Collect the Cash: Four Keys to Getting Paid with Dee Bowden
EPISODE: 63
You made the sale. You delivered the work. Now comes the part a lot of business owners would rather avoid: asking to be paid.
In this episode of Sales as Service, I’m talking with Dee Bowden, founder of Collect the Cash and a revenue recovery expert who has recovered more than $100 million over the course of her career. Dee makes the case that accounts receivable isn’t simply a back-office function. It’s part of sales, customer service, and the overall client relationship.
We talk about why unpaid invoices usually have a story behind them, how to investigate what actually happened without immediately assuming the worst, and why the confidence required to collect your money is built the same way sales confidence is: through practice, coaching, and repetition.
In this episode, we get into:
Why the sale isn’t complete until the money is actually in the bank
Dee’s Four Keys to Collect the Cash: problem solving, customer service, gratitude, and relationship building
The common administrative issues hiding behind unpaid invoices
Why asking to be paid doesn’t have to feel confrontational
How to build the confidence to have uncomfortable money conversations and keep the client relationship intact
LISTEN TO THE EPISODE HERE 👇🏻
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Dee Bowden: Everybody that we admire who's great has always been scared. They've always lacked some piece of confidence. But what do, what do they do? They got coaches, they got mentors. They sat and, and did the reps to get better at whatever they do. Take sports, take acting, pick your thing. They've always had somebody that say, "Okay, this is how you do it.
This is not how you do it."
Tam Smith: Welcome to Sales as Service, the podcast designed to help you change your mind about sales, literally. I'm gonna help you change the way you think about selling. I'm Tam Smith, your host, sales bestie, and pitch partner next door. If you're tired of bros with biceps telling you how to crush a million dollars in your sleep or battling imposter syndrome on your own, you've come to the right place.
All you need to do is listen, then take action. No gym membership required. Let's get started
Welcome back to another episode of Sales as Service. Somewhere between landing the deal and cashing the check, most sales conversations just stop. There's a kickoff call, maybe a few balloons, and then the invoice goes out, and everybody assumes the money is just gonna show up, and it usually doesn't show up on its own.
My guest today has spent more than a decade proving that the sale isn't actually finished until the payment clears, and that getting there takes the exact same confidence it took to win the business in the first place. Dee Bowden is a revenue recovery specialist who's recovered more than 100 million in outstanding invoices over her career for everyone from solopreneurs to government agencies.
She's the creator of the Collect the Cash framework, and she treats every unpaid invoice the way a good salesperson treats an objection, as a story worth understanding, not a fight worth avoiding. Here's my conversation with Dee Bowden. Dee, thank you so much for being here. Welcome to Sales as Service. Tam, thank you so much.
Dee Bowden: I, like you, I've been excited about this 'cause I just knew we were gonna have a ball having a whole conversation about sales, collections. Most people are like, "How does sales and collection go together?" Listen, we gonna give you, we gonna give y'all the really good story. Well, to kick us off, tell us in your words, who do you help and how do you serve?
Who I serve is this. So, I've, I've had a career as a, as a, uh, contract closeout specialist. So I've s- I've served government agencies. But now I want to collect the cash. I work with small and medium-sized companies and solopreneurs who have corporate contracts and government contracts, and then they h- have that heebie-jeebie moment when they're like, "Uh, D, I don't like to go back and ask these people for my money, but I need to get paid."
I'm like, "Exactly." So we're gonna d- we're gonna... I help them go back and get their money. The second piece is to deal more importantly with the confidence, because I realize the reason they don't wanna go back and have that conversation, because they don't feel confident. But I say it this way: as confident as you were to pitch your services and ask for the, ask for the business, you gotta be just as confident to ask for the money.
You gotta... They go together. Sales and AR, they go together. Love that. And this is impressive. You've recovered more than 100 million over your career. Mm-hmm. What first pulled you into revenue recovery? So everybody says to me, "So D, how... Who wakes up and says, 'This is what I wanna do'? You know how you go to, you know how you go to school and you're like, career day.
Oh, you know, you have firemen, doctors, and engineers. No, you decide you wanna recover money." So what had happened was about 30... Mm, it's been over 30 years. I used to work for an engineering consulting firm. I got my start literally as a data entry clerk, then accounts payable clerk, and then I saw my first contract administrator, and that's when I learned that in larger businesses, there's somebody that administers the contracts who deals with payments, vendors, all the things.
And so when I, y- you know, basically came up the ranks, when I got promoted to be a contract administrator, it was for the construction division, and that, my team was building a water filtration plant. And the prior administrator, I guess it was just th- that project was a lot, and so when I, when th- when they said, "Hey, D, welcome aboard and welcome to the team.
