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Josh Schachter:
Hey, everybody, and welcome to this episode of Unchurned. I’m Josh Schachter, founder and CEO of UpdateAI and host of Unchurned. I’m here today with Damien Howley. Damien is a executive an executive in customer success and author of the latest book, Control Your Customer, a Guidebook for Customer Success Managers. Damian, thank you so much for being with us today.

Damien Howley:
Oh, thank you for having me, Josh. It’s a pleasure.

Josh Schachter:
So, let’s start out. You you wrote a book, and we’re gonna talk a lot about that content. I’ve read it myself, and and I’ve really enjoyed it and found it very educational and and really, really helpful. Tell us all about your experience in CS and what you’re up to.

Damien Howley:
No. I think that’s a a perfectly nice way to ask. So I’ve I’ve been in software, in SaaS for the last 20 years. I’ve been in customer success roles, for the last 10 years, 11 going on 11 years now, mostly at smaller scale startups. So kind of focused on the, you know, hyper growth stage of a small startup in a lot of different spaces around the country. And I currently serve as chief customer officer for a startup out of Charlotte, North Carolina called Whip Around. So my you know, to answer your question, right, my my background and my experience of just living in the SaaS world and the customer success world, I’ve had, over a decade of exposure now to to engaging and interacting with customers.

Josh Schachter:
And tell us very quickly about Whip Around and about the organizational layout under your purview at CCO.

Damien Howley:
Yeah. So Whip Around, we we’ve digitized the, fleet management experience. So in order to keep your fleet safe and compliant on the road, We’ve done this through managing everything from the vehicle inspections all the way to the maintenance and repair process. And so, we’ve we’ve got thousands of customers, that that use our software literally 3 to 4 times per day per vehicle. Pretty pretty high velocity growth. So I’m the chief customer officer here, and, I run the the post sale experience, everything from implementation, to customer success and support. I also see over op internal operations and and a bit over, you call it, sales engineering, some of the technical aspects of the sale. So, yeah, that’s kind of the summary.

Damien Howley:
Great.

Josh Schachter:
You spent your time writing a book. Why did you write this book, Control Your Customer?

Damien Howley:
Yeah. Look. I I wrote this book because, in various forms and fashions, I’ve been teaching these concepts over the past 10 years. And it’s, of course, evolved and matured, and they’ve taken on different, kind of unique flavors as I’ve gone from large enterprise customers down to smaller, more like premium plays and and government and so on and so forth. But I found that I had a real hard time teaching at scale. So when I got my last company, it’s a company called Passport out of Charlotte. I had maybe 25 CSMs. In teaching this content at scale became massively laborious.

Damien Howley:
I mean, I spent a ton of time side by side on phones with with the CSM, with the customer. And it worked. I mean, it was highly effective, but I never got everybody. And so I said, you know, what if I just, what if I had a starting, like a starting place where the entire team knew the plays and the entire team had the same vocabulary. And everybody just knew what we were you know, what our plays were and and and how we were gonna go and approach these things. And truth be told, it was, you know, it was a a Google doc, like a 15 page Google doc that was pretty half assed for the better part of a decade. And only only in the last 2 years that I say, well, I’m gonna I’m gonna take a little bit further and and really flesh out a lot of these concepts.

Josh Schachter:
Half assed is an interesting choice of words because you use a really strong vocabulary in the title of your book. Control your customer. It’s not how to build meaningful relationships. It’s not how to, you know, create more influence and exposure, etcetera. It’s control your customer. And you talk a lot about those concepts. So what is controlling your customer in a nutshell mean?

Damien Howley:
Yeah. I mean, I I think maintaining control of your customer means that you are calling the shots. And, you understand and architect the outcomes of your future as that contract owner or that account manager or whatnot. The idea is that it’s an intentional, proactive, like, strategic way to look at your customers. And there are thousands of times where I’ve experienced a customer derail a meeting or, you know, hijack a conversation or a sale or, take you off some of the things that that would ultimately deliver longer term value for the customer. And so it’s a bit of a mindset that the control is up to you as a CSM and that you you can very quickly lose or gain that control. And if you’re if you’re cognizant of of what it takes and and how to read the room that you can remain in control. It’s not this like this die hard desire to control everything, but just more of a philosophical positioning.

Damien Howley:
There’s a lot more in your hands as an a CSM than a lot of people think.

Josh Schachter:
Yeah. That makes sense. And it sounds to me like it’s it’s more of a finesse and an art, and a and a soft soft science. You talk about the different tactics in that. But, actually, no. Before we get into the tactics of that, you wrote this book for folks that are learning and and ramping up their own careers. And I’m just sitting here, what are some of the biggest mistakes that you see people who are still learning about customer success make in the function?

