The Pavilion Podcast
The Pavilion Podcast

Episode · 1 year ago

Ep 14: A Jungle Gym Not a Ladder feat Daniella Bellaire


A Jungle Gym Not a Ladder feat Daniella Bellaire

But hello everyone and welcome to therevenue collective podcast. I am your launch host, Justin Welsh, member ofthe Los Angeles chapter a revenue collective. In inside of these episodes we're goingto feature ideas and conversations that are inspired by ongoing discussions within the revenue collectivecommunity across the globe. In inside of revenue collective there has been a lotof chatter around career navigation, especially around positioning yourself to get ahead inside ofyour organization or the next company that you join. We're going to cover thatin a little bit more inside of this episode with our guest head of salesfor point of sale at shopify, Daniella Blair. Before we dive in withDan Yellow, a few quick notes. If you're out there listening and youwant to join revenue collective, visit Revenue Collectivecom and click apply now. Ialso cannot forget our amazing podcast sponsor, outreach, the number one sales engagementplatform. Outreach revolutionizes customer engagement by moving away from siloid conversations to a streamlined, in customer centric journey. Leveraging the next generation of artificial intelligence, theplatform allows sales reps to deliver consistent, relevant and responsible communication for each prospectevery time, enabling personalization at scale that was previously unthinkable. Okay, let'sget the show started with Dan Yellow Blair. Our guest today is Dan Yellow Blair. Dan Yella is a two time head of sales with four years ofexecutive leadership experience. She is currently the head of sales for point of saleat shopify. Shopify, I'm sure you're all familiar, is a one pointfive billion dollar Revenue Company, in arguably the best multi channel Commerce Company,providing tools like e commerce, pos banking, fulfillment and capital to help businesses ofall size grow. Dan Yella, welcome to the show. Thanks somuch. Really pumped to chat with you today. Justin I am also pumpeda chat with you, and before we do that, you know, I'dlove to learn a little bit more about your journey to becoming the head ofsales for Pos over at shopify. Yeah, for sure. So currently had asales for shop by retail, which you know, really is multichannel platformcentered around point of sale for retail businesses. Tons of fun in building and scalingin the last little while, especially through covid. But you know,if we take it all the way back. You know, I grew up inan entrepreneurial family, single mom, and you know what happens when youhave a single mom, you end up taking your kid to work. Sothat's really where my sick of my sales career started, and I like tosay at the age of twelve, growing up in in a business where Iwas working at my mom's Ba and I remember toting around a little cart andselling fresh cut soaps to her customers and that like as etched in my mindas my first true like hustle. So, you know, moving along there throughhigh school, worked for my mom and then really got my first tasteof sales. After that, you know, realized I wanted to go to businessschool after graduation. Like so many graduates, I was unsure, whatdo I do? What's my next step? And at the time, and thiswas by like over ten years ago, it was like women can do recruitmentand hr and that's like a really safe thing to do, and soI thought, okay, you know, I'll I'll try HR and see howthat goes. And fast forward. It was a total it was a totalbore. It wasn't for me. I really liked in the recruitment piece,the aspect of sales, but I couldn't control my commodity. You can't predictpeople showing up to interviews, etc. Etc. So I realized I wantedsomething more. Stumbled and fumbled my way, as most twenty something year olds do, ended up in banking, banking sales, which was also, youknow, for those of you banking sales, I apologize, but a little bitof a total bore as well. And so for me it just wasn'tthe culture that I think I was hungry...