Here's over a million dollars in unpaid invoices, and that's your first task as the new contract administrator. We need you to get-" No pressure. No pressure at all. Just, just come on in here. Just get the, get the, get the coins. So I'm like, "Y'all, y'all have over a million dollars?" But Tam, here's where it really got personal for me, because here's the thing.
So my former employer was a prime contractor, and they had subcontractors or small businesses that were supporting them. And because the prime didn't get paid, the small businesses didn't get paid. Mm-hmm. Yeah. And when I realized that if I don't figure this out, you know, my company's not gonna get paid for building this water filtration plant, and then all the small companies that were supporting them, you know, from laying pipes to all the things, they're not getting paid.
And I, you know, it became more f- 'cause I thought about it, I said, "Wow, so if they're not getting paid, that means their teams are not getting paid, there's their families, there's all the..." I mean, this, this thing just kept, kept going down. I think it's like the total trickle-down effect. Yeah. Absolutely. And so when I saw that, I said, "Okay."
And one of the, one of the, what really kind of started this whole thing was when, when I finally untangled this over million-dollar- And I was sending invoices. One of the subs came up to the office and they're like, "Hey, who's Dee?" And I'm like, "That's me." And they're like, "We just wanna say thank you for untangling this m- this mess so that the primes could get paid so that we could get paid so we could actually pay our services, uh, meet payroll, take care of our families.
And we appreciate that you, like, you went and untangled this mess. 'Cause we have been trying to figure out, we, you know, we're waiting for our money, and we don't know why we're not getting paid." And that's when, that's kinda how it started, and then, you know, it's kind of been this problem-solving journey, and then the...
I'll tell you about the four keys in a little bit. But it's, it's been those, it's been those four keys my, my whole time. And then I realized that, you know, I'm a, I actually have fun doing this. I think it's just, you know how you wake up and you kind of feel like, "I didn't expect this to be my thing," but it becomes your thing, it becomes your jam.
That's what this is for me. I wanna hear about the $6 million in 60 days story. Absolutely. Happy to tell you about it. So 20 years ago, I used to work for a small IT company outside of Boston where I'm originally from. Sam, and, and you're listening, guys, you all know how it is. You, if you, if, if, if you've ever worked in corporate, government, or nonprofit, it's usually this, "Welcome aboard.
Welcome to the team. We're so happy to have you, dot, dot, dot." But in my case it was, "Hey, Dee, welcome aboard. You're gonna be part of a collections team, and, uh, here's your cubicle, and here's your list of accounts, and it's worth $8 million in outstanding invoices." It's the same story I sh- And I was like, "Hold up.
Y'all, y'all, y'all sold $8 million worth of IT services, software licenses, computers, all the things?" "Yep." I'm a part-time person. They got senior people doing this work, and I said, I literally said to them, "So none, none of y'all can figure out how to get this money? Nope." And your... And this is what they said to me verbatim, "Your resume says that you know how to collect money because you've already collected this much money for the, for the, for government agencies."
I said, "Right." I said, "Okay." So I just got quiet, and in my, in my quiet space I got my download, which is this, which became the four keys. And so in 60 days I collect $6 million as a part-time person, and then what I thought was going to be the, you know, sales and service part of this was gonna be salespeople were g- were going to get their commission because we had collected this money.
And I thought me and my team were gonna come downstairs to these beautiful white envelopes, 'cause I just knew they were coming downstairs and going, "Hey, D. Hey, so-and-so. Hey, so-and-so. Hey, so-and-so. Thank you so much for collecting all this money." Nope. The CEO says, "Listen, we made an executive decision, and we're deciding today that we're closing the company, and we're letting 100 people go, including you, right here, right now.
You got 30 minutes to go get your box and all your stuff and leave the building. And oh, by the way, here's your last check." Nobody saw that coming. We sure... Me and my collection team, we certainly did not see that coming. I mean- Yeah ... I think later there's, there, I'm sure there was probably either financial issues that we just didn't, you know- Yeah
we didn't know about. But the fact is that I went to work as a part-time person. I did my part to help my team and, and I thought I was- Mm-hmm ... helping my company, you know, stay afloat. Yeah. And we, you know, we, we got, we got told to goodbye. And so as I tell that story, I normally tell everybody, I said, "You know, there's usually...
Everybody usually has something in life that jars them, that makes them go, 'Did this really just happen to me?'" You're like, "Yeah." And then you go, "I don't wanna be here again." And then on top of this, I, it's not until I started telling the story again, when I go back to my, my beginning when I was, I shared about working for the engineering consulting firm and those small businesses, now I realize why this is such a big deal for me.
