Heroes of AR – Episode 3: Dee Bowden’s Four Keys to AR Success

In this episode of Heroes of AR, Pradyut Hande sits down with Dee Bowden, Founder and Author of Collect the Cash and one of the most recognizable voices in the AR and Collections world. Dee has spent over two decades in Accounts Receivable and Credit across both private and public sectors, including recovering $7.5M in unused federal funds for the U.S. Coast Guard.

Over the course of their conversation, Pradyut and Dee unpack her four keys to Collect the Cash: problem solving, customer service, expressing gratitude, and customer relationship building; and how they play out in day-to-day AR operations. They explore how to collect without damaging customer relationships, what really blocks teams from embracing automation and AI, and how finance leaders can build more resilient cash flow in a volatile economy.

For anyone in AR, finance, revenue operations, or sales, this episode offers a realistic and practical prism at what it actually takes to turn booked revenue into money in the bank.

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What are your four keys to “Collect the Cash,” and how did they originate?

PH: What better way to start this conversation than with something you're super passionate about: your four keys to Collect the Cash. These include problem solving, customer service, expressing gratitude, and something that often goes under the radar: customer relationship-building. This forms the foundation of your work. It would be great if you could tell our audience a little bit more about this core philosophy.

DB: Thank you so much for having me here. Usually when I talk about Collect the Cash, everybody asks me, “Where did you get this from?” So I'll tell you a short story.

I was working for this small IT company. And; you know how it is when you get hired. They say: “Welcome aboard, here’s your cubicle,”. And then they say, “Here’s an aging report worth $8 million.” And because I've been doing this a long time, the first thing I thought was: “Okay, what's the problem? How did you sell $8 million worth of IT services and not get paid?”

So that was the first thing that jumped out. Since I'm a person of faith, I got quiet. And; the four keys came up:

1. Problem solving: Answering the question of: What’s the story behind why these invoices haven’t been paid?
2. Customer service: We're in business to take care of our customers. If there’s an issue: a data entry error, a missing PO number, or anything else; your job is to take care of that customer and give them the best experience possible.
3. Expressing gratitude: This one is big for me! You know how it is when you finally get someone on the phone in Accounts Payable or at the client, and they say, “Dee, the reason we haven't paid you is…”. Whatever the issue is, you’d be like “Oh my gosh, thank you.” I believe in saying thank you for helping me identify the disconnect. And; it really came from the bottom of our invoices. Over the years, I’ve seen so many invoices that say, “Thank you for your business.” That taught me two things: Every client appreciates that you have a solution to their issue, It’s a reminder to be grateful for every customer that chooses to do business with you

4. Customer relationship building: This often goes under the radar. I’ve been in Accounts Payable and Accounts Receivable for over 20 years. To me, building relationships is about the person who:

1. Takes my phone call
2. Answers my questions
3. Helps me figure out where I’m stuck
4. Gives me the information I need; so I don’t make the same mistake again

At the same time, we have internal customers: the people we work with; and external customers: our clients.

If you don't build good relationships internally and externally, things don't move. Things don't get resolved. I’ve worked in both the public and private sectors, and I’ve learned that building strong and sustainable customer relationships is critical to cash flow efficiency.

TL;DR:

Dee’s four keys came from a very real moment: being handed an $8M aging report and thinking, “How did we do all this work and not get paid?” From there, everything she does in AR comes back to these basics:

• Problem solving: Every unpaid invoice is a story to understand. Fix process gaps, paperwork misses, or misaligned expectations
• Customer service: Make it easy to pay. Clean docs, fast responses. Less friction, more clarity
• Expressing gratitude: Thank customers for transparency; shift the tone from confrontation to collaboration
• Relationship building: Cash moves when people do. Cross-team collaboration and customer partnerships unblock payments and protect revenue.

Together, these four keys turn collections into a mix of detective work, service, and partnership. So; you’re not just chasing invoices, you’re keeping revenue you’ve already earned from quietly leaking out of the business.

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How do you collect with confidence; without being ghosted or damaging customer relationships?