...and looking for at the time.And then, Lo and behold, one of my friends, as it somehowhappens, one of my friends was like, yeah, you know, this companythey're hiring, like tex s ails, was really popular. Now you canget on, commission, you can make so much money, like you'dbe graded at you've such an outgoing personality. And I thought to myself like Oh, you know, that's really interesting, commission they're going to train me.So I ended up at a company called soft choice, and that was, you know, me find my tribe quickly, became top performer. Thenmentor, you know, building and scaling enablement. From there, then becamea manager. I like to call this the sort of jungle gym approach,and then building and scaling teams and after four years I was leading mid marketfor Canada. And then I got another sort of friend over wine, asit happens, and you're chatting and this friend said, you know, he'dbe really great in the startup world and I was like, Oh, startup, yeah, key, that that sounds really interesting. And it's like, you know, hey, this company just got seed funding their Canadian youknow, it's the next toby loot key from shopify. That was literally whathow it was pitched to me. And you can really grow your career.And at that point I was hungry for learning, hungry for knowledge and Ireally wanted to stretch myself and it was super scary, but I took theleap. So ended up joining a company. That's really how I got into exactleadership and I sort of just fell into it and learned a lot alongthe way. I did two years at a company called seven shifts. Soscaled from employeed twenty to employ a hundred and fifty, went up to,you know, zero to eight million, and are are and and then atthat point, similarly, you hear from Your Peer Group. Oh, shopifiesdoing this really cool thing with point of sale retail. Two years had passedand I thought, wow, I really need to invest more in myself andalign myself to others. You know, they are smart and building and inthe startup community it's really the network that you have and not more so thepeople that are in the startup that you learned from all the time. andBoom, the rest is history. Here I am, I'm almost a yearin the role and it's been in a wild, wild ride building and scalingthis team. So we were about three people when I started and were almostat fifty. As an ORC congratulations. I know shopify is such an awesomeand awesome brand. I mean when I think of a like really key brandsor they're just one that stands out, especially through the COVID crisis. Soyou know, one thing I hear is you. I heard words like,you know, fell in or you know, took this sort of jungle gym approachin you really have this sort of nonlinear path to leading sales and youknow, when I talk to sales leaders sometimes they have a very straight linecareer growth, AE, manager, director, VP. Now you've been in HRrecruiting, finance, enablement sales. Can you talk about the benefits ofthat particular type of journey as you've made your way into into shopify? Yeah, of course, and I think it's so valuable because, for so manydifferent reasons, you know, you pick up things along each opportunity. Inrecruitment I realized I wanted to do sales and that was the lightbulb that wentoff. And in banking I realized I really loved sales, but I didn'tlove the product and I wasn't passionate about what I was selling. And sonow I knew I needed to do sales, I needed to find a product Iwas passionate about, I needed to work for a company that I believedin, their culture and their vision, and so that led me to techsales and I was like wow, you know, I love technology. It's, you know, the way we're doing things in the future and I canreally get behind and the company invested in one of the big draws was theyinvest in their new talent. They had a twelve week training program when youjoin. Those were things that were unheard of to me at the time andI was like wow, I can really benefit from this, and so thoseare the things that sort of all those little nuggets led me to where Ineeded to go. And then, you know, with with my role beingin sales, a soft choice. It was this interesting path where I wasin sales and in order to get into sales leadership, which was interesting,I had to step outside of the sales org to get a bigger, broaderLens. That was sort of how it...

...was position to me and I thoughtat the time, well, that's really crappy. I just want to bea sales leader. You know, you're twenty something, you're super naive andnow, in hindsight, I look back and I think, wow, youknow, that opportunity reporting into hr for the time being, that's where enablementlived. I built out, you know, and iterated on this twelve, twelveto sixteen week training program it was one of the biggest Aha moments ofmy career. Where now I can, you know, I can build outtraining content, I can facilitate, I can coach my managers better, Ican coach my reps better, and I learned so much in that time andit only led me to be a better sales manager and ultimately a better exactleader and a better people leader. So really crazy how those little nuggets alongthe way lead you to to where you are and it really is built upwhat I'm able to do now and scaling shopify. I love that. Youyou know, I heard you say I had to step outside of sales orI had to get a different perspective active and I think when we think abouttraditional career pathing or growing your career, you know there are some really obviousthings that you can do to push your career forward. In one of thoseis just perform well right, hit your performance benchmarks, especially in sales.But I think when you have this sort of different or non traditional career path, there are things that you have to do outside of that, as youmentioned. So what are some other key areas that you know you focused on, maybe outside of even sales, or stepping outside of sales and into adifferent department? What did you do outside of work to position yourself to continuegrowing your career into the executive leadership role where you're at now? Yeah,so, you know, I think earlier on in my career I very muchrelied on what was being given to me within within my company to be successfuland I then saw peers around me really upscaling quite quickly as it related tolike leadership and exact leadership, and I thought to myself, okay, I'mmissing something here. Like, you know, there's only so many things I'm goingto learn of what sort of being fed to me. And I thinkpeople who are in bigger companies at times, you know, I've interviewed managers orlike I've been, you know, at this x company, this telecomcompany or whatever it is for eleven years and that's all I know and that'sscared me. And so I quickly realized I needed to go out and Ineeded to learn from people who'd done it before. And I you know,we talked about this a lot as sales leaders, but it's such a simplebut true thing. So reading became a big passion of mine, and I'llbe honest, you know, I didn't love school, I didn't love theformal education system. So to me to go and buy a bunch of booksand make time to read it was like a but I quickly realized if Ilove the content and I love the topic and I'm passionate about it, I'mgoing to get into it, and so I just started crushing books. Sothat was the big thing. I also made a decision to take, youknow, additional courses. So I took different types of coaching courses, Itook different types of leadership courses. I ended up later in my career,most recently, doing a word in program for exact leadership on data analytics,and so I'm still learning to this day. And then, you know, outsideof just going out and seeking knowledge, it's the Peer Group, right,it's finding people who've done it. I started combing my Linkedin I startedasking people for introductions and that really lit me up and little fire and themore I built relationships and the more I talked to people, the more Ilearned and the more opportunities that came to me. So you're consuming information inthe form of books, you're taking courses, you know, you're going in,you're doing some classes at Wharton, you're establishing your network outside of work. All those things are are things I love seeing like and when I seesomeone doing those things, I know they're ready to start to step up anddo a leadership roll. But you know, oftentimes other folks at your organization maynot see you doing those things. How do you raise your hand likehow do you go into your organization and say I'm consuming this, I'm doingthis, I'm expanding my network. How do you stand out in an organizationand use the things that you're doing to continue to grow that career trajectory forward? Yeah, for sure, you know.

