Common mistakes leaders make

Peer Sales Agency - Ketchup Popsicles Podcast Episode featuring Jamie Pieper

Thank you for tuning into Ketchup Popsicles, the podcast about getting leads and closing deals. I’m your host, Ryan Mack. Let’s get started.

Meet Jamie Pieper

Ryan Mack: Well, thank you for joining the Ketchup Popsicles podcast. Today, I have a guest, Jamie Pieper. She is in charge of sales at Peer Sales Agency, and we wanted to bring her on to talk about common mistakes that sales and marketing leaders make, and how to recognize that you might be coming into that… and how to avoid it in the future.

Jamie and I were talking yesterday and kind of laughing that we run into these issues regularly. I’m excited to talk about some of these things and get your perspective, you’ve got a really amazing background in sales, you’ve been doing this for a while now.

Jamie Pieper: Yeah, a little while.

Ryan Mack: So you were a top producer in sales for 15 plus years, I know that you came from Southwestern Consulting, which that’s a really great background when it comes to a process and the fundamentals, the discipline to document. Talk to me about how that maybe shaped your career a little bit…

Jamie Pieper: Yeah, I actually started with Southwestern in college with one of their sister companies – selling door-to-door, so that’s where I really started selling. I had no idea what I was doing, and they’re like, “Look, we have a process, we have a script, and if you do these things, you’ll be successful.” And I was. So, that’s where I started, and then more recently, I was working with them with another sister company on the coaching and consulting side, and it’s been amazing. I’ve talked to thousands of salespeople and sales leaders and have learned a ton for sure.

Ryan Mack: This conversation got started because we were recognizing coaching opportunities, really, with some of our clients and the marketing and sales leadership that they have. More alerting them to potential red flag behavior, we had Peer preach a lot about accountability, ownership, awareness being abundant, and so we’re always trying to promote the ability to recognize when you’re doing something that’s leaning towards, maybe, a behavior that is gonna have a negative consequence.

Then it just kinda transitioned into, “Well, we should probably talk about just these common mistakes that we see,” and we can start with on the sales side because I’d really love to understand what you’ve seen in your career – if there’s any difference between small business vs. enterprise level. I think that’s always interesting because we do have sales reps that are more transactional, and so they’re getting high volumes, lower dollar amounts.

Then, we have your enterprise folks out there that are [on] 12-month sales cycles, very intense journeys with a lot of stakeholders, and then everyone kinda in between different industries.

Common Mistakes by Sales Leadership

Jamie Pieper: I was thinking through this, and it’s funny that you mentioned, “you’ve talked to thousands of people, there are any common threads,” and really… It’s almost always the same.

I think everyone thinks they’re special or unique, and certainly, there are differences among the different types of businesses, but in general, the principles are the same and the mistakes that people make are the same, and one of the first ones… And this is appropriate, this time of year, ’cause they’re talking about goals, and everyone is setting their 2022 goals and their Q1 goals, and they’re seeing that their leaders don’t always provide the big picture vision around those goals and having that revenue transparency, like the “why” behind the goal.

So, companies have this big revenue goal, they divide it out among the team, everyone has a quota, and that’s it: there’s no connection to the goal, no background, and it’s just like this arbitrary number to the sales reps sometimes.

Ryan Mack: Yeah, well, we see that with companies where they have the BHAG or some huge, annual goal. This is what it’s gonna be, this is why it’s important to the leadership team… but then there’s never an explanation of what you’re trying to do as an organization if we get more revenue, and what we’re going to build out, and what products we’re going to go to market with.

Do you think that these companies do it because they think we can’t handle it?

Jamie Pieper: I think they think they [communicate the why behind the goal,] but they don’t. Or maybe they mention it at the kick-off meeting, and everyone’s like, “Yeah, okay, but what does that mean to me here in… Let’s say Omaha, Nebraska, when my headquarters is in Los Angeles? What does it mean to me?” Because everyone has an income goal, and people will say, “Well, it’s my goal because that way I can support my family or live the life I wanna live,” but at the end of the day, a goal is just a number with a bunch of zeros behind it, and that’s not very motivating when you’re overworked, overwhelmed, frustrated, tired, and so having a bigger connection to that goal and leaders can help individuals do that.

