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Welcome to the Sales Transformation Podcast, the definitive stop for leaders driving change in the sales world. Hosted by Kevin Warner, we dive deep into the minds of Founders, CEOs, VPs of Sales, and Sales Development Leaders from trailblazing startups to industry-leading public companies.
Our mission is simple: to illuminate the path to extraordinary sales leadership. We explore a broad spectrum of sales territories, from the intricacies of Founder Led Sales and Outbound Sales to the transformative potential of Technology in Sales and Social Selling. Whether it's mastering your CRM, optimizing conversions, scaling sales teams, or engineering a complete Sales Transformation, our conversations are set to challenge the status quo and redefine sales success.
With a new content every day of the week, we bring you unfiltered interviews with the luminaries of sales, people who have not just succeeded but transformed the way we think about sales. Kevin Warner also shares sharp, tactical sales tips every week, packing decades of sales wisdom into bite-sized insights.
So, if you're ready to rewrite the sales rulebook and learn from the best in the business, the Sales Transformation Podcast is your ticket. Write us a review, share the show, and join us on this journey of sales evolution. Let's transform the way we sell, together!
Welcome back to another episode of sales transformation brought to you by Leadium. Today, we have Leandra Fishman, c r hoe at Apollo IO, joining us to share her journey in sales leadership. Colin, back to you.
Collin Mitchell:Alright. Welcome back to another episode of sales transformation brought to you by Leadium. I'm your host, Colin Mitchell. And today, I've got Leandra Fishman on today. She's the CRO over at Apollo.
Collin Mitchell:Welcome to the show. How are you?
Leandra Fishman:Hi, Colin. Thanks for having me.
Collin Mitchell:Yeah. We just realized that we're pretty much neighbors, so that's pretty cool.
Leandra Fishman:I know. Go East Bay. Right?
Collin Mitchell:Yeah. Yeah. Have you been in the the bay for a long time or no?
Leandra Fishman:Yeah. Actually, I spent my whole entire life in the bay. I was in the South Bay and then on the peninsula. I recently came over to Oakland probably about 6 years ago and, yeah, just enjoy the diversity, the walkability, and, and being close to the city.
Collin Mitchell:Yeah. Awesome. Yeah. We love it. We moved here recently, but, love it.
Collin Mitchell:Well, before we jump in here, just give us a little bit of background on yourself before we kinda jump into the topic today, and then we'll sort of take it from there.
Leandra Fishman:Awesome. I have been in sales my whole career. I think going on probably about 35 years now. So it's been quite a while and I never planned to get into sales. I kind of joke, you know, with people.
Leandra Fishman:What do you wanna be when you grow up? Because I don't think a lot of people grow up and say when I grow up, I wanna be a sales rep. Maybe unless you let you have a parent or you've seen kind of, you know, somebody that's that's in sales. But I kinda stumbled into sales, and I've had an awesome opportunity to experience a lot of different company sizes from, you know, 10 person startups to Fortune 500 companies across a lot of different industries and verticals, consumer hardware, enterprise software, manufacturing services, and really the fun of these different stages and being able to be at every single level, you know, as you as you kinda have had different experiences in your career. And what I'm really most passionate about is solving problems, building teams, and really helping make an impact in a way that I can measure it in terms of revenue.
Collin Mitchell:Yeah. I don't think anybody, grows up saying they wanna be in sales. Most it's most people, it's their plan b or c, but there is a lot of people doing a lot of great work to try to change that.
Leandra Fishman:Yes.
Collin Mitchell:You know? I think that for for a long time, you know, sales has kind of been a dirty word, but, you know, there's there's a big difference between people that do it right and not. And so I'm just kinda curious, you know, what made you stick with sales?
Leandra Fishman:Yeah. I stumbled into sales really coming in from my first job in a sales office, but working in kind of the customer success area. So I was just assigned to accounts, and I was a little bit of a mix of, you know, kind of order processing and account management and, you know, kinda administrative work, but what I loved is solving problems. And to me, I never considered it sales. I don't think I really knew what sales was at that time, But what I loved is building relationships and solving problems and then seeing how that impacting was helping customers, you know, propel their business forward with whatever product or service that that I was selling, but also, you know, really seeing the impact that it had been on a company in terms of growth.
Leandra Fishman:And so I think that that whole energy and essence of really grounding myself into being of service really resonated with me.
Collin Mitchell:Yeah. And at what point did you, go into sales leadership?
Leandra Fishman:Yeah. That's an interesting journey because I never had a plan for my career. I was never like, oh, I wanna get to, you know, this this stage or this position. Actually, I told I was told very early on that I wasn't gonna be successful, because I actually didn't have a college degree. And I didn't grow up with kind of that environment of kind of education and so I was, you know, wasn't in a kind of a nurturing family environment that was really stable.
Leandra Fishman:And so I kinda navigated my way, I think, for my my first, you know, 18 years, with a lot of kind of unsupervision and and, independence and and didn't really think about, you know, what was my potential or I didn't think about what my career opportunities were. So when I got into sales and I was like, wow. This is kind of interesting here. I went to the the VP of my organization, and I said, I think I think I'm good at this. I think I wanna take the next step.
