Andrew Conley: From Overwhelmed to Overachiever: Mastering Sales Pressure Without Breaking

Welcome to Go to Market, a podcast for RevOps, sales, and marketing leaders to dive deep into industry insights and best practices. Go to Market is sponsored by Fulcast, the go-to-market cloud. My name is Amy Cook, and I am so excited today to introduce you to Andrew Conley, a go-to-market leader and advisor who's working at companies like Qualtrics and Workato. Andrew, how are you?

Doing well. Thanks for having me.

Good. Thank you so much. I appreciate that you are willing to come back on after being on the podcast once. Glad it wasn't a horrible experience for you.

And, um, I loved it.

It was so much fun and we had such an engaging discussion. And one of the things that you said really struck me as so relevant and important that I wanted to have you come back and talk specifically about that one piece, being the constant pressure of sales and how you handle it. I think that some of the advice that you gave us in the previous podcast was super interesting. And as someone who has done sales before and is very happy to be in marketing instead of sales, I can't wait to learn all of the tips and tricks and on how you survive and thrive.

Yeah, and I'm excited to talk through it. And I don't know if I, I survive and thrive. I think there's always ups and downs, but excited to talk through it. You know, when you brought up this topic, it actually made me think of this meme I saw on one of these sales accounts I follow, and it had a it was kind of like a before and after of different people. And it had a before of someone that was sober and then they started doing drugs for a certain amount of years and kind of their before-after pictures. And then they had a salesperson before and after and they just aged drastically. So it said after getting into sales, it just ages you and you know, it is a stressful, constant grind, but I think there's a way to find happiness and peace in it.

That's awesome. And I think the people who do are some of the most capable, smart, and interesting people and also very secure. Like it's, super interesting to see the real veterans like yourself who have been able to find that middle ground and that peace like you're talking about. So just getting right to it, what are some of the pressures? Let's start there with the pressures that sales has. I mean, you've got your number going up all the time while your territory is shrinking all the time, right? You have to eat what you kill. And what are some others?

I think it's just the constant expectation to deliver, right? I mean, sales has a really short memory. You know, what have you done for me lately? You could have a fantastic year the prior year, but if you're not doing well now, your job's on the line. And so I think it's a matter of how do you deal with the short-term, but also the long-term planning, right? And I like to kind of think of this analogy of as an individual, if you don't have, let's say, a roof over your head and food to eat, that's all you're focused on, right? And It's all that consumes you. But as you get your basic needs met, you can start thinking about, oh, well, I need to eat more vegetables, or I need to do cardio, or I need to do something to take care of myself. I think sales is similar where it's like, if I'm not gonna hit my quota this quarter, it's all you can think about. It's all you're consumed by. And so it's like this constant pressure to say, how do I hit this quarter? Um, and, and I think there's a way to find this balance between what you're doing now and what you need to be doing long-term. But if you can't get to the point where you're confident and secure in like what it looks like now, it's really hard to ever start thinking long-term about your career progression, your long-term decisions, right? And so So finding that balance is tricky.

Yeah. So you're like in this constant state of where is my next meal coming from? Almost like the survival mode, right? Instead of thinking strategically of how your career path can grow in the long term and where you eventually wanna end up. Is that right?

Exactly. Yeah. That's a great summary. And I think in sales, a lot of that comes down to where's your pipeline? For me as a sales leader, I mean, that's one of the most important things that I focus on cuz I think if you have adequate pipeline, not only is your sales life better, right? Like, I think you feel more confident, you have multiple ways to hit your number, but you also have peace in the way you communicate with that, with customers, right? Like, there's not this weird urgency to close deals unnaturally, to push deals that aren't ready to be moved. In sales, that all happens, and sometimes you have to try to say, hey, I got to close everything I can. But when you have adequate ways to hit and a lot of different opportunities or pipeline, it's more natural. And your customers feel it, you feel it. And it also transcends from your business life to also your personal life, right? Like, there's less stress at home, there's better relationships in my personal life when I have adequate ways to hit my number because I'm not as stressed, right? And doing this in a while, I think it used to be much more stressful every end of quarter. My wife said over time, like, end of quarter, Andrew didn't come out. And it's like, it's gotten better. So I, I think there's this, this natural pressure every end of quarter to deliver. But if you can have adequate pipeline, you don't have that pressure, that stress.

