to fill today just in the scope of the industry and as it's changed so much over the years yeah i mean it's a really good question i think like the main thing is i i think people go into events we have a lot of events both in person And I think that in terms of the events, people will go into like planning a con like an industry conference, for example, with the best of intentions.

And then candidly, like I think all of them just seem the same. And we go because like we feel like we should. And there's, you know, there's a lot of people to meet. And so there's value in bringing a lot of important people together into one room. So we go. But these tickets are expensive. And, you know, you get away from your family and sometimes you're traveling. And I just, I was.

I've been disappointed with a lot of industry conferences and gatherings over the years. So for me, I'm like, well, it would actually get me excited, like to just like to actually want to go to one of these things. And we try to always answer that question and keep that front of mind when we're doing our events. We want it like inevitably, business will come up and networking will happen, but we don't want it to feel like this stodgy, like professional event. We want real people to have like real relationships with each other.

We want people to feel humanized and we want to be a fun, you know. And I think what's also really important is we want to eliminate any gatekeeping. That's something that's always been incredibly important to me. I've had, you know, women who have been mentors of mine in the past who taught me that, you know, you have to gatekeep. And you have to keep certain things close to the chest in order to, you know, to move up and to do well and this and that. And like I bought into that because I didn't know anything other than that for the longest time. And then I just got to the point that I was like, I can't help but think there has to be a better way of doing this. Like if we really like are under the philosophy, have the philosophy that like if I help you and you succeed, it will have us both succeed.

together and it's not this competitive thing but like we can truly lift each other up um then like it's totally possible to do that and it just takes buy in though you know if it was and if it was just me preaching this and you know not our hundreds of members buying into it as well it wouldn't exist um but thankfully you know our members really have bought into that philosophy um and it's really wonderful to see in like this crazy world especially that we live in that lay people can just genuinely still be there to like support each other and help each other out absolutely and then in terms of just the way that the industry is evolving so much and changing and you know there's new platform trends in ways that we can connect with influencers and work with them and collaborate um

what's the secret to keeping whim just valuable and relevant in this ever-changing industry and how are you as the leader at the forefront, keeping yourself up to date on things and trickling that down as well? Well, there's like the nerdy answer. There's a bolderable answer. Which ones do you want first? There one, but I would love to hear both. I'm so curious.

I know. I was going to say both. Yeah. Okay, well, the nerdy answer is I'm like such a tech geek. And like I automate and use AI and do all sorts of stuff to be, able to keep my team really small and lean and our business really buttoned up and still have like over 600 members and you know thousands of people who know about us right and who were in our ecosystem in some capacity because I mean I had my last agency we had like 12 people I think on

staff at our highest point and only like 20 clients like it was like the ratios were very different right um and i from a business perspective i think that you know you can run the type of business that i wanted to run this time around was very different was more in line with like having 600 members and a handful of staff right um and so yeah we use tons of amazing tools that i'm experimenting with all the time to try to find new stuff that can help me and systems i'm like such a nerd when it comes to creating systems and we systematize everything but we have you know community engagement tools to be able to help facilitate conversations there's platforms that we use to be able to host our virtual events and all sorts of

tech we have a developer that's full-time on our staff that helps us continue to be able to develop you know them and and make sure everything's like maintains that it actually functions properly so that's the nerdy answer and then like the vulnerable answer is like it's hard to do it's not easy and sometimes I feel like I'm not doing a good job of it to be completely honest with you like it's probably one of the hardest parts of running a community is constantly having a pulse on what people need and I feel personally responsible to help people um like it's a business it's not like I can help you if I if I you know no one's no one's signing up to whim with like thinking like oh

Jesse because I'm signing up to whim Jesse's going to help me get a job but I like I can't help but feel a little bit responsible to do everything that I can to like help people with things like that um and so I think about that like at night when I'm going to sleep you know like I these people are investing in me and I want to invest in them and I really want to make a difference that I really want to help people and it's a hard market out there right now and I have talked to countless amount of people who are so talented been through I spoke to someone today who's been through like 10 rounds of you know interviews for one company and still doesn't get the job it's like I want to be able to help I want to be able to like connect you with somebody at least

who can help move you through the process and help you finally land something that's great So I try to do the best that I can, but the truth is, like, I wish I could do better, you know. I'm trying to always find a way to do better, I guess. Yeah. Well, thank you for sharing that. That was really beautiful. And as someone who has been through this crazy job market in the past six months, what you're doing is incredibly valuable.

And not many people are doing that. So thank you for taking that space and helping to elevate, you know, other women particularly in this crazy job market. And speaking of the community side of things, you've shared a couple of little micro stories, but I'm curious if there's one story that stands out specifically to you from the community that really reminds you why you started it in the first place.

It's a really good question. You know, it's interesting, right? Because we could have just been people in influencer marketing, but we're women in influencer marketing. and you know we're women's focused organization and we've always been like that from the beginning we have men who are part of the organization we have non-binary people who are part of the organization we certainly not going to turn anybody away but like it's very very important to me to uplift women in business because I feel like I wish I had that when I was first starting out so in terms of

like what's important and reminds me of like why I continue to do this and like why why I, even on the hard days, I still want to do it. It's because it's really like mission focus, like what we do. You know, it's not, and that feels different from when I was a talent manager. Because, like, candidly, like, you got very transactional. Right. And it's sort of like, it lost a little bit of the heart. But now, you know, I love when we get like, you know, people right out of school