And as a woman in sales,you know, and I hate to throw the woman card, but it'sjust so true. It's as a woman in sales, eat your and I'llspeak for myself as opposed to all women, but you're more inclined to be morehumble, your less inclined to brag, your less inclined to be boastful,and I felt like that for a very long time and so it reallytook something inside. I mean to say, okay, you know, I have. I've been selling since I was twelve years old. Dan Yellow,you know, pull it together and you know, share the knowledge that you'relearning and consuming with others and reference that knowledge. And so that's what Istarted to do. I started to talk about the courses I was in andnot just showing up to a meeting saying a yess, guess of courses I'mtaking, but you know, when it was socially appropriate, saying yeah,actually I'm enrolling in this program. You know, even to my to mydirect manager, this was recently, it's like, Hey, really love thiscourse. Looking for something on the data analytic side, as we're doing financialmodeling, and I'm thinking Warton is the way to go. Here's why,you know, here's my take on why I think it could be really valuableone. I wanted him to pay for it to I wanted him to knowand also validate that it was the right move. And you did. Andand then it became in a conversation, you know, Oh, Danielle's takingthis word in program did you know? Or Oh, you know, andso I think just feeling confident enough to say, you know, these arethe things I'm doing, are these are the things I'm learning, and thenreferencing them in your day to day and your job, and I think that'ssuper important to do. You also don't want to take credit for something thatyou somebody wrote in a book. You want to be honest about it andyou want to provide others the same opportunity to learn like you did. SoBook Recommendations, Course Recommendation. So it becomes this really great way of,you know, discreetly talking about your accomplishments and what you're doing helping the company, Helping Your Peer Group, helping your team to be better by referencing whatyou're learning. And Yeah, it doesn't it doesn't hurt at all that peopleknow that you're doing those things. So really important to do that. SoI know you mentioned earlier that you know you didn't want to play the womancard and I can appreciate that, but I also heard some really interesting thingsin there. I heard confidence, I heard boasting and, you know,a as someone who let a relatively large sales team myself, I just seethat men are more frequently to approach me and boast or be confident or raisetheir hand for that, that promotion. And I'm just curious for some ofthe the the women listeners who are out there, was it just a momentin time where you gained that confidence, where you decided that you wanted toput yourself out there more, or was there something specific that happened that helpeddrive that forward? Yeah, that's really good question, you know, andI'll be honest. Justin like I'm in my s, my early to midS, and I would say that it's something I still struggle with you know, transparently, and I tell not just the women that are in my orgor in a cross functional Org, but also the men. And you know, there's something that's called Imposter Syndrome. It's real. It's not just somethingwomen face, at something men face. But you're right. You're right that, you know, men are are typically more inclined to put their hand upand be a bit more boastful, and so I'm constantly battling that and tryingto trying to get a fine line between pumping myself up, you know,believing in myself. And one of the great ways I've found, even justin the last, I would say, four years of my career, ismentorship. And so I thought, you know, after I'd learned to didall the books, you know, took the courses, met the Peer Group, built the network, I was like something still feels like it's missing.And I actually met with a peer he was leading VP sales at a similarsized company in the city and he and I were chatting and I was like, you know, tell me a little bit about how you're growing, howyou're devlving, and he mentioned something called an exact coach and I was likewow, and he said, Oh, my CEO recommended an exact coach andI said nobody recommended an exact coach. To me, that that sounds interesting, and so I saw it out. An exact coach and then subsequently afew mentors, and so I've tried to find diverse mentorship, you know,different backgrounds, whether it's fortune, five...

