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


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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.


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