The Sales Hacker Podcast
The Sales Hacker Podcast

Episode · 3 months ago

182: Build a Sales Team from the Ground Up w/ Michelle Pietsch


In this episode of the Sales Hacker Podcast, we have Michelle Pietsch , VP of Revenue at Dooly , which streamlines sales workflow and saves reps 5+ hours per week. Join us for a standout conversation on building sales teams from the ground up at high-growth startups.

What You’ll Learn 

- How to handle massive growth expectations

- The importance of investing in infrastructure in the team

- Hiring SDRs to create demand

- Why the discovery process is always an improvement area

Show Agenda and Timestamps

- About Michelle Pietsch & Dooly [2:10]

- Building sales teams from the ground up [8:08]

- Being in the early growth stage with sales [11:15]

- Effectively coaching reps for improved performance [16:40]

-Improving the discovery process [18:57]

- Paying it forward [25:10]

- Sam’s Corner [27:01]

One, two, one, three, three. Hey everybody, it's Sam Jacobs. Welcome to the salesacker podcast. Today in the show we've got Michelle Peach. Michelle is the VP ofrevenue at Duly, a really interesting company that provides connected workspaces so that yourability to update your crm and sales force is improved, reduces complexity from YourCompany and saves your reps five hours per week in busy work and things thatthey don't want to do. So at any rate, it's a great conversationand she's been building companies from the ground up for a really long time.Before we get there, we've got three sponsors. The first is outreach.Outreach has been a long time sponsor of this podcast and we're excited to announcethat their annual series, unleash summit series is back. This year's theme isthe rise of revenue innovators. Join the new cohort of leaders who put buyersat the center of their sales strategies to drive efficient, predictable growth across theentire revenue cycle. Get more details and save your spot at summit dot outreachdot I. Oh. The podcast is also sponsored by pavilion. Pavilion isthe key to getting more out of your career. Our private membership gives youaccess to thousands of like minded peers, dozens of courses in schools through PavilionUniversity, and no for onzero workbooks, templates, scripts and playbooks to accelerateyour development. Pavilion members get hired twenty two percent more quickly, are paidfourteen percent more on average and get promoted thirty four percent more rapidly than theirpeers. Those are some amazing stats. Unlock the career of your dreams byapplying today at join PAVILIONCOM. Finally, Demo Stack. The product demo ismake or break for your deal, but tailoring the story is tedious work.Demo Stack turns weeks in two minutes, so you can deliver custom demos atscale. No more ACME INC dummy data. With demo stack you can edit dataand charts with a point and click and show product stories that win dealsfaster. See how world class sales organizations use demo stack to accelerate revenue atDemo stackcom. Now, without further ado...

...less, listen to my conversation withMichelle Peach. Hey, everybody, it's Sam Jacobs. Welcome to the salesackerpodcast. Today, we are excited to have on the show Michelle Peach.Michelle is the vice president of revenue at Duley, the rapid growth sales SASScompany that recently raised eighty million dollars to pioneer the connected workspace for revenue teams. Michelle has a long history of developing and scaling sales teams for fast growingstartups. Prior to joining duely, Michelle served as the VP of sales adriftand associate VP of sales a data dog, where she successfully grew the sales teamfrom the ground up. Michelle, welcome to the show. Thanks forhaving me. Sam. We're excited to have you. So we like tostart with your baseball card. Your title is vp of revenue. Your nameis Michelle Peach, but not everybody knows Du lie. So, in yourwords, the company you know? Just tell us. I mean there it'sbeen a story in the press that would that I've read about recently, overthe last couple of months. But in your words, what is duly do? Yeah, so for a sales wrap and sales managers. You have yourdata in your meeting notes all over the place and reps don't update sales forcebecause there's a lot of Admin work and that impacts of sales managers. Sowe're duly reps, take meeting notes and update sales force with one workflow andview, which ultimately eliminates the duplicate effort ensuring that your sales force, instance, is always going to be up to date. And we are saving salesreps five plus hours per week. So just really eliminate all that busy work, all of the noise. And for me as a sales leader, Ihave dealt with US my entire career, both as an account executive but onthe leadership side, where I have to constantly hit up reps to ask forupdates of their forecasts or what's going out with deals. So that helps withall of that grunt work and removes it. Amazing. I mentioned that you justyou know you've recently raised eighty million dollars. But from like a sizeof the organization, rough ar are I...