...hundred company, scale up, startup, women, men of all sort of shape, shapes and sizes,and that has been phenomenal. And my last, and I'll wrap this upwith my last conversation, and she'll know who she is when she hears this, but my last conversation with one of my mentors was, you know,her asking, tell me a bit about what's going on, tell me abit about what you're doing, and I said, you know, you know, we overcame covid we did this, we did that, we scaled,we pivoted our business, we did all these things. And I was likeyeah, like, wow, it's saying that. Allow, that's a lot. She's like you, she's like you go like high five, like youneed to. You need to shout that from the rooftops. This isn't thetype of relationship where you need to be muting you know, you need tobrag right now, like this is phenomenal work, and I thought to myself, wow, like if this, if I don't feel safe enough to doit with you, I won't feel safe enough to do it with others.And it was a really interesting exercise. So the Tldr here is, youknow, seek mendership and don't just paying everyone you know on Linkedin, butbe very deliberate about it and what you want to get out of it,and it's been very helpful for me. I love that and as someone whohas also suffered from imposter syndrome nearly his whole career, it is very itreally resonates with me and I think it's such a challenging syndrome to overcome.And and when you repeated what you had done out loud and heard your accomplishments, I'm sure that helps. That's that's often what I do. I goback and I review my accomplishments and I say, if this didn't have myname on it, what I think that this person did well and that that'salways been sort of a way to help me out with with imposter syndrome.So I love the fact that you brought that up that's to me. That'sa very relevant topic today. I hear being talked about quite frequently and I'dbe curious maybe you know you've had these mentors, you've had executive coaches.I'm going to assume in before I do Daniell, I'm going to assume thatyou've also mentored some people. Is that correct? Yes, absolutely so.When you get, you know, a mentee and they look at you andthey say, wow, you're leading sales, you're an executive leader at what isarguably, you know, one of the greatest companies in the world rightnow, how do you think about giving them advice? What, or maybethe top two to three things that you try and distill down and pass alongfrom your experience onto folks that you might be mentoring? Yeah, and Ithink you know some of the things we I've mentioned, but I think it'sreally important to allow yourself to fail as a big thing. I think youknow, Kitty Corner to imposter syndrome and you know, not being someone whobraggs is someone who thinks they're just not doing a good job and is afraidto fail or admit failure, which I think is like even worse and sortof tries to brush it under the rug. So the first thing really is,you know, be vulnerable, and I wish somebody had told me thatin my twenty S. be vulnerable, admit what you don't know, seekknowledge, seek guidance, seek mentorship for that. The other thing is,you know, an invest in yourself, and it's similar to how I've embodied, you know, practice what I preach and embody what I've done over thelast really more so in the last for to, for to five years.But invest in yourself and that could be seeking mentorship, you know, seekingknowledge, it could be mental health. You know, we're living in aworld right now where people always feel like they're on and they're in front ofa screen, and so maybe maybe investing in yourself means taking on a newactivity outside of work to help with your mental health. And I do alot of things like that outside of work to help with my mental clarity.And so for sure, be vulnerable, for sure. The other the otherpiece there. And then I would say, lastly, align yourself, and thisis a pretty broad one, but align yourself with a company and alignyourself with a leader who is going to, you know, invest in you andyou believe in and is going to help raise you up. That's alsoreally important, because you can be at a company that may never give youopportunities. You can be, you know, reporting to a manager who may neverreally deeply invest in you, and that's at every level. You know, one of the big reasons I joined... five is how many smart peoplewere in this building. Not Anymore, but how many smart people were wereat this company and and who I'd be reporting to and who they would bereporting to, and I knew there was a lot to gain from that longerterm in my career. So I would say those are the three pretty bigthings. Those are great. Don't be afraid to fail, so be vulnerable, remember to seek knowledge, guidance and mentorship. Other words, invest inyourself. That's a huge phrase. That, I is one of my favorites,and then aligning yourself with a company and a leader who will invest inyou and raise you up. So three excellent pieces of advice from Daniella Belairand Daniella. We are kind of wrapping up our time here and that meanswe have one more segment left and it's what we call our quick fire five, and it's just five questions where we get top of mind real answers fromexecutive revenue leaders like yourself. Ready to go? That's go. Let's doit cool. What is a book that changed how you think about business?Oh God, so many books. The one that is amazing right now thateverybody should check out it's an awsome talent book called antifragile. The summary Is, you know, simple concepts to live an anti fragile life. We knowthat we're supposed ton of allatility, disorder, stress. How, in an antifragileenvironment can you thrive? And I love that concept, specially as covidhits. As you know, we're all working from home right now. Theconcepts in that book, like the one that really sticks with me is makesure that you have your soul in the game of what you're doing and buildredundancy and layers. And as an executive, building redundancy and my plan for htwo was like the best thing I could have done and a hundred percentrecommend this book. Awesome. What's something on heavy rotation in your music playlisttoday? I mean, I have to be really honest with you, Iam not usually a big lady Gaga Fan. I love her as a person,but haven't really been big into the music and I secretly have an obsessionwith sort of house music, you know, great dance music, and her newalbum CHROMATICA is absolute fire and it's on heavy rotation my household, mywife and that's all we listen to, just solid beats around the house.I think her neighbor was a really annoyed with us. That's awesome. Hermakeup artist is actually quite famous now and she went to my high school inmy home room. Little known fact. They're from a very small town,Chesterland, Ohio. That that brings us to number three. You. Whydid you join revenue collective? Yeah, so, yeah, going back tolike you know, the themes and the narrative of our discussion are just seemlesslykind of flowing together, but it really was the network in the community andI had heard from similarly a peer of mine. We were having a conversationover beer and it was like hey, oh, have you you know Iwas? I was actually asking asking some some feedback on some marketing stuff wewere testing and as like do you have any idea like what we should dohere to Dada sales led versus self serve classic question and he said, ohwell, why don't you ask the revenue collective? And I thought, Oh, who's the revenue collective? You know, and he's like, okay, wegotta get you hooked up. You got to get a tap into thiscommunity. And so that's what it was. It was community. It was evenjust the trust, because when you're part of a community like revenue collective, it's the trust to be able to sort of freely open up and shareyour playbook versus, you know, when you hit a people on Linkedin,they're not always willing to go that deep with you, and so it's beena tremendous asset and building new friendship. So I saw a bunch of peoplethat I knew and I'm also making a lot of new friendships all over theworld. So shout OUT TO LAURA OUT IN LA at Ringdon. A madea new friend recently with her and that was through revenue collective, and soI'm loving the ability to connect with people outside of my city as well.Lawer's amazing. She's great. I've had a lot of chance to hang outhere quite frequently because I'm I've been in La for the last four years andyou know, I joined revenue collective as an og when it was just fivepeople going out to lunch and dinner in...

