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Interesting Conversations with Strangers, with Alexandria Smith [Episode 841]

Alexandria Smith is the Head of Sales Development at Headspace, the mindfulness and meditation app. Alex has had a very unconventional path to her current position. Lots of adventures, like living and working in an ashram. Talk about foreshadowing! Alex did something that more sellers should do. Go out and experience the world before diving into your sales career. Go explore and meet a range of people who aren’t like you. You’ll learn how to connect with people with whole different perspectives and experiences. It’ll help to you be more human. And to have interesting conversations with strangers. Which is our business.

Episode Transcript

Andy Paul: Alex. Welcome to the show.

Alexandria Smith: Hey, Andy. Thank you so much. I’m so happy to be here.

Andy Paul: we’re excited to have you here. So where we’ve been hanging out during all the goings on here.

Alexandria Smith: I actually just recently got back from a trip from mammoth and I visited there for the very first time. And it was such a special trip camping for a week. No service trails, hiking, waterfalls. It was incredible and definitely needed it too. Cause I. I feel like it was the first time that my partner and I have, I can’t even remember I’ve taken a trip just together.

One-on-one him and I. So it was definitely very needed and a very successful trip.

Andy Paul: Oh, good. Now, did you like meet right before the shutdown or

Alexandria Smith: Oh, so actually I met my partner back when I was living in San Francisco and, I was taking some time actually out of being in the corporate sales world. And during that time in San Francisco, I was teaching yoga full-time and I had met my partner through yoga, through one of the other teachers that I worked with.

And. Definitely one of those situations where we meet once we haven’t stopped hanging out and now we’re going on being together for the last four years.

Andy Paul: Wow.

Alexandria Smith: I know.

Andy Paul: Starting to get serious. Let me one on a camping trip.

Alexandria Smith: Hey, everything gets serious during quarantine. I’ve

Andy Paul: Yeah, that’s right. Yeah, I know. Yeah. my wife and I noticed that, we, yeah, we had never spent that much time together, 

Alexandria Smith: I think a lot of,

Andy Paul: with one of us with one of us traveling out without one of us traveling, yeah. Ever. Since we’d been together.

So it was like she went by, I had to go back to New York a week ago for her job. And it was like, 

Alexandria Smith: Yeah. Whoa.

Andy Paul: Maybe we haven’t been apart for a long time. yeah. Yeah. so let’s, we’re gonna talk about you and Aras Airbus, favorite subject and. I found it really interesting. So you’re at Headspace and for people that don’t know Headspace, it’s on my phone. I know it’s on millions and millions of phones.

So tell people what headspaces

Alexandria Smith: Okay. Yes. So Headspace is a health and happiness company, and that sounds obviously very broad, but we provide resources and solutions for mental health support. Specifically through a meditation is what we’ve been known for. A lot of people don’t even realize that Headspace has actually been around for 10 years, but really.

mindfulness and meditation and alternative ways of discovering your own healthy habits, is one of the reasons why headspaces become very popular for people right now. And obviously are really in a very, important partner that’s always available, specifically in some of these most trying times that we’re in, but.

Andy Paul: I’ve ramped up my use of it, in the last six months. I hate to mention a competitor by using both Headspace and calm. And, yeah, I know people swear by it. And I remember being, even before the pandemic, I remember, talking to a guy, a friend he’s a president of a. Was VP at a very one on tech, big tech that man moved to be president of a startup.

And by me we’re talking about kids and moving and all this pressure of being a startup and said, how do you do it all? And he says, damn, 20 minutes a day on Headspace.

Alexandria Smith: Nice love to hear that success story. And, there were a lot of, Other amazing companies that are out there that are very much focused on, the idea of obviously helping people to improve their health and happiness. So I always encourage people to, look around and see what works best for them.

But I’m of course, I’m so happy to hear that you get 20 minutes of Headspace. That’s great.

Andy Paul: Yeah, that was, yeah. I started with Do five minutes at a time. So five minutes, something, 10 minute meditation. And then, one thing I like about being calm, they have these breathing exercises that I’ve, I really like. but yeah, I cycle through those and yeah, the last six months have been good times to use them.

