taylor desseyn

guidance counselor 2.0 · episode 433

the winding road w/ leslie greenwood, co-founder of women wednesday

mar 26, 2025 · 30 min · with leslie greenwood · hosted by taylor desseyn

key takeaways

  • leave a job when burnout hits and you've lost your ideal life profile, not just when money runs out.
  • network in communities where your actual customers are, not everywhere; linkedin is where b2b go-to-market leaders live.
  • people buy from people, not companies; build trust through vulnerability and authentic conversation over product promotion.
  • don't wait to network when job hunting starts; begin two years prior so you start at zero or better, not negative five.
  • step through doors when the path is clear and you see the opportunity; your five-year plan will change anyway.

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about this episode

leslie greenwood shares her winding career path from retail to startup exits to community building, and why networking before you need a job matters.

full transcript

auto-generated from the audio, so expect a few typos. the audio is the source of truth.

alrighty we doing this thing good morning good morning from a very rainy Nashville it is supposed to rain four to six inches over the next few days so I may just float away to be totally Frank so TBD right now we're still good it is also raining in Dallas and 49 degrees and it's gross and I feel like I'm in Ireland yeah yeah yeah you know it's funny uh I I read some stat like a year ago or so where technically Nashville has what was it is it Nashville has more rainy days than Portland we just don't get as much rain as Portland or or

vice versa we have more rain than Portland um it's kind of crazy yeah it rains a lot here but um good morning everybody happy Tuesday excited for this episode this morning I know I say always am excited but I am excited I mean you know I I think I think when your job and we'll get into Leslie's background when your job is to meet people um and and to have really good conversations if you are wired that way I can get you pretty excited so I am excited for this morning excited to have this conversation with Leslie and again shout out Alicia novin for making

the introductions um uh Alicia novin and I started back our series unghosted which is our uh which is tor's resume LinkedIn critique series that we're doing once a month um and so Alicia and I are back doing that alici and I made this connection um so shout out to him also the power of connections as always um but again if you are tuning in welcome we're starting to see people tuning in um please say hey would love to hear from you again what I always tell people is this is a networking really platform I started this show five years ago next month and I started

this is just a way to give back to the engineering community and really over the last year what I've realized this is really a this really a networking show where this is a meet I guess it's a Meetup you know we can call it a Meetup Leslie there a virtual Meetup where you come hang out with a wonderful speaker uh you can connect with people in the chat um and make some friends again it's like I tell people and I see some people doing it shout out Richard uh he's not here yet he usually Tunes in but shout out Richard he's starting to do what

I always say I say if you connect with every single speaker that I have on the show and you connect with every single person in the comments your network is going to be insane and that's what I want I want you to network off the back of me so please connect with Leslie again but send her a note tell her you saw her from obviously the show so she knows where you're coming from um before we dive in Ricardo TAA Mark Chris Daniel there he there he is there he is Alicia good to see you buddy Ro it's great to see y'all this morning Nashville

traffic yeah yeah yeah if it just rains in Nashville things going nut Stephen also Dallas got crazy traffic I was in Dallas in December for a conference crazy crazy traffic in Dallas um Jonathan it's good to see you again this morning all right so Leslie enough of me yapping let's get the people what they want who are you you what do you do and we'll go from there awesome awesome well uh again I want to shout out Alicia um when we first talked we Alicia and I had never met so Alicia is just a random internet connection who sent an email nominating his boss for

Wednesday women and then connect me with all these amazing people and so he's like how do you know Alicia I'm like I don't totally don't but we had a great call and here we are today so um let's see who I am and what do I do so um I am lesie Greenwood I am the founder of two companies one is chief of Angeles consulting which is my um Community Consulting business um I used to be the VP of member success AT Pavilion so probably similar to what you have at torque you know about professional development but this is for goto Market professionals and um

now I do that for a living on my own um I'm sure we'll get into my unemployables which I would I think I just am um for my own sanity and benefit um so I love working for myself and then also I am the co-founder of Wednesday women so if everybody would please follow Wednesday women it is a platform just to uplift executive women leaders so um oftentimes and and just like you kind of mentioned at the beginning connect with these people follow them um increase your network oftentimes these women that have these amazing titles we don't know who the women are behind them and