Leandra Fishman:Yeah. He said, do you have a college degree? And I said, no. I don't have a college degree. And he said, you're never gonna be successful without a college degree.
Leandra Fishman:Now this was a shocker to me. Like, I was like, oh, I I didn't understand this was a thing because I didn't grow up with that type of environment of, you know, kind of that family or friends or parents, like, nurturing young minds, I was just, like, oh, I'll just figure this out. And so at that point, I recognized, like, that had a ceiling, and I started to feel really insecure because I thought I'm not gonna be successful. And if I'm not successful, that means I'm not smart. And if I'm not smart, then, you know, I'm not good enough.
Leandra Fishman:And so I really kinda started a little bit of a spiral. So I was like, okay. I gotta go back to school. But, you know, I didn't feel like I was really clear about what I wanted to do, and so I wasn't passionate about it. So I just kept my head down.
Leandra Fishman:I just, like, worked really hard, and I just recognized in a sales organization, the only thing that people care about is the number. Yeah. That's all I talk about. Not the
Collin Mitchell:degree. That's that's changed a lot, though, I think. You know?
Leandra Fishman:Yes. Yes. But back in the day, it's like you hit the number, you're good. You don't, you're bad. And I recognize that when you take really good care of your customers and you solve problems like that number just it was coming naturally.
Leandra Fishman:But I also recognize that, you know, there's going to be a ceiling for me and so I didn't think a career was possible to get into leadership. So I spent about 3 years being, you know, kind of like an inside sales, you know, type rep in customer service and then kind of jumped into that next layer and then had a little bit more sales responsibility. Didn't even know what a commission plan was or understand, you know, hitting those numbers and making that extra money. Spent another 3 years on getting into field sales. So it's probably about 9 years into my career until I went to a start up, and there was an opportunity that, as a start up growing to hire a manager or a director of that team.
Leandra Fishman:So about 9 years in, I felt like I had kind of mastered, you know, the art of being a great salesperson. So I went to that VP, and I said, I I think I I can be a leader. I think I can be in management. And he says, you can't be in management. You don't have the experience you don't have the background and I looked at the job description and at the bottom it said college degree required Now, again, because I didn't have that background and I had felt very insecure about it, I was like, oh, I get it.
Leandra Fishman:This is like the ceiling that a a degree gets you to get to that next level. And so I said, you're right. This person's amazing, and I don't have, you know, all of this experience. I said, why don't you go find that person? In the meantime, can I do the job for free?
Leandra Fishman:I didn't ask for the title. I didn't ask for the money. I was just like, I think I can just help. And so can I just do it while you find that person? And 6 months later, they didn't find the perfect person.
Leandra Fishman:They realized she's not doing such a bad job, and that was my first step into leadership.
Collin Mitchell:Leadership. Wow. That's pretty bold.
Leandra Fishman:Yeah. It's it it it really comes from just wanting to serve. And so when I got that first step into leadership, a lot of my peers were older than I was that had more experience because at that point, I was 27 years old And I was like, what do I know? What am I gonna teach them? But I really had that mindset of, like, what can I do to help?
Leandra Fishman:What can I do to help you? I was at corporate. They were in the field. And so I just said, like, how can I help you be successful? And so I think a lot of really my leadership traits grew out of helping set strategy, remove obstacles, and getting out of the way.
Leandra Fishman:And it's fun when you can help people, you know, kind of expand their own opportunities and their own success and win. And so I've really always had that mindset.
Collin Mitchell:It's a it's a crucial mindset for for leadership because I think a lot of people get into leadership for the wrong reasons, and many get into leadership too early. Right? We we've all seen, and I was top performer to leader, not ready, you know, which you're then learning at the expense of your team, which can be, you know, disastrous. But kinda curious in that first experience in leadership where you, you know, sort of took ownership for, you know, your career trajectory there, You know, took a step of, you know, not getting the title, not getting the pay, but taking on the responsibility. What were some crucial things that you learned in that, say, first 6 to 12 months?
Leandra Fishman:Yeah. It was such an important time because I didn't know who I was as an identity of a leader. And so I read a lot of books. I think the one thing I've always had in my life is just like a deep curiosity of learning and knowledge, and I am a book reader. If you've got a great book, I wanna hear about it because, I I love to read and learn.
Leandra Fishman:And I just thought, okay. How do I sneak knowledge information? And the other thing that I think was really important that I really tried to embrace was just listening. You know, just like you have to be a good listener if you're a salesperson, you have to be a good listener if you're a leader. And really kind of honing a little bit of my understanding, not having to have all the answers.
Leandra Fishman:Answers. I think that that sometimes we think when we get into a leadership position, we have to have all the knowledge, but really kind of treating, like, the the team is like they're actually in the trenches. If you ask them what the problems and issues are, they will tell you, and often, they have the best, you know, solutions to those problems. And so I really just recognize that I don't have to have all the answers. Really listening to my team and leveraging their expertise and their experience and helping elevate them as how everyone's gonna win.
Leandra Fishman:Yeah.
