Episode 214

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Published on:

21st Jan 2025

Getting scrappy | Shawn Stiffler

Episode 163: Shawn Stiffler doesn't care what stage you're at - there's always room to innovate.

⏱️ Timestamps:

00:00:00 - The sauce button

00:02:13 - Customer success starts with scrappiness

00:03:42 - Resourcefulness in scaling success

00:06:16 - Scrappy or just doing more with less?

00:08:35 - Creative solutions: An AI budget workaround

00:10:40 - The restaurant lesson: Shoot the deer

00:11:10 - Cultivating risk-taking within safety

00:12:47 - Signing off with lessons in action


📺 Lifetime Value: Your Destination for GTM content

Website: https://www.lifetimevaluemedia.com


🤝 Connect with the hosts:

Dillon's LinkedIn: https://www.linkedin.com/in/dillonryoung

JP's LinkedIn: https://www.linkedin.com/in/jeanpierrefrost/

Rob's LinkedIn: https://www.linkedin.com/in/rob-zambito/


👋 Connect with Shawn Stiffler:

Shawn's LinkedIn: https://www.linkedin.com/in/shawn-stiffler-68947773/

Mentioned in this episode:

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Transcript

[Rob] (0:00 - 0:13)

There were times where I would be like, his name is Budo, my business partner. I was like, Budo, we're out of sauce. And he was like, Oh, okay.

Go hit the sauce button. And I was like, sauce button. He was like, dude, there's no fucking sauce button.

Go figure out how to make sauce. I don't know how, he was like, I'm going to figure it out. I was like, okay.

[Dillon] (0:26 - 0:40)

What's up lifers and welcome to the daily standup with lifetime value where we're giving you fresh new customers, success, ideas, perspectives. Every single day. I got my man, JP with us.

JP, you want to say hi?

[JP] (0:41 - 0:41)

Who do you?

[Dillon] (0:43 - 0:56)

And we've got Rob with us. Rob, can you say hi? All right.

This is what happens now. You've got peer pressure. We have Shawn with Shawn.

Do you want to say hi? Or do you want to say, who do you?

[Shawn] (0:57 - 0:57)

Who?

[Dillon] (1:01 - 1:19)

And so this is where I know when the alliances are struck, because now I've got to be the Scrooge that says, I am your host. My name is Dillon Young. There will be no hootie.

Who's it's not that kind of day guys. Shawn, thank you so much for being here. Can you please introduce yourself?

[Shawn] (1:20 - 1:47)

Yeah, my name is Shawn Stiffler and I am the director of success and operations at Dr. Genius. A little bit about me. I started there roughly 10 years ago and worked my way through frontline support, account management, customer success, built those functions on the way.

And here I am now I manage all things, post-sales. 10 years. It's going to be a little rare these days with a lot of the job hopping around.

[Dillon] (1:48 - 2:13)

So 10 years. Yeah, it's not as rare as I thought it was, but every time I hear it, I am like, wow, man, like you have kids, right? Did you have kids when you started there?

That's like a crazy way for me to envision. Yeah. That's wild, man.

Yeah. Wild. Shawn, you know what we do here?

We ask one simple question of every single guest, and that is what is on your mind when it comes to customer success. So can you tell us what that is for you?

[Shawn] (2:13 - 2:24)

Be scrappy. That's what's on my mind. And that's for customer success, individual contributors and leaders.

I was thinking about what's really on my mind. That's be scrappy with problem solving.

[Dillon] (2:26 - 2:58)

And I think that this is an interesting juxtaposition we've now created by no, we did not try to do this, but to think you've been with a company for 10 years. I don't know that I've ever worked for a company that was even 10 years old, whether I worked there for 10 years or not. And so I've got this idea that at a certain point, you don't have to be scrappy anymore.

You've got your processes figured out. You've got your hierarchy, your accountability. And so like scrappy, no, man, we got it figured.

We just need people to plug in as widgets. And it sounds to me like you're saying, no, that's not the case. That's not the case.

[Shawn] (2:59 - 3:00)

Not the case.

[Dillon] (3:00 - 3:02)

Say more, tell me more.

[Shawn] (3:03 - 3:41)

So there was a LinkedIn post recently, but it had to do with placing leadership and even individual contributors. And in the post Zerp era, just a feeling like there's a widget or you just plug in or you turn a on button and things work. And that's not the case.

So being scrappy is you don't have budget approval, but you still have the problem you need to solve. All right. So what do you do with that?

I mean, you can't buy a CSP, but do you have a CRM that has some capabilities, something native, something you can build out. May not be as good as some of the big name CSPs out there, but it's better than nothing. So that would be an example of scrappy versus just throwing your hands in the air that I can't solve the problem.

