The Pavilion Podcast
The Pavilion Podcast

Episode · 1 year ago

Ep 94: Running Start-Up Sales w/ Michelle Pietsch

ABOUT THIS EPISODE

Ep 94: Running Start-Up Sales with VP Revenue at Dooly, Michelle Pietsch

Part of the "Thank God it's Monday (TGIM)" series hosted by Tom Alaimo.

All right, welcome back to the Revenue Collective podcasts your host tom Alamo. Thank God it's monday. This is where you learn the tips, the tactics strategies that G. T. M. Execs need to get to the next level. So before we get to today's episode, I want to give a quick shout out to our sponsor. This episode is brought to you by drift. More than 50,000 businesses use drift to grow revenue and increase customer lifetime value faster drift helps their customers align sales and marketing on a single platform to deliver a unified customer experience. Where people are free to have a conversation with the business at any time on their terms, learn more at drift dot com and I've used drift before and I love it. So let's get to today's conversation. I've got Michelle peach on the line. Actually coincidentally former VP of conversational sales at drift, former A. V. P. At data dog. Former inside sales manager at you test worked inside sales at E. M. C. And is currently the vice president of revenue for Dooley. You might have seen that recently. They just landed a series B for $80 million. Who? That's a lot of cake. So there's a lot of exciting stuff going on at Dooley. I love talking to Michelle. Let's go straight into our conversation. We're gonna learn a lot about her history, a lot about women in sales, a lot about how she's driving the revenue plane at duly on such a great growth track. So without further ado let's get straight into our conversation. All right Michelle. Good morning welcome to the podcast. How are you? Good. Thanks. Thanks so much for having me. Yeah. Well I've got a fellow bostonian on the show. It's always good to connect with people in New England when I'm across the country. I know I love it. My companies in Vancouver Canada. So I'm always referring to east coast stuff here and it doesn't follow the same, so happy to be checked. I didn't know that Vancouver, I feel like is or maybe just Canada in general, I feel like it's kind of like on an uptick in the tech world, I don't know if that's just me or like following Shopify and some of these other companies, but it seems like they've got a little bit of momentum going, They do, and there was a chatbots company aid. I just got a pretty big round of funding out of Canada. So shop of I a to duly kicking off. Yeah, that's awesome. That's awesome. I'm excited to have you on, not only because you are a fellow bostonian, but you've had an amazing career in sales. So there's a lot that I want to get into first and foremost, what I'm looking at. Your linked in. I see just a ton of amazing companies that you've worked for. Obviously a duly now at drift before that at Data Dog, Before that the list goes on and on. So walk me through a little bit of, you know, like how you've chosen some of these opportunities, like what do you look for in a company when you go...

...there, because you seem to have time to a lot of these companies really well as well. Yeah, so I enjoy working at the startup level where I have the opportunity to scale the team basically from the ground up and when I'm interviewing and looking around it with the opportunities, it's really about the leadership team number one and then the product. So am I going to learn and be challenged by working for these leaders and do they know what their vision is? How confident are they about their vision and how excited are they about their vision and where they want to take the organization and then products. So is the product something that I can get excited about and behind, is it a pain that we will solve and help other people be successful when they're using our products? So those are the two main things and I've had the opportunity to work for some amazing leaders and the products early on were awesome and evolved drastically over the years that I've worked at these organizations. So I'm really excited to do that here at Dooley. So your VP of revenue? Right. Yes. Can you walk me through what the thought is there between that and being like a typical VP of sales? I'm sure it seems like an intentional kind of change of of terminology to maybe follow like a chief revenue officer type of path. Yes, exactly. So that's that's the ultimate goal is to follow the C. R. O. Path but also managing all of the revenue in the organization today. So not just the sales team but eventually growing out and account management team. And then we have other pieces of the business that drive revenue that will eventually oversee and provide guidance to help us accelerate our revenue and then maintain our customer base. So my focus is all of the revenue within the organization. Okay. Got it. And you're selling to salespeople? Yes, I have the pleasure to sell the salespeople which is excited. Yeah, I just started doing that this year over at gone and I was selling to other people before that. But there's something special about selling to a C. R. O. Or VP of sales because if you do a good job I feel like they really they get it, they appreciate it and they'll they'll go with you on that sales process on the path. They're not as resistant. But if you mess up like they'll let you hear it and they'll tell you about it. That's been my experience so far. Exactly. There's very little room for error. But I like it because we can get we're on the same playing field, right? So we're going to ask you discovery questions. We're going to try and unpack the pain in your process today and we're going to ask for next steps and I want my reps to go in for the hard close. But we can also say you know what? It's under a quarter. You just be real with me. Are you going to sign like salesperson, a salesperson? Is this a deal or not? As opposed to you know, typically selling to engineers, you can't be real with them.