they may not be out there shoot you know tooting their own horns and so our job is just to toot them for them and um and yeah so that's that's that's what we do there and um you know I've done a lot of other things but I'll let you kind of drive me through that track because we could be on that whining Road for a long oh I know yeah yeah and it's so tough right I love having deep conversations and and we and I try to keep this 30 minutes so people can Hop On Hop off and kind of go to their next meeting

so yeah lot to cover today shout out to all the comments I see you I've been trying to throw everything up Roxy loves Leslie you know Roxy I said the same thing I I told Leslie as well her glasses are fantastic so um all right so look at your background we have a lot to go over I I think the big thing uh that that I kind of want to highlight Le at least launch off with is is is you you had the ninet to-5 for five years at Pavilion and then you just let and you just you just went to go do your own

thing right you moved on and and you kind and I think that that scares a lot of people um I know before I joined torque I was thinking about doing that um you know I know a lot of people don't know where to start a lot of people you know kind of tired 9 to5 can you just kind of give General thoughts on where you're at Pavilion and and really what made you jump yeah um you know I was at Pavilion first as a member then um you know pitched myself to be the VP of member success so kind of like you I was in

charge of all things uh content strategy everything and that was when we were going from 2,000 to 10,000 members I was just there for two years I'm still a member I still participate um so we went from 2,000 to 10,000 members in two years we also built the entire learning curriculum within member success I was Finance I called people to pay their bills because otherwise they'd end up on my churn sheet and by God I was not going to have churn you know if I could save a churn off my kpis I was going to do it so I called many of people on collections

not my favorite job um and so you know I think it was just time it was time it was a mutual decision and you know it was I was so burned out I did not know like when people talked about burnout I will tell you I was just like poo poo people p up your big boy pants let's go and then it hit me like it had been coming in a slow roll and then it finally just hit me to the point like I was I mean I was shot um because you know as you know 247 community and I love being in there with

the members and I love helping and even though I had a team of 18 at one point there was still always so much to do so if you all are not appreciating your community managers it is smooth like a duck smooth on top and there are wheels going all the time everything's burning all the time everything's burning all the time and it took 18 people for it to look like Smooth like a duck on top yep um and that was working like way more hours than we ever should have so so um and you know as as I transitioned out I you know I talked

to a mentor and the mentor said I want you to create an ideal life profile and what that was was tell me what you want your life to be and write that down and then we will work on a job to fit into your life I don't know about the people on this call but I have never done that I've always fit my life into my work and that was a really kind of cool idea to me and you know it came on that Consulting was the way you know that I wanted to do it I am a reall y great early stage Scrappy person

who becomes really indispensable and kind of annoying um once they get really you know like we start putting structure in and I'm just busted against the walls for structure and um that's why I'm unemployable like I'm just not I'm not meant for structure but I love the awareness though right and listen I mean I I I know you know we're obviously joking a little bit but but like I think and that's kind of that that was one I'm a little like I think we're a lot alike I mean just obviously learning your story real time I'm kind of that same way I I I Buck

I push back against pretty much everything and the nicest way possible and but but when I was interviewing like for this next role like I was very like hey this is what I bring this is what's not going to work take it or leave it and I don't know if you can speak to that that just like how important I guess getting to that mindset is because if you take a job that's not a fit I mean you're going to be miserable oh 100% And I will tell you the there's I this is a quote that I've used in two interviews in both my last

two jobs which was I will play inside your sandbox but you have to tell me where the boundaries are yeah if you don't I will be running down the beach building something else not building something else that's not important but you know in that early stage land where everybody's doing everything right like just like we did it in at Pavilion we build everything and um and I said I understand I also need a Long Leash but I and and I acknowledge that it's long enough to hang myself yeah and so I mean I was very clear in both interviews that that is how I work

now granted that's not gonna work for everybody no it's um I'm 54 so I'm in a different stage of life I'm not trying to exit a company I'm not trying to be a billionaire um so I don't know I don't know that I suggest that for all of your people but like I think mindful of that would be good on what's where you think your boundaries are on that 100% so um yeah I I and I agree with you on that 100% so talk talk about you move on from a pavilion I think a lot of people you know try to figure out what to