...mean you don't have to answer anythingconfidential, but where are you in your growth? How many people work there? That kind of thing. Yeah, we are really small. We havea big presence out in the social media world, but I started in Marchand we had thirteen employees and we're around fe employees today and fastly adding moreto more engineering and product side. On the air side, we keep thatpretty close to us, but we are growing and have some pretty lofty goalsahead of us. Amazing. How did you find the job you're working?I Sam you're a you're adrift. I mean those are drifting data dog ortwo pretty high profile companies. What was it about this opportunity that excited you? Yeah, it's funny because I left drift to be a stayathome mom.I had my second son last July and thought I'm going to take a breakand really just spend time with the family and didn't think I work for quitesome time until Chris, our CEO, asked to meet with me and Isaw a demo dulee and it just solves a pain that I felt for solong in my career. So it was a no brainer to take this roleand do what I typically do, is building and scaling the sales team hereat Duley. So I'm really excited about that. Well, that's that's incredibleand congrats on your on your second son. Thank you. So let's dive alittle bit into your background. How did you, you know where you'refrom. The common question is because I still I've been doing this for threeand a half years now, recording this podcast, and nobody has ever saidthat they have a quote unquote traditional sales background in terms of how they gotinto sales. So how did you get into sales? What was your entreeinto the world and and and just tell us a little bit about your career. Yes, so right out of college, two weeks out of college, Istarted at EMC's sales program because I really didn't know what I wanted todo, but sales just seemed like the natural step for me. I wentto school to be in PR and communications.

I had a number of different internshipsin PR and I noticed that the ability to make a lot of moneyand control your revenue wasn't really there. And at the same time I wasbartending and waitress saying and knew how to upsell from, you know, thestake tips to the flame and yon the bottle of wine, and I enjoyedthat. So I had a feeling that I should go towards sales, butno one knows what they're going to be doing out of college. Ended upat AMC, went through the sales program and realized that the larger organization reallywasn't for me, because crushing goals and getting like very little recognition and notseeing that reflect in your paycheck as a bdr wasn't for me. So Iwent to applause, where I got my experience in the true startup world andthat it took off from there, where I was a Bedr and at thattime we called it grass roots marketing. Had No idea what I was gettingmyself into. Didn't really know what a startup was, and I learned somuch very quickly about outbound prospecting, how to talk to prospects and close dealsat a really young age, right out of school. So it kind ofjust happened naturally. What did applause do? What does applause do? So applausewas called you test back in the day, and it is crowdsource bugtesting. So you hire people to test your applications for bugs and you coulddo that on different platforms and different environments, which were super powerful for some ofthese the world's largest organizations. When they're rolling out an application, youneed to make sure it works. Amazing. And so what have you learned overthe past? You know. I mean you've been at data dog,you've seen some really incredible success and now you're working at a really well fundedcompany that's early in its growth, and... of the things that you mentioneda few minutes ago was, you know, what you do is you build salesteams from the ground up. How do you approach that? You havea framework? Do you have a methodology? Do you have a seat? Youknow, how do you figure out what to focus on? For example, tell us a little bit about, you know, your philosophy. Ifwe were to hire you to build out our sales team, what would youdo first and how did you think about it? Every organization is different,and that took me a little bit of time to realize. It depends onwhat you're selling, who you're selling to, and I it really starts with listeningto your customers, listening to the current employees that are there and identifyingour super powers and the value that we bring to the market. So beforeyou put any type of process in place, it's important to understand what we actuallydo, what our customers are saying, what they love what they hate aboutour product, and peel back the layer of the onion there to identifyokay, what's our discovery process look like? What's our B flow look like?What type of sale is it going to be? Is it more transactionalor we focusing more on mid market to enterprise? So early on it's identifyingtop of funnel. We know who's coming, who's raising their hand, and whatdoes that look like, and then putting the standard process in place fromthere and knowing that the first two times is probably going to fail and beingokay with doing experiments and and being okay with those experiments not necessarily sticking.So with the organizations that I've built, the team that they have had multipledifferent trajectories of where the sales process was going and what that overall growth looklike. So at data dog is super, Super Transactional, your standard plg motion. Before PLG was even a thing, we had people coming in, raisingtheir hands and bind without ever talking to a sales rap and drift wasa little bit different, where we had...