Wow, that is so interesting. And that speaks very true to me in terms of how I can best support sales as a marketing leader. One of the things that I'm working really closely with our sales team on is building that pipeline. And I noticed that when we kind of take it account by account and I try to get them things in their ICP that are really important, it builds that trust so much more. And I never really thought of it the way that you've described it, which is it's a stress relief for you. And it's not out of any other reason. It's not like you just want it fed to you. It's not like you're not willing to work. It's not even a rational thing. It's almost an emotional thing, right? Is that what you're telling me?

Very much so. And I think that once you have that peace of mind, I think people behave differently, right? When you're kind of backed in a corner versus when you have adequate coverage and it allows you to go back to like my, my previous analogy to think more long-term and say, oh great, we have enough to hit this quarter, but now let's think about next quarter or the next 12 months or the next 2 years. And to be a better leader because you're actually not just focused on the immediate needs, but you're focused on the long-term needs because your immediate needs are met. And I'm always thinking, I actually created this standing meeting called our Pipeline Council, and it was a monthly meeting with everyone that created pipelines for the sales channels, including partners, marketing, SDRs, sales leaders. And we had our targets and we'd say how we're trending towards it. So it was an accountability touchpoint, but it was much more of like a collaboration saying, hey, what's working, what's not working, how do we help each other? And we all had our metrics that we needed to hit, but it was this way for us to come together. And plan for the near term and the long term and say what we need to do from a pipeline generation perspective. And that ended up being actually one of my favorite standing meetings because it allowed for us to have that alignment. So marketing, sales, partners, even sales leaders were all on the same page of where they were at and what they needed to be doing.

Oh my gosh, I love this. So I'm going to do this myself. I'm supposed to be reporting the pipeline number in our executive meetings. So I'm going to set this pipeline council. Thank you so much for the idea. I love it. So when you talk about pipeline, do you have a certain expectation of what marketing should source and what sales should source? And like, do you think of it in terms of that? Or do you just think of it in terms of like, it's a number? The way I think you're thinking of it is more like all the different ways, like you described, right? Like you wanted to have a variety of ways they're coming in.

Yeah. And I think definitely a variety. If you asked me 10 years ago, earlier in my career, I'd be like, 100% marketing. I don't want to do any outbound, but I think as I've matured and learned, I think it's good because not all pipelines created equal. And you look at dollars in and dollars out, right? When you're kind of owning the business, the number, you have a certain amount of budget and where do you want to place those chips, right? Where do you want to put that investment? And you can look at kind of the immediate, what does $1 in get in terms of dollars out? And different channels are going to be different. There's also this curve over time. So if you think about like a partner channel, for example, you may put a lot of money in there to invest in building strategic partners, whether channel partners, ISV partners, and it may not yield much, but it's kind of this hockey stick where once it starts clicking, you get a lot of return from it. You may think about AE outbound where it's more linear. And once you kind of figure out the outbound, you hire another AE, you get a certain amount of output and you can kind of expect a certain amount of AE outbound activity or revenue. You know, marketing on paid, there may be diminishing returns where you spend more money on ads and you actually get worse return on ad spend. And so it kind of has a diminishing curve. And so you have to kind of think about where you're at in these different curves of the pipeline channels and what's right for your business. There's not a right or wrong answer of like, hey, we need 20% from sales, 30% from expansion, 50% from marketing or whatever. Like there's going to be varying splits and it depends on where you're at in those maturity curves for each channel. But I think it's always important to assess what's the ROI currently and where do we guess we are on this curve as we spend more money or invest more into it? Is it going to get better? Is it going to get worse? Is it going to be linear? And trying to understand that investment arc. So that's kind of how I think about the split there.