[Dillon] (3:42 - 3:58)

JP in your role as working with a larger set of customers that each can get less of your time and attention, but you're working at a company that is doing. Okay. How does scrappiness rear its head for what you're doing?

[JP] (3:59 - 6:08)

I'm actually just perfectly described it, right? No CSP, right? But we do have Salesforce.

A lot of people have Salesforce, right? Salesforce has some capabilities. Let's create a command center or a dashboard to address this problem.

And Hey, maybe in the future you can get the CSP, but for now, this is what we have to do. And I can see how maybe once that problem is solved, well, there may be some other issue that arises where the ideal solution probably commonly it is budget approval. That's probably going to be a common issue.

So being scrappy to me is all about being resourceful. And I think there's an organizational resourcefulness. In other words, I am not skilled at building a Salesforce dashboard.

So that is something that hopefully my team can do, right? Like my leaders, they can support me in that way. So there's scrappiness in that sense.

And then I think there's my own scrappiness, which I think has to do with. I've been taught this in my CS journey, driving accounts. And before I pass it, I was wondering what you would say as opposed to what, and you said, throwing your hands in the air, Shawn, and that is something I experienced earlier on because in CS we inherit these accounts and they're not ideal.

Right. They come in, they've got all kinds of issues and there can be a temptation to when you encounter an issue that is really difficult, or especially if you're in scale, let's keep it real, especially if you have a lot of accounts, there's a tendency to want to just throw your hands in the air and not really try to address it at all. But I think that's the wrong approach because it's easy to be like, ah, sales didn't do their job.

And that's why I have this poor fit customer, this and that is like, I think being scrappy is taking that ownership and looking at what you can do and making an effort there instead of just simply saying like, oh, I don't know what to do with that. So I'm just going to leave it. You know?

[Shawn] (6:10 - 6:15)

Totally agree. Totally agree. Yeah.

Yeah. That's I agree.

[Dillon] (6:16 - 6:41)

Shawn, I want to ask a question that is going to sound 100% combative, and I don't say that to say I don't want it to be. I say that just to prepare you. Maybe the answer is no.

Is calling it being scrappy, just lipstick on a pig for the much maligned phrase, do more with less that we keep hearing and that people are tired of hearing?

[Shawn] (6:41 - 6:53)

That's a good question. I think that's a good question. I think it, the answer, it depends, which seems to show up a lot, but I was really trying to avoid that.

I'm like, oh, the election is over, Shawn.

[VO] (6:53 - 6:55)

We don't, I know, I know.

[Shawn] (6:55 - 8:33)

I was trying to avoid it depends and it just naturally came out. Oh, it's fine. It's fine.

So I would say from my context, no, but I understand how it can be depending on how it's used. So you may truly have a resource issue or you may truly have constraints that existed pre some event, and maybe that's just the nature of the business. And you really need to problem solve.

So when I think of scrappy, I think of problem solving. It's just a short word that everyone understands to identify something. I think of problem solving in my context.

When I hear it, I try to filter it through. Okay. You're just problem solving, but you could definitely slap lipstick on a pig with using that word.

Nah, just be scrappy. But I think of it as problem solving and that's where a leader can do it down to individual contributor. You don't have to be a manager.

I have a specific example. We got denied on budget for an AI tool. So AI was a subject.

I was like, do I talk about it? Or everyone's talking about AI anyway, I ditched it, but it's related to problem solving and being scrappy. But so we got denied budget just because we have competing priorities and it's a tool that would help out with sentiment that's native and Salesforce.

And it was disappointing. I did a simple Google search. Does open AI have an API that works with sentiment?

It does. Well, we have engineers on staff and so now it may not be the best. It may not be as good as a platform that's already built that you can just pay a fee for.

But what we are going to get is this case through natural language where this email appears negative, here's some automations flag, the account manager flags, CS flag, if it's something with onboarding flag, whoever that's scrappy to me, problem solving.

[Dillon] (8:35 - 8:39)

Rob, why don't you jump in with a couple of minutes we have left?

-:

Yeah. I'll tell a quick story because honestly, I feel anger coming over me. And why do I feel anger?

I feel anger because I'm thinking of all these times where I, myself and people I've worked with have refused to be scrappy and we'd rather just take the, either the complaining route or the overly methodical route that does not get the result fast enough. So the story, I think the guys might know this one. When I graduated college, I was like, I'm going to start a food business.

And I spent months planning it, thinking about branding, trying to secure an investment so that I could open up my first location. And, and I was just hanging out talking to this guy who owned a restaurant. And he was like, dude, it's been months.

