In a recent webinar, Doss Co-founder and CEO Wiley Jones sat down with Eileen Tobias, a finance leader with over 30 years of experience at companies like NetSuite, Dropbox, and Komodo Health, to discuss one of the most critical operational workflows for any business: order-to-cash.

For those unfamiliar with the term, order-to-cash encompasses the entire workflow from when a customer places an order to when payment is received. As Eileen put it: "Order-to-cash is really that workflow that captures how you're selling items or services or software to your end customers, how you're invoicing them, and then how you're ultimately getting paid. It's the lifeblood of any company—if you're not successfully selling and collecting, your company is not going to last very long."

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Why Order-to-Cash Matters at Every