do on their own right I think there's many different Avenues you could develop product you could do Consulting kind of maybe a Services based thing what was kind of your thought process because I kind of went through that too I was like do I create another Market Talent Marketplace do I you know do I do con you know content Community like what like talk to me where your head was with that because I think that's a really important kind of next step for people W to go on their own you know I thought I was going to do customer success because that was my background

and actually I didn't know I was a community Builder until I left Community until I left Pavilion and found out oh wait I'm a community strategist I this is what I do right um I talk to a lot of people um I also you know I Heard lots of ideas I'm telling you what I in the first two weeks I was told to write a book start a course start a podcast start posting on Twitter and uh let's see Twitter and Tik Tok yeah like I need to do all these things and like you know sell PDFs and all this kind of stuff and it

just got very overwhelming and yes I did try that I had a podcast I tried to start a course but that was not for me um you know so I think it's very easy to get distracted by all the ways that you can do it I think it's really finding like what do you love to do and really kind of take in all the feedback and then maybe you put it in chat GPT and tell ask it to tell you themes and explain your personality and say what would you recommend because the there are so many things that I did try that I really it

would not have served me and I'm still actually figuring that out like I didn't know my ICP for my business for 18 months like I finally got it at 18 months like it is specific and very narrow and Niche yeah so it's still an evolution I you know I kind of want to dive into a little bit Roxy comes in exhausting I I I do want to talk about kind of the networking side of things and kind of like doing the Tik toks and the twitters and the podcasts you know obviously I'm out here and you know I'm doing the whole thing and and I'm

very blessed to have support um to do it um but I did it by myself for a very long time and and obviously you tried it and it's a lot talk about just the power of just just getting yourself out there at least right because I think you know I again I want to shout out Richard um Richard hopped in here um um you know and and and and he's starting to like follow up and like hang out with my guests and like do calls and he's he's doing it public and it's very simple very methodical and he's not he doesn't have a podcast he's

not posting audio recordings all he's doing is he's doing a picture and he's posting a recap on LinkedIn just talk about how you don't always have to do a lot to be effective that was the biggest waste of my time to be quite honest my audience is on LinkedIn yeah I work with go to market leaders yeah zos VPS of sales marketing customer success they're all on LinkedIn y um and so I diverted my efforts into places is where they weren't um they also all of my business comes from just I mean for your audience and I'm sure you do this as well you tell

your people and I can see you doing it here is now is that like be in community with people you plant your seats you give without expectation and one day you will after you tend and sew and pull a bunch of weeds you will harvest yep all of my business comes from Community with a t gental small amount from LinkedIn so it's actually like it's more like a person from my community will tag me in a post in LinkedIn that will start a conversation so I all of it comes there it's like a 100 per.

I want I want I want to dig in that a little bit because I still think I think LinkedIn I made a post about this Friday a nd a lot of comments a lot of thoughts I still think LinkedIn is like the most underrated platform like like in terms of business like in my perspective if you are in the B2B space and you're like dtoc Tik Tok Instagram everybody else in my opinion should just live on LinkedIn what are your thoughts on that talk to me just about your findings more on LinkedIn yeah I um I'm definitely a LinkedIn girl I try to post almost

every day yeah um you know it's it's hard because some days you're like no one looked at my stuff no one cares um all that kind of stuff and which is the reason why you should just go ahead and post because no one cares and no one read it so just go out there and start um I probably had what maybe 500 followers and they were realtors for my first tech job when I started yeah you know and I have 177,000 something and you know you get the notes from now and then that says you know I really loved what you said it helped me

today because I was having a bad day yeah um and you know that will happen but yeah no 100% And honestly I don't talk about business a lot on LinkedIn I will occasion obviously community and networking is such a part of my life yeah um I talk about that but I'm not talking about my company I'm not talking about my wees I'm not talking about my services sure um people do business and I actually don't even post on my company page anymore people do business because they want to do business with me they don't do business they don't care about my company and so me

establishing trust and authority and a vulnerability that allows me to create rapport with people quickly and easily is the most important thing for me and sometimes that means I'm just gonna say Yeah I you know what I listen this is this is the hot take here I think what Leslie just said people want to buy from people people don't care about companies I I mean my hot take is I think that's that way across the board I do too and I think that's why Community teams are so important in today's day and age we I people want to buy I want to buy from Leslie