Damien Howley:
Yeah. I mean, the for me, the biggest mistake that I see, and I I I see it time in and time you know, time out is is that the interpretation of the customer experience is derived from one contact. And that, you know, the the CSM naturally latches on to one customer contact, and and it’s generally somebody who is using the software and that they kind of represent the entirety of of that customer based on the input from one one individual or a very small quantity of individuals. They they don’t understand that the customer could be a collection of 100 or if not thousands of employees, all of which may may have a hand in using your software or extracting value from your software or even the ultimate you know, success or camp termination of your contract. Right? Like, that that it’s not single threaded experience and that each of those threads requires variation and and tailoring to to how you mature and engage them.

Josh Schachter:
How do you set up a new relationship with a company, with a customer as a company, in a way where it’s not single threaded? Like, what do what do we do to get the most enriched multithreaded relationships with customers?

Damien Howley:
I mean, it starts in sales. Right? Like, the the selling process, depending upon what what ARR you’re selling at, right, it’s gonna dictate really what level of the organization you’re able to sell at. But ideally, your your sales process is also multi threaded and has multiple stakeholders, has an identified economic buyer and user buyer and and, you know, degree of influencers. And that translates over into a healthy and organized implementation. And so those relationships are should be formed presale, in my opinion, and and should be carried throughout the duration of the relationship. Now post sale, the frequency and kind of touch of these interactions is gonna vary. So really, you’re not gonna pick up the phone and and talk to, you know, a a CRO on a daily or weekly basis. But you certainly, have to touch them at some with some frequency, and they have to be part of your, you know, your your cohort of of individuals that you’ve developed relationship and deliver value to.

Josh Schachter:
And and you talk about a framework in the book. Can you describe that for us?

Damien Howley:
Yeah. I’m assuming you’re talking about the value versus relationship framework.

Josh Schachter:
Well, there’s that. I think there’s also the you you have, like, the is it STO framework as well? Whatever framework you think is most helpful in this regard.

Damien Howley:
Well, good. Yeah. So the STO framework is something that I’ve probably drawn on a whiteboard close to 7000 times. I mean, I don’t have no idea where I’m coming up the number. But the the point is the the STO framework is a massively simplified, you know, kind of segmentation of your customer contact That your it’s s is strategic, t is your tactical contacts, and o is your operational contacts. So your strategic contacts would be, you know, very senior up at the c level, vice president level. They have higher budget authority. They think differently.

Damien Howley:
They care about different objectives. They value different types of interactions. They even have different tolerances, and and they they have different timelines that they are looking to solution and and, achieve their objectives. As you move down that pyramid into the tactical, the dynamic of what they care about, what they value changes. And also the the the, kind of the the timeline or the arc of of, you know, when they expect to achieve their objectives, it reduces. And then when you get down into the operational, the operational would be much more hands on individuals who are using your software. You think of it as a sales rep or a support agent or an accountant. Right? Like, what they care about is much more product oriented.

Damien Howley:
It’s much more focused on the features. Their their tolerances are different. Their values are different. Their budget authority is different. And so this framework is, again, a very simple segmentation of your customer contacts. And when you start to segment your context this way, you realize that the way that you interact with and that the programs and the collateral and the messaging and all So that So that’s the the STO framework, and, obviously, it’s pretty substantial because I wrote a book about it. Right? It goes a lot deeper than that. But there’s, it’s been a massively useful tool for me.

Damien Howley:
And that’s over the last decade, I’ve been using that.

Josh Schachter:
Conceptually, it makes a lot of sense. And in practice, how do you implement the estimate? Like, do you go through this exercise with with your CSMs on a whiteboard or in software to map out all the relationships through the framework?

Damien Howley:
Yeah. I mean, so we it starts with teaching. And then once they’ve got the concept right, there’s a lot of coaching about how they the different expectations of how you interact at different levels. Ultimately, we do end up flagging all of the contacts, all of our engaged contacts in in our CRM, so that we we understand at which level we are engaging our customers. We NPS based on the SEO. We do cross sell marketing based on the SEO. We do, you know, QBR is based on the SEO where I’ll just bring I’ll do like an an EBR really, an executive business review with just tactical strategic contacts. We’ve done product release notes based on the SEO meaning, right, like what you’re highlighting in your product release notes to a strategic buyer is vastly different than the the value that you should be highlighting to a hands on operational user.

Josh Schachter:
So you’re segmenting out. You actually segment out. I I wanna, you know, kinda double click into this because I I think it’s a I mean, it sounds like an like an amazing idea, or an amazing thing to do. You in your CRM, let’s say it’s Salesforce. I don’t know if it is. You actually classify all of the contacts in an account so that you you can enumerate and segment out each of those contacts into the different categories.

Damien Howley:
Yes. Every single one. Every every engaged contact. So anybody who we’ve, you know, had it been able to identify where they sit in that in the STO.