...a great, great brand recognition outin the market. So everyone was really really cure various for we treated asif it was a PLG emotion. But at the end of the day wereally need to do like qualification and proper discovery in order to make those customerssuccessful, and that was one of the instances where, like, we didn'ttake the time to actually listen and learn and identify those true superpowers for ourcustomers in order for them to be successful. So, putting your your traditional salesmotion in place, there you're a dueling now. How do you thinkabout I guess there's a natural tension, I would I would presume, butI could be wrong, between the amount of money that you've raised, inthe growth expectations that are implicit in that money, and the reality that it'spretty early stage company and there were thirteen people there a few months ago.How do you balance that pressure? Do you balance that pressure? Do youjust try to hire higher higher? You know my experience when, and youmight know this just from from knowing a little bit about me or not,but my experience is sometimes companies raise a ton of money and then there's thishuge pressure to hire ton of sales people before they before there has been anydiagnosis, a top of the funnel, before you figure it out how you'regoing to generate leads and generate opportunities. How are you balancing that tension nowthat you're a duly where you've got this massive amount of capital on the balancesheet which implies, you know, a couple hundred million dollar valuation, butthe reality is that you're pretty early in your growth stage. Yeah, Sam, and that is yet we pressures the right word. It is setting theright expectations with everyone involved at the state Jeck level, in the organization andalso at the board level, because we are very much seed company, orreally early series a, but with a lot of money, and we havebeen in learning mode since I started in March. There were no sales reps, so we had really very little resources or understanding of, you know,where this thing is going. So when you have all of that capital andexpectations to build and grow super quickly,... can fall on your face relativelyquickly because you hire two quick and you don't have the the resources, theprocess and the understanding of where we are going to run to. And thatwas something that I set early on with our CEO that I will not justthrow bodies a number because we got a ton of funding. We need tounderstand how we can be successful and map our priorities the right way and knowingthat we are still very much in learning and growing phase and as we startto have more conversations with prospects and customers. Were learning every single day. SoI spend most of my time coaching and listening to calls with my salesteam to identify, okay, what is our process going to be? Now, for example, we're starting to see a lot more mid market companies raisetheir hands, so that's something that wasn't there two months ago. So it'sreally it is a it's a tough balancing act, but setting the right expectationsearly on was really important for me with my CEO that I will not justthrow bodies at a number. We need to make sure that we have ourducks in a row before we do that, because I've made the mistake in thepast where we've listened to okay, you have x amount of funding,now go hire twenty people. Six months later we have to fire fifty percentof them because we just we weren't ready. I've made that mistake too. Yeah, been they're done that. I don't want to do it again.Yeah, me neither. Another thing that I sort of like discovered, orwhich is also hard sometimes to pitch to the CEO, is, Hey,I don't want to hire reps necessarily. First thing I want to do ismaybe hire a head of revenue ops, and maybe I want to hire ahead of enablement and maybe I want to hire, you know, a recruiteror some kind of sales or revenue focus talent acquisition person, like building outthe infrastructure of the revenue team before just hiring Reps. have you sequenced itthat way or you know what's how are you thinking about building infrastructure as youhire the actual closures? Yeah, that... exactly what we're doing. Ihired headed of Red Bops in June when I only had three sales reps atthe time, and the idea for her role is to really understand our dataand put the process in place for marketing off C S OPS and sales opsso we can figure out where to focus, as opposed to bringing in a bunchof sales reps. I think it's really important to hire salesops or revopsreally early on because they are you're basically guiding light and they're my like numberone person that I spend most time with to just put the mechanisms in placeand if you without the actual tools needed in order to understand top of funnelMatrix, top a funnel data and also see and customer success data. Youreally can't figure out where to go without that, in my opinion, andthat's a role that people wait too long to hire, because once you startto unpack it, after you know selling for twelve months, they're like,Oh wow, we should not have segmentsed that way now let's change it.I want to do it the opposite way and have someone put that in placebefore we actually do, you know, segmentation or tiering of accounts or orgrating of leads and stuff like that. But for the sale side, Ialso hired an ASTR team earlier than I normally would as well, and that'sfor us to really just to penetrate the market and get as many hands onleads and contacts as possible to bring people to duly, and it is ait's at one ratio right now, which you don't typically see this early on, but it's an experiment that I'm willing to take. I support your experiment. Thank you for it's better to have...