Because in my career when I went to work as, as a, in the con- in this construction division, there were small businesses that got impacted. I went to work for a small business. When we went out of business, I lost my job. Mm-hmm. I'm like, "Okay, this, this, this is not cool." But, and then fast-forward to COVID. Now Tam, I don't know if you're a big theater person, but I am.
So when Broadway shut down, you know Broadway has, has these theater houses. Those are all businesses. They've got sales and contracts and vendors and actors and people and food and all the things. And I'm like, so Broadway shuts down during COVID. There are no shows running, which means there's no sales running, which means there's no cash flow running.
And I'm like, "And so nobody's gonna talk about this. Really?" Seriously? Mm-hmm. And so that became the thing where my book coach finally said, "D, your why is that you want small bus- small, medium-sized business owners to win. Teach us how to win, how to go from collect the cash. The sale is not complete until the money is actually in the bank."
And why does that matter so much? Because everybody celebrates the sales, and as they should. Sales, it's usually, uh, uh, like I'll say it based on my experience, it's been salesperson g- you know, lands this new contract, lands this new thing. Oh my gosh, here's the kickoff meeting, here's the balloons, here's all of the tchotchkes, here's all the things, and that's great, and it's yay because that, hey, that's revenue coming into the business and all the things.
But after they land the sale and after the work gets done, we, collection people, AR people, we gotta get that money. Mm-hmm, mm-hmm. And then we have to untangle whatever, whatever great promises they told them on the front end, we have to untangle that and get that fixed so that actually the money comes in, gets, gets in the bank.
And so I just had this heart for making sure small business owners understand this. As confident as you were to ask for the business, you have to be just as confident to ask for the money. The sale and payments, they go together. You don't, you don't get the sale without the payment, and you know, obviously.
And I don't know h- how much of that is just, it's, it's a fear thing, it's nerves, but I'm like, but if you, if you pitched and won the contract, you gotta see it all the way through and get, get paid. It's just, it just makes sense to me. But what, what do I know? Well, well, I, I wanna know what you know. Like, what is your magic?
What is your secret? Like, what are you... Do you feel like that you- Are doing different to be able to have the success that you have doing this work. Well, first of all, great question. Well, first of all, I'm a person of faith, so I don't... My success comes as a part of me being a person of faith. That's number one.
Number two, when, remember in, in the earlier story I said I got quiet and I got my download. So I have a framework, it's called the four keys to collect the cash. Mm-hmm. My four keys are the following: number one is problem-solving. Problem-solving is this. It's two things. It's what had happened was, because every unpaid invoice has a story.
If you got- you haven't gotten paid, you gotta get the story behind what happened. Mm-hmm. Did it go to the wrong person? Did they forget to put the contract number or the purchaser number? Did you send it to your former contact at said company and that person has moved on? Or their account, you know, if you, if you deal in the account space, so so-and-so is managing your account, and so now so-and-so is no longer on your account, it went to some- went to another person, but they forgot to let you know, so you been keep sending stuff to the same email and you're like, "Why isn't this getting responded to?"
Because that person already left, and they forgot to let you know that your, your contact, let's say it was Tam and now it's me, or me, now it's you. And so you don't know this, so you, you just... I mean, and that's what we do. I mean, you build the rapport with that person, so you just keep sending your stuff.
And then you're like, "Why isn't this getting fixed?" And, or, "Why aren't they responding?" But you don't know that there's, that somebody else has taken over your account. So the first, so the first key is problem-solving. What had happened was, which is basically what's the story behind why they haven't paid you?
So that's key number one. Key number two, customer service. Tam, I know you know probably better than, than most that, you know, customer service is everything. And everybody's, everybody's definition of customer service is different, but most people ask me, "How do you put customer service in, in collecting outstanding invoices?"
Very simple. You know how when you order something from a store and you get... Let's say the best story. You ordered 10 sets of sneakers, you got your little box and you're like, "Oh my gosh, I'm gonna get all my favorite sneakers." You open up your box and there's t- there's supposed to be 10 and there's only eight, but you paid for 10.
First thing you're gonna do is 1-800 whatever the name of the store is. "Hi Tam, this is D." "Oh, T- D, before we can, before I can, uh, help you solve the issue, we need to confirm, you know, your name, your account number, what did you order, when did you order it, da, da, da, da." And then what you want them to do is listen to your story a- and to explain to you why when you paid for 10 sneakers, why are you short?