Josh Schachter:
Do you track the engagements so that you you know kind of your frequency and who you’re engaged with and and who you might not be as engaged with?

Damien Howley:
You track all engagements, all phone calls, emails, text messages. It’s, you know, just through modern day technology. Right? And and then so when I’m looking at a CSM’s portfolio, I’m able to see how many levels of the STO that they’ve engaged across their customer base in a particular time frame. So I can say, well, hey. Your your top ten largest accounts, you’ve got really rich engagement at the s and the t, but you’re kind of thin on the o. But when we get to your 11th 12th largest account, I’m only seeing you engage at the operational level. So we need to put a plan in in place for you to elevate and move up the ladder and secure a tactical contact or a strategic contact.

Josh Schachter:
Damian, I’m not I confessed this to you earlier. I’m not a I’m not a a CSM myself. I I never have been. Just a just a fanboy of the industry and the function. But what I’m told from let’s keep assuming that you guys are using Salesforce. What I’m told from from folks is that it’s always wildly out of date, like all the different stakeholders that are input into that system. How do you maintain the discipline? Because I I think I think what you’re saying is is just such a golden bullet for people. But how do you maintain the hygiene of that data in Salesforce? Is that a challenge?

Damien Howley:
Yeah. It it’s it’s a challenge. I mean, it’s it’s manual, right, in the sense. Like, you can you can get some insight at some point. Like, you can enrich and get the the latest titles and such. But, really, it’s gonna come down to the CSM and their read on on the level, whether they’re strategic tactical or operational. But it’s not a high bar. I I’ve had teams before that I said, I need you to be engaging 2 of the 3 levels of the FTO.

Damien Howley:
So that means one contact at, let’s call it strategic, and one contact tactical. So that’s 2 contacts in that account. That’s a smaller account. But, right, then they’re interacting with the customer, and they’re identifying different contacts and different targets and then flagging them accordingly. And so it’s it becomes pretty intuitive through just through a lot of customer interaction, really. That’s the hygiene is an active CS team that is very proactively, interacting with your customer base.

Josh Schachter:
Maybe it’s sales folks that I’ve spoken to that have told me it’s been a mess trying to get those those databases, to have good hygiene. Maybe CSMs are are a little bit more vigilant with that, which would make sense.

Damien Howley:
Well, it’s you know, as a CSM, right, you might get 100 of hours with certain contacts per year. Like, it it all depends on the dynamics of your business and, like, how enterprise you are versus how dot market you are. Like, that that number is gonna gonna vary wildly. But the point is you get substantially, theoretically, you get substantially more time as a CSM with your customers in your context than a sales rep in a sales cycle. And so the ability to massage and mature information, the information should be much richer post sale.

Josh Schachter:
Yeah. Makes sense. In in your book, you seem to discount the idea of keeping your customer happy. You you verbatim, you call it irrelevant. So let’s like, tell me more. What what what’s what goes into that statement?

Damien Howley:
Yeah. I I edited that part of the book a lot. I’ve I’ve had these interactions over the years, Right? When I talk with people and they’re like, you don’t care about customer happiness. I I do care about customer happiness. I have I mean, I personally have been, you know, on the front lines with what I would consider some of the happiest customers on earth. I just don’t think it is the primary point of index that it is that it should be sought after as the the the first, objective. It is to me, it is a lagging indicator, And and it is a result of delivering value, delivering to the customer’s objectives, and standing up something that you can then build an exceptional relationship on.

Josh Schachter:
On a scale of of 1 to 10, 10 being the highest, what’s the value of quantifying the value to the customer that they’re gaining from your product? Like, how important is that? 10 being like this 10. 10. Okay. And what’s the the the value? What’s the number 1 to 10 of keeping your customer happy?

Damien Howley:
Yeah. I’d probably say, like, be safe, right, a 5, maybe lower.

Josh Schachter:
That’s a pretty big delta between the 2.

Damien Howley:
Well, you gotta think about why people buy software in the first place. Right? It’s they’re not buying software to extend their their list of friends. And that’s that’s a a harsh, this kind of a harsh, you know, connection there. But it’s they’re they’re buying software in order to accomplish a particular task or an outcome, a business objective. And they’re buying software in some cases to amplify their own, you know, their own career or their own personal lifestyle. And so I just I mean, maybe maybe I’m too hard pressed on it, but it’s I find that, the richest relationships I’ve ever formed with customers have come on the heels of exceptional value delivery where we are we’re executing on all fronts. We’re meeting their objectives. We’re helping them grow their business.