PH: We know that customer relationship building is critical, and customer experience is so important because when you're chasing your customers to pay, you don't want that to become a point of friction. But; things do get heated. There can be extreme circumstances where the collections team is hard-pressed for time, chasing targets that seem unattainable.

In such a scenario, how can your framework actually help businesses collect without being ghosted or eroding existing customer relationships and trust?

DB: Great question. First, I believe you have to see it like this: “How do we win?” And; when we win, we get paid. That’s the first thing. Secondly, you have to see yourself as a solutions provider; whether you’re using technology or you’re a person on the phone.

If you're on a collections team, as your aging grows, you’re hearing: “We need to meet X amount of dollars”. If you don't change your mindset first, you're not going to do anything different, because all you can hear is: “I’ve got to meet my quota.” We understand that's part of the business.

But; the other piece is: “How am I going to approach this from a solutions perspective?” You might have clients that are sometimes challenging. So you need to ask: “What’s the problem?”. Sometimes it's as simple as asking: “Clearly, when we signed this deal, we might have missed a step. What did we miss?”

You often don't discover that until after the contract is signed, the sale is made, and you go to collect the invoice and realize: “Oh, I'm missing some information. I'm missing X, Y, Z.” If we don't go back and fix that, the problem is likely to run on an endless loop.

They need to know that you care about them. This isn’t just about collecting the money. Your customer needs to know:

• You’re sorry there’s been an inconvenience
• You want to come up with a better solution; so you don’t make the same mistake again
• You want to continue a great relationship because you value them as a customer
• You’re gathering lessons and best practices so you can be better for the next customer

TL;DR:

• Stop leading with pressure: Lead with problem-solving to collect without getting ghosted
• Shift from “hit the number” to “how do we win together?”: Act like a partner, not as a Collector
• Treat tough accounts as joint troubleshooting: Find misses, fix process gaps, share ownership
• Protect the relationship: Empathy + clarity + respect → honesty, callbacks, and payments without burning bridges

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As businesses scale, what habits or gaps stall the collections process?

PH: We come from an enterprise background where we help businesses use Accounts Receivable automation to do a lot of this at scale and speed. Volume and velocity keep increasing.

You spoke about customers helping themselves or feeling more in control of the process. Components like customer portals, self-serve, and automation prevent repeat mistakes. As scale increases, the organization’s maturity level also has to keep pace: technology adoption, empowering people, optimizing processes. In your experience, what are some habits or gaps that stall the collections process in such a scenario?

DB: Most of us AR folks who join any new organization are familiar with this: “Welcome aboard. Here's our process. We've done it this way for X years, we may have tweaked a few things, but this is basically how we do it.”

When you introduce anything new, most people don't like change. And; depending on the industry or agency, when you introduce a new thing, you have to take into account that the people doing the work already have existing modus operandis and checklists.

Now you want to introduce a new process: a new system, a new way of seeing things. But; one thing that often doesn’t happen is that we don’t give people enough room to get comfortable with the new idea.

We usually say:

• “Here's the rollout.”
• “This is how we're changing it.”
• “Take this class, take this webinar, and go.”

We forget the human part: “I need a moment to adjust to the fact that we’ve changed our system. I still want to be a top Collector, but I need to understand how the new system works.”

I think that’s one of the issues. Business and life always grow and change. The fact that we're talking about AI and AR in the same breath is a change.

Those of us who’ve done AR are used to manual processes to deal with invoices, spreadsheets, and email trails.

This is a tool to help you do your job better.
You have to make sure the AR team clearly understands understand:

• “This is not taking away your job.”
• “We’re helping you do what you do better.”
• “We want you to be comfortable with the tool, use the tool, and also show us where we can improve the tool so we can help you do your job better.”

When that conversation is had: AR teams stop feeling threatened and start seeing technology as an enabler that makes their job easier and more efficient.

TL;DR:

• Change fails without humanity: New tools break when teams aren’t given time, clarity, or emotional space to learn a new way of working
• Automation triggers uncertainty: If “replace” is left unaddressed, adoption stalls; acknowledge the concern openly
• Reframe the narrative: Tech is there to elevate roles, not erase them - make the job easier, faster, and more effective
• Invite ownership: Include teams in feedback and improvement; security + respect unlock real adoption and real speed

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What role can AI play in AR automation and a human-centered tech stack?