Why don't you, why don't, why did you get eight and not 10? Customer service for that b- that business is they listen to your story. They're gonna either say, "Tam, first of, on behalf of said company, we apologize because we should have shipped 10 sneakers, and, uh, we're sorry that we didn't ship you 10. We only shipped you eight.
Number two, we're gonna do something to fix this. We're either gonna give you a credit. When we get the new sneakers, we're gonna send you an extra pair for the inconvenience." They're gonna do something to make it right, because that's what you expect when you call in for customer service. You expect them to hear your story- figure out the details, figure out the mistakes, and then fix it so that you stay on as a great customer.
'Cause what they don't want is you, you to go on any part of social media and go, "I just had the worst experience with such and such and such and such and such." And now you know, you know it better than I do. All it takes is 30 seconds of a video gone viral 'cause somebody had a horrible experience with said store or said whatever.
Mm-hmm. I share that story to say my part of customer service with collecting outstanding invoices is, on behalf of my employers and now obviously the people I work with now, is I have to make sure that I am getting into the weeds, asking the right questions, looking to untangle what happened so I can do this and then get it fixed so that they will go, "Okay, hey, D, you know what?
We're sorry. Yeah, we didn't tell you that your account got moved from this person to this person," or, "We didn't tell, tell you that we changed billing systems from this to this. We didn't tell you that... Oh, we changed our email. You know, instead of it going to admin at such and such, now it goes to info at such and such such.
We didn't tell you none of that stuff, so you didn't know that." So my approach with customer service is that I'm responsible for making sure that my clients and, and my former employers have a, have... know that I, when I'm on the phone, that there's a good experience and I'm going to, I'm going to handle the things correctly.
Um, also part of customer service to me is if you make a mistake, admit it, admit that you were wrong and say sorry. Take ownership. That's it. Hey, Tam here. Most consultants and service-based founders are great at delivery. Referrals prove it, but referrals aren't predictable, and you've avoided sales because you think you have to be something you're not.
Tam Smith: Sales isn't pressure or cringey tactics. It's connection, starting conversations, recognizing when you can actually help someone. The hard part? Doing it consistently. That's why I built the VIP Legion pipeline system. It gives you a repeatable way to book three to five sales qualified meetings each week through relationship first outreach, not cold pitching.
Dee Bowden: Ready to create opportunities on purpose? Book a free alignment call using the link in the show notes. Sales is a practice. Let's make it consistent. I don't know, to be honest, that I had thought about revenue collections as part of customer service. A- and I appreciate you putting it in that field, and I, I am picking up that you have a very, like, relationship first, curious approach to what you do.
Yep. Um, which Prior to this conflict from outside in was not, you know, I know you, so it's what I expected. Yeah. But for the, let's just say the industry or the- Mm-hmm ... the, as a whole is different. It's true. Well, 'cause, okay, there's two things. One, when you hear collections, most people think of a debt collector, medical bills, things like that.
That's consumer debt, that's not what I do. We're... When we're talking about business to business collections, or AKA accounts receivable, we're talking about people who have contracts that do, you know, pr- have deliverables, that have things that are required on, you know, a 30, 60, 90-day calendar. That's the, that's the world that I come from.
Mm-hmm. And my peers, th- those of us that are in, like, order to cash or, uh, procurement to pay, we know that customer service is part of it because after the sales people get la- land the work, we're the ones that have to af- after all the balloons and all the- ... everything goes away, we're the ones that have to un- untangle whatever mess was created.
So we, we, we, when I say we, I'm talking about my, my buddies on LinkedIn. There's a bunch of us who, who have been in, in this industry long enough that we learned that customer service was one of the ways we did things, and how we did it was... So my third, so my third key is called gratitude. One of the first things I said to you was, "Thank you so much for the opportunity."
Remember I said, I think I said it to you in my email yesterday. Mm-hmm. "I'm so excited for this." And I said, "Thank you." People are like, "So thank you? You, you say thank you?" Yeah, because if you, if you've ever gotten, if you've ever gotten an invoice for a bill from said company, usually they'll say, "Thank you for your business."
You've seen this, right? Mm-hmm. Okay. Oh yeah, for sure. So, so all I did was take that one line from, from the bill and decided that gratitude was gonna be one of my keys. And here's the other thing. I don't know if you've had this problem, but I certainly have. In order to collect the $100 million that I've done, the $6 million in that short story I shared earlier, every time somebody took my phone call, helped me untangle where the invoices were and why didn't we get paid, and it's like, oh, hey...