Damien Howley:
And those are those are the happiest customers ever. And we we all have them. In in the book, there’s

Josh Schachter:
a few concepts that caught my mind. I only wanna go into one more, of these concepts. The rest, well, people have to read the book. But I want you to choose. So here are the ones that really captured my my my attention that that we haven’t spoken about. This idea of a value to relationship matrix kind of, you know, dovetailing on on our conversation so far. The idea of celebrating every win, this commitment scale that quantifies what you’re committing to, the concept or the notion of levering everything, using a bad cop in your, you know, tactically, and firing a customer as being sometimes a proper approach. Let’s explore 1, Damian.

Josh Schachter:
What should we go into?

Damien Howley:
I I don’t know. Let’s go into, celebrate everything.

Josh Schachter:
Cool. Good. That’s the one I wanted to go into anyways because because that one was, like, it was eye opening to me. So what is this idea of celebrating everything?

Damien Howley:
Yeah. I mean, it’s it’s a really simple concept. I mean, it’s the shortest chapter in the book. Right? Like, so it’s, I guess I I might might not have picked the best the best topic here. But it is this this idea that, that everything you do for the customer, is in some way quantifiably delivering some value. And, you know, it kinda ties a bit into the to some of the other concepts that you mentioned. But I found that, like, you know, I might at larger companies, I might organize a meeting with product team to to provide some direct customer feedback on a particular feature. And I will I will go back to customer and celebrate that.

Damien Howley:
I mean, I will I will broadcast that to them and take that victory for me as a as a CSM. Literally say, I went out of my way. I did this for you. I’m doing it for this reason because I believe in in, you know, the value that we’re bringing to you. And so, I mean, it could be anything from setting up a meeting or you get an issue resolved or you get a ticket escalated or you get, in some cases, you know, you get a a term in the contract, changed or reduced or whatever the the the the valuable activities that a CSM does are just so broad, but so regularly distilled down to, like, binary outcomes, which I just I can’t buy into. Right? Like, I I I have these CSMs who will work for for, hours and hours and hours for customers. And then, you know, it’s it’s, maybe not as appreciated or understood, or the value is not even translated over to the customer. So celebrate everything is this idea that you should take the wins, communicate with your customers when you’re delivering value in whatever capacity.

Damien Howley:
And over time, these are very nominal, but increasingly, you know, they increase your reputation and your value delivery with that customer.

Josh Schachter:
I I loved that that was my favorite chapter. Honestly, it is the shortest chapter. It’s a really short chapter. Maybe we could post it somehow alongside when we when we publish this podcast. But it was my favorite because you you know who’s really good at celebrating wins? Sales. I was able to get that that price negotiated for you. I was able to go back to my manager, so on and so forth. And, you know, of course, then that’s acknowledged and so appreciated by the customers.

Josh Schachter:
But, see, yes, sometimes we don’t, you know, do take the time to really celebrate all that we do. And it’s not always obvious to the customer that we did have to go to bat for them or that there was work involved in this. I I recently asked the customer success manager to marry me, Not not liter in literal terms, but she was so helpful to me and went so above and beyond. You know, it was from a company called High Touch. There you go. That’s my shout out to them for the the tremendous work that she did. And I but, of course, like, my role being what it is in the industry, like, I want to make sure I acknowledged all that. But most people, I don’t think necessarily would, always be so cognizant of these efforts.

Josh Schachter:
The the some of the examples that you give, they opened my eyes, like, this idea of celebrating that you were able to fix a bug or escalate a ticket in subtle ways, not like throwing confetti or whatever. Right? But, like, hey. We were able we were able to really, you know, ramp up the the the the the the resolution of this issue that you were facing. I was able to escalate that, as opposed to just apologizing, over apologizing for it. Right? Like, turn it into an opportunity to solve their problem. And and, I I don’t know. I I just felt like for me personally, there were lots of things that I do for customers in my role and, again, like, handling support issues, plug fixes this, that, where, like, yeah, you’re right. Like, in very soft ways, you can turn this into in into a celebration of of of value that was delivered to them.

Damien Howley:
Yeah. And if I can add to that, Josh, I’d you know, it’s I I don’t know how many chapters in the book. I I suppose I should know that. There’s, like, 25 chapters. A lot of them are tactics. Right? And, like, this is just one of an aggregate, one of many ways to to incrementally drop value to the customer. And and I just think it’s something that’s overlooked. And you’re right.

Damien Howley:
Like, sales, they nail it. In CS, maybe it’s I don’t know what the the dynamic is of the CSMs and why they maybe there’s just a it’s not as natural to go and and and claim those. But whatever the case is, there are I just believe in mathematically and continuously, maximizing the value that’s delivered to the customer. And back to the other topic. Right? And that value delivery will outshine any troubles or any challenges in the relationship.

Josh Schachter:
100%. Damien Howley, CCO, author of Control Your Customer, thank you so much for being on this episode of Unturned.

Damien Howley:
Thank you so much, Josh.