And then, like you were talking about, even just seeing the big picture of what it means, operationally, what that could look like for the company. We even talk about that at Peer, if we have a goal like, “This is where we wanna be. We need to make sure that if we bring on these new clients that we can support them, but we have the bandwidth, the resources, so the clients have a successful experience, so the sales reps have a successful experience.” So, there’s so much that goes into that goal, other than just, “Here’s the number.”

Ryan Mack: That’s interesting. I do believe that there’s this weird gray area that both the executives and sometimes the sales teams try and avoid when it gets into how deep do I go in the P&L? They’ll be very transparent with you above the line, and when it comes to just the revenue, but when it comes to how that revenue then is being distributed down through the organization, paying for things, they get really worried that they’re going to be judged on the way that the organization is spending money, and that’s probably a conversation for another time too.

But the revenue transparency, I like what you said: if a goal is just a number with a bunch of zeros behind it, it’s not very motivating, and so you gotta get to the next level down. What impact could this goal have on the professional or personal lives of the associates? So, you’re kind of saying if sales leaders would take the time to break it down a little bit better, even if it’s individually, to make sure that it resonates with each individual, they could you see that going a lot further.

Jamie Pieper: Absolutely, and then you have this: we have a goal, and then maybe there is even a vision or some emotional connection to it, and then we’ll see, “Okay, well, here’s your goal,” and there’s no plan to achieve it, and there are no activity expectations and no accountability.

And salespeople are like, “I don’t even know how I’m gonna do this.”

In sales, Ryan, how do we usually define success?

Ryan Mack: Revenue.

Jamie Pieper: Revenue! Results. But how much control do we ultimately have over this? Not a ton. We can’t make people work with us or do business with us, and so that’s why salespeople get overwhelmed and stressed.

They just see this big end goal and panic, and so having leaders be able to show the team how to hit the goals – and break the numbers down, and reverse engineer it into those controllable activities. The calls that they’re making, how many people they talk to, follow-up touches, the emails they’re sending, the meetings they set: that’s all stuff that’s in our control.

Then, tracking it. Not just doing it, but actually tracking it. I’ve seen companies have leaderboards, which is amazing because there’s transparency and visibility across [the organization.]

And lastly, celebrating not just the end result, but the activities that lead to that end result.

Ryan Mack: Yeah, okay, so first:

  • These leaders are failing to come with enough transparency to give people context into why a goal, why something is important, and why we need to march. So that’s the first issue.
  • Then, there’s not a well-defined plan to go and get it.

I really like what you’re saying about that. If you’re being judged on a number at the end of the day, that can feel very overwhelming because you don’t have control over so many components in that deal, and you’re being judged on something that you might impact 30 to 50%.

So, not only is having a plan a better way to be, but it will help the salesperson have more engagement with their day-to-day activities because they’re in full control: I can control how many people I call, I can control what I say to them when I’m on the phone, what I email them. What materials I think would be helpful in the journey, I can control all of that.

I just can’t control how they’re going to respond to it, but I’ll do the best that I can get to that.

It’s interesting, I feel like I’ve run into that as a sales rep in the past.

Jamie Pieper: Yeah, yeah, I’m all about controlling what we can control.

Because if you don’t, then you’re gonna be on a constant roller coaster and be kind of miserable. So: control what you can control, and trust that if you do the right things, the results will follow. And yeah, having a leader that can help you break that down and see what [those activities are] is helpful.

And then the last thing I was thinking about on this topic, or that I hear salespeople say is that they don’t have the tools or the resources they feel that they need to be successful, which is super frustrating, ’cause here they are: they have a huge goal, they’re working their tail off, and they’re like, “But I’m not getting support, I don’t have resources, I don’t have anything to share with my prospects and with my clients.”