A- and the, the real blessing was when somebody explained to me, "Hey, D, clearly you didn't understand that for this, for this customer, with this purchase order, you gotta have the purchase order, you gotta have the receipts, you gotta have this and this and this and this, and clearly nobody told you that. So I'm gonna take five minutes and explain to you what you need to do so you do not make the same mistake again.
Hey, do me a favor. Get your notebook. You know, you have old school. Get your... Oh, you know, now it might be, you know, type it on your phone. But old school, get your notebook and write this down. Make a, make a, make a template of it and write down step one, contract number, step two, this, receipts, whatever, da, da, da, da.
Make yourself a template, and then use... This is the template that you use every month from here on, and this is how you do that." The gratitude came from the, the pe- the people over my career and with clients who have taken the time to explain to me the steps I missed. And so I said, "Okay, I'm using gratitude."
And then when I saw invoices that says, "Thank you for your business," because here's the thing people forget. When you pitch your services or your product or your whatever, people have a choice with who they do choose to do business with, and when they pick you That means that you did a really good job, and you obviously, your solution solves their problem, so they are trusting that you can deliver, you can solve their problem.
You're gonna provide good customer service. You're gonna be grateful that they picked you. And then the fourth key is relationship building. You're gonna take care of them, and it's not gonna be just transactional. You're going to take care of them as a good customer, and preferably, if you do it really well, you'll get repeat business, and then they'll tell their friends, and so on, and so on, and so on.
And you've done this work- Mm-hmm ... for everyone from small business, government agencies. Is there anything that changes in the de- approach depending on who's on the other end of the invoice? No, because basically, I'm doing the four keys, whether it's a small business. So if I give an example. So one of, one of my friends is a professor.
She reached out to me, and she's like, "Dee, I have a contract with this major university, and I'm, I'm struggling to get my money." Now, she's, you know, credentialed and all the things, but what she said was, "Dee," when I mentioned earlier about the heebie-jeebies, she was, she was one of the people with the heebie-jeebies.
She was like, "Dee, I don't, I don't like confrontation. I don't like doing this stuff, and I don't feel confident." And I said, "Okay, so here's the first thing. Before you, I can get you to get on the phone and go get the money, we gotta, we gotta address the confidence issue because here's the thing. You were credentialed, and they, they selected you to do this training, which means you checked all the boxes.
You gotta trust that if they selected you to do this work, they're also going to pay you. We just gotta figure out what happened to your, your invoice and your contract." So we t- we talked for a few minutes and walked through f- the, the four keys, and in 36 hours, she got her money. 36 hours. And it's a, it's, if you, if you go on LinkedIn, u- under my name, it's this thing, a post called Story Time, and she tells what we did in 30 minutes.
So that's one So I say no, but I say, I, I maybe I should say it this way, no with a caveat. On, you know, the government side, it's, it's not, it's, it's not normally a 30-minute phone call. It's normally, okay, I gotta start with internally first. So it, it would be, um, the financial people, I gotta get the records, and I gotta make sure that our records demonstrate all the things, and then I have to reach out to the vendor, and I have to go talk to them and get their financials, and make sure their financials match our financials.
And if there's a discrepancy, whose fault is it? Is it their fault? Is it our fault? And then there's the how do you fix this? 'Cause then there's, you know, data entry errors that have to be done, and unfortunately people don't do a lot of good, really good quality control. They kind of fly through stuff, and then you're like, "Oh, so this has been sitting here for a year or two.
Nobody caught it." And then you gotta untangle that. So you're still doing the four keys. It gets elevated because obviously if you're doing it with a solopreneur or a small business, it, that's a small thing. But, you know, the government agency and I've gotta deal with the government side and the vendor, so I'm dealing with b- both sides.
Oh, also, and I'm dealing internally, so I'm dealing with finance and contracts and systems and IT. You know, the list goes on. Just gets more complex. Yes, ma'am. Yeah, yeah. You see, you see this beautiful gray hair? This is why it's so happening.
I wanna go back, I wanna talk about the confidence piece a little more. Sure. 'Cause I definitely confront that a lot just on, like, on the sales side of the business- Mm-hmm ... and that hesitation to, there's a lot of hesitation and resistance and like the, the first step, you know, it is that, that mindset piece.
Absolutely. Like, if you peel back all the layers, is it really just, like, you know, fear and resistance and lack of confidence to ask those questions? I think it's a couple of things. I think, number one, um, if you, if you, if you go based on these beautiful social media streams, it looks like everything is, like, magically delicious, like that cereal we used to eat as a kid.
