Episode 323

full
Published on:

24th Jun 2025

Tighten the loop | Monica Stewart

Episode 273: Monica Stewart wants to know how we get to value sooner.

⏱️ Timestamps:

00:00:00 - Intro

00:01:31 - The big question on customer success

00:01:48 - Vendor mishaps and lessons learned

00:05:27 - Why traditional sprints fail

00:07:04 - Rob's show and tell inspiration

00:08:33 - The power of focused sprints

00:11:03 - Internal dysfunction challenges

00:12:21 - Positivity and customer engagement


📺 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 Monica Stewart:

Monica's LinkedIn: https://www.linkedin.com/in/monica-stewart/

Transcript

[Monica] (0:00 - 0:19)

They're supposed to have built something that they then show you, you QA their work, you give them feedback, you like show them some more advanced stuff. Then you do onboarding workshop number two, which is like the second part of whatever the thing is. And like, of course, depending on the product, you're going to break this up into nine days.

[Dillon] (0:28 - 0:50)

What's up lifers and welcome to The Daily Standup at lifetime value, where we're giving you fresh new customer success ideas every single day. I've got tortilla Rob with me. Rob, you want to say hi?

What the one? And we've got JP with us. Incredulous.

JP, can you say hi?

[JP] (0:50 - 0:52)

Hey, I love a good crate, baby.

[Dillon] (0:53 - 0:58)

And we have Monica with us. Monica, can you say hi?

[Monica] (0:58 - 0:59)

Hey, good to be here.

[Dillon] (1:00 - 1:11)

Good to have you here. And I am your host. My name is Dillon young, Monica, as if you need an introduction, your second time here, can you introduce yourself?

Is that what I say there?

[Monica] (1:11 - 1:30)

Yeah, I think that's what you said. I introduced myself. It is an honor to be invited back.

This was fun. The last time that we did it, I think it's going to be fun today too. My name is Monica.

I'm the CEO and founder of MSD consulting. I help you be SaaS founders get from one to 10 million ARR by building a scalable revenue systems. And I've been doing that for 15 years.

[Dillon] (1:31 - 1:47)

Tight. That is a tight pitch. I love it.

I've got to work on mine. Monica, you do know what we do here. We ask every single guest one simple question, and that is what is on your mind when it comes to customer success?

So can you tell us what that is for you this time?

[Monica] (1:48 - 5:26)

Yeah. Okay. So, um, I've been thinking a lot about like, how do you get that time to value tighter and how do you keep the people that are going to influence your contract from slipping away, and this is really top of mind for me right now.

Cause I just went through a cycle with a vendor that I brought into one of my clients and they did not do this. So like, I'm not working with this client anymore since like two weeks ago. And I get a Slack message and they're like, Hey, we have some really great new ideas for the company that you brought us into, like, you think we could get something on the calendar?

And I was like, yeah, man, I mean, I can talk to them, but I'm actually not working with them anymore. Did you know that they have a new VP of sales? When you talked to him and they were like, uh, and I was like, Oh man, what went wrong with this rollout?

You know? Cause it was like the time for them to review their six month pilot obviously did not get renewed. And I realized that there was like, yeah, there, there, it was, it was all right, everyone's friends.

They're all okay with it. But it was like, when we were doing the whole onboarding, it was just this feeling of like, okay, are we done yet? Are we done yet?

Are we doing the thing? Are we doing it right? And I remember I kept asking them, like, is this what we should be doing?

Like, you know, our situation, what are we missing here? Or is this like the training wheels are off or riding the bike? Like, you know, you're looking at us and you're like, yeah, I've got it.

It just never really felt like I knew whether we were being successful or not. And like, I'm a pro at this, you know? So like, if I can't get it, what's missing here.

So I would love to hear what you guys think about this. I've been playing around with this idea of an onboarding workshop. So instead of like, you set the thing up, you do the training, you put the product in their hands, you kind of make it feel like a bootcamp and here's roughly how it goes, let me know if you guys have ever done anything like this.

I'm sure that I'm not the first person to come up with this idea. Maybe I am. So like you do the kickoff, everybody's there and you lay out, this is what we're going to do for the next, let's say four to six weeks, probably four to six week program, right?

Everybody is there. All the people that sign the contract, all your executive stakeholders, knowing that that's the only meeting that those people are usually ever going to attend. Right?