Collin Mitchell:Yeah. I I think that, that can be hard for a lot of first time leaders. Especially and it can also be a little bit frustrating. Right? Because you're like, oh, I know what needs to be done, and sometimes you almost just wanna do it, and that would be the simpler path.
Collin Mitchell:Right? But, you know, allowing your team to have a voice and let them find their own solutions and empower them is is the right, you know, place to come from as a leader.
Leandra Fishman:Absolutely, Colin. You nailed something that was really hard for me when I moved to being a second line leader. So when I was a first line leader, I was like, okay. Either the team's gonna figure this out or I can figure it out for them. And I actually moved from consumer hardware into enterprise software.
Leandra Fishman:And I thought, oh, this will be easy. You know, the the quotas were so much lower because when you're selling, you know, consumer hardware, you're selling multimillion dollar, very, very large deals. And when you're selling software, especially in the in the early days of SaaS, these subscription based models were very small. So when I had the opportunity to switch into enterprise software, first of all, I didn't know anything about enterprise software. I hadn't sold it before.
Leandra Fishman:But I thought, oh, a couple $1,000,000 worth of quota? No problem. I could do that in my sleep. And then I recognized it's not the one deal. It's the 100 deals.
Leandra Fishman:Right? I couldn't just close the one big deal to save the day. And then I also recognized that it was the team that needed to close those 100 transactions. And all of a sudden, I was like, they don't think they can. And so I recognize just, like, how our own self belief system can really kinda put a a ceiling and a lid on what our potential is.
Leandra Fishman:And when teams don't think that they can win, it really prevents them from being successful. And so I had to learn that I can't do the work for them. I need to teach them. So what I did is I really thought about, okay, if I was doing this job today, I learned the product. I created a system, like, in my own mind, and then I taught it to them.
Leandra Fishman:And in 6 months, we did more revenue than we did in the entire year prior, and I didn't pick up the phone once. And it wasn't because the team didn't have the tools. They didn't believe that they could, and they just didn't understand how the right strategy. And I didn't want them to fail either, and I certainly, at that point, you know, wasn't gonna let, enterprise software take me down in terms of a a new or vertical and industry to conquer, and to conquer, and it was a fun ride on that on that area. Yeah.
Leandra Fishman:So what were some things specifically that you worked with them to build up
Collin Mitchell:their their confidence?
Leandra Fishman:I'm a big believer in, first of all, just having a system because I think sales is a numbers game. And in so many aspects of it, you need to have some structure and some process to really understand how you get what's at the top of your pipe all the way through. I think the second thing that's what's really important is not just that system. It's like, what are those key metrics? And how do you measure yourself and challenge yourself to understand, okay, at every aspect of that funnel, like, it's gonna continue to fall out.
Leandra Fishman:And how do I learn the lessons from those? And I think that's the fun thing about transactional velocity and actually love the SMB commercial space is that you have so many transactions that you're going. You can really start to see the patterns and the trends. Mhmm. And really just got the team to believe in themselves.
Leandra Fishman:I mean, that's what I think is the hardest thing in sales. If you don't have confidence, your customers feel that, you don't feel, you know, strong enough and really understanding maybe your product or the market or just know the value that you have in solving problems, really making sure that people understood. What is our product differentiation? What's our value? How can we help serve?
Leandra Fishman:And always doing what's right for the customer. I'm a big believer there's only really 3 things that you can control. The first one's your attitude, the second one's your effort, and the third one's your intention. And I think in sales, sometimes the intention can get a little bit squirrelly because we're all, like, pushing for the win and the dollar. But when your intention is to help and serve and make an impact and a difference and solve problems and add value, I think the universal lines of everything around that.
Collin Mitchell:Yeah. You're you're you're right. The intention is the tricky one.
Leandra Fishman:Yes. Especially when one gets involved. Right?
Collin Mitchell:Yeah. Especially, you know, with salespeople who, you know, large portion of their compensation is tied to commission.
Leandra Fishman:Yeah.
Collin Mitchell:You know, it can be it can be a challenge to to manage that intention. So how do you help your team with managing their intentions, you know, with the goal of serving customer and, you know, whatever their best interest is?
Leandra Fishman:Yeah. It's such a good question, and I think it's something that we all need to stay grounded in. It's like reminding ourselves ultimately the customers who are here to serve. And in looking at those that customer journey, I'm always about the best customer experience at the lowest cost to serve. And so I feel very unattached to kind of the outcome in a way if the outcome isn't really around what's best for that customer.
Leandra Fishman:Because in my mind, kinda you're creating I call it sales karma. Yeah. Yeah. You're creating that energy where that is really gonna serve you or it's gonna come back to bite you if you're really trying to gain the comp plan or or force a solution down, you know, a path where it's really not gonna benefit the customer. You really just don't have that right grounding.
Leandra Fishman:To me, I always ask, like, what's what's in the best interest of the customer? And sometimes that's gonna lead you to a yes or a no. But I believe in the collective energy of when you do the right thing with that intention, you know, it it'll all, it'll all work out in the
Collin Mitchell:end. Thanks for tuning in. Please don't forget to like and share so we can help more people transform the way they sell.