Then they go to marketing [for enablement materials] and just expect too much out of marketing like, “Hey, we need X, Y, and Z tomorrow,” which isn’t fair or reasonable, either.

Ryan Mack: But the three things that you listed, those are common things that we’re hearing: why we’re doing it, having no plan, or at least not a good plan, and no tools. These are easy things to fix, and there are a lot of templates out there!

Jamie Pieper: For sure. And I think you can look at any executive at any company and they will see this in some way, shape or form, no matter the size of the company, so it’s pretty universal.

Okay, so I’m gonna flip it on you then, ’cause we were kind of touching on marketing and hey, sometimes sales expects too much out of marketing or vice versa. So, on the marketing side, what do you see mistakes that leaders make?

Common Mistakes Marketing Leaders Make

Ryan Mack: A good question. And we deal with this a lot.

Yeah, I would say probably first and foremost, it’s that the marketing leadership doesn’t establish a relationship with the sales leadership.

Empathy is, I think, a foundational block in relationship building, and you need to understand what a day in the life is like for the people that you work with. I think leadership is very good at empathizing with the individuals that report to them because they’re hearing about the daily struggles and experiencing the wins with them, but breaking across silos and going over to an area and being able to see themselves not as separate departments, but as phase one and phase two of the entire sales process. Marketing leaders, the ones who struggle, don’t see themselves as part of the sales process.

They think marketing is not sales, and I would say that marketing is absolutely the very beginning part of the sales process, and the more time you spend with the sales team, you start to understand what they’re running into in the field, the conversations that they’re having, how the competition is positioning themselves, where maybe your product is falling down and how they have to speak around it, gathering all of that information allows you to promote the product upstream much more effectively.

It makes the sales team’s drive a lot easier, which then results in them being able to execute more activities, generate more revenue… The thing I see the most is they almost… talk shit about each other! “Oh, sales, they are always coming in, last minute, and they don’t understand how hard it is to…”

Yeah, you’re right: it is hard to get stuff thrown on you and be told, “I need this tomorrow.”

Yeah, that sucks, but you could have just pro-acted a little bit, and started to understand what they need when they’re gonna need it, and probably eliminate 90% of that reactive behavior.

And then the stuff that does come up, you’re probably right in there with them, saying, “Yeah, this is a company objective that we’re trying to go win this deal, and so it’s all hands-on.”

On the other hand, the sales team doesn’t… They don’t recognize how valuable marketing can be in pushing their products and supporting the kind of middle-of-the-funnel nurturing that you gotta do with your prospect. You get that meeting, you leave a good call feeling good, and maybe the next step will be like a demo… but there might be three weeks in between that good-feeling meeting, and the demo. And that’s three weeks that other reps from other companies are gonna get in there, so marketing can help you and check some stuff that just keeps them on the line.

[Marketing wants to] help you, and the more that these folks talk, I think the better off they’ll be, number one.

And I think number two, they’re not as honest with themselves or with their stakeholders on reporting results and holding themselves accountable to the downstream impact – the lagging indicators of how much money did we generate, how much promotion did we do, what was the return on that investment?

Talking about generating a lead, we get too wrapped up sometimes in those metrics, those are leading indicators. But who cares? How many discovery conversations that I get to have this month, how many demos that I do, how many proposals did we send, how many deals did we win? Those are the four things that matter, and I don’t think marketers like to talk about three of them very much… because they’re like not really in control of them, so [they say,] “I’m gonna put a DMZ between this top-of-funnel lead generation and the rest of the sales process.”

And there it is again, this inability to wanna own the fact that they’re the top part of the sales process. I don’t even know why we have the word marketing, it’s just pre-sales, sales, and post-sales.

Sales-Marketing Alignment Starts with the CEO

Jamie Pieper: Yeah. Okay, so I guess this is the million-dollar question: but how do you bridge the gap?

Ryan Mack: Yeah, good question. I think it starts at the very, very top.

It has to start with the CEO, and first, the CEO needs to understand the value in the Marketing Department, and if they’re not using it… talk about just not leveraging a rocket booster that you have.