Oh, that's very interesting. And I see it's not just the sourcing, but it's also, like you mentioned, what's right for your business. And I think that that comes in terms of industry and it comes in terms of the stage your business is at, right? So I had an advisor who's also a good friend of mine who has built multimillion-dollar companies from zero all the way through several hundred million. So she's been on the executive team there. She has a kind of a rule of thumb where she says the first $10 million come from the founders, period, end of story. From there, then you can expect a lot more to be coming from marketing and a lot more to be coming. Would you agree that different stages of the business have required more outbound from you as an AE versus marketing? Or— and, and, and like, also I think like B2B versus B2C I think is different. But tell me how you kind of think about that?

So I wish I was an expert on, on all of this, and I can only say from the experience I've had, both the companies I've worked at are B2B SaaS, and I've come in later stage than 0 to 1 or even 0 to $10 million. It's been 10 to 15 or later when I've come in. But I would agree, I've talked to a lot of early stage companies, both that I've advised for and interviewed with, and it does seem like there's this founder-led sales kind of in the beginning, and it's them selling their vision, selling their network, really doing a lot of that. That transitions hard for a lot of companies to say, how do we now go scale this? And in doing that, you want to have other channels, whether that's outbound, whether that's marketing, whether that's partners or however that may look. And so my opinion is I don't think I'm qualified to fully answer that, but I do know that it evolves as you scale a business and depending on which industry you're in. A lot of companies do a lot of PLG motion and that works great where it's led by the product. It's a freemium to premium and people come in through that way. Sometimes it is, if it's enterprise SaaS, it is a lot founder-led sales. And so I think that vary based on industry, based on, um, you know, stage of the company, but that's what you should always be assessing is how does that pipeline balance change over time, because it, it shouldn't stay the same regardless of where you're at in the journey.

Yeah. Oh, I love that. And that is such a great perspective. I'm always fascinated to hear about your perception of pipeline because you guys are the ones that are affected the most by it, right? So we should really be listening to you the most about it. All right. So I think that is so insightful to me that having enough pipeline helps you stay in the game, helps you feel better about it. What else do you do to just keep you even-keeled and steady as you're going through this?

I think finding ways to de-stress is super important, right? And I think adequate pipeline's one of those ways. Other ways outside of professionally, I enjoy getting outside.

Mm-hmm.

I enjoy being in nature. Summertime, it's easy in Utah. I like to hike or mountain bike. Even just going for a walk helps me de-stress. Last time we talked about cold plunges. I feel like if you start your day with a cold plunge, it can't get any worse. I mean, it's, it's awful, but there is this unique sense, you know, when I go out and exercise, you know, it's a de-stressor for me, but that can take an hour, an hour and a half depending on what I'm doing. And in 3 minutes in a cold plunge, your body just gets so stressed that it's just like so intense for those 3 minutes that you're in there that when you get out, you just feel this rush of endorphins and you just feel so happy that your baseline is no longer just freezing cold and you're outta there. Yeah.

Yeah.

And so I found that as kind of my cheat code, cuz honestly, when I'm at the end of quarter. I'll do that daily. It really helps me out. So these are like tips and tricks, but they're ways to kind of make sure that I'm relaxed. I think too, it gets easier as you get further in your sales career to have more of a perspective because the variability of where you land is, is not as great. And what I mean by that is if you're an individual, especially if you're selling enterprise type accounts or deals, one deal can make or break your quarter and you're hoping that deal comes in and you either get 150% of your number or 20% of your number if that deal comes in. Doesn't. As you get further into your career, there's less variability because there's the law of large numbers, there's more deals, and it's less of how far are we going to be up or down. Like, there's some variance, but it's not as drastic as when you have just 1 or 2 deals.