I don't want to buy from the company I I know Leslie's going to take care of me right and that's one thing that we're I'm very passionate about torque and what we're building like people want to people are going to want people resonate with Jason people resonate with bana people resonate with hea people resonate with me in all different ways and they're gonna want to be a part of us because of us not because of torque and I think like if you're in if you're in marketing for company marketing like you need to get over yourself a little bit uh because it's not because you

all aren't the ones moving the needle it's the people moving the needle and you do it right the people move the needle for you because they love your company and they will talk about you and a quick segue into Wednesday women which is My Accidental business you know we got 10,000 followers on a business page crazy which is crazy in a year um LinkedIn throttles business page is FY social media people yeah and in a year with all organic because people resonated with what we said our tone is still vulnerable and open and it's still you know probably a little bit too much founder Le

but it's it's going to have to be that way because people want to buy from us um or do business with us um so yeah yeah so talk about women Wednesday a little bit more um you know I know I know uh you know there's a lot of people in the chat how can they get involved um just kind of just kind of give the give the chat kind of a high level overview of that yeah give you my elevator pitch love it give it to me probably haven't practiced it or had enough coffee this morning we can Workshop it now don't worry yeah no

it's it's on the front page of our website if you go to wednesdayw women.org the first part says we are here to celebrate executive women leaders you should follow uh let's see follow learn from and be inspired by I love it the our goal is to g et more women on stages podcast and panels in more LinkedIn feeds because of course what you hear when you see the Manel folks this is a term Manel a panel of all men yeah they're almost always white dudes yeah um when you see the Manel people will and you call somebody out on it or you ask they say

well I didn't know any women experts yeah yeah that's not an excuse because there are many out there and if you follow Wednesday women you can meet two every week and add them your your follow list um and then sharing their authentic voices you know I have calls with women that are amazing like they have t CMO of grammarly have learned of Albertson's you know Fortune 50 companies but what people want to hear the title's great it's flashy they want to hear about the woman behind the title and so that's what we focus on so we're very our presence is is LinkedIn we're actually not

a community um we are just a movement and we talked about this a little bit on our call yeah it's just it's just a movement so follow us the things like comment engage follow the women that we we present to you every week um we just for for your group because I know you run a little bit more technical we just finished a series on women in privacy okay privacy uh cyber security and risk they are the ones that have the unsexiest jobs that really no one really wants to have to deal with but they do all the day um I think I might have

seen one of them on this call too um and just we did a whole series just highlighting women in in privacy and it was really it was a really amazing thing that's awesome you know I do want to I want to kind of pull kind of recall our oneone conversation we had because I think it's I think for the people watching um they obviously know kind of what we're trying to do on the torque Community side of things and and whatnot um I I do think our chat a little bit about do do people need another Community right and you and I were chitchat about

that like women Wednesday you you know you said it's more of a movement not a community can we unpack that kind of a super high level give me your thoughts because we had some good Baner around that um during our one call yeah and actually I mean it is really one of our things like we believe that executive women have really too much to do already already we we can probably agree on that um and they don't need to have to go somewhere else to spend 15 minutes to get value um our goal is to deliver value without expectation and I think that's that's why

that's part of the verality of what we do is that we don't even the women we feature it's like fill up my form for 10 minutes and engage with the post yeah and I will blast you all over social media yeah um so yeah I mean I think and I used to teach a class on this it's like there's communities that you love and engage with and I when I say engage it's two times a week for 15 minutes um there are some you keep because you might have a question you might want to ask in there it's not one you're really engaged with but

you just like might have a technical question and they're really ones that you need to just take off your slack side panel you know and just get rid of them or your Discord side panel or I don't know works but like you just need to get rid of them and clean them out because it's mental clutter to take away from the places you can really learn grow and make those connections that will make a difference in your job and I know you talk a lot about this but like if you start I'm just going to lay this out super I'm gonna be as plain as

