Become a Creator today!Start creating today - Share your story with the world!
Start for free
00:00:00
00:00:01
Amanda Schlegel
14 Plays1 hour ago
Thanks for listening to our episode with Amanda Schlegel.
To keep up with or connect with Amanda:
✨Amanda’s LinkedIn: https://www.linkedin.com/in/amandaschlegel/
✨ Amanda’s Website: https://www.amandaschlegel.com/
✨ Email Amanda: amanda@amandaschlegel.com
To stay in touch with Meredith and Medbury:
Follow Meredith on LinkedIn: https://www.linkedin.com/in/meredith-farley/
Follow Medbury on Instagram: https://www.instagram.com/medbury_agency/
Subscribe to the Medbury newsletter: https://meredithfarley.substack.com/
Email Meredith: Meredith@MedburyAgency.com
Recommended
Transcript
Introduction and Amanda's Background
00:00:03
Speaker
Hey, Amanda. Hi. Good see you. It's really nice to see you too. Thank you so much for doing this interview with me. i feel like our listeners are going to love hearing your story and hearing from you.
00:00:15
Speaker
For folks who don't know you, can you say who you are and what you do? Sure. Amanda Schlegel, and I am new to Boston. I moved at the beginning of the year, so I'm settling in, and I am a go-to-market strategist.
Career Journey at Tech Giants
00:00:34
Speaker
I've f led sales teams in tech companies like Microsoft, Samsung, IBM, and I have started my own consulting practice where helping startups build out sales teams whenever they're ready to expand as well as helping them figure out if they're even ready to do that, just where they are in the go-to-market track. And so yeah, happy to be here.
00:01:03
Speaker
Thank you. So, yeah, where you are... sitting in your really cute kitchen. You're in the South End, right? So I always forget. I always want to say back bay, but South End. And I feel like we should say like before we started recording, you were talking, youd recently moved and talking about getting things organized and just what a mess it is sometimes. i But I'm really happy that you're here in Boston. i have to say every time we talk, I really appreciate it so much. We met through the networking group, Chief, which great yeah group if anyone listening has been thinking about it.
Transition from Marketing to Sales
00:01:33
Speaker
And i love talking to you because I feel like in all my years of like corporate, was in like a chief product role, chief product officer role for a bit where I interface with the sales team a lot and a COO role where I did a lot of sales teamwork, but I've never actually been on the sales side. And it's such a beautiful art and science and you have so much wisdom and knowledge about it. And I also love the integrity that you – take when you're speaking about or guiding.
00:02:04
Speaker
And so thanks for doing this. I feel like anyone listening who wants to hear all about sales, this is going really good interview. How did you end up here? And I don't mean Boston, though, if you want to talk about you can. What was your career journey up till now? You mentioned IBM, Samsung, Microsoft. You've worked at so many incredible places. Yeah.
00:02:24
Speaker
It's one of those things where I never set out on this trajectory, just as opportunities come up, you I just took them. I had started my career in marketing and spent about 12 years marketing. i Enjoyed being in marketing. i feel like I learned so much. It made me a really customer-centric person. So I always think about the customer on the other side, and I credit marketing for that. And I think about messaging and how you stack up against competition, what kinds of questions to answer before you talk to a customer.
00:03:04
Speaker
All of those things I learned from being in marketing. I think when I thought back in those days about sales, I really never saw myself doing it.
00:03:18
Speaker
It didn't seem like a job for smart people. I know that sounds like really rude, and but it did it just did it It didn't seem like a job for smart people, and I had no interest in it, and didn't think that I would ever be good at it either.
00:03:34
Speaker
well And I started interacting with customers a little bit and I was really loved it. i love still to this day, love interacting with customers and new people and Then as i started to learn more about sales, I realized that especially certain types of sales roles are really strategic and you really get to see the impact of what you do because the numbers don't lie and it can be a very invigorating and challenging role.
Key Traits in Salespeople
00:04:08
Speaker
And so I became a lot more interested in
00:04:12
Speaker
transition from marketing to sales when I worked for Samsung Mobile and I managed the Walmart business for Samsung Mobile. And from there, I just knew that I could never go back to just a straight marketing role.
00:04:29
Speaker
And that sort of set me on the trajectory for being in tech, even though i had this free retail CPG experience and Samsung was still like the CPG and dealing with retail. and I still to this day love retail, but that job is what really changed the course of my career because from there I went to Microsoft and that transition was because Microsoft was looking for people that had deep industry experience as they were transitioning to become a cloud company and
00:05:07
Speaker
it sounded like a crazy proposition at first, but it was also really intriguing. And from there, I ended up like being on the road to big tech. And so one one opportunity led to the next, led to the next, and that's how I got here.