It's not, uh, number one. Number two, I think because, number one, my first entry into this, into this field was, as I shared, I got promoted to be a contract administrator, and my, I kinda... You know how you get thrown into the deep end of the pool? Mm-hmm. That's kinda how I got, I got thrown into the deep end of the pool.
So I didn't, I didn't really have ti- I didn't have time to have struggle with confidence. I was promoted. I had a job to do, and there was an expectation that I was going to figure this out. Now, over time, in talking to people, I've learned that sometimes, you know, if you, if you've had, if you've had challenging experiences, and if you haven't done the personal and the professional development to understand how to address this, you can spin, and you, y- you can keep spinning.
So I was fortunate that I've, I've had great, I had great mentors in my career, so, you know, I, you know, I, I don't want this to come across like I, oh, I've always been successful. Oh, absolutely. I, h- No, absolutely not. I made mistakes like anybody else. But what I've always done is I've always been a l- I've always been a student.
I've always, you know, invested in myself. And when I was fortunate to have great mentors and when I first got into this and learning how to present, you know, basically present my case when I'm trying to recover this money, and I'm trying to untangle this, and this, that, and the third, and then learning how to appreciate the people who helped me, who kind of like the story I said earlier, people who helped me untangle why this didn't work, and then here are the steps and this is why.
I think the other thing around confidence is that I feel like confidence is a decision. You just have to decide. I mean, you can do like this. You can see my hand here. This is confidence. And then, and the other hand is this is you. And in the middle is they're gonna go from being like this to being like this.
But you have to decide, and you can do it scared. You can do it afraid, but you just gotta, you gotta do it. 'Cause here's the thing. Everybody that we admire who's great has always been scared. They've always lacked some piece of confidence. But what do, what did they do? They got coaches. They got mentors.
They sat and, and did the reps to get better at whatever they do. Take sports, take acting, pick your thing. They've always had somebody that say, "Okay, this is how you do it. This is not how you do it. I advise you to do this." If you're following tennis right now, they, every, every time you watch tennis on TV, you always see the players looking at their coaches.
The coaches have already, the coaches have already been advising them on what to do when you get on this court, when you play so-and-so. They give advice them with the best strategy for how to play against that opponent, opponent. But what have they done before they get on the court? They've had reps.
They've had repeat sessions. They've had the coach, coach or coaches pour into them, you know, obviously build them up emotionally and remind them who they are and that they're great, this, that, and the third. And they've also told them to have fun. Also told them, "It's okay if you're nervous. It's, it's okay if you're not, you're not feeling 100%, but don't forget all the hard work we've done to get you here.
Now get out on that court and let's go." I love that. Like, okay, I'm, like, gonna, like, just save that clip and replay it every time I need a little pep talk. 'Cause that's, I mean, 'cause that's, uh, Tam, that's, that's what... I mean, if you, if you think about it, that's what we do. I mean, I'm sure in your, in your career, if, if you did sales- Yeah
I'm sure you ha- you've had, you've had mentors that, that have advised you, "Okay. Hey, Tam, when you deal with this customer, there's, you know, there's, there's steps one through five," and then you finally figure it out, and then you're like, "Oh, I know what to do." Mm-hmm. And you might be like, "I'm a little bit nervous," but then you're like, "No, no, I, I, I closed this customer, this customer, this customer, this...
Okay, it's the same thing, but this customer's a lit- little more challenging, a little more whatever. Okay, great. But I already have a baseline 'cause I already know how to close. I already know how to sell. I, I already know how to have my conversation. I just need to remember, okay, take this baseline, take these reps that I've already been doing.
Next level is, is this customer." Okay. And here's the thing. If I get them, great, and if I don't get them, okay, I will learn from that, and I will figure out how to make the adjustment so I go... I land the next bigger fish, but I'm not gonna be not- Mm-hmm ... I'm not gonna stop fishing. I'm gonna keep fishing. It's a great reminder, I think, that it's like from the outside in, you, e- especially when you're talking about, you know, sales or any kind of money conversation, is that we all just came out of the gate good at this.
And, you know, that, that remi- uh, 'cause y- that, that reminder that, you know, it's just reps- Mm-hmm ... and being coachable and teachable- Mm-hmm ... and every opportun- like, uh, you know, ev- I mean, it's that whole there's, there's no failures. You know, there's just lessons. You know, it's really true. You know, so whether it's a, it's a, a win either way 'cause you're either gonna, you know, win, or you're gonna learn something from it that's gonna make you that much better for the next one.
Tam Smith: I can think, like, one of my early mentors, you know, even starting this business was, you know, "Tam, you're not gonna be able to think your way through this. You gotta just, you know, get it, get out there, and get some reps in and start practicing and start learning," and it's so true, so I appreciate that reminder.