who are just so hungry. like oh i love that energy when you have like someone who's like in their young like early 20s and just hungry to like just you know succeed in life and they're eager to learn and they're open to advice and like that is just i'm such uh like i will help anybody who gives me that energy um and it's just it's like i'm i feel very lucky that i get to do that for a job and like call that my job um so just being in connecting women because like then, you know, you meet one incredible woman and another incredible woman and putting them together and like seeing what they can do. I've seen people like start businesses, you know, from relationship that they formed in women. And it's really

incredible just putting the right people and matching them together. Yeah, absolutely. And as you've already shared, even just in that last question, just your passion of supporting women in business. And I'm just curious overall, just in your time building WIM, what are some of the biggest challenges that you've seen women in influencer marketing face? And how can women overcome those challenges as well? So I'll be honest. The biggest challenge I see women face in WIM is themselves. I think that we're fortunate that we're in a world where like there's a lot of discrimination in our world. They'll get me wrong, but it's much, much less against women that it used, certainly than it used to be. But what I still see that drives me crazy is just a lot of

women who are so smart, so talented, and they get in their own way and they doubt themselves, or they lack confidence, or they're a little risk-averse. And I look at them from the outside. I'm like oh my god you could do such amazing shit sorry I don't know if you can curse on the yeah you're all good you can do such amazing work and you can like knock it out of the park and how you have something here and I see it from an outsider's perspective and I can hype them up all day every day and I do but at the end of the day like they're done like they have to get out of their own way they have to believe in themselves and it like again it sounds kind of cliche but like it is very true um you know with people interviewing asking for raises you know

wanting to start a business but you know scared to go off on their own like I hear of these circumstances and scenarios all the time um and it can be scary like I don't want to you know sugar coat it like it's it can absolutely be scary I was even scared like of all people like I was scared when I launched my first business too when I launched my second business even you know after I had experience of doing it once before but I'll tell you I would I would be very hard pressed to go and work for somebody else again like I love working for myself I love the freedom that I have and the flexibility and the I don't know there's just so much good that comes from it and so you know my ideal situation professionally might look very different from yours like you

might want to work for Google, you know, or the, you know, your favorite brand in the world, you know, that's your dream. Um, but I, I, I, I, you know, I want, I wish that basically people could see in themselves what I see in them. That makes sense. Yeah. No, definitely. Um, and I think while we're, while we're kind of forward looking here a little bit in terms of, uh, in terms of influencer marketing, I'm curious. Obviously, things are changing rapidly and maybe this is a little bit of a difficult question to ask. Where do you think it's heading in the next three to five years or so? Yeah. I mean, I can tell you a little bit where I wanted to head. I can't imagine where things are going, especially in this world. But like, I just want to see people take more chances.

Creators take more chances and more risks. And brands, too, I think that people are playing it very safe because of, like, things like cancel culture. and things like that, which I just hate because it just, it like prevents people from, you know, creating some really interesting work and really like, like, I come, like, you know, I come from like a theater background. So like I'm that like artsy, artsy girl who like wants to see like people experiments with cool art. Um, so my hope is that people feel comfortable enough to be able to experiment and create really beautiful work. Um, and have the space to be able to, to fail and have it be okay to do that and learn from it and you're not be canceled or not

be you know like just whatever it is I don't want them to have this like we need to create a world where people can learn and I think that that's really important and the same goes for you know people who are on the brand side you know or agency side and working on campaigns you know I I think like we're all humans and we're making the best decisions for what we know and what we have with the information that we have at the time. But I'm just sort of tired of people playing it safe. I feel like I can't really. Like I thought influencer marketing would sort of be a little like further ahead than it is.

Currently, I think when a lot of us who are there like in the early days, like it, the most exciting part about it was all the promise that it had. It was like this uncharted waters and, you know, we saw the potential there. And then for a lot of reasons that I probably don't have time to get into it, it kind of stalled a little bit. So I would love to see people take more risk. I would love to see people, you know, work with creators in more dynamic ways. I'd love to see brands, experiments a little bit more and really like differentiate themselves from each other. but mostly I'd love to see us like live in this world where like it's okay to do that because

I also understand why people are nervous to do it. So it's a big ask for three to five years. Maybe it's good. It's good to start thinking about how can we at least semi get there in three to five years and then maybe in 10 years we'll be fully there. So it's a good intention to set, I think, even in the next few years. So thank you for sharing that. And thank you for sharing just everything, how you've built WIMM. Again, thank you for providing such an amazing resource to professionals in the space. I know a lot of people absolutely love it, including us, and so thank you for that. But we would love on that to know how we can stay in touch with you. And then also learn more about WIM for those who would like to join and be a part of it. So let us know all of

the details there, if you don't mind. Yeah, and of course. So definitely follow us on Instagram. at I-AmW-I-I-M, that's I-A-M-W-I-I-M-W-I-M-W-I-M-W. Same is for our website, I-A-M-W-M-D-com. And those are the main places that we're at. You can learn about our membership, which is, you know, just as you get access to, like, the most incredible women who are equally as obsessed with this industry as you are and can be able to, you know, network with them,

partner with them, you know, use them to cast your campaigns. there's so many different features and tools that we have at mentorship program. So it's a great way to just connect with other women and just to meet each other and being community with each other. So that is the best way to learn more. Amazing. And I'll have all those links below in the show notes. So be sure to check that out. But Jesse, thank you again so much. We really appreciate you just joining us and being here today. Thank you for having me. Thank you.

Thank you so much for tuning in to this week's episode. If you enjoyed this conversation, I would love your feedback. And if you're ready to take things to the next level, sign up for my weekly newsletter in the show notes. You'll get weekly career and marketing insights straight to your inbox. And if you have an idea for a future marketing happy hour episode, shoot me an email. Hello at marketing happy HR.com. Thank you again and I'll see you next Thursday.

Thank you. Thank you.