Alexandria Smith: Absolutely. And this is a really special time for us as an organization to be supportive to our community members and provide them with other resources and tools in order to help address a lot of the challenges that we’re facing in our day-to-day lives right now. And so it’s really also even pushed.

Us as an organization outside of the box and thinking of new ways that we can partner with even other amazing people like John Legend, who just started as our yes, with our new chief, as their new chief music officer, which is incredible and the focus of the playlist. So there’s a little bit of everything for everybody on there.

If, meditation is something that, some people are not ready to explore yet, or, there’s a lot of different types of content that can help you, introduce yourself to different ways of thinking and operating.

Andy Paul: Yeah, no. I urge people to have these on their phone. but you’re. You’re on you sell the business though. 

Alexandria Smith: Yes.

Andy Paul: so I found that fascinating is when you and I first met, or I first heard of you and before we actually had met, and as I was like, wait a second, I know Headspace, but they sell to businesses as well.

So tell us what you sell to a company

Alexandria Smith: Yes. And I also had the same reaction to, when I discovered that they had a B2B side of Headspace, that was really interesting to me. When I saw the job posting that they were looking for a sales development manager, I thought, what do they need a sales manager for? I’m already paying for it.

So I, of course I was excited to take the call and learn more about what Headspace was trying to accomplish and. essentially where we are now is, we were like the startup within the startup for a little while. And now we’re obviously excited that we’re going to continue to invest resources.

But essentially what Headspace is doing now is that we are providing an enterprise mental health solution to organizations, to help partner with HR teams to improve the health and happiness of their workforce. And it’s customized. It’s data-driven and we do leadership workshops. This is obviously all inclusive of course employees, having access to Headspace provided by their employer.

So my team, the sales development function, We are sitting in UK, we’re sitting in North America and we are continuing to expand, but essentially our role is to introduce this enterprise mental health solution to organizations and to of course, partner with them and continue to develop our products and enterprise solution.

Andy Paul: Interesting. So give us a, what’s the ideal customer profile for you guys for on the B2B side.

Alexandria Smith: It’s really hard to say right now, if you have a workforce that is in need of any sort of mental health solution, which I believe at this point in time, if you are operating you qualify. So I think that we’re obviously still figuring out, but we have been very successful, in the organizations that we’ve been partnering so far with.

Like Google is someone that we have partnered with. And, as far as the ideal customer profile, It really just depends on what the organizational needs are, but at this point in time, we’re really still figuring it out. Of course, we have some strategic ideas that we think would be great with certain organizations, but it’s a little too early to tell.

And the great thing about mental health is it doesn’t discriminate. There’s not like a one size fits all or a profile for people who qualify for something like this. It is literally for everyone.

Andy Paul: Yeah. I mean off the top of my head and not because this is a sales podcast, but I would think I’ve been on this kick for awhile if I think any organization with a sizable sales organization would be an ideal prospect for this because you ever watch the show. Billions.

Alexandria Smith: No, I’ve never seen it before, but I have heard of it.

Andy Paul: So about a hedge fund, high pressure trading environment.

And one of the key employees is an on-staff psychiatrist, no mental health professional, but when the traders had a slump, when the, personal doubts, lose their confidence, whatever guava consultation in the office, I’m like, and you see this on sports teams, right? Professional sports teams, they have got staff.

Yeah, psychologists and sports psychologists and so on. and, these are all performance-based organizations. And so sales is a performance-based profession. And yet we spent so little time focused on that aspect of it, the mental health and the mindsets and so on.

Alexandria Smith: Definitely. I would say that Headspace is definitely very appealing to that particular part of the organization. I know from firsthand having a career in sales, that this is something that no doubt, a lot of the, stereotypes that you would think about when you think of sales organizations could absolutely use a dose of a break and meditation, mindfulness pausing because, If you work in sales, your time is money.