00:05:26
Speaker
Amazing. When you meet people, do you ever think, oh, they would be a good salesperson? Do you feel like you can pick up on what makes people good at that? Yeah, it's interesting.
00:05:38
Speaker
i when I meet people, um care so much more about who a person actually is whenever I meet them. And maybe that's why working with clients is so fun because you're trying to uncover who they are and how you can help them if you can.
00:05:56
Speaker
And just building that rapport is my favorite part of sales. So I don't really, whenever I just meet people in general, don't normally think that unless I've met someone, because I have met a couple of people before who were in different functions. So like operations, for example, and They had just vibrant personalities and were very curious and had some of the characteristics of salespeople and have actually said to me, oh, sales, because people always think that salespeople get paid a lot of money. And, you know, they usually do get paid more than marketing or operations, those functions. But there there have been people who have made comments to me like, oh, I just don't think that I could ever do that. But it would be nice to make more money. And if I think that they have it, then I've said it. But I don't initially think that. But when I'm interviewing people for sales roles, I know exactly what to look for.
00:07:03
Speaker
Can you say a little bit more? Like what are you assessing Because I know you help your clients sometimes hire. Is that right? Absolutely. Yeah. okay So yeah. What's your approach there and what do you look for? So my my first and foremost, a really great salesperson has to be endlessly curious.
00:07:22
Speaker
Because especially if you're going to sell ah tech or some other really complicated product or service, you've got to be endlessly curious.
00:07:33
Speaker
You've got to be really comfortable with not knowing everything. So things being nebulous, ah you' you've got to be able to live between lines. which sounds easier than it is. i know for myself that when I made that transition from Samsung to Microsoft, learning to live in a nebulous world did not come naturally to me at first. I did did not like it. I did not feel like I had enough control over what was happening around me because when you're selling really complicated products and services,
00:08:08
Speaker
It's not a job you do by yourself, regardless of what people tell you. It's really not. And so, It felt like lines were really blurred where if you're selling like a consumer product, it's very clear where pick up and within a certain role and somebody else takes over or vice versa. And, but tech sales, it's very nebulous. So being comfortable with that, being able to have, be able to focus and still drive towards something,
00:08:44
Speaker
in a shakeout. That's part of it. Being very organized. I'm sure that there are successful salespeople that are very disorganized, but i wouldn't place bets on it for building out an organization, especially one that you want to have great success because your you're going to have a lot of moving parts. And so the organization helps manage that.
00:09:11
Speaker
And then Another really big characteristic of a good salesperson is not always knowing the answers and then asking for help.
Sales Discipline and Team Dynamics
00:09:22
Speaker
You are likely going to have to depend on other people sometimes to help you lead me through a conversation with the customer. So you can't really have a big ego about it. I always say that sales is a team sport.
00:09:34
Speaker
So yes, it's very individual. You have an individual number. You've got to hit those, hit those markers. But at the same time, you're on a team. And it's if you think about a sports team, for example, everybody has a role. Everybody knows what they have to do. And you get judged from the impact that you make as an individual player. But you also contribute greatly to the team. And I think sales is the same way. So you need confidence and willingness to learn.
00:10:02
Speaker
But don't come with an ego because that destroys the culture really fast, actually. and And then I think being very disciplined is the other like major characteristic. Again, yeah, I'm not that I'm not even an athlete, but I think that these, that there's a lot of correlations between like characteristics of a good athlete and somebody who's a good salesperson, because You have to have discipline, especially when you're going after new revenue. Your days will be filled, sometimes doing monotonous things, and you have to trust the process that prospecting, sending those emails, or making a phone call, or building rapport with a customer or a contact within a company that then is going to eventually lead you somewhere. You have to trust that process, and you have to just keep doing it, and you have to trust that
00:11:01
Speaker
that it's going to pay off in the long run and it's can be really grueling. So not everybody can handle that. It's very easy to get doubts about how well you're doing or your ability to perform whenever you're starting out and, or if you're starting with new accounts or, You don't even have accounts yet.
00:11:22
Speaker
So yeah, I think yeah it's really asking a lot of someone to to be a great salesperson. But that's those are the things that I look for whenever I'm talking to someone. And usually you could tell by the energy level and then by the stories that that people tell.
00:11:40
Speaker
And then every once in a while, you can get fooled by a salesperson because they are selling. But I think that I've either gotten really lucky hiring or I'm pretty decent at being able to pick out talent. it it's Thank you so much. I find that so interesting. the When you're talking about a comfort level with ambiguity, like sometimes it's a kind of nebulous role or how you fit yourself into the se the environment might feel nebulous and or
00:12:13
Speaker
being comfortable being in that kind of gray area where you, as you were saying, you just need to trust the process and you need to take steps every day to move toward the goal and just trust that it's some, it will get there. That's really interesting. I never thought of comfort with ambiguity as such.
00:12:30
Speaker
An important part of the sales, i don't know, persona is not the right word, but the toolkit one needs to have. And I can also see like how there's, it seems to be me a lot of tension in the sale, the ideal salesperson persona, because it's someone who's willing to sit and be disciplined and do the work and trust the process and do boring things. But someone who's also deeply curious and wants to connect with and talk to people. And it's a lot. It's definitely unique and can really burn people out if they're in the wrong role.
00:13:02
Speaker
But I think one thing about leading salespeople, it's something that I've done that like I'm not the norm, I think in the corporate roles that I've been in, but I don't think anyone should ever be punished for stepping forward and saying, you know what?
00:13:18
Speaker
I don't think I'm good at this. I don't think this is where I see myself. I think when someone comes to you and says that, you help direct them somewhere else in the in the company. I've done that multiple times. Most people will just put them on a tip and fire them. I don't think that's what you should do because I think that everybody has value.
00:13:40
Speaker
And i think really great leaders find value in people and put them where they can thrive and where they're going to be successful. And it does not, it doesn't benefit the sales leader, for example, to go through that, move the person where they can thrive yeah because that value, it just may not be in the role that you're in. And then you can open up and it's, to me, it's just,
00:14:07
Speaker
a much more humane way of dealing with it, but also faster. and you don't have to go through all the things that you have to do to fire someone. But yeah, I mean, it's really, I think it's a fun, it's a fun job, but it's a fun job for the right people.
00:14:24
Speaker
Yeah. So I know interviewing and building out sales teams is such a big part of what you do. Can you talk about the other ways that you work with and collaborate with and support clients?
00:14:36
Speaker
Yeah, depending on how big the team is or how deep the organization is, can impact how how much an executive leader gets to how many, how often that they get to meet with customers and what they actually do. I've found that over the years, the higher that you go,
00:14:57
Speaker
You're just a figurehead at that point. And I'm just being honest about it. You're just a figurehead and you're showing up to meet the other leaders with within the client organization.
00:15:08
Speaker
but I think anytime that i get to have interaction with a customer, whether it's solving, cause this actually did happen to me a couple of years ago. i had a young account manager on my team I was She wasn't sure she wanted to do sales, but she was very honest with me. and We kept working and, but she was very open to coaching and she had a couple of different mentors and she would always come into my office and talk to me.
00:15:39
Speaker
And i had a customer that called, up that was one of her customers and said, Hey, she never returned to my calls. And so I was like, I've kind of believe that this might happen with her.
00:15:52
Speaker
We talked about it and she said, actually, it's the other way around. And she was able to show me like all the emails that she had sent him. She had left voicemails and documented them in CRM, which is another reason why you want to be disciplined as a salesperson. It's a really good CYA tool too So anyway, she was able to back up what had happened. So I called him and just said,
00:16:21
Speaker
hey we want to help you and tell me what you need right now. And i'm going to work with Julia and we're going to get this done. So we did. And he told me what he needed. And then i had the opportunity to meet him in a couple of weeks. We were going to a conference and he agreed to meet with me and gave him my mobile number and just said, if you ever need anything, please reach out to me. And that was all it took. You just need to smooth things over. is this like is this was this a performance issue? is it a chemistry issue? Because sometimes that it happens to everybody. And if it was a chemistry issue, I would have just switched out the account manager
00:17:06
Speaker
But we were able to handle it without doing that. But that was one, one option. But at the end of the day, you want to make sure that the customer's needs are being met.
00:17:18
Speaker
But i also think that you have to be fair with the salesperson too, and not punish someone. if they didn't deserve it. So I always like to make sure that I do the due diligence on that as well and make sure that I understand what's happening. But whatever it is, but those are the most, those are mostly the interactions that I have these days or helping solve issues like that. So sometimes for your clients, you're coming in and you're serving as a leader who's you are mentoring and training and coaching, but the sales team, but you're also stepping in to like troubleshoot and you handle the call from the angry customer or disgruntled and be like, okay, this, let me categorize this issue.
00:18:03
Speaker
Let me, I don't know smooth over is the right word, but let me ameliorate it with some nice personable steps and help to prevent clients from going from disgruntled to canceled clients or clients you've left. And then what about when you're, it's, I know you work with some early stage startups too.
Advising Founders on Scaling Sales Teams
00:18:22
Speaker
So so have you ever had a founder come to you and say, I think I need a sales team. Do you help them evaluate when they're ready to build something?
00:18:31
Speaker
I have a framework that I use to just help walk them through. Because there's a psychological perspective, especially when it's a founder, or about readiness. And then there's also the financial piece. So it's a math problem.
00:18:48
Speaker
How much do you expect a salesperson to generate and revenue and you can get it like a cost per head? And then how much revenue will each salesperson produce? And does that make sense with what you're selling?
00:19:05
Speaker
Or is there another way to to sell this? So helping somebody figure that out and then the Also the psychological part, I did have a situation with a founder who really was ready to make investments and wanted to drive all those things, which again, you're a founder, you want to drive your business, but couldn't let go of certain things. So when I came in, this was a cert tech services company, which adds some
00:19:39
Speaker
complexity because if your services, what are those services? Who are all the partners that you're working with? And this particular founder had a hard time letting go of like contract negotiation. he didn't even have any of the services that his company provided documented anywhere. And that was the first place I started. Everything has to be documented because in order to in order to grow and teach another salesperson. They've got to have an idea about what it is that they're selling. And so we got that part done. And eventually i talked the CEO into implementing a piece of software that would allow for for writing the contract. So you could go through and
00:20:25
Speaker
pick, okay, the customer wants this type of service and it calculates the price because you can't, there has, again, it has there has to be a framework for how you price things and how they're structured.
00:20:38
Speaker
And so you have to be willing to let go one of the information out of your head and share it with other people and be comfortable with other people. having that information and then sharing it and then maybe doing something a little bit differently than you would do it as well. Maybe yeah they call customers at a certain time of the day and that's not something that you would do or maybe they did not think to discount a certain service that you as CEO have done ever since you started your company. And that doesn't make it bad. It actually makes it good because you're making more money. but And then the biggest thing is trust doing all of that and sharing the information and allowing for a structure to be put into place so that not only could one sales person come in and pick it up and yeah go find customers and then bring them back in and sign them up on a contract and then get them set up and executing with the the team that does that.
00:21:42
Speaker
But you've got to allow for multiple people to do it. And that just requires a lot of trust. So there's a conversation to be had that there as well with people who are thinking about hiring sales teams.
00:21:57
Speaker
Yeah, that's super interesting. Do you find that trust is that one stumbling block that you find a lot of founders have where they just like, it's really hard to let go? Or is it just but every now and then someone where you're like, ah, I think because it's something that you built yourself. So yeah, I think accepting that other people are going to be a part of this and they're going to work hard for you and work hard for the company. yeah yeah you You've got to come at it from that frame of mind, because if you're coming at it from the other way and you don't trust and you don't think that somebody is going to work as hard as you and don't think that somebody can do as good of a job as you, it's going to be really hard to scale.
00:22:46
Speaker
Yeah, totally. Because then you're going to be you ah focused on the wrong things. You're going to be, you left out this line and this email, or you're going to be nitpicking about things that really don't matter. Are you bringing in customers? Are we bringing in money? Am I, as a salesperson, bringing in enough money to justify my being here?
00:23:07
Speaker
And are if we turning a profit on me taking up this seat? Those are the things that a CEO should be focused on, but when they don't have trust, they do, they nitpick and they go, okay, but this person showed up two minutes late to this meeting, or it's all these things that really don't really matter when it comes to moving the needle. So the trust, the trust is a really big part.
Education and Guiding Principles
00:23:36
Speaker
Why do you think you're so good at these things? like It seems to me like you're really good at the people side and understanding like patterns and archetypes of people and what makes a good hire. You also are so tapped into the structure, the process. And it seems to me like you, because you've been involved in so many organizations at so many different moments and at so many different levels of small versus scale, you're really good at knowing, okay, this is the moment and the step in the process where we do X, Y, Z, and here's exactly how we do it. What do you think in you is just so drawn to this kind of work and why do you think you've been so successful at it?
00:24:16
Speaker
Thank you, Prith. That was a nice compliment. I think that from the people side of it, I've just always been interested in people and behavior. And my bachelor's degree is in experimental psychology.
00:24:29
Speaker
I forgot that. You told me that. There we go. Thank you. Okay. and And then my MBA is in strategic leadership. So I like to say I've majored in the soft skills. I think my education helps a lot. It helps me identify patterns. And I think also is it's probably my personality but also i think my education is responsible for how i think about people and and the way that i view things which helps me connect the dots i love learning new things i like building new things i remember when i first started at samsung i had a really difficult customer
00:25:12
Speaker
Everyone was intimidated by him. He was a guy, really big guy, like tall, just big guy, very big presence, would drop F-bombs all the time. If he got upset, everyone knew about it.
00:25:26
Speaker
Could be very intimidating. But I kept showing up in his office because he invited me and I knew that I just had to trust the process and that eventually I would win him over and that I would figure out all the things that I needed to know to put all the pieces together. And so I did, i just stuck with it. And the funny thing about this guy in that role is that i would go to Miami a lot meet with him,
00:26:00
Speaker
call my husband in the airport, Miami airport, up probably six or seven times. I had a meltdown and I'm talking like falling just and crying as just in public and didn't care because that's how distraught I was after meeting with them. oh like And I kept going, kept going. went over his trust so much that I was the only person in all of Samsung that he would talk to. Like he wouldn't reach my life bosses and calls or emails. Like I was the person he talked to, got this company to go to Korea for the first time ever. Is it because Samsung's a Korean company, they loved for customers to come in and visit them in Korea.
00:26:50
Speaker
And this company had never done it in the 13 years that they had done business with with Samson and talked them into going and they came. And again, perseverance, curiosity, a little bit of crazy. Like i being think back, like, why did I do that?
00:27:09
Speaker
and My life could be so much easier, but, but I wouldn't have had all the fun either. Man. I love that. i think that's great and inspiring. I think sometimes when there's difficult relationships with clients, know,
00:27:23
Speaker
Yeah, it takes so much resilience and perseverance to keep showing up the way you did. When you say trust the process, it seems like that, like you've said that multiple times throughout the conversation, that seems to be like a foundational thing for you where you're like, you keep showing It really is. feel like it's a guiding principle for me because – Whether you're talking about sales or, and I'm in a transition of my life now, you do have to trust the process that you're going to get to the other side and that things aren't going to line up and they don't always turn out the way that you expected.
00:27:59
Speaker
But the unexpected things are the fun things. Like i look back on things that I've done in my career, the things that I've learned, the people that I've met, just experiences that I've had.
00:28:13
Speaker
And I feel good about it. I don't feel like there there was plenty of hard things in between. Lots of tears, lots of confusion because I did the hard jobs. I really did. But I also think that as a female, I just was determined that I was going to do the hard jobs. I'm going to show up because even if it feels hard and it feels like sometimes you have to do things that you feel like you shouldn't have to do and, or tolerate something that you shouldn't have to do.
00:28:45
Speaker
i wouldn't change any of that. I do think that I'm at a point now where I'm past those days where I'm not going to tolerate things because again, it's a trade-off. Like I was willing to tolerate things because look what I'm learning. I always call it like collecting my puzzle pieces and and this and also i think because I'm an honest person, if i can't win you over by being honest, then we probably shouldn't be dealing with each other.
00:29:16
Speaker
I love that. I think what you just said, I feel like it's something I've thought of too or felt it but never put the words in. it Put it into words in that when you're young or younger and you're doing really hard stuff, you're learning and you're willing to tolerate things. And then the more and more you're just providing like wisdom and a service, you you guys are getting a lot from me. I don't really need to to deal with X, Y, Z. Yeah. Or because I'm like, i I have a lot of puzzle pieces now. I have a lot of puzzles, so I don't need to collect as many puzzle pieces anymore.
Contact Information and Conclusion
00:29:51
Speaker
I'm sure tons of folks listening might be like, how could I meet Amanda? How could I work with her? Where should we send them? I know you have a website. We could put your website in the link into the show notes. so if you're listening, can just click over anywhere else that we could direct them.
00:30:05
Speaker
Yeah. can email me at Amanda at Amanda Schlegel dot com. And yeah, we can throw your LinkedIn on there too. yeah LinkedIn. Thank you so much, Amanda. I appreciate it a lot. All right.
00:30:19
Speaker
Have a great afternoon. You too.