New York, and it's so coolto see how big it's gotten. I think there's on, no, twothousand, three thousand members now, and in the quality of person inside ofit and the the network and the relationship you can build is just awesome.So so glad that you are in it. And that's a kind of lead intoa next question. would be really interesting to know what is a skill, and this goes back to maybe boasting or being a little arrogant, butlike, what's a skill that you believe that you were world classing? Yeah, so it's a good question. And you know, going back to mebeing not the person, how the person has to push myself to Bragg God, this is terrible. Justin's making me think of what I'm an expert at. Oh, he's such an Asshole, and I really am. And soI thought to myself, a great exercise, Danella. You know, pull ittogether. You're great at some things, and so I think for me,you know, the two things that really came to mind, especially inwhat's happening right now, is really just change in execution I'm a huge driver, you know, through and through, I make it happen. Whether it'spandemic or not, we get things done, and so really aligning teams and goalsvery well. So top down, like aligning teams to broader visions andgoals and executing on that, that change, and making sure that everybody's bought in, because that's really important when you're trying to move a ship and andthat, I feel, is something that, you know, I'm quite proud of. Awesome. Lastly, give the audience kind of like a life mottoor a principle that they can take home with him today. Oh God,life motto or principle, I think you know, in the simplest form,just be a constant learner and be adaptable. I think that so important to beadaptable in any stage of your career, because the only thing you can dependon is constant change, especially if you're in a high growth environment,and that's part of the draw for most people and for me. And andjust it be intentional, and I say that you know I'll repeat it,but be intentional about investing in yourself at any level of your career, becauselearning shouldn't end right so that would be my two cents. Danielle has somuch good stuff today. This was a ton of fun. Tell everyone howthey can get in contact with you if they'd like to reach you, gettingup on Linkedin. I'd love to chat. Love to make more new friends.So the bubble are on Linkedin and we can go from there. Cooland your revenue collective slack handle. It is at Daniella tr for Toronto.Awesome, Daniella. Thank you so much. It was great having you on theshow today. Learned a lot x one conversation. Have a great holidayweekend. Yeah, you too. Thanks so much. Just inteers. Thankyou.

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