You're not going to be able to get on their level on the same page. The same way that you can with a sales rep. We're all going through it. We all have a number over our heads and where we come in, we're going to really focus on helping you move your deals forward. But that is where the conversations usually lead at the end of the month. Hey, sales after sales rap would be real with me. And that's, that's something that a lot of other sales people don't get the opportunity to do when I'm on sales calls with other sales. Perhaps I also test them. I'm looking for them to identify the pain. I'm looking for them to set that next step with me. So I know that everyone is doing the same thing with my reps to do. You ever call it out? Like, um, sometimes we use Sandler at dawn and so sometimes we'll do like an upfront contract and Either they'll make a okay, that was a good one. Or I'll just be like, how is that upfront contract? Just because I know that they know what's going on. Do you ever make a comment if someone selling, do you like that? Yes. And I always praise them for setting next steps. That's something that I find sales reps don't do. You just leave the daily hanging and it's left out there and for my team, I want them to definitely get next steps and a firm handshake at the end of the call. But when someone does that, I praise them and I wait and if they don't like man, you missed an opportunity. So it's it's always coaching. I'm always coaching no matter what. Yeah, I mean, you have to, if you don't have next steps then you don't have a deal. That's what I was told, like my first year sales and it's always stuck with me. I praise the person that taught you that. So I'd love to get into, you know, we were talking a little bit before the podcast about, you know, women in sales and being, you know, underrepresented. And I'd love to kind of go down that thread with you a little bit and hear your thought on, you know, both women in sales and then also women in sales leadership and where your head is on, you know, where we are today. Yeah, absolutely. This is something that I'm very passionate about, especially over the last few years in my career, I have noticed that we see a lot less female sales reps entering the sales world and I'm not too sure why. I think it starts at the leadership level, at certain organizations. We need to start embracing it. We need to start welcoming more females into the sales world. And I think it's the messaging that we put out there at the executive level. We need to make it more normal for moms to step into the sales world, little bit of flexibility. I think over the last year, we've proven that Females are not just females. Everyone can have the flexibility and still do their jobs. It's not necessarily that mentality of you need to be on 24/7 and that is something that has changed over the last few years. When I first started sales, it was very much go, go...

...go. And there was a point where I thought there's no way I would be able to have a family like I could barely handle my dog and be a sales leader, let alone Children. But there was an article Harvard Business Review put out a year ago and it highlighted women in sales and female sales leaders and sales reps are typically number one and no one talks about that. No one ever highlights that. So I want to start highlighting that more. I want to, I want sales leaders and organizations to start thinking about how you can embrace it and be more welcoming to female sales reps and sales leaders. Something really passionate and near to dear to my heart. I remember that article. Do you remember what some of those traits were that women possess that made them better. I know I'm putting you on the spot from a year old article here. Yeah, I don't, I wish I had that in the back of my head. But for me personally, I think it's females and especially moms were female sales reps and sail leaders. You're able to balance a lot and accomplish a lot in a very short amount of time. And when you have something you have a goal, which is typically a revenue goal, females have the ability to take their goal and they chip away at how they're going to get there. And because we're typically in a time crunch, we can put our specifically process in place in order to achieve that goal and it's more about focus routine and balance. Yeah. And I feel like, I mean now we're, I'm generalizing, but I feel like women have sometimes like this, this sixth sense like this, such a high level of emotional intelligence as well with people and can really like tend to show, you know, more empathy and I think that we're now living in a world where that's more recognized and sales is less about like Wolf of Wall Street, you know, smiling doubt, close them on the phone, hard, hard clothes and it is more about like you're on this process together. You do need to really do a good job of doing discovery and understanding pain, matching that pain to how you can help like all these different things that it is a lot more of An art. I feel like then it's just like a science of make, you know, 200 cold calls and like just get people's credit cards over the phone that benefits people that can, that can make that human connection. Yeah, you're spot on. I mean no one likes to be sold to right and no one likes that aggressive sales tactics, especially the way that people can buy today. You can buy anything without ever talking to anyone. And if you have to speak to someone you most likely don't want to be berated with a bunch of paying questions. And this is this isn't just for females, but having that ability to be empathetic and listening is really important. And I think females are...