day if you start networking when you're looking for a job you are too late you should have started two years ago so if yall are not networking now almost all of us are going to need a new job in two years two to five years yeah you you are in such I I see it every day you are in such um a negative you're starting at negative five correct instead of starting at zero or plus 10 if you're not properly networked yea h yeah and again that's you know really the goal for torque and you know um you know my this is a little bit

more job search oriented Briana who who you've got in touch with is obviously hers is a community focused one you have Jason who really is highlighting just people in Tech more along their career Journey but still um you know along their Tech journey and then hea um is really in my perspective like basically our our really Mexico latam version of Jason's podcast and so you know really for us we we want to provide you I mean if you message Leslie right after the show and go hey loved your conversation saw you on she's going to get back to you right that's how this networking starts

and that's what really my ultimate goal for torque is is for you all to just Network off the back of us because Jason's got a hack I mean all of us have hacking communities um and so so that's what you know again we're super passionate about but I agree with you if you are waiting you are behind very very behind yeah um so as as we kind of again time flages we're having fun with friends as we kind of wrap up here in the last seven minutes I I do W to really kind of really let you kind of say maybe some words we haven't

gotten to or or encouragement or anything that that's still on the top of your mind that I haven't asked any questions about you know I guess my encouragement because like we did call this podcast or this show uh the winding road yeah um my journey in my career has been from retail to um you know just regular business to my first accidental job in Tech where they gave me a 100 shares and we exited to a 200 to a fortune 250 I mean seriously people this never happens but I thought wow this is great this is how startups work yeah um um to you know

to customer success to being a stay-at-home mom for two years like I have it on my LinkedIn profile it's kind of my like you know when people put their X Fang stuff on there I'm like I'm an ex stay-at home mom like I just put i t out there because I'm like I'm gonna be fancy too so yes I used to just change poopy diapers and like read to my kids hug hug um so um I think my you know and then coming to you know working at Pavilion and increasing my network and now being out on my own and being asked to be on

these podcasts I was talking to my mom before this and she's like when did you become so social like when did you like when did you like doing this stuff and I'm like I don't know but you should maybe watch me on LinkedIn today and you know and then you can see yeah um but um yeah so I mean it's just it's so different like someone called me LinkedIn famous the other day I'm like dude I'm a Midwestern housewife a 54 year-old midw Western housewife that's still how I see myself so like where you're at right now is not a dependent of where you're going

to be um I think we talked in our conversation this is lesle v17 there are at least 10 more versions of me and I may not be doing any of this stuff in four years um so I don't know I guess the the the the uh words of encouragement are for those out there looking to make a move or are in the middle of making a move is like you know follow follow the path when a door is open and the path is clear you very well may need to walk through man I I that's so good that'll preach as I say you know for

me I I I think yeah I was talking to my I was talking to my wife about this too uh the other day um we we were at dinner and she was like she goes it's funny to you've completely transitioned your career without ever really like seamlessly and and and went from a tradition heads down recruiter to essentially marketing community in the dev world right and I really resonate with what you said I think a lot of us can get so caught up in what's your Five-Year Plan what's your 10 year what's your threeyear and it's like to me like that's not even a thing

anymore for me it's like where am I at presently where do I want to go and let's continue to work through t hat when an opportunity arises I think you're right step through the door I think a lot of us an opportunity can be yelling at us in front of us and we're like nah right so like I think like having Community around you having people around you to encourage you but then like when you see when you see the lane go yeah yeah which there's two asterisks to that is that many people walk around with blinders on correct so they're not looking for the

doors because they're in the spot like they think they're in the spot well the spot always changes so you know take off the blinders to look for the doors and to be realistic about what a clear path is I mean I took a job the job that brought me down to Dallas and I knew the path wasn't clear but it was my first VP roll but I was fired eight months later after removing my family AC cross country but we were meant to be in Texas it got me my next VP role I love it and um you know and I got hired back by