Dee Bowden: Absolutely, and I'm so glad you said that because even if you take this example right here, doing a podcast, oh, my gosh. Mm-hmm. My my, my very first one- My goodness. Number one, I was so stiff. Number two, I did not relax and let my personality show and just, just th- I was trying to be super buttoned up and all the things and, and, and I was so tight.
And I finally got, got with a coach who said, "Okay, D, here are some things you need to remember. Smile. You're funny. Let your personality show. You have great stories. Let me show you how to, how to add them in and then, and you, you're a teacher, so teach through your stories." Mm. And give some people, give people with them they can, they can walk away from.
'Cause I think, knowing one of your questions was, you know, what are they gonna walk away from? Well, preferably they are gonna, they're gonna hear the stories. 'Cause most of us, we learn, we, we've always learned by story. Mm-hmm. We've always learned by story. Let's jump into our fast five. All right. Let's do it.
Your best advice you've ever received about sales or business development. One, you have to continually invest in yourself. What's something people are always surprised to learn about you? How much I love Ferris wheels. So h- has that always been, always been a love? Yeah. I have loved Ferris wheels since I was a little kid.
I don't know if you grew up going to the amusement parks- Mm-hmm ... and you loved the rollercoaster. Mm-hmm. Okay. Mm-hmm. See, so you, you were that thrill-seeker. You loved all that stuff. I loved the Ferris wheel. Why? 'Cause it was slow, peaceful. I didn't want all the twists and turns. Mm-hmm. I needed, I needed the calm.
And then I learned that Ferris wheels are all over the world. People, they're in, they're in London, they're in Dubai. They got them all over the United States, and I, I, I absolutely love a Ferris. It's one of the best things for me. Love it. What's one task you've happily handed over to AI? Right now I haven't had, I have not handed a task over to AI, um, only because I'm on the, the, the, the new part of learning AI for this.
I think one of the things that will be helpful is, like, once I can take a, a class and learn, okay... 'Cause here's the thing. There's two things to that question. Number one, I feel like- Everybody has been on this, this, this bandwagon about, you know, AI is great. Well, there's two things. AI is great, number one.
Number two, AI's gonna take over your job. Number three, you're gonna be replaced with AI, dot, dot, dot. You know, so there's all this fear with stuff, so there's part of it. Now, so there, there's that. Number two, I have not seen how to put AI into what I do because a lot of my stuff is still relationship based, it's personal based, and what I, right now I don't feel comfortable with using AI where I have to still get on the phone.
I still have to do calls and talk to people, especially because I'm talking about a lot of money. So- Right ... me having a little bot popping up to, to say something- ... that I... No, that's not gonna go over well. So I'm saying that to say I'm ack- I'm acknowledging that that's a concern for me. But also it will probably be that I need to, I will probably have to take some kind of training, some kind of, to figure out how to, how to bring AI into accounts receivable and then understand how it, it will help me do my job, do my job and do my services better.
And then, like, what's iteration one? Like, where, how can I test this out and go, "Okay. All right. Oh, how, I didn't, I didn't know AI could do that. Oh, really? Great." And then once I, once I, once I get that first light bulb and I can see how it does it, then I'm like, "Okay, cool." Because, one, I will have faced that fear or faced that concern, and then I'll, then I will do what I need to do, which is go invest and learn how to do it and then implement it and then go, "Okay, so iteration one is let's take the class, let's learn, let's test it out."
And then iteration two will be, "Okay, D, we got a whole system here. Let's go." What's your go-to way to recharge after a busy week? Time by the water. I, I hear that quite often. And if you only had one hour each day for business growth, how would you spend it? For business growth? Mm-hmm. I'm reading a book. Hmm.
Nice. What are you reading now? There's a book, it's, it's a, it's a, um, compilation. It's Speak to Sales. Yeah, that's what it is. That's what I'm reading. Ooh, I have to write that one down. I have not read that one. Yeah. Well, I want to thank you so much for being here. This has been a really, um, enlightening conversation.
And where can folks find and connect with you online? Well, first of all, Tam, thank you, and thank your audience. So for all of you that are listening, I'm on LinkedIn, so type in Dee Bowden, linkedin/dee-Bowden, that's one number two. My website is collectthecash.biz. And also, as a gift for your audience, y'all can come to my website and get, go to collectthecash.biz/freebie.
There's a thing called Five Tips to Collect the Cash. It's a free download. And then, so for, uh, for anybody who struggles with the heebie-jeebies of getting paid, I walk you through, here are five simple things you can do to collect your cash after you've made your sale. Because don't forget, collect the cash.