...a small number of reps with tonsof opportunities high fiving and everybody's sitting quote and closing deals then two hundred repsand no leads and then you fire half of them, like you said earlier. Right, right, exactly. So one of the things that you know, you I think you're good at, you've prided yourself on in the past, is is coaching, how to effectively coach your reps. and you alsomentioned earlier in this conversation that you know you're spending a lot of time onthe phone listening to calls. Maybe you're using, you know, something likeGong or course or what have you, but try not hear what our customerssaying, what a prospect saying. How do you need to think about thesales motion, the sales process, the talk tracks? What Are Your keysto effectively coaching reps that you can actually drive improved behavior and performance? Yeah, it took me a while to learn this through many, you know,failed attempts of watching other leaders come in above me and putting a process inplace. It just doesn't we simply just doesn't make sense or aligned with thebusiness or the rep stay in the life and then trying to roll out aprocess to sixty reps who just look at me like you have no idea whateverwhat we do all day. So I have now realize it's best to understandwhat the reps are doing every single day. What does their day in the lifelook like? What's getting in their way, what's working, what's notworking, and listening to calls and identifying coaching opportunities for each individual rep,and then also on the team side, is really important, but getting onthe reps level, so spending more time on a one to one basis anda team environments as well, to just hear, okay, what are youhearing on calls? What's getting in your way? For I just got offa forecast call. I got into the second deal and one of my repsis chimed in and said Hey, have you, has anyone else been hearingx, Y and Z, and we spent that entire forecast call just tryingto unpack that and help them identify how...

...they can get over overcome that objectionor get better when that comes up, as opposed to just like focus onthe deals, focus on the forecast, and I think it it's really importantto figure out what they're spending their time on. So, for example,at drift we were constantly rolling out new tools. Every tool that we rolledout the reps, no one logged in and they were like. You realizethat you just gave us five tools to learn and to implement and I don'thave the time or energy to do that. So figuring out what's getting in theirway and how you can minimize that that noise is really important and italso gives you the opportunity to build their trust in your ability to help them, especially when you're identifying areas of improvement, gaps in their process and taking thetime and over it's really just about listening. You mentioned that the onething that you can always that always bears improvement is the discovery process. Elaborateon that. Yes, I don't care your a hundred million in revenue,you're crushing it, I guarantee. There are reps that are just still failingat the discovery process and and it's maybe because I am spending a lot oftime listening to calls, but you miss the opportunity to dig deeper and identifywhat I call like a golden nugget really early on on calls and discovery issuper important to identify how you can position the value of the product, howyou can actually help your prospect and reps need to always be working on discoveryand you see even your top reps get super comfortable because they're your top repand they start to skied over some questions and they miss the pain. Theycan't tie value back, and it's something that I will always be working onwith my team. One of the experiences I had sort of to your lastpoint, your last coming about time value back, is sometimes when I've beenteaching discovery or trying to coach reps or... or just been part of teamsthat have been doing it, we spend so much time talking about asking effectivequestions that you hear reps on the phone and they they just they start askingso many questions and you could tell they lose the threads somewhere in them allthe conversation and they're not sure how to take any of these answers and relatethem back to the product, tying it back to value. How do youhow do you coach people to do that? That's a question. That's what I'mdealing with today. I think it's narrowing it down and not asking it'salmost like less is more, especially if you get a metric. You getone metric, focus on that one metric, dig a little deeper and then identifyin our demo. Like you, it could go it could be aten minute demo where you can get to the Aha moment or you can beshowing someone forty five minutes of Duli but without actually identifying that core metric orpain point. It's really hard. So once you get one one thing reallyearly on, stop there, ask a few more questions, know that youhave amor at the end of the call or at the end of the salesprocess to throw back at them. That is easier said than done, though, and I've seen it with my reps, for example, just at a callyesterday. Had unbelievable metrics and just didn't know where to go from there. And it's the it's practice makes perfect and identifying. Okay, what elsecould you have asked with this one metric? You got the pain, ask thetwo or three more open ended questions and then go to the part ofour platform that ties back to that and then that's it, because people don'twant to be on a pain funnel call for for fifty minutes where you're justdrilling them with questions, and then that you lose them in the demo becausepeople's attention spans are very short. So try and less is more, shortand sweet. Yeah. Also, the other thing is that people are aware, you know, especially for your tool right, because you're probably set upselling to heads of sales, enablement or crows or vpieces of sales. Theyare acutely aware of when it's a rep...

