June 16, 2022
E63: How Can I Help with Kate Leidy

On this installment of RRH, we’ve got the fabulous Kate Leidy. Long-time tech seller turned founder. Currently helping formerly incarcerated humans break into tech sales. And we talk about how these radical conversations are landing with sales leaders.


On this installment of RRH, we’ve got the fabulous Kate Leidy. Long-time tech seller turned founder. Currently helping formerly incarcerated humans break into tech sales. And we talk about how these radical conversations are landing with sales leaders. 

Topics Discussed

  • Where does passion come from? (1:19)
  • What happens after you experience a great sales culture? (7:45) 
  • What to do when you’re not sure what you want to do next, career-wise? (10:02)
  • How are tech sales leaders receiving the Strively/re-skilling game plan? (11:04)

 

Resources Mentioned: 

Transcript

Amy:

Uh, what's up human. Welcome to the revenue real hotline. I'm Amy. more importantly, I'm excited. You decided to do. Today. I know you've got a ton of options and I appreciate you. This is a show about all the hard and uncomfortable conversations that arise while generating revenue and how to think or rethink what you're doing, why you're doing it. And then of course, How to execute differently. And like I said, I'm happy you decided to come along for the ride. Don't forget to follow the show wherever you listen. So you can be notified each time a new episode drops. And do me a favor friend. Don't tell anybody about the shell. Let's keep it our little secret. I'm Amy Rahab check. This is the revenue real hotline. Enjoy the lady. Welcome to the revenue rail hotline friend. I am honored that you have, have made time for us today for

Kate:

your honor. I'm so happy to be here. Thank you. Welcome.

Amy:

Welcome, welcome. All right. So Kate, why don't you tell our listeners a little bit about who you are and what you do every day, and then we'll dive. We'll take it from there.

Kate:

My name is Kate lady and I am the CEO of strive Lee and I prepare people who are coming out of the U S prison system for careers in tech sales.

Amy:

That was a pretty concise,

Kate:

you can count on me for brevity.

Amy:

I mean, I just, I respect it so much. I want to say that again for listeners, for anybody. Kate's mission. She works with people coming out of the prison, U S prison system to help re-skill them. And I would imagine breathing a great deal of belief into them and treating them like human beings that are not lost forever and giving them some hope and a brighter path and to not just a pretty baller profession, but a high earning profession. As well. And so Kate, on the off chance, you haven't heard this yet today. Thank you for doing what you do. Thank you for being the only person that I know. And I know a lot of people that's doing anything like this, and I think it's fucking awesome. I think it's awesome.

Kate:

It's an honor. And a privilege

Amy:

RA. So, how did this passion for incarcerated humans? Like I'm, I'm remembering a stat that you said, or that we talked about once, but 75% of people that are coming out of the prison system

Kate:

return return.

Amy:

75%.

Kate:

That's insane.

Amy:

What a waste. And so it's like looking for housing, it's a problem. Looking for jobs. It's a problem. I mean, and even I think about like the, the Ray of hope, what was it Florida last year that voted to make, um, a felony conviction, not bar someone from being able to vote, which was then, oh, so again, not even being allowed to vote, but that was overturned by the public, but then the governor like human. W whatever it's too disruptive to the, the voting blocks. Um, so that's a different story, but anyway, I think it's awesome. How did this become a passion for you? Elsa story friend. Yeah, I,

Kate:

I grew up in tech. Um, I, I joined my first startup in 2004 and had the opportunity to go from, you know, little tiny startup all the way through IPO with Rackspace. Um, and then I went on to, um, Six more startups. Okay. Um, and then by the time it was, you know, 2018, I was on my seven. I was exhausted. I was completely burned out. I could not find joy in my job at all. I didn't want to show up. I wasn't really showing up. But I had a friend, my best friend shout out to IVU Vinson who said. Why don't you go be of service to someone and see if that helped you to have the opportunity to go to Solidad, which is a state prison, um, here in California, in the valley and volunteer with Hartnell college to teach employment skills. So how to write a resume, how to present yourself in an interview. I'd never been to prison. I didn't know anyone in prison. I had no idea what to expect. And I went in that day and beat guys completely blew me away. I just, um, immediately saw a room full of talent, people who are naturally curious, who are ambitious, who, who asked really great questions. And I thought these guys would make fantastic salespeople. They would make great tech, sales people, someone should start a nonprofit. Not being me, of course. Um, and you know, being a single mom, I'm a mom of two, three young kids, two young kids and one grown kid. And so starting a nonprofit, it's not really make a ton of sentence, but 2020 happened and you know, the world came screeching to a halt. My company immediately, you might not have. Uh, my kids when I moved in with my parents, um, so that we could do distance learning and they could help me and just get through the pandemic and in a little bedroom, in my parents' house, I just started building the program. And in November of 2020, we put our first group of five women through it completely changed my life in every single way and the best way. Wow. So many things that he has

Amy:

had there. I just started putting programs together. I just want to write that down. Okay. So. Have you ever read conversations with God? Have you ever read this book? I know the book,

Kate:

but I don't think I've read it. And if I did, I forgot.