Hmm, that makes a lot of sense. And it kind of goes to the pipeline also. If you've got a whole bunch to work with, you can't predict the future, right? So some things are going to fall out and some things are going to go that you didn't expect. And so that's a very helpful perspective as well. So you've got this de-stressing with Pipeline, you've got de-stressing by keeping yourself physically fit through exercising, cold plunges and things like that. What do you do mentally to keep you just at the top of your game mentally?

I think life's about perspective and putting into perspective. I mean, yes, B2B software or whatever you're doing, your career's important, but it's not like we're curing cancer. I mean, it's all relative, right? I want to do the best, I wanna perform the best, but I think having a good perspective. Is super important. And so for me, it's helpful to kind of always reset. Some people do meditation. I've tried that. I'm not great at it. I could probably get better at it, but I think just keeping the perspective of like, look, if I'm doing my best, we've tried everything we can. This is the best I can do. And if I've left it all on the field, I, I can't be disappointed. So that, that's also helpful from like a mental perspective to know that if you're trying everything you can, you're doing everything you can, this is your best and that's where you're at. And so that's also helped me get through a lot of end of quarters. It hasn't always been great, right? Like I've had some really good end of quarters where we've done really well You know, I've had quarters that have been disappointing and it's stressful and you gotta shake off the loss and you can kind of say, hey, that was rough, but you know, on the next quarter and how do we get those ones in here in queue then the following quarter quickly and then move on.

Yeah, I really like what you said there too. Thinking about like, you know, this is not the same thing as cancer. And I think that that for me also is very helpful. I am pretty intense when it comes to making sure that I get my job done and If I ever feel like I'm falling short, I take it super hard, as most of us do, right? Because we all want to do well in our career and things like that. And so sometimes I think about it and I'm like, okay, what's the worst that could happen here? Is anyone going to die? No. Are, are all my kids safe at home? Yes. I keep this perspective in mind because my dad spent 50 years in the entertainment industry with tons of ups and tons of downs, and my mom was so great and steady. And I was like, Mom, how do you even handle this feast or famine mentality, which is so common in sales, right? And she goes, you know, I always just think to myself, what's the worst that could happen? The worst possible thing that could happen is that we could lose all of our money and end up in a homeless shelter. I think I could do that. So I'm like, hey, that's, that's a great, great perspective. So I kind of try to think of the exact same thing of what you were just saying. Is just really keeping everything in perspective. Meditation for me just stresses me out more. I start, my mind goes down a rabbit hole and I can't do that. But for me, trying to keep things refocused on my kids is really helpful for me and doing things like that. So like, I love what you said there about the strategies. How important is the community with other sales leaders to you? Is that community aspect important?

Yeah, I think so. I think for me, community of other sales leaders, I have some amazing friends that I've made over, over the years. Working through some really great companies and we go to lunch, we stay in touch, we text often, and that really is a great support because they know what I'm going through, right? And so they can relate. So that's great. I'm lucky to have a strong family life, a wife and kids that helps me reset and kind of align on my priorities and what matters most. I think having that ability to depend on others is key. And to your point, it's super important, but the stakes aren't that high. And what's the worst that can happen, right? Like, do your best and, and it all works out. And so those are easier said than done. Like, it's easy to say, hey, don't stress so much. Like, it's all gonna work out. It's easy to say, it's hard to live, but I think as you practice it, it does get easier. And I've seen that over my career.

Is there ever a point where you've told a rep that maybe doesn't have the sales chops or abilities that they should maybe think of something else or find different career? Have you ever had to have that conversation with somebody?