...really good at listening and understanding what the prospect and customer is saying and how you can map that back back to your product, being able to solve that pain. But empathy is number one, I think that you should start testing for in the interview process. Not necessarily. I'm going to go through the sales process like like a bulldozer, like a bullet trying to chop. You know, like that's where I think most of my top female sales reps are like that and that's why they're successful and I imagine that maybe it's happening now, definitely in the past, where you mentioned when you first got into sales, it was like, oh, I'm never going to have a personal life if I want to do this because it's just so crazy. And I imagine that once women maybe decide that they want to have a family that they're more likely to either get into a different career where it's not as high pressure or they stay as a sales rep where there's more flexibility naturally than being in sales management. So I'd love for you to talk about that because you do have both, right, you're the VP, you've been a sales leader at multiple great companies and you do have, you know, two young boys and you're doing it all. So I'd love for you to talk to someone that might be in that situation. That's at that pivot point about how you make it work, how you, how you are successful in all these different areas. Yeah, absolutely. I have two young boys, three and 9.5 months old and there was a point where I thought there's no way I'm going to be able to be a sales leader and have a family. So let me just, despite continued to just focus on crushing my career And there comes a point where you have to figure out how you're going to balance it all. And it's 100% doable for me specifically, it's all about routine and identifying your routine in your day to day and how you can balance work and life. And some people might say there is no work life balance, but you can make it however you need to make it in order to be successful. And it goes back to my previous comments of where companies should start to think about adding that flexibility and making it normal for, hey, I'm going to need to block off my calendar 3 34 to go pick up my kids, But we're also at 100% of our goal or were pacing at 100% of goal and you feel comfortable with doing that. And you can also look back at everything you've accomplished in your career to get to where you are today. It's really about understanding what you need to do in order to be successful. And it's harder for females to see that because there aren't a ton of female sales leaders. And I think most companies prior to Covid didn't necessarily make it normal for females sales leaders to shut down for a few hours to take care of their families, but we need to break that cycle. We need to do it soon.

And what part of that also relates to you mentioned a little bit about like trying to show your son's like as they're growing up like that, this is possible to, and like this could be something that could happen in their lives with a wife or you know, however they decide to live their lives. But like also kind of being the example of, hey, I'm being a great parent, I'm being a great wife and being a great, this that, but I'm also like crushing it as, you know, a sales leader and you know, my professional goals and ambitions that I have and being able to do all those things. Yeah, absolutely. I'm very goal oriented. So I set specific goals for myself, whether there's short term goals like weekly, quarterly, monthly yearly and that is what motivates me to show my boys. But hey, you can, you can be on the soccer field and you can also take a call to close a deal at the same time. And it's just setting those goals and showing them that if you chip away at your goals, you can achieve whatever you put your mind to and that isn't just necessarily in sales or sales leadership. It's really just anything in life is being motivated to just go the extra mile and I'm willing to literally run through a wall to get to the next level and to help my team be successful and to be there for my family. And those are just specific goals that I have set in place for myself. And I suggest everyone just put down goals whether their daily weekly, monthly yearly And check them off as you go. They could be really small goals, whether it's achieve your metrics for the week before Friday or what I want to lose 10 lb by summertime. Just small things that you could just check off, but you can also feel accomplished when you're done at the end of the day. Yeah. And I think the parent thing is so important like to me, you know, I had a mom that was, you know, is a badass, like, you know, sales and marketing leader growing up and she was doing her thing, but she was also there like to pick me up from school or if I was home sick from school and you know, I'm not going to say her age, but she's still out there now. She was just on a flight yesterday to New Jersey, like trying to get this like deal done for her startup that she's working at and like to me that was inspiring to me to share, like as a boy that like she's out there crushing it and like attracted me to my fiance who is a better sales person than I am and like doing all these things too. So I feel like there is a really strong effect to like, growing up as someone with a mother that is like doing all of those things. And to me, I've always found that inspiring and I'm I'm almost like sometimes like if I'm, you know, feeling like lazy, I was like, are you kidding me? Like, like for in the back of my mind, like come on, come on, tom you got it, You got to pick it up a little bit. Yeah, Good for your mom. That's awesome. See like that I look up...