...that's just asking questions because they weretold to ask questions and it feels like an interrogation, not a conversation exactly, and you can also tell when there's a script in front of them,which is painful. So trying to make it as conversational and helping your prospectas opposed to just drilling them with questions because you know your manager is goingto ask, makes a lot of sense. Last question I have before we sortof talk about your influences and mentors and things like that, but you'rein an early stage company. I don't know. Do you have a quarterlyor monthly goals for the team? We do both right now and that's simplybecause we didn't really know much about our our run rate or where business isgoing, but we're going to go quarterly next year. Makes Sense. Myquestion is this. I've found, but you know, and maybe, maybe, maybe just have an experience this I've found it can be. You know, the job of sales leadership can be. I mean the job of an eightis very hard. The job of sales leadership or reven the leadership isalso hard. And one of the hard things I found is that you buildup so much energy and commitment and enthusiasm and passion for the quarter and hittingthe number and, you know, pulling deals forward and clue and clearing outthe pipeline so that you can hit that quarterly number and then it all resetsback to zero. You know when the next quarter starts and the reality isthat for duly to be a world changing company, that's going to take probablyfive, six, seven years. And there's you know that's going to betwo thousand and twenty four, twenty eight quarters of that kind of roller coasterof energy ups and downs. How do you pace yourself? What's your mindset? How do you think about making sure that you were prepared for, youknow, a two, three, four five year journey as opposed to,you know, a shorter journey with the company? Well, that's a verygood question. For me, it is really identifying small goals that you canchip away out and then, very long...

...term goals that you can chip awayout so you always have something that you're racing to achieve. So, forexample, if we do quarterly goals it, I have my team specifically focus onchipping away monthly and then also chipping away weekly. So I will dothe same, but I think more long term, for six months out andchip away there, but from a numbers perspective and, you know, keepingthis thing going for the next three to five years, knowing that there aregoing to be ups and downs and understanding what your your ultimate goal is,either, you know, acquisition or IPO. This being my fourth start up,nothing really surprises me anymore, so nothing phases me. I just needto understand how we're going to get there and make sure you have the propergoals in place and then back it into, you know, weekly, monthly,quarterly expectations for myself and then also for my team. Thanks a lotof sense, Michelle. It's been great having on the show. One ofthe last things we like to do is just pay it forward a little bitand figure out who it can be. Books like it can be, youknow, grit by Angela duck worth. It could be like a great book. You've read it could be a great boss that you've had, a couldbe a mentor could be a board member, but could it's just people or ideasthat have had a big impact on your life that you think we shouldknow about. When I frame it like that, what comes to mind?My previous zero, Josh Allen at Drift was a great mentor. Josh andI had, I think, a good working relationship where he was one ofthe first leaders that provided feedback and then I also provide feedback. So wehelped one another grow and and learn from. You know, books and what Ireally like to read or what I when I'm my favorite books is Pattymccord powerful. That was an awesome book...

...because it ties back into what I'vedealt with a lot with growing startups and the mentality of the employees from likereally early on and as you grow. I just like the way that she'sshe's no bullshit and that's how I hope and want all leaders in a startupto act. Yeah, I think Josh Allen probably be my favorite leader thatI've worked for so far. Well, we are all fans of Josh Allenover here, so you're not going to hear anything sent from US Michelle,it's been great having you on the show. We're going to talk to you onFriday for Friday fundamentals, but if folks are listening and they want toreach out and get in touch with you, what's the best way to get intouch? What's your preferred method of contact? Linkedin Michelle Peach at Dooleyand maybe remind people how you spoke peach pie ts. H Awesome, Michelle, thanks so much for being on the show. Will Talk to you onFriday for Friday fundamentals. Thanks so much. Same. Hey everybody. Sam Jacobsand Sam's corner really enjoyed that conversation with Michelle Peach. Really really talentedearly stage sales builder, leader, revenue leader, and she's taken on agreat job at Duley, which is a really incredible company. We talked abouta lot of things. A couple things just to underscore, and if youknow me, you've heard me talk about this one million times, but Michellehas inherited a situation where they've just raised eighty million dollars and I think dule'soverall raise over a hundred million dollars, and yet they're a very, veryearly stage. I mean I think she said Post sad pre series a,like really early, right, really early. There were thirteen people that worked atthe company when they had eighty million dollars on the bank, which iswild. But the point is this. With eighty million dollars comes very,very high growth expectations, and the mistake that Michelle did not make, butwhich less experienced people might make, would be to take those growth expectations.First of all, it just turn up the intensity and the anxiety metre inside, right internally. You just you're be...