Money is time, you’re on the clock. you’re grinding, you’re doing what you need to do to get to where you need to go. And oftentimes everything else falls on the second and third and fourth priority after, hitting your goals. So I definitely hear you on that. And I do think that this is attractive too.

Sales organizations. And that was a no brainer. When I first joined the team, I thought that was a huge opportunity. And then of course, being in this position, we’ve been able to learn so much more about all the other departments, but also receive a tremendous amount of stress and the type of work that they do.

Andy Paul: well, and I think obviously it’s magnified during the shutdown period cause, yeah, I’m sure you’ve experienced it. I’ve experienced it. I look at my wife’s work where, yeah, she’s basically eight to five on zoom, which is just nuts. Because every little. I used to pass you on a hallway, and exchange has not become a scheduled zoom meeting.

And, yeah, and I think just in general, in America, we’re famous worldwide for being obsessed with work.

Alexandria Smith: Absolutely. I think that rings true. I took some time away from the corporate world and I traveled abroad for a year solo by myself in South America and visited, but  Argentina, Chile, and Colombia. And. When you travel and you spend that kind of time away from America, you learn very quickly the things that are part of our culture that are not necessarily normal or other way, they’re essentially you learn that there’s actually other ways to operate, but to your point, it’s just very much embedded in our culture in America.

Andy Paul: Yeah. I think you learn other places that happiness is not based on possessions.

Alexandria Smith: No doubt about that. So connection, experience, joy, and moving at a slower pace. So we don’t miss the moment and we’re present with the people that we love and the things that we’re doing. And it’s so interesting because I’m sure that we can all. Think of a time, if not literally 10 minutes ago, where we might be multitasking and we’re not as present and not one-on-one with that person we’re talking to, or that scheduled zoom call that you’ve been on for eight hours.

So it’s just something interesting that we learn.

Andy Paul: question for you then with your team? First of all, like roughly how big is your team?

Alexandria Smith: my team is so teeny tiny right now. I have five people on my team. And go ahead. No, go.

Andy Paul: and I took it when the shutdown happened. Yeah. Everybody’s working from home. How’d that go for you?

Alexandria Smith: Yeah. It definitely brought us so much closer. And this was one of those moments where I was actually thinking about two, at some of the organizations I’ve worked at, I’ve managed 20 SDRs. and we had 11 STR teams globally. And that type of demand to do remotely would have been so much scarier than obviously, what is being managed right now with my team, Headspace.

And in the beginning, There’s just so much constant communication. And the first thing that I was focused on of course, was the health and safety of the people on my team. And that inherently wanted me to, check in with people, constantly have phone calls and calls, and also right away establish boundaries.

Hey, If you don’t feel like showing your face on zoom, that’s fine. If you need to move this one-on-one, if you want to just hop on a call, like really give people space. I think that was a really important part of the transition as well, is giving people space to be able to get themselves set up, in a place where they feel like they can succeed.

And they’re in a Headspace quote unquote. That’s also very positive as well, and that is a process they talk a lot about. everything that’s been happening with COVID and I can relate it to the stages of grief, in the beginning it was absolute chaos and then anger, and then, acceptance and freshman year where you just go through these different phases.

And I felt like we were all going through that together. And so I have really. Focused so much more on just the people, part of the job. And when I focused on that, we were able to, for sure navigate the rest of the stuff. That work in some sense, almost felt like a safety net, not to say that it was easy, but there were so many other hard things that were going on externally that I felt like that was the most important place for me to support and focus.

Andy Paul: And yeah, we are customers during this time interested. It’s something you could think, okay, this is discretionary. Maybe not top priority, or have they said no, actually we’re pretty aware of what’s going on with our people that actually having a resource like this and offering this type of resource to our employees is actually more urgent now than it was back in January.

Alexandria Smith: Absolutely. for the people that reached out to us for support during this time, they were absolutely looking for ways in which they can support their employee population. And of course, we were incredibly grateful to be what we would consider almost a first responder when things really started to get.