...to someone like your mom. Um I have a funny story. I I left my previous role because I thought I was going to stay at home mom. It didn't last very long. Uh And a lot of people told me that it wouldn't last very long. And my 2.5 year old one day said mama is really good at doing the dishes, doing the laundry. She's always vacuuming. Mama is really good at cleaning. And I thought, oh man, I need to get back to working because mom is really good at doing a lot of other things and just cleaning. And I need to show my boys that I don't want them to just think of me as folding laundry all day. So that's my goal just to show them how it could be done. That's awesome. I love it. I love it. So you joined Dooley? What like four or five months ago? Yes. I started March one. Okay, so there's a lot of folks that are, you know, it's a hot job market right now, especially because of last year there is so much, so much turmoil and everything going on with Covid and people unexpectedly getting laid off and and things like that. So like what's like your mindset for the 1st 90 days or so? Let's say I'm coming in and I'm going to be the VP of sales or revenue at a startup. What should I be mindful of in the 1st 90 days to really kind of hit the ground running? Yeah, I've been spending a lot of time listening to gone calls. So I suggest purchasing a tool like gong or course and getting in there and listening to what your customers are saying, what your prospects are saying. Especially early on you have to understand how, where your product is going. Is there a product market fit yet? What our prospects saying? What do you need to do on the product side in order to take this thing to the next level? And I spend a lot of time listening to calls that we completely bombed calls that we did really well on. And that is giving me an indication of where we need to set our sales process and also what we need on the product side. What we need from customers success. What do we need from onboarding? It's really important for I really think everyone in the organization this early on to listen to what people are saying about your tool and any suggestions that they have, any gaps that we have in the process. So it's actually been pretty amazing most of our product team. Listens to our calls are CeoS and they're on the weekend, so that's been pretty awesome to see. So let's get a little bit more specific. So how many reps do you have? I have three wraps today. So the team is pretty small. Okay. And do you ask them to like tag you and ones that went well or not well or you kind of just pick them at random? We do both. So they tagged me on calls where they really needed help on or they were stuck. We also do weekly film reviews. So I will pick a call that I listen to and I'll take chunks of the call and I'll have the sales reps, listen to the...

...call on a team call and they give each other feedback On where they think that they could have improved or places that they've done did really well. And then on the product side, I listened to calls, I listened 3-5 calls a day and I tag my product team in there and then they get in there and then they write feedback and where they need to improve on the product side. So it's a, it's every day. Yeah, I mean you can you crank that speed up there and you can go through gone calls. It's also listen to it on your phone. If you're out for a walk or folding laundry, didn't, you can get through a couple of calls, but it's really important right now for where I am, I'm trying to understand what we should do from a sales process side, which are on boarding look like how does CS get involved? So there's a lot of pieces and I'm really thankful for gone. This is not a paid ad man, I should start swinging, gone. So let's say, you know, you're, you're looking through all these different things and these are big challenges for startup, right? Like how to onboard, like how the past the customer success, like how we can change the sales process maybe to accelerate deals or whatever it might be. Like when you're getting all these ideas, you're listening to a ton of calls, how do you or how will you prioritize which one to really spend the meat of your time on moving forward? Right now? It's sales process. So that impacts the way that we service our prospects and our customers. So understanding how we asked for are paying questions, right? How we are unpacking the pain and then how are we showing the value on these calls? That's number one and then that will impact the sales methodology that we're going to put in place. I haven't put one in place yet, but I think that's important also for aligning sales process and the sales methodology. Then when it comes to the customer side, what does our on boarding look like today? It's really, we're working on that. So listening to the calls and understanding what is important for the customer in order for them to see the value really quickly in the tool. And that's number two. That's like the second on my list. So first process then onboarding, how are we servicing our customers and then we'll just unpack the rest from a product standpoint. Yeah, I love it. And I love the collaboration there. Any tips for like coming in and working well with It sounds like you have a good relationship with the product team working well with product with marketing, all these other functions that you have to flow with while also, you know, hitting and exceeding your numbers. Yeah, I think collaboration is really important, especially in the world where most people are remote. I think it's understanding how other individuals on the team like to communicate. So I'm a big video person. Instead of sending a slack, that's paragraphs long, I'll send a minute...