Yeah, unfortunately lots of times. And I think whether I tell 'em to not have a career in sales or if it's just not a career doing this type of sale, that depends. But I think it's not easy. Being in sales, but I, I do think anyone can learn it. And I think that not everyone can be successful at every type of sale, but I think that sales isn't like a personality profile. Like this personality is going to be good in sales. I think there's some inputs that lead to certain outputs. And I think that there's kind of like a skill-will diagram of like, what's your skill and what's your will? And I'd rather bet on the person that has high drive or high will, um, than has high skill, especially if they're intelligent and they can learn because sales can be learned. And so in my opinion, I always assess people based on that skill-will and say, where are they at here? And if they have low will and they're not really trying, that's a very different conversation than if they're trying, but they're just not aware of how to do it. And so the way I look at it is I, I really wanna assess them. And oftentimes I'll have them plot themself on this. I'll draw it on a, a whiteboard and say, where do you think you are on this chart? And dot where you are. And then I'll dot where I think they are. And then we'll discuss. And so this idea of managing someone out of the business because sales maybe isn't right for them really comes down to, do they want to be here? If so, why do they want to be here? And what drives them? Because yeah, sales isn't for everyone. Luckily for me though, a lot of the people that I've been working with in my career have been in sales for a while, and so they kind of already know this is what they want to do. Earlier on, I did work with a lot of people that just moved into sales, and you have a lot more of it when it's more early stage sellers.

Uh, that makes a lot of sense. They're like trying it out to see whether it's a good fit for them and that kind of thing. That's super helpful. Yeah. So I think the take home from the topic in terms of how do you manage that, the stress levels and everything that goes into it, is you kind of have to have a solid understanding that you feel confident that you can do it and that you've got the will and And that indexing on will, even over skill, maybe you index on will and adaptability or will and intelligence or whatever, that you can learn those things and you can be successful.

Exactly.

That's awesome. How do you help somebody who's on a PIP? How do you help get them off the PIP and becoming productive?

Yeah, so it's interesting because I've had a lot of experience with this and there's people that you can manage up and then there's people that are managed out. And I do think a lot of it comes down to their drive, not always, but most of the time, but it's always a matter of Has this individual been coached? Do they know the inputs that lead to the outputs? Are they doing the inputs, at least the minimum expectations? And those inputs could be, are they making effort to have calls? Are they having meetings? Are they preparing for those meetings? And if they're not, were they aware they should have been doing this? In most cases, yes, but some cases they didn't get a lot of guidance. And so you have to make sure they understand what are the leading indicators that affect the lagging indicators. Lagging indicators being either building pipeline or closing deals. And I think when it comes to a plan, it should never be a surprise. It shouldn't be a situation where someone's on a plan and they, they didn't know they were gonna be put on a plan. They should be aware. And so I kind of like to have this idea of a coaching plan before a performance improvement plan. And what I mean by that is when things start trending down, the manager should come to that individual and say, hey, you're not where you want to be. Let's figure out how to do this, right? So maybe they've missed the quarter, maybe their pipeline's not where it needs to be, but there should be a conversation and there should be some sort of conversation before a plan. It shouldn't be a surprise. And so a coaching plan is much more of, hey, what can we do together? What do we need to work on. And then a PIP, in my opinion, is much more formal. It's where a coaching plan didn't really turn things around, and so we actually have to come to writing out a contract. This is what needs to happen by these milestones. And those milestones could be a full quarter, maybe broken down by month, could be one month broken down by weeks, and you can decide what the length should be. I like to give a longer runway for people that I think have the will but maybe not the skill, so they can show improvement on the skill. If they don't have the will you can have a shorter plan because it's much more focused on, okay, I need to see these behaviors. And if you're not doing these behaviors after 1 week, I don't think you're gonna do it after 2 weeks. Like you just, you don't have—

That's so insightful. Yes. So the will is something you can turn on or off or skip very quickly.

It's the skills.

And it just shows what an excellent leader you are to be able to see the difference in that and be able to give the ramp time needed in order to develop those behaviors. That's amazing. Well, is there anything else that you wanna say, like final words to all of the sales leaders and also reps listening to this podcast?

I don't think so. I think sales is not easy and everyone in this knows that. I'd love if anyone has any other tips or anything I missed that if they wanna reach out, cause I'm always looking at ways to get better and to learn more from those around me.

Well, thank you so much. I really appreciate your time, Andrew, and thanks again for diving into this topic.

Thanks, Amy Cook.

It's great being on here.