A bit more challenging, those first couple of weeks of March when everything started to shut down. And so the conversations that we’re having with people are very real because they’re about people’s health and people’s safety. And also with a lot of companies, having to do for lows and layoffs, We are there to support them in all of these really challenging decisions or tough conversations that they’re facing with the people that they’re, essentially, providing for us. So it was incredibly humbling and it was okay. So very therapeutic to connect with strangers over the phone too, when people were also so scared that they were, like when are we ever going to go out again?

So we would get on the phone with some of these strangers and have these very vulnerable conversations and. I just thought it was such a special moment to meet other people in

Andy Paul: So getting on the phone with customers or prospective customers.

Alexandria Smith: both. And when I say, members are how we refer to the people who were onboarded, our Headspace for work products, but I would say prospects, customers, people in general.

Andy Paul: interesting. So do you prescribe for companies when they buy subscriptions? Do you also have Hey, here’s how we suggest you use it. Here’s a program to follow. Here’s how you’re going to roll this out to your employees. how do you onboard people internally in something like this that you know is not like, Hey, it’s not like a CRM system or you’ve got to use it for your job.

it’s like a, I don’t call it a perk, but it’s, It’s so how do you, how do they, how do you help the people, the companies that purchase from you, how do you help them? That’s an onboard their own people.

Alexandria Smith: That’s always something that our company is working on as far as adoption and engagement and education. That’s very much where the, I would say customer success side of initiatives. come from when we do onboard someone, who’s purchased our Headspace for work enterprise solution.

but to your point, yes. we put together a rollout plan and of course we have to partner with these organizations and how, in which, and the ways in which they roll out communication to their employees. And so we work with them to design a plan and a launch, and a lot of times. we have found that organizations tend to really be open to rolling something like this out, or maybe already have it in their mind as an initiative they want to do for a particular time.

For example, world mental health day, that’s coming up on October 10th. This is a great time to be talking about mental health. And when you have these days or times where we take time to recognize a portion of how this can be beneficial to people, I think people see, a nice value in doing that simultaneously.

And so long story short it’s customizable. Of course we do. emails and newsletters and webinars and all that good stuff. but it’s very much the partnership with the specific organization we’re working with.

Andy Paul: Yeah. I think it’s, as I said before at the top, especially in sales, I know corporate wide, but in sales, Yeah, sales people need to do a better job of paying attention to it just bit by bit. Hey, we’re seeing on LinkedIn and other forms where now people are quite frankly having the courage to stand up and tell their stories.

And we just need more of that, but also provide more resources for people. And I think this is so the example I gave before is. Yeah, I think, I firmly believe that any sizable sales organization, maybe a hundred sellers, 200 sellers, I don’t know the exact number is at least on an outsource basis.

You should have access to that type of mental health support because it is, and sales is, and all jobs are stressful with this as extremely stressful work. You, we are compounded by what’s going on today. And we expect people to be at their best when they’ve got kids at home and all these other things that are going on, fear of getting sick and we don’t provide any support for them.

And again, this is such a stressful role, managers, if you’re listening. There are resources like Headspace and others, but pay attention to your people because, Hey, they find it extremely hard to talk about. And that’s why I applaud the people that do speak about it. Like Richard Harris, who talks about it online, LinkedIn a lot.

And this should be part of the standard. Package at all times, not just during a pandemic for asset sales organizations of a certain size and for smaller ones, there are, on demand resources and so on. It’s just gotta make sure people understand that it’s available and to take advantage of it.

And that’s not, yeah, not, they’re not looked down on for wanting to do that.

Alexandria Smith: Absolutely. I think that’s, just how we look at acquiring another sales tool to help our sales people be more efficient from a metrics standard. We have to be looking at. That this is a human being and what else more can we be giving to this person? It’s not so tactical, that’s going to put this person in the best place to succeed.

And I think that the challenge right now is, twofold. And you touched on this, but just want to highlight the fact that. There is a lot of education and learning that still needs to happen first. And then of course, in conjunction with that, there needs to be access to these types of resources.

And those are the two biggest barriers that we’re trying to provide people. And I think just meditation and mindfulness, in relation to workplaces in general is the conversations that we’re having. And. leaders now more than ever have a responsibility to address and support people in these areas, but they don’t necessarily know how right.