the parent company the next day so I just took the three month Severance and took my old job back I me me a break um so but yeah it was it was definitely an eag hit but so like yeah just be honest about what the the what a clear path looks like if you're climbing over wire it is not a clear path correct 100% that's so good um all right so I do kind of Rapid Fire here um with the guest again thank you all the about this say what you didn't tell me about any rapid yeah I never tell anybody about it rapid fire

questions but uh handful of questions uh first off Leslie um Valentine's Day is quickly coming up what's your goto Valentine's Day candy oo um oh oh they have pink M&M's I love Eminem So the the the Valen day I'm just gonna go themed no they're the same I love it I love it um next question I tell everybody um if you were to wake up tomorrow and I tell you that you can't do what you are doing now but I will pay you the same like money's not a problem I pay the same whatever what hobby would you pursue can you pay me more though

sure why not okay um I would travel I would just travel I would travel and I would go I mean this is my other networking tip when I travel I go into my community and I drop in their local channel and I say hey I'm gonna be in San Diego next week anybody want to grab coffee I would travel around the world and have coffee with is great Just Vibe out a coffee shop exactly uh outside of traveling and and and obviously coffee uh what are some other Hobbies you have just fun things you like to do outside of work uh o h you're talking

to a startup grind workaholic um so um I do like to read and oh oh well I guess this is not really a hobby but I love trash TV like I think that's a hobby yeah all the Real Housewives what's your goto trash TV Real Housewives of everything I will watch all that my husband makes so much fun of me my wife loves it too oh yeah yeah so that's that's that's my um that's my hobby which is unfortunate that but that is true I love it I love it uh obviously want you to always ask people um to give shout somebody in the community

that who's doing some really cool stuff so if you want to give uh any anybody specific shout in in women Wednesday yeah yeah yeah um Let me give a shout well I'm gonna give a shout to my co-founder Melissa Moody okay um she was a CMO and co-founder of a company called gated she is a product leader but also marketing leader so um she probably loves a little bit more of this technical stuff than I do um and yena and I will not say her last name georgevich I will put it in some comment somewhere okay U but she's looking for her next role she's

an amazing podcast producer marketing she's an amazing writer um and uh she works with us as a contractor but um she's looking for her next role so I'd love to get her in touch with someone who can really appreciate her talents the way we do I love it that's awesome um and then uh next question any books or I know we just talked about TV shows was there any movies books anything you've rea d lately that you just really enjoyed uh movies or books uh oh yeah well this this is easy if you looked at my LinkedIn post from yesterday it was all about Wicked

it was about Defying Gravity and just take that yeah so it really kind of ties into this conversation so favorite movie right now is wicked I'm listening to the soundtrack it gets me hyped about just like you know I'm just gonna go do my and and people you know just need to watch out I love it that's awesome last question as we wrap up again thank you all so much for tuning in this morning um we'll be back tomorrow with my guy Nick Taylor um at 9:30 a.m Central um to talk about how to navigate really big conferences for networking so hope hopefully see y'all

there tomorrow um because I'm going to Amsterdam in two weeks to speak and it's a 7500 person conference and I'm terrified uh last question the show is called guidance counselor 2.0 because we had guidance counselors in middle school high school and college but now as adults we don't really have anybody turn to and just ask for General career advice if you could go back in time and tell young Leslie something about career stuff what would it be biggest piece of advice um forget about money and Status ah do something that you're passionate about and the money and Status will come if if if that's important

to you but like I think status as I was younger was very important to me like I want to be a doctor or a vet or something because that was important and I never did do any of that stuff um so yeah do something you're passionate about and then figure out what your superpower is try then you can articulate it very easily so good so good yeah and it's like Jason just said well Jason's hosting a devops panel later today um so it's gonna be a great conversation so uh go check out our torque Community page on what time that is I don't know exactly

what time that is but anyways thank you'all again Leslie thank you stay on so I can say bye to you backstage uh but y'all have a great Tuesday uh if this resonated if this episode resonated with you would love for you to share this obviously on your LinkedIn um obviously connect with Leslie um and support Wednesday women and uh y'all have a good one we'll see yall tomorrow morning 9:30 centr everyone

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