...video to just get my points out there. Other people really like email. They'd rather just communicate via email. So, understanding that first is really important and then spending a lot of time early on with these individuals is really important to build that relationship, collaborate on these ideas. So for example, I have one on ones with the VP of product. I want one for VP of marketing and yes, every single week. And it's sometimes we might not have necessarily a pressing matter, but it's just like building that relationship, collaborating with them across the board, like on the personal level, because we don't get to see them in the kitchen, we're not going to be able to go grab lunch or go for a walk around the building quickly. So building that relationship, understanding how they like to communicate and then overall collaboration across the entire SLT or strategy team is really important, yep, I love it. So, I'm curious like throughout your career, like what resources have helped you a lot? And this could be like, you know, books, this could be podcast, this could be people you follow on Youtube or instagram and it doesn't have to be sales related, it could be self help, it could be psychology really. Any topic is fair game. I'm just curious. Anything that has impacted you, something that you're into right now that you recommend to other people, anything like that. That stands out. So, one book that I read typically this early on at the startup level is impossible to inevitable. That's something I always turn back to. And then I like john Barrows an open view, open view puts out awesome content. Um I like getting the emails on the weekend and scrolling through their blog posts there really P. L. G. Focused. So that's where the organizations that I've worked at have been P. L. G. So they have a lot of good content that they put out and then john Barros, I've, I really like the way that he thinks about sales and the sales methodology. So he's someone that I follow and use his nuggets with my team pretty often. He's awesome. He's my favorite, he's my favorite sales leader influence or whatever person. Yeah, me too. Yeah. We uh, they invested in him at when we were at Tech Target. I bought his online course, done a few podcasts with him. He's a good dude. And uh, I feel like kind of balances the line of like the art and the science. I feel like of sales, which some people, I think maybe lean too heavily one way or the other. Absolutely. He's a really good human. So, and you can feel that with the way that he coaches and goes back to my earlier comment about being empathetic during the sales process. I think that's important. And he has that really good balance of being a good human on the sales side and also getting to the point to, and he's a bostonian. Exactly. Which doesn't hurt, right? So how much of your time you're spending a lot of time listen to calls, trying to think about process. I imagine at the size of dually, you know,...

...for every company, every deal matters. But for for, for your size, like every deal matters. You've got three reps. So like there's probably a lot of deals that play. Like how often do you find yourself getting into deals and actually selling versus saying, Hey tom this is the rep like this is all you, you let me know what you need. What's your thought there? That's a great question. So I'm not the type of leader that will take over your calls. I don't think you're going to learn if I'm running your sales calls so I will join calls where we need to, we know we're going into like a pretty heavy discounting negotiation where I'll come in and play good cop, bad cop type of scenario. But from a coaching perspective, I'd rather I'll be on the call and I'll jump in when needed when the rep is really struggling or we're just stuck and it goes back to all right, I'll jump in and be that type of person that will um ask the tough questions that the reps seems to be a little bit uncomfortable so they can learn how it's done. But I don't, I'm not a big believer in actually running the calls and that's where it goes back to the sales coaching opportunities when you have a type of sales recording or call recording tool, you use those opportunities to coach everyone on the team after the fact to, so it's either on the calls, I'll slack them. Some people get thrown off by that. But then at the end of the day, just listening again and then giving feedback. I feel like there's been a lot of articles written about this, but like there's so much truth to that. You know, I don't know what you're, what those three reps where they are in an age, but I imagine that they might be millenials, given that it's like, you know, a hot, cool startup Dooley and so like from my perspective, a lot of like young sales reps, like we thrive on, like we love the coaching and um you know, I've got a director that just like just coaches, like, yeah, I call him the professor because he's just always just like teaching people something. And so I feel like that's a huge plus for anyone that's listening that, you know, maybe they're focused on all these other things, but haven't had time to do the coaching. Not only does it make your team better, but it also keeps them bought in. I feel like on the mission and keeps them excited to work there because they're, they're learning and growing. Yes, absolutely. Coaching is so important and I've seen a lot of sales leaders fail at that and it's probably because we have a lot of other things that are on our plate as well, forecasting, hitting the number. But it is, you're doing your team in the service. If you don't understand and identify the gaps that they have in their process and it could be something little, it could be your, their emails need to be tweaked a little bit or the way that they start the calls. Are...