Which is the education part that we’re solving for. And then the access is okay, what are the resources? And that’s part of it, but it definitely starts with the conversation awareness, And the education and building the access.

Andy Paul: I think part of it requires, culture changes in many organizations from yeah. Oftentimes in sales is any sign of weaknesses, like blood in the water for sharks. And you looked at as being less than, and. Yeah, no, that’s not exclusively in sales, that’s what we’re talking about here.

And yeah, as leaders, you have to make that change. Yeah. Make it available to your people, these resources available to your people. You have to be in a position to have these conversations where people feel empowered to be vulnerable about what’s going on and help them.

Alexandria Smith: Absolutely. And that goes back to what we really just talked about, which I would love to expand on is that the responsibility. I’m the leader. This is a time more so than ever that if you’re in a manager or leadership position, that you’re probably having conversations with yourself in the mirror, hopefully that you’ve never had before and asking and challenging yourself.

Yes. In a way where you have to do different things, to put yourself in a way where you can be supporting others to the best ability and. Being open to these types of things was once a choice. And now I would say it’s an absolute necessity in a requirement. If you’re going to continue to lead people through this time,

Andy Paul: I agree, but I think that the problem is, and I’ve talked about this often in this program is that it’s the way we structure sales and most large organizations and even smaller ones, but we assume that because somebody has achieved risen to the level of, CRO or VP of sales or what have you.

Is that they are somehow magically imbued with all these qualities, right? That they are not just a sales expert, they’re a human development expert. They’re a human potential and performance expert that they know how to motivate people. They know how to. That’s unfair. They haven’t been trained on any of that.

Now, ego wise, let me think they’re really good at it, but they’re not right. and you look at other performance-based organizations. I often talk about professional soccer. Because I love professional soccer, their staff is full of specialists. In various levels, aspects of performance and mental health being one of them, we’re in a performance business.

People. We want people to perform better as we need to give them the resources and we need to enable them to operate, in an environment that’s not driven by fear. And that’s what starts at the top is known leaders at the top, feel that can’t admit they need help.

Alexandria Smith: That

Andy Paul: they’d be perceived to be weak.

And then it filters on down the chain. Everybody’s afraid to say anything because, Oh, I’ll be perceived to be weak or they think, I don’t know something. And so we run this whole business from a perspective of fear, as opposed to having this open mindset of growth mindset. Even though people claim they have it, you really don’t have a growth mindset.

If you. Can’t support people who have challenges and mental health issues oftentimes caused by stress at work.

Alexandria Smith: Definitely. And I think the level, I just think the level of fear that people have is due to their lack of awareness. And what exercises are people doing? To, cultivate more awareness in this situation. So that way we can act and respond accordingly and also means, okay, to show the emotional side, I feel like that was my, I feel like that’s been a superpower of mine in my management and it’s, I guess one of those things, like I can’t help, but to be my authentic self, if we’re spending that much time together, but that is something that I’ve.

Gained more respect throughout my personal and professional career development, than anything else is just being raw and letting people know for sure that I don’t know something, but I will absolutely. It’s all about followup, right? It’s w we can, who’s supposed to know anything or everything for that matter.

So I think that there’s a lot of different factors that come into play when we’re considering, like, why leaders aren’t necessarily. made this change for themselves and you’ll for sure. It’s always going to be hard to steer the ship for other people. If our leaders aren’t invested in making those changes.

Andy Paul: Yeah, absolutely. Okay. Here’s a question for you.

Alexandria Smith: All right.

Andy Paul: You lived in an ashram, so that’s fascinating. So tell us about that. When you know, what stage in your career did you do that and where was it and what I’m very fascinated by.

Alexandria Smith: I would be happy to elaborate on that for you. I’ll back it up just a little bit. Cause I think the context before is really important. So my first sales job was in New York city and, had the opportunity, it was really low paying, but could have, uncapped commission situation, but it was definitely my ticket out of Florida.