PH: AR automation and AI are no longer just buzzwords. They're part of core products and solutions. But; there’s an overload of information out there. Organizations need to separate the wheat from the chaff, the hype from real value. In your view, what role can AI play in AR automation, and how can it amplify the capabilities of a human-centered tech stack?

DB: There is a lot of information out there.

What often happens is we just bring in AI and start going. We never go back and say: “Do you see how this maps to what you used to do? We’re not saying don’t do it the old way; we’re saying: do it this way, plus add this, and here’s how it connects.”

That’s one of the reasons people resist: nobody is connecting the dots. To make it more human, this is where my four keys come in again: problem solving. Therefore if you want me to use AI and automation in your company, help me understand:

• How is this a problem-solving tool for collecting cash?
• Why are we doing this alongside what I’ve already been doing?
• How do I connect the dots between AR, automation, and AI?

When you see me not just as a “Collector,” but as part of the solution to help us collect cash with confidence…and; you help me make it make sense, then I can say: “Okay, this is a tool. This improves me. I grow in knowledge, skills, and abilities. Now I'm actually a resource to the company internally and externally.”

So when we introduce a new system or customer portal to customers and they don’t understand something, I can:

• Simplify customer experiences
• Maximize value realization  
• Match expectations on customer service

And; then the customer says: “Oh my gosh, thank you so much. I’ve been struggling. I didn’t understand all the things inside the portal.”

Now you’ve built a better relationship. They feel like you go above and beyond for them.

TL;DR:

• Show people a clear “before vs after” view: How AR work looked pre-AI and how AI actually changes the same steps
• Explain how AI helps them solve problems faster: Fewer manual tasks, quicker dispute resolutions, real-time inbox summaries, dynamic account health scores, and more. Instead of just thrusting another tool minus context on your team
• Position AR teams as problem-solvers using AI: Not people being replaced by it
• Understanding and alignment are key: When teams comprehend and trust the tool and the underlying technology - they serve customers better, build stronger relationships, and the business gets paid faster

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Do your four keys to “Collect the Cash” show up differently in B2B vs. B2G (government) work?

PH: You’ve worked with both businesses and government agencies across the public and private sectors. You’ve made some “impossible” recoveries, like the $7.5 million recovery of unused federal funds for the U.S. Coast Guard. In your philosophy of the four keys, how does it show up differently for B2B and B2G organizations?

DB: Honestly, I don’t believe it shows up differently. For example: when I worked at the Coast Guard, when I got hired they said: “Dee, we have hundreds of contracts where the work has been done, the performance period has ended, and there are excess funds sitting on the contract.”

I didn’t know anything about closing out these specific contracts, so I had to learn it fast. That’s problem solving.

Once I got it, I realized:

• There are thousands of contracts
• There are thousands (really, millions) of dollars waiting to be collected

So the question becomes: “How come this much money is still sitting on the books after the contracts have ended?”

Next, customer service:

I’m doing customer service on behalf of the Coast Guard and I have to interact with:

• Different branches of the Navy
• All the vendors who have those contracts

Then there’s expressing gratitude.

I’m working on closing out old contracts: say the contract was awarded in 2020, ended in 2022, and then it just sat there. The work has been done; the money is still sitting there and nobody’s asking why.

I’m thankful for:

• The people who go into the system
• The ones who confirm the vendor did the work
• That the final invoice was submitted
• And that they’re not owed any more money

Then I have to build relationships to get them to sign the documents: like the contractor’s release form that says:

• “We, X company, worked with this agency.”
• “This is how much the contract was worth.”
• “This is how much we got paid.”
• “We have completed our services as per the agreed upon terms and conditions.”

So to me, it’s not different for the public sector or private sector.