What's taking so long? And I was like, well, I'm waiting on an investor. I'm waiting on this person who's doing my branding.

And he was like, come here, sit down. He's like, I'm about to get sunned. He's like, I'm going to tell you a quick story.

He was like, my first language is Turkish. And in Turkish, we have this parable that a kid goes hunting with his dad. Kid sees a deer.

Kid looks up at his dad and says, dad, can I shoot the deer? Turns around and the deer is gone. And he's like, so shoot the deer.

Like you see the deer, you can kill it. Okay. And I'm sorry, PETA, I'm not a hunter and I've never hunted.

And I don't have any killing bones in my body. But the point is that was like, that became a principle of our restaurant. We ended up partnering together on a restaurant and scaled it.

We scaled it to four locations over seven months. And the way we were able to do that, zero outside investment was, and we didn't make any money, mind you, but like we bootstrapped the whole thing because we had this principle that we are always going to do more with less. So I remember there were times where I would be like, his name is Budo, my business partner.

I was like, Budo, we're out of sauce. And he was like, oh, okay, go hit the sauce button. And I was like, sauce button?

He was like, dude, there's no sauce button. Go figure out how to make sauce.

[JP] (:

I don't know how.

[Rob] (:

He was like, I'll figure it out. And I'm like, okay. And then I'm running to the basement, trying to scrap ingredients together.

And this became like the foundational principle. Everyone who's worked with me in the past has reported to me, these poor people, they all know this story because I see it all the time. Like I see people like me in my past overthinking, overanalyzing and trying to apply this Ivy league framework.

So like really simple situations at times.

[Shawn] (:

Don't overcomplicate it. Yeah.

[Rob] (:

Yep. When there's, when there are scrappy solutions available.

[Dillon] (:

I will say though, there's one piece of this that I think we're not talking about and that is operating within a organizational culture that rewards that and does not punish it. And that is a very thin line. And I think where people get caught up is they don't know where that line is or that line keeps moving or that line is not drawn straight.

And so for as important as I think it is for people to have a default to action mentality, there's also got to be from a leadership standpoint. And Shawn, maybe you want to talk about this though. We're almost out of time is how you foster that sense of safety for your individual contributors to make those types of decisions.

[Shawn] (:

I think that's a great question. And a hundred percent true. There's context.

That's where it depends, comes from to answer your question. I'm responsible for six or seven teams, 50 ish individuals and different disciplines. So the way I foster that is go do and document why.

So if it blows up, there's no point reprimanding or coaching on the end result necessarily, because if something's on fire, it's on fire. We got to put it out. I want to understand why that happened because I could really help there and understand your steps you took.

So go do have a default towards action, but think about why you're doing it and just document it and understand it. So if we do sit down to talk about it, we can just go through the steps and then I can help guide if there was a misstep potentially. And then if you did really well, then great.

Let's keep doing that.

[Dillon] (:

Very cool. I love that. Great way to end it.

So that is our time. Shawn, thank you so much for being here. Fantastic topic.

And thank you for not talking about AI, but mentioning it so I can put it in our SEO and we get fantastic traffic.

[JP] (:

Get the algorithms going. Yeah. Thank you.

[Dillon] (:

You know the game. You're welcome back anytime with that attitude. But for now we've got to say goodbye, Shawn.

All right. See you all.

[VO] (:

You've been listening to The Daily Standup by Lifetime Value. Please note that the views expressed in these conversations are attributed only to those individuals on this recording and do not necessarily reflect the views and opinions of their respective employers. For all inquiries, please reach out via email to Dillon at lifetimevaluemedia.com.

Find us on YouTube at Lifetime Value and find us on the socials at Lifetime Value Media. Until next time.

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The Daily Standup is the flagship podcast on the Lifetime Value Media network, cohosted by Dillon Young, Jean-Pierre "JP" Frost, and Rob Zambito. We're publishing daily and sharing the most diverse and unfiltered array of guests. Tune in to hear industry titans and newbies alike chopping it up, sharing their hot takes, workshopping their current challenges, or just giving Rob another new nickname.

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About your host

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Dillon Young

Dillon is a career Customer Success professional, having done tours of duty in Technical Support, Training, and Implementations as well. He did Sales that one time, but doesn't like to talk about it. Since 2019, he has been a people leader in CS orgs for early stage technology companies, primarily in the financial and human resources spaces.

Dillon founded Lifetime Value in 2023 with the vision of delivering entertaining, educational, and non-biased content to this exciting profession *without* selling (gasp) an ebook.

So far, so good.