So then for the next couple of weeks, you're working with your team, you're working with your users, but instead of doing a training and then having an office hours session, you do like half the training and you're like, okay, first we're going to do a profile creation workshop or like whatever the thing is. And you walk them through, like you show them how to do one part of the thing that they need to do. You let them breathe for a week, you come back the next week, they're supposed to have built something that they then show you, you QA their work, you give them feedback, you like show them some more advanced stuff, then you do onboarding workshop number two, which is like the second part of whatever the thing is.

And like, of course, depending on the product, you're going to break this up in different ways. Same thing, let them like you could even do this as two 90 minute sessions where you're co building with them, or you could do it as like training, then they come back, whatever is appropriate. The idea is, is that by the end of the thing, they have created something in the product with like their own data, their own users, their own models, whatever it Then when you do the wrap up, you bring everybody back because you're going to demo to them what their team built in that time.

[Dillon] (5:27 - 5:54)

This is you've been on the show before. So you know what my brand is. So I'm going to come and tell you why this won't work.

JP's favorite personality quirk of mine. But actually, no, I think why, why I think this doesn't happen often, is because I think we've evolved to turn it into this like sprint, because of how difficult it is to get people to keep showing up.

[Monica] (5:55 - 5:55)

Yeah.

[Dillon] (5:55 - 7:04)

And I think that's a product of a number of different things. You own a very small piece of their resource pie when it comes to time and attention. And I think we've also started to hire implementation people that are very just like task oriented.

They're not, they're not salespeople in any capacity. So they're not selling this experience. They don't make it fun.

They don't make it engaging. It really is like, and then you do this and you do this and you do this. Yeah, yeah.

And so I think those are probably the two and they might be like a chicken or egg sort of situation, right? But I think, yeah, absolutely. That's the right way to think about it is to make it more engaging, make it more bite-sized, make it more involved on their part.

But I think there are challenges that have created the scenario that we're in today. And maybe we should re-review it because now we have like different technology and different whatever that can make this easier. But Rob, why don't you jump in here?

I'm sure you've had this experience.

[Rob] (7:04 - 7:13)

Yeah, in different forms. And Monica, you're actually inspiring me to fully bake something that's been half baked in my notes for some time.

[Monica] (7:14 - 7:14)

Nice.

[Rob] (7:14 - 7:26)

Which is part of customer show and tell. So I was like, I was thinking to myself, show and tell. Like I was thinking about my nephew doing show and tell in school.

And I was like, what if we did show and tell with our customers?

[Monica] (7:27 - 7:29)

Literally, that's it. Yeah, yeah, yeah.

[Rob] (7:29 - 7:37)

Like instead of what if instead of a QBR, you know, you show up and you're telling the customer how they did. They're like, look at my progress.

[Monica] (7:37 - 7:38)

Look what we made.

[Rob] (7:38 - 8:33)

And then look what we made. I like that was really good. What we made.

Yeah. And I think that's really cool. And it's not just QBRs, but I think it also it reminds me of all the way back to your last episode where we left that episode saying like, no more snooze fests when you kick off a new client.

Yeah, time to value has to be tight, has to be fast. And one of the things I've been working on with one client is we took their onboarding process that was week over week, over week, over week with these meetings where people would show up forgetting what they talked about last time, and we condensed it down into a one day onboarding sprint, which was really interesting where it reduced no show rates. So Dillon, that solves part of the concern you had.

Clients would have quicker time to launch. Like we basically modeled off of the experience, kind of like when you have someone come install wifi in your house, like shows up and then they leave and then like, you're done.

[Monica] (8:33 - 8:33)

And then you have wifi.

[Rob] (8:34 - 8:53)

Yeah. And then you have wifi, it's done. So they're happier.

We also hypothesize that clients will learn better if they're more focused for a defined period of time. And they literally shut down all their distractions too. Like they're not showing up to a training call with their email up.

So less task switching and less burnout risk for CS teams as well.

[Monica] (8:54 - 8:54)

Totally.

[Rob] (8:54 - 9:17)

We're not task switching and going back and forth and managing a big book of clients that we have to constantly jump between. So it's working really well for multiple clients at this point has worked well with me for me in the past. Got a shout out, former guest of the show, Tajay Conkright, friend of mine who initially gave me that idea, like probably like eight years ago or so.

But I like this idea.

[Monica] (9:17 - 9:19)

Do you do those in, in person?

[Rob] (9:19 - 9:20)

Sometimes.

[Monica] (9:20 - 9:21)

Yeah.

[Rob] (9:21 - 9:25)

It depends largely on the affordability of the model, enterprise way more likely.

[Dillon] (9:26 - 9:32)

I have a question, but before I ask it, JP, I want you to, maybe we're on the same wavelength here. So why don't you go ahead?