So I took it and

Andy Paul: get out of LA, get out of Alabama.

Alexandria Smith: Yes that too as well. So I

Andy Paul: And what were you selling?

Alexandria Smith: so it was called a single platform. There were basically the first people put in venues on the internet. So if you wanted anything other than your name, address, and phone number, when you’re a restaurant or a small business, you would essentially pay a single platform, a subscription fee to have your information listed anywhere, and you could update it whenever you wanted.

And it was the right place, the right time. And. It was a startup and I was one of their first sales hires. And then the company got acquired. We started hiring 10 people per month, 120% sales floor, super duper competitive. I was a full cycle. Eight didn’t have STRs back then. I was the SPR. I was the marketing manager.

I was the customer success. Yes. A hundred cold calls today. And. I was in the top 3% consistently quarter over quarter, had the opportunity to become a part of the management team, did that for them for two years. but truly any, I, I don’t come from money. This was like the first time that I’ve ever made money, seeing money.

I don’t even know what to do with it, but I knew that I didn’t want to go to another brunch or go shopping in Soho Saturday after Saturday. Yeah. I quickly realized that I was definitely searching for more. I’d also just developed a really healthy work-life balance, which is a whole other story, but long story short, after that trip, I basically quit my job, sold my things, had an eat-love, pray moments, and went and bought a one-way ticket to Brazil.


Andy Paul: why Brazil?

Alexandria Smith: so funny story. I had gone to Brazil about six months prior to deciding that I was going to quit my job plan, do my thing. and I had such adventurous friends in New York, born and raised in Manhattan. Totally pushed me outside my comfort zone all the time. And. she, her and I think we made like one of her first, commission checks that we were very proud of.

We were both working in sales and she said, let’s close our eyes and pick a place on the map and let’s go travel, celebrate. And I thought, Oh God, that’s so wild, but let’s do it. And the place that we picked was Brazil. And then we went to Brazil for three weeks. I came back from that particular first check and said, wow, There is more to life.

I want to explore that if I’ve got money, like that’s what I want to use it on. I want to live, I want to explore, want to learn another language. and that’s really what prompted the trip. So I obviously plan to plan and plans. No one saw me for like months, of course, Paris and talk to me for a couple of

Andy Paul: Yeah. So you just quit your job

Alexandria Smith: Yes,

Andy Paul: and hopped on planter Rio or Sao Paulo

Alexandria Smith: that’s right.

Andy Paul: just by yourself,

Alexandria Smith: I started off, at carnival with, five of my friends and we traveled together for two weeks in Brazil, and then people left me on my journey, which was when the deep, scary, awesome, exciting work started to happen. And I felt like there was a massive transformation happening month after month, I was just transforming into a different person.

Andy Paul: what was doing then?

Alexandria Smith: Definitely confronting fear, death, anxiety, being overwhelmed, body issues. you name it, safety, right? Being a female on my own, traveling, not knowing the language. Probably some of the biggest fears are that a lot of people haven’t stepped into a lot of unknown and a lot of unknown obviously causes fears, but I’ve really learned to actually seek the unknown now.

And it’s not so scary anymore, which is why. When I got back from that trip I came back to the States. I had a moment when I was in Peru, I stayed at a meditation house in the sacred Valley for 10 days and I thought, Oh my God. How do I feel like this all the time? What is happening here? I had just made a promise when I got back to the States that I was going to really, learn so much more about breath, work, yoga meditation, and see where it comes from.

And did a ton of research. So long story short, I got back to the States and I decided New York was a place for me anymore. I had just a little bit of money left. And so I went to San Francisco and at the time I was interviewing with different corporate companies, not feeling it

And, but very passionate about this yoga and meditation breath work, San Francisco is a hot spot for a lot of different types of practices under those Januaries.

And but I was really looking for a very authentic experience. And so I found this Ostrom called the yoga society of San Francisco and I met the teacher there. His name is brick Shaw, and. I had an overwhelming amount of emotion meeting him and just feeling like this is the person that I want to learn from.