Tam Smith: The sale is not complete until the money's actually in the bank. Fantastic. Thank you so much. Thanks again to my guest, Dee Bowden. I love how Dee reframes confidence, not as something you feel before you act, but as something you decide and then back up with reps. And that applies whether you're pitching a new client or picking up the phone to ask where your payment went.
So here's your sales as service challenge this week. Pick one invoice or one client who's gone quiet on payment, and don't assume the worst, just reach out and ask what happened. Maybe your contact changed. Maybe something got lost in a system update. Listen for the real story and say thank you for the business either way, and write down what you learn so you're ready the next time it happens.
Dee's work is such a good reminder that follow through is part of the sale, not separate from it. All right. That's it for me this week. Remember, sales is an act of service. It's about what you give, not what you get. And when you serve well, the ROI always follows. I'll see you next week. You've just listened to the Sales as Service Podcast, the podcast to help you shift your mindset around selling.
The executive producers for the show are Jess Milanes and me, Tam Smith. The show is produced by KNWN Media and Studio 349.
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We spend a lot of time talking about how to make the sale.
How to find the right prospects. How to start the conversation. How to communicate value, navigate objections, follow up, and ultimately get someone to say yes.
Then the contract gets signed, everyone celebrates, and sales moves on to the next opportunity.
But there’s one pretty important step left.
Getting paid.
That’s the point Dee Bowden, founder of Collect the Cash, made during our conversation on Sales as Service: the sale isn’t complete until the money is actually in the bank.
And for a lot of business owners, that last step can be surprisingly uncomfortable.
You may have had no problem pitching the project, negotiating the scope, or sending the proposal.
But when an invoice becomes overdue, suddenly the conversation feels different.
You don’t want to be pushy. You don’t want to damage the relationship. You start wondering whether you should give them a few more days.
Dee’s perspective is simple: bring the same confidence to collecting your money that you brought to asking for the business.
That doesn’t mean becoming aggressive. In fact, her approach is much more relationship-driven than that.
It starts with curiosity.
One of my favorite ideas from our conversation was Dee’s belief that every unpaid invoice has a “what had happened was” behind it.
Maybe it went to the wrong person.
Maybe your contact left the company.
Maybe the purchase order number was missing.
Maybe the client changed billing systems and nobody told you.
Before assuming someone doesn’t want to pay you, find out what happened.
That’s where Dee’s Four Keys to Collect the Cash come in: problem solving, customer service, gratitude, and relationship building.
Instead of approaching collections as a confrontation, you’re solving a problem with the client.
What’s preventing this invoice from being paid? What information is missing? Who needs to be involved? What can we do to move it forward?
That sounds a lot like good sales to me.
We often think customer service happens during delivery. But the payment process is part of the experience, too.
A confusing invoice creates friction. So does sending it to the wrong contact or failing to understand your client’s payment process.
And when something goes wrong, how you handle it matters.
Listen. Ask questions. Take ownership when the mistake is yours. Help untangle the problem.
You can protect your cash flow without sacrificing the relationship.
The other part of this conversation that stayed with me was Dee’s take on confidence.
She describes confidence as a decision, but that doesn’t mean you magically stop feeling nervous.
You build confidence through reps.
That’s true when you’re learning to sell, and it’s true when you’re learning to have money conversations.
You make the call. You ask the question. You learn what worked. You adjust.
And eventually, a conversation that once gave you the “heebie jeebies,” as Dee calls it, becomes another normal part of running your business.
So if there’s an unpaid invoice sitting in your accounts receivable right now, start there.
Don’t avoid it.
Don’t invent a story about why they haven’t paid.
Get curious. Find out what happened. Solve the problem.
You already did the work of earning the business and delivering what you promised.
Now finish the sale.
✦ YOUR SALES AS SERVICE CHALLENGE
Pick one invoice or one client who’s gone quiet on payment. Don’t assume the worst. Reach out and ask what happened.
Maybe your contact changed. Maybe something got lost in a system update. Listen for the real story, thank them for their business, and write down what you learn so you’re better prepared the next time it happens.
Dee’s work is a good reminder that the follow-through is part of the sale, not separate from it.
RESOURCES & LINKS
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TAM SMITH
I’m Tam Smith-Sales Growth Strategist and Founder of Studio Three 49. I help service-based founders find, connect with, and convert right-fit clients through predictable, sustainable outbound sales solutions.
No pushy pitches. No bro-marketing. Just simple, structured systems that turn connections into clients.