-:

I mean, I'll just quickly add, I think that in my experience, when it comes to keeping customers like engaged with something that they got, I think Dillon, something that you said caught my attention, something that I've learned, which is when you talked about the resource pie, like it's like something you don't have control over, right? Like I, I am representing the solution that I have, perhaps that is only going to be, but so much of this customer's budget, and if it's only so much of that customer's budget, then they're only going to give me so much time. So that I would say that falls under something that's not in my control.

The other thing that this made me think about was, I don't know, I'm losing, you know, how things start to run away from, gosh, it, it was company dysfunction, internal dysfunction. You do not see. So I have learned that, you know, cause I'm typically liking keeping people engaged is usually like one of my strong points, but I have seen that if a customer is dealing with a lot of internal dysfunction, like you, it doesn't matter if you're coming out like Johnny Carson, Johnny Cochran, Johnny Knoxville.

I don't care. All the Johnny's can come out. If they are having internal dysfunction, they cannot hear you over their own internal dysfunction.

So that's the other thing too, that I just wanted to call out.

[Monica] (:

Yeah. I mean, you guys know that like, I come at this from like at least half sales perspective, because I do that too. And I only work with companies that sell enterprise.

So in my mind, I'm like, okay, they bought it for a, there's a thing that they want to see happen. Right. And if we leave them to their own devices, the likelihood that that thing is going to happen is less because of all the reasons that JP just said, like we only have certain resource share that potential resource share is the most available when they sign the contract, internal dysfunction, shitty implementation teams, all of that.

So it's like, how do we basically like force them to do the thing that they said that they wanted to do in the shortest amount of time possible? And I'm like, if it still doesn't work, it still doesn't work. But I think Dillon, all the points that you brought up earlier are the reasons that this doesn't happen now, but I would challenge you and say, like, maybe we should be changing those things.

[Dillon] (:

So here was my question. JP didn't go in this direction. Did they do anything right?

This company that you used as the example, like did they set the foundation properly? Did they find out who the decision makers were? Did they map the organization?

Did they tell you what the journey was going to look like? And then it just like petered out. Is that what it was?

[Monica] (:

They did all of those things. They didn't tell us what the journey was going to look like. And I think that that was really like the miss.

And it's like the, so in thinking through, like, what do we want to solve for here? The thing that kind of made that team lose interest is we never, we never got positive reinforcement. We never got like, that's amazing.

Look what you guys did already. Like, good job. Like, keep going.

Just like anybody needs to, when they're learning something new. So we were like, we're not really getting like, yeah, we're getting value, but we're not, we don't really feel like rewarded from this thing. And so it kind of just became less compelling over time.

[Dillon] (:

Rob had to jump, but he had a good analogy about the cable installation. And I think that what more often happens is a company buys a service that is not as simple as a cable installation and we treat it like it is, and we don't go through this process of like, think about if you had to turn on your modem every single day and you had to like configure your IP every single day and every time you wanted to do a Google search, you had to like set some sort of, that's kind of what we're dealing with, right? Like the systems we sell are much more complicated. And I think often we instead treat it like it's a cable service.

Oh, send it and forget it. It's not going to be a problem. And the customer, unless you really hammer home that it's not like that.

I mean, it would be ideal for them if it was like that. So they're going to treat it like that unless you kind of like pull them in and you engage them in a way that is like, no, no, no. I really need you here with me to see how this goes.

Monica, that is our time. I love this topic and I love the way you're thinking about it. I also think the one, the other thing I thought about is time to value, you can pull it so much earlier or time to first success, whatever it is, if you chunk out the process, like you talked about, and it's not the cable guy after two hours of being in your house and drilling holes in your nice hardwood floors and whatever else they do, doing the speed test and saying like, Hey, check this out.

You're all set up. Like if instead they, they, they kind of like every once in a while updated you on like, okay, so I did all this and now all I have to do is this. Like you'd probably feel a lot better about the process and you know, Domino's pizza tracker, small wins.

Yes. Yes. I love it.

Monica, you're welcome anytime, but for now we do have to say goodbye.

[Monica] (:

Great meeting with you guys.

[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 general inquiries, please reach out via email to hello at lifetime value, media.com to learn more about advertising on the daily standup and the lifetime value media network. Please reach out via email to advertising at lifetime value, media.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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About the Podcast

The Daily Standup
Delivering fresh new customer success ideas every single day.
Do you want to know what other customer success and post-sale professionals are thinking about, struggling with, or succeeding with?

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.

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