And he also took a very particular interest in what I was trying to accomplish and knew. He just looked at me and knew I was doing some soul searching and

Andy Paul: at that point, let me interject that at that point. Did you have a goal in mind?

Alexandria Smith: I wanted to get my yoga teacher training. I did, I wanted to get my yoga teacher training, learn it more. And then for the most part, I wanted to teach, that wasn’t right away. It was more so I wanted to just learn it, but I love to teach and anything that I love, I inevitably end up teaching it to other people.

Cause I’m obviously such a big advocate for things I love.

Andy Paul: But at that point, were you thinking, yeah, I’ll find my way back to business at some point or to sales, but was that in the back of your mind or was it like, no, I’m on this journey and I don’t know how it’s going to turn out.

Alexandria Smith: So while this was all happening, I really started to love this studio in San Francisco called ritual hot yoga. I ended up hanging out there all the time. Becoming friends with the teachers became really good friends with the owner Lindsey. And, she learned about my background. She learns about what I am doing or trying to do at the current time.

And she said, I could really use your help. Like I’m trying to grow this business. I want it to be the soul cycle of yoga. I want to grow multiple locations. Will you come on full time with me? To be a business development manager and open a couple locations and I’ll sponsor your yoga certification.

You can teach and do whatever journey you’re doing right now. And, and at the time it was, that was an easy yes for me. But when you talk about, I probably took a 70% pay cut from what I was doing in tech. So I had a completely different lifestyle change for a couple of years as well, and being in the Bay area, doing the reverse.

And it’s really interesting to see the way that people treat you too. That’s a whole other thing.

Andy Paul: when you’re not making money.

Alexandria Smith: Yes, exactly. Or when you’re not working in tech or talking about tech.

Andy Paul: yeah. Yeah. so based on that experience then, yeah. It seems very logical that you ended up at Headspace.

Alexandria Smith: Very serendipitous. things work out and. At the time, it got to the point where I had swung the pendulum all the way, the mental health way full-time yoga decided it wasn’t going to be me for a long term, but it’s such, it’s obviously a part of me and a part of my life forever. I had done this self work right for the last three years.

Traveling, learning about yoga, living in this Ostrom. Teaching and living in a completely different lifestyle. I was so eager to actually go back into the business world. It’s just so interesting the way to be changed. I was so stubborn before, and then two and a half years later, I was like, I have things to give other people.

I would love to go back to sales. I love sales. I love working on commission and being in control of what happens and how much I get paid based on my performance. And I was so excited, but I was interviewing, I was still teaching yoga full-time for six months. And it was so interesting because some people thought that maybe I all of a sudden, would it be qualified to do a similar job as what I was doing before I was doing yoga because I took time to do

Andy Paul: yeah, the world has changed so much in those two years.

Alexandria Smith: Yes. And. And then Flexport was the company that I actually moved to LA with. So in San Francisco I found Flexport, they reached out, they loved my background. They loved the fact that I took this time off. They were looking to hire their first sales dev manager. And, they said that. they were growing really fast.

They’re probably going to have 10 teams in the next year when I thought, wow, this is such a great opportunity. And it ended up being a great fit. And so I moved down to LA to open up their LA office and run their sales team down here and then expanded it to six other offices. And so that was before Headspace.

And then, and, I had a really interesting experience there, logistics. Nothing is more complicated than that, especially selling it. I definitely, I definitely felt like there were times though, that I was sitting in the room with some of the smartest people I’ve ever met in my entire lifetime.


Andy Paul: Great room to be.

Alexandria Smith: Definitely. And it got my operations muscle super strong. and I have a really heavy load in conjunction with sales enabled. I am very deep in data and operations and savvy in that area, which I think is another super power. but Headspace had, I ended up actually reaching out to me through a mutual connection of someone I used to work with in New York.

Eight years prior. So never underestimate your network or people that you work with, or the reputations that you build, even if it’s the worst experience, try to do your best job. Other people will remember you for that.