[Leveraging your marketing department is] gonna make everything better for your sales team, which will result in more money for your company. So, I think it starts first with the CEO, making sure that marketing and sales are working closely together. I don’t mind it when they put them under the same roof. That’s a really good starter. And then as corny as it is, they gotta start doing stuff together: they gotta have team-building exercises, they have to have strategy sessions and workshops and opportunities for the marketing individuals to spend quality time with the sales individuals.

Sales always has annual meetings, [and so Markeitng] being present for those annual meetings, not only presenting in the meeting, but then sitting in and listening to the rest of them. And then I think, over time, they start to see the real individuals behind the roles and I think it just blossoms from there.

Jamie Pieper: Yeah, no, that’s interesting, ’cause I’m thinking… My background is so heavy in sales experience, and now being at Peer and seeing some of our clients that do such a great job of really having a good synergistic relationship between marketing and sales. It’s amazing, it’s a win-win for everyone! Versus maybe the clients that don’t [have sales/marketing alignment], or prospects or other people that we talk to that don’t…

Ryan Mack: Trying to think if there are any other mistakes that I see between the two of them… I think communication, empathy, accountability, not pointing fingers…

I don’t see the value in anything in pointing fingers, I just don’t get it. I mean, there’s always more that we can do as individuals to positively impact the consequences… I don’t see how blaming works, and maybe the last thing that I would say is, it kind of falls along the lines of the reporting… And it feels tactical a little bit, but: funnel analysis.

I know it’s really in the weeds, but talk about deep diving into every stage of the buyer’s journey and figuring out why [prospects are] falling out from stage to stage, what we can do to keep them in… What we did wrong, what we can change…

I’ll tell you what, if there’s anything tactical that you want your team doing regularly: funnel analysis is it, to me, because it is the ultimate exposure of where your processes and tactics are falling down. When people jump out of your funnel, you’ve failed somewhere in that process. Either failed to clearly connect the value to the pain that they’re having, or whatever – you didn’t get through. So, they fell out and it is honest, it’s honest work when you get into that funnel analysis because you can’t hide from those numbers at all.

So yeah, just a little tactical thing that maybe some sales leaders and marketing leaders can implement to avoid mistakes.

Jamie Pieper: Yeah, I agree. I don’t know that I would add anything to the list. Yeah, I think the big ones, like you said: communication, having some empathy, not blaming each other. That would be a really good place to start.

The mistakes we make

Ryan Mack: Yeah, okay, so to wrap it all up, the mistakes that we’re seeing:

  • Lack of transparency
  • Lack of planning
  • Lack of tools
  • Lack of communication
  • Lack of empathy
  • Lack of accountability

Those are the six main things that we talked about. Actually, I took some notes, and I wanna get us back together here in a few weeks and talk a little bit more about the sales process.

I think it’s a really great opportunity for Peer to have someone with your background. What we’ve learned from you and the information that you provide is… It’s really been eye-opening for us. I think a lot of people, when they think about salespeople, think about the art of the deal. You’ve shown us how much science really is behind it, and how to improve those statistics every day and get better.

I would love for you to share some of that here in the near future, so I’ll holler at you and see what your calendar is looking like.

Jamie Pieper: Sounds good. See, I love podcasts, although I say I’m about 25% self-development podcasts, and the other 75% is true crime, but… Yeah, that’s alright!

Ryan Mack: That’s great. Well, I appreciate you taking some time today to break this stuff down, I hope everybody found it really powerful.

Want more insights into unlocking the potential of your sales team? Follow Jamie Pieper on LinkedIn or send her an email.

Want to be the next guest on Ketchup Popsicles? Follow Ryan Mack on LinkedIn or send him a message.

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Ryan Mack

Ryan Mack is the CEO and co-founder of Peer Sales Agency. Fueled by his drive to help companies reach their revenue goals, he puts his decades of experience in sales, private equity, and organization leadership to work for Peer’s clients.


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