Amy:

This is like never a book that I would have picked up. Okay. So I was raised in a fundamentalist Christian household. The only role in high school was if you're not in church on Sunday, like you can't go out the following Saturday. I did everything in my power to try to like bend my father as well on this one, nothing worked. I speak about this on the other episodes of whatever. It's not. But when I turned 18, I wanted nothing to do with it. Right. So I would have never picked up this book, but I did one of the, like Ryan holiday does these challenges and he does this read to lead challenge and it changed my life. But one of the challenges that day was like, go talk to somebody that you respect and trust and ask them for the book that changed their life. And then when. And so I was working with a professional coach at that moment. Um, her name was Laura, and so then she sent me to conversations with God and I was like, God damn it. Like I gotta, now I gotta read this. Anyway. It was. Life altering. And that long diatribe was all to say that there's a line in there and it talks about remembering. And so think of the word, remember, and imagine a hyphen in between Ray and member. And so this kind of plays on your girlfriend's advice that she gave you your friend's advice. They're like go be of service to others and see if that helps you like part of our experience on this plan. It is to remember. That we're here for each other. And the challenge though, is that in order to make that sustainable, right, we need to take care of ourselves first, which it's, it's very counterintuitive, right? It's like that, you know, put your own oxygen mask on or fill up your own damn. I have no use to anyone. I thought that that was beautiful. And I like, I almost want to like, be friends with your friend. Like if I could have somebody in my ear like that to remind me of that kind of stuff.

Kate:

And also just on that note at the theme time I was reading, how can I help by Ram Doss? So it all perfect storm.

Amy:

Yeah. And I love it. I just started putting it together as you started creating first and then like great things come through. Okay. But before we go into the Australian, I want to talk about this seventh organization and being burned out.

Kate:

Okay.

Amy:

Let's do it. I I'm trying, I don't want to put my own like biases onto the conversation, but I don't know if we've ever spoken about like my, my red pill, blue pill analogy when it comes to culture, right. When you've worked at a great place, it's like you've taken the red pill and you can never unlearn what that feels like yet. And it makes the. Places that are not like that, which is about 80% of them boy, way fucking harder, way harder.

Kate:

I mean, Rackspace to me was like, it was the greatest job I think I'll ever have. And then it's like being in love with someone who's super great. And then you guys break up and you have to go. Other people and you're like, well, no one will ever be as good. I stopped person. So every company I went to, I was looking for, I was looking for a Rackspace and I couldn't, I couldn't find it. Um,

Amy:

I, I, I, I can relate to that. And this is why Ryan Walsh and rep you, um, was episode number one, right? Because that's the history of the Lord's work as far as I'm concerned. And so we're going to start with that, but I think a lot of people can relate to. Let's talk about though, this what happens after. So Rackspace was what number was at in the seven one

Kate:

number one. Okay. Okay.

Amy:

Um, what did it feel like? Let's say on. Attempt number five or attempt number six. Talk to me about the self-doubt that starts to creep in at that point, or like, sort of just where was your head at it?

Kate:

It's not even like, I don't even think that's the right.

Amy:

Okay. Well tell me what it was. I mean, it's

Kate:

self doubt. It's like impending doom. Like I knew in my heart of hearts, I was not, I couldn't do it anymore. I was never going to. I was never going to be good at it, but also if you don't have some, like, if you don't know what you can or want to do, then it's very problematic. I had no idea. I didn't know what I wanted to do. I didn't know what I was good at anymore.

Amy:

Yeah. So listeners, if anybody can relate to that, one of the things that I found to work very well in moments like that is to think about what I don't want to do first. And kind of work my way into it from that. I also speak about, um, finding sales enablement and kind of going through my resume and like looking at all the bullets on the resume and forcing myself to put them into three categories, loved it, hated it in different. And that, that helped me to kind of get a little bit closer. Um, but like Kate, like where you, like, where you hitting her number, like where, where was the doom feelings of doom coming from? Was it about like I'm a, I'm on a PIP and I'm going to be fired again? I've

Kate:

been on a PIP, definitely messing up. They couldn't care. I just couldn't care. I didn't care. You may lists, I went to the. Trail and I walked and cried. That's what I would just walk and cry and I would listen to podcasts about whatever. I don't know, just trying to get inspiration.

Amy:

So you just started creating the program. I like, I think that that's so baller. All right. So let's go back to struggling. So walk us through, like, what happened when you created the program? Like, how does one even does, do you go and knock on a prison door and say like, Hey, like I want to, you know, like how do you even start to form those relationships? And then I'm very curious to hear about what the conversations are like with sales bosses or sales leaders. Um, Who could potentially be pulling from this candidate pool. So like, just walk me through the process and then we'll go to the, like, how is the market received this?