...super freaked out every single day thatyou're not living up to these massive expectations. And you know, you could imaginelike a revenue model where, like Michelle's, she said she started inMarch, so it's like that's the end of q as A. Qtwo is, you know flat, q three is a little bit up, but thenque four you're supposed to all of a sudden show five hundred percent growth andbe at, you know, ten million an Rr, up from one inMarch. And that's not going to happen most of the time. Maybe sometimesit'll happen, but most of them it's not going to happen. But thething that really happens, though, is you feel that pressure and say yousay and the board because oftentimes, although it's changing, but often times theydon't know how to build a company either. So they say, you know,go hire ton of Reps, go hire thirty reps. you know,every rep generates two million a R are. If we hire thirty reps next yearwe'll have sixty million. And that's not how it works and that's thatwould be a big mistake. And so Michelle has made a couple smart decisionsthat I would or scored and sort of bring to you. The first isthat she's invested in infrastructure, in the team. First and foremost, Ithink she only had a small number of reps, and yet what did shedo? She hired a head of revenue ops as, I think, oneof her big hires, and she made that hire only a month or twointo her her journey there. Secondly, she hired bunch of SDRs. Right, so in steenators hire and twenty Reps. they've got a one to one ratio. What is she doing when she does that? She is creating demand, she is focusing on creating infrastructure, scalability, that's the revenue operations higherand she's investing in creating demand through SDRs and correspondingly, what you're going tohave is a smaller number of reps correspondingly, but reps that feel supported. Right, they've got infrastructure around them, they've got demand generation and strs creatingopportunities and leads. Those people are far more likely to be successful. Canyou imagine a world where there were no SDRs or where Shell is being chiseledmaybe on like, you know, a specific kind of ratio, one hundredand twenty five, one str to five reps, which doesn't really do anygood and there's no revenue laps. And she just hires reps, traps,traps, because the CEO, in this case it would be Chris Hartforkinson,who does understand these things. But let's say it wasn't. Somebody is enlightened, as Chris all of a sudden you're...

...just you're being asked to hire allof these people and, as Michelle said, then what happens? Three months later? You fire half of them. Fire half of them because they didn'thave any deals to work on. Well, why don't they have any deals?Well, because you don't never process, because you have an infrastructure and becausehe didn't have demand. So she's doing it the right way. First, focus on creating demand, focus on creating opportunities, focus on creating infrastructurethrough revene APPS, and then from their build out the sales team with scalabilityin mind, and I think that's going to work. So I really likethat conversation with Michelle. Before we go, we want to thank our sponsors,of course. The first is outreach. Remember that they're bringing back the unleashsummit series. So get more details and save your spot at summit dotoutreach dooh. We're also sponsored by pavilion. Think about these stats. Pavilion membersget hired twenty two percent more quickly, are paid fourteen percent more on averageand get promoted thirty four percent more rapidly than their peers. So thosenumbers speak for themselves. Unlock the career of your dreams by applying today ajoint PAVILIONCOM. And finally, Demo Stack. Product Demo is make or break foryour deal, but tailoring the story is tedious work. So see howworld class sales orgs use demo stack to accelerate revenue at Demo stackcom. Thanksso much for listening, everybody. If you haven't joined the sales haacker communityyet. Please think about doing that. If you haven't given us a fivestars on Itunes, please think about doing that. If you want to getin touch with me, can you can email me Sam a joint pavilioncom orlinkedincom forward flash the WORD IN FOR M F Jacobs, but otherwise I willtalk to you next time.

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