...there little abrasive or they just go right to the point of just understanding how they can improve in their day to day. It could even just be the time management. I find a lot of people need coaching on time management and how they're managing their day, but spend time with their reps, try and identify where they are lacking in their day to day process whether it's listening to more of their calls, joining their calls for understanding their forecasts and their deals, not just asking what you're committing best case unpack that unpack where those deals are, it could be a very small miss and the next step, but if you coach them on that, it could help them get that deal. I love it. So I've got a few more for you in kind of like a quick fashion. Is that cool? Michelle? Yeah, Okay, so we talked about going, but sales and I'm sure usually, but like sales tools or any type of like tool, I guess technology that you can't live without that really helps you out. I'm not a big tool person to be honest with you. I feel book and paper, maybe no, get rid of the note fucking paper. That's where duly comes into place. I think for me, the email sequences, tools have been really effective. I'm not going to name any specific ones because I've had horrible experiences with some, but my team loves them. So my team loves to be able to get creative with the emails sequences that they're sending and not have to think about it after the fact, although we customize all of our messaging, it gives them the opportunity to organize their day, better to make sure that their cadences are going out and so they don't miss a beat. That's probably the number one tool that I would buy outside of some kind of call recording. And do you like the sibling? I do have a sister. Okay, so let's say your sister is taking on the role of VP of revenue at a fast growing startup and you could only share one piece of advice with her. What would that be? Oh, I didn't know. I had no idea where you're going with this question. I would say don't get overwhelmed. I feel like there's always going to be a fire to put out, but tomorrow's a new day, so don't get overwhelmed. It is what it is. That's great. That's great. And then the last thing for you is obviously we're on the revenue collective podcast. You know, community. I'd love to hear any tips that you have that either that you leverage this community or just like networking in general and the philosophy that you have for that with your career. Yeah, I am loving the slack revenue collective. So I haven't been very active, but I read and scroll through every day what people are saying the women's revenue collective has been really helpful, especially with the way that other female sales leaders are coming up against issues whether it's with their rex or their managers and how to...

...navigate those tough conversations. So that's been super helpful and I highly suggest getting in there. The guru has been helpful to. So the app that you can get in there and and search for certain things. I search for some job descriptions that I had to put together. So that was really helpful. That's great. So any pieces that we didn't get to today before we let everyone know like where they can connect with you and where they can learn more about Dooley. But anything else that's like burning top of mind that we didn't touch on? No, I think we've covered it all. It's been great, awesome. So first of all, Michele thanks for being so generous with your time with, sharing your wisdom for the community. So just if people want to learn more about Dooley, people want to connect with you. Like what's the best one of the best places to do that? You can connect with me on linkedin Michelle ph on linkedin checkout Dooley and I'd be happy to walk you through a gemma. I got one more thing for you actually. I forgot. Mark has promised me to get on that hot ones like spicy wing challenge and he's been blowing me off for like six months. So are you sure you're gonna do it? Everyone that's been on since it's been brutal. Have you done it? No, but I'm apparently in line too. So you and me both. All right, this is a public accountability. I'm gonna tag Mark. Gonna send this to him. I want to be on it with you and I want to get some hot wings. Let's do it. Let's do it. We should do it in person to see how we're both in boston. We'll suffer in person life. Yeah. There you go. That's awesome. Well, thanks. Michel. Really appreciate you. Coming on. Awesome. Thanks so much. It's been great. All right, everyone. Thanks for checking out that episode of the Revenue Collective podcast. One more shout out to our sponsor drift. This episode was brought to you by them. They are the new way businesses by from businesses. You can learn more and get the conversation started to drift. Dot com can learn more, connect with me on linkedin. My name is Tom Alamo until next week. Get after it. Thank God, it's monday. Have a great week. Peace. Say something. Mm hmm.

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