Kate:

I honestly, I had, I didn't have a ton of faith that it would be received. Um, but I have, I had a mentor, Kathleen Nielsen, who has a ton of experience building businesses and I'm experienced in nonprofits. And I told her my idea and she was like, I love it. Let's just start playing. So we started pleading and I, I didn't have a lot of faith, but I dunno it looking back, it's a card to even, it feels like a blur. It's hard to say exactly how it all happened. It's like it just unfolded and every single step I've taken in building this program, um, it's like the path is just like, oh, like just being created in front of me. And I am just taking steps and it's just. Happening just going. Um, and so the first group that came to our program, wonderful five women. Um, and they trusted me to guide them. And I will tell you, I'll still tell you a story of one of them. She's on our board. Margaret Maloney. Okay. And, um, when I met her, she had experience, um, she had experienced, uh, she just didn't know what to do with it. Um, she really wanted to be in tech, really wanted to be in tech. And I was like, I think I can help you. And so she came through the program and she was the hardest working person I had ever met in my entire life. I've never seen her tire and I pushed her really hard. Like I do everyone, um, because I want everyone to be the best when they leave our program. I didn't have any hiring partners. No one really knew what I was doing. I'm going to meet a few announcements, but I was like just doing my, my research. Okay. Well, who do you want to work for? And we kind of zeroed in on gone. We didn't have any connections there. So we just went in the old fashioned way, like send your resume. And then we did a cover letter with a video that she recorded 47,000 times almost to the point where I, like I thought in center breaker, but she just never. Okay, but okay. And so every interview she went through, we spent so much time preparing and coaching and growing is a very difficult interview process. They don't it's a lot. Um, and so when she finally got the offer, she called me on the phone. It'd be, I was crying. She was crying. We were so excited. But then we were like, okay, now we have to get through the background part of it because no one knows.

Amy:

You're having to disclose it yet, or you have a chosen to wait until, right. Okay. That makes sense.

Kate:

It were a fair shot, but then, you know, when it's time to disclose and you disclose because we want to be transparent and it's just a better way to be. And I will give credit to gong. They gave, you know, they gave her every opportunity and she had the ability to explain herself. They hired her. She actually moved out from Arizona. She moved down the street from me because she doesn't know anybody in the bay area with her daughter and her daughter and my son go to school together. No, they're both at the same school on the season break at a sleep over last weekend. They're very good friends, but more importantly, Margaret's got hired as an STR. She got promoted to senior SDR and then this month she got promoted to AAE and she's already. Closed two deals.

Amy:

Congratulations, Margaret. That is awesome. And now she's

Kate:

looking a board of directors and, obviously Shannon, one of many examples of why this makes

Amy:

sense. Okay. So. I know I've thanked you a bunch of times, but I'm going to say, I'm going to say it again. Thank you. Thank you. Thank you. Okay. But now let's talk about how this conversation is received. When you go talk to some sales bosses or sales leaders that are looking at participating in the changes on the diversity and exclusion front, which is now what I call it. What, what are those conversations like Kate? Like for real, the good ones, the bad. What? Like, where, how is this being received? What's working. What's not shockingly.

Kate:

I would say like 95, 90 8% of conversations are like, okay, great. Let's get him fired. Really. There are some times that it, HR of course is like, well, what kind of backgrounds are we talking about? Like the most part they want to hire from us. It's shocking to me because I honestly didn't know how it was going to be received, but I'm actually, um, I'm kind of proud of the tenant community for that.

Amy:

that wraps another installment of the revenue real hotline. I'd like to thank my guest for being so damn real and for sharing their insights and for, of course, being so much. And I'd like to thank you to listeners. It means the world. And I appreciate you. If you have any thoughts or comments or experiences, you feel inclined to share head straight over to revenue, rail.com. There's a new join. The conversation feature on the right side of the page. I am all damn ears. Final thought. We are introducing a coaching aspect to this. So anyone who's brave enough to dig into an account strategy or outbound strategy set. That's where we kick things off. Please do follow the show wherever you listen to your podcasts. So you'll always have the latest episode. Download it. If you want to contact me, I'm at Amy at revenue. real.com. If you want to follow me on social Twitter is Amy underscore Rahab check, and LinkedIn is linkedin.com. Backslash Amy rev. This episode was produced by the fabulous Nian Fiedler Iraq man. And I appreciate you too friend. And of course, whatever you do, don't tell anybody about the show. Let's keep it at our little secret until next time. All I'm Amy. This is the revenue real hotline, happy selling.

Amy Hrehovcik Profile Photo

Amy Hrehovcik

Host of Revenue Real Hotline Podcast

Kate Leidy Profile Photo

Kate Leidy

CEO @ Strively