That’s how I was able to collect $7.5 million because I used my four keys and said:

• These contracts were awarded and the money’s still sitting here
• I have to figure out the process to get the money back
• have to build relationships and get the vendors to sign the paperwork and confirm everything is done

TL;DR:

• The four keys to “Collect the Cash” is a replicable playbook: They don’t change between B2B and government work
• Working through the keys: At the Coast Guard, Dee used them to track down why millions were still sitting in unpaid dues on closed contracts, then unwind the mess step by step
• Solve for “X”: What happened, who needed to confirm what, and which documents had to be signed to release the money
• Proof of the pudding: By combining problem solving, service, gratitude, and strong relationships across agencies and vendors, she was able to recover $7.5M that would have otherwise remained uncollected

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How can leaders future-proof cash flow in a volatile economic climate?

PH: You’ve seen the evolution of AR over many years. The pandemic was another inflection point: businesses went bankrupt, bad debts were written off. And now, in the current economic climate: things are turbulent, unpredictable, and volatile. What would your advice be to business owners, CFOs, or finance leaders today? How can they future-proof their cash flow strategy and be more resilient in such uncertain times?

DB: How can a CFO, a director of finance, or an AR director manage this better? Go back to aging: 30, 60, 90, 120 days and then ask yourself, “Where are we?”. Have a collective conversation on how to handle your overdue payments.

If we’re not having a conversation, we’re missing:

• What additional support is needed?
• Is it only an AR issue?
• Is it also a Sales issue?
• Do we need to involve the account managers?

We have to understand:

So if you want to future-map this, have a real conversation. For example:

• “We have $5M, $8M in outstanding invoices across 30/60/90 days.”
• “I, as the CFO, can’t manage all of this by myself.”
• “I need all of you to help me solve this.”

Ask:

• Is there an issue on the Sales side?
• AR folks, where are you stuck?
• Do you need training on technology?
• Do you have a relationship with the Sales representative who brought in this business?
• Is there anything they know that you’re missing when you make those calls?

You can absolutely use technology. But; address it from the standpoint of: “I don’t want us to lose. I don’t want the business to go under. I don’t want anyone to lose their job.”

I’m saying:

• Be solution-based
• Have the conversation
• Use technology and people together
• Set clear goals

And; when you collect the money: Celebrate your wins.

We forget how challenging AR can be. Just make sure you celebrate the people who helped you hit that goal. That’s part of how you future-map as well: Have the meeting, ask the questions, give people a chance to share feedback.

Because at the 60,000-feet level, leadership sees numbers on a screen. They’re not the ones facing customers daily, trying to collect.

TL;DR:

• Start with the basics: Look at your aging - 30/60/90/120 days - and get brutally clear on where the cash is stuck
• Don’t treat it as just “an AR problem.”: Bring sales, account managers, finance, and AR into one room and own it as a business issue.
• Ask real questions: Where are we stuck, what support is missing, what’s broken in the process, what context does sales have that AR doesn’t?
• Use tech with people, not instead of them: The goal is to protect the business and jobs, not just to plug in a new tool with limited training or adoption context
• Celebrate your wins: Set clear cash targets, work together to hit them, and when the money comes in, celebrate the team that made it happen. That recognition is part of how you build a resilient cash culture

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5 Strategic Takeaways

1. Shift the mission: Collections aren't “get the money”. It’s fix the blockage. Treat every unpaid invoice like a root-cause puzzle: what broke (PO, scope, data)? Who needs to fix it (AR, AP)? With that mindset, customers stay in the conversation because they feel helped, not hunted
2. CX = Cash flow: The path to payment runs through the customer experience. When you respond fast, clean up your side of the process, and show gratitude for the transparency, customers feel respected. That respect compounds into cooperation and cooperation clears aging buckets
3. People > Platforms: Even the best system can’t unstick a payment if no one’s talking. Revenue moves when AR, Sales, Finance, and AP connect the dots. High-trust relationships create shortcuts: faster answers, faster documents, faster confirmations. This is what actually accelerates cash inflow
4. Tech with trust: Automation and AI are enablers and accelerators. Not a replacement. If AR teams fear what it means for their job, adoption stalls. But; if you map automation to their workflow and show how it reduces grunt work (triage, data chase, templates), they’ll pull the tech into their process with pride
5. Cash culture. Not firefights: In 2026, the CFO can’t be the only one worrying about liquidity. Sustainable cash flow needs a shared operating rhythm: common dashboards, clear prioritization rules, and celebrating milestones like “days to dispute resolution” or “DSO drop.”