Andy Paul: yeah, I think it’s fascinating and I think that. Yeah, either as a fuel, seeing this as an individual contributor or as a hiring manager is yeah, for me, the key lesson and I. As much as possible, try to do this as is, bring people in who have this diversity of experiences and into your sales team, not just don’t hire guys like me.

I went to college and went right into sales, but yeah, people went out and experienced something. And even if they took a break in their career, I remember once hiring a guy who drove a bread delivery truck. Yeah. and he’s had a fabulous career. He was excellent at it. at sales, other people with diverse backgrounds, that’s, I’ve always wanted people to have that different perspective.

I hired a lot of engineers from the sales people. Yeah, you would think from a, you met them, traditional Salesforce, Oh, they don’t have the personality, Bob, the sales DNA, whatever, blah, blah, blah. And these people just crushed it. Because they had these different experiences.

They related to people in a different way. Customers love them and we just need to increase our commitment to bringing more diversity in the sales because it works.

Alexandria Smith: Yes,

Andy Paul: it’s not a, not an obligation. It works. You want, probably the reason we perform at consistently low levels in many industries and sales is there’s no diversity of opinion about whether we should be doing it differently.

Alexandria Smith: that’s right.

Andy Paul: Everybody’s operating in lockstep.

Alexandria Smith: Absolutely. And I think that you made a really good point when you were talking about that specifically. And I just think that again, why do we think that way? And I find myself like, how am I a unicorn that I want to build the most diverse and inclusive team like that is, seems to be something that like, that is one of my.

Number one purposes and responsibility as a leader is to do that. And I think about that every single day. And I thought about that even before, obviously a lot of things have become awakenings where people within the last couple of months with everything that’s been going on and. It’s so important.

And that’s why I love the sales development function so much. It’s expected that I’m not going to hire people based on their seven years of experience. Like I am looking for straight up potential character, hunger drawings, and, obviously a working relationship, a partnership and. I think about this all the time.

And I, it still is obviously so surprising. the teams that I’ve run have been the most diverse teams within a lot of the tech organizations that I’ve worked for. And I recognize that’s a problem and don’t get me wrong. There’s definitely a whole much more that I can do that we can do to continue to build upon that.

But I want to see that running through the veins of sales organizations, we’re so guilty of that.

Andy Paul: yeah. Yes. In 20 words or less. Yes. Am I saw a, sad recently. Let’s see. I think I have it here. 78% of people working in sales in the U S are white and 61% of those are male. you do the math. That’s white men who make up 30% of the U S population hold over half the sales jobs.

Alexandria Smith: Yes, and I bet that’s even scarier when you get to the sales leadership level, but that’s another conversation for another

Andy Paul: Oh, absolutely. Absolutely.

Alexandria Smith: it’s not surprising to me at all I learned, but I also learned this game for men and I have them to thank for that. However, again, paying it forward. I just really hope that we can and power more leaders to be focused on building diverse and inclusive things and getting access to the opportunities for people of color and for women.

And that should be a priority. And I think it’s, but also there needs to be a lot of partnership from organizations. I think that some organizations that are scaling really quickly, like we used to have hiring deadlines. When we were scaling out, one of the organizations I was at that was, and what do you do when you’re in that kind of position, when you want to wait, for, a diverse set of candidates to be able to make this decision, then you’re on these deadlines and not your whole existence.

As a manager is tied to that in some sort of way. there has to be alignment that’s not the right way to approach hiring.

Andy Paul: Yeah, absolutely. All right. Alex, we’ve run out of time, but it’s been great speaking with you.

Alexandria Smith: Yes. Thank you so much. This was a great chat.

Andy Paul: how can people connect with you if they want to learn more about your story and what you’re doing in Headspace?

Alexandria Smith: The best way to connect with me, stay connected with me is on LinkedIn. And I am trying to grow my professional network there. So I of course would love to hear from you comments DM, or if you have any fun projects that you’re looking for, you want to talk a little bit more about mental health or how, you can even talk about your own or your workplace.

I’d be happy to support.

Andy Paul: Perfect. All right, Alex. Thanks a lot.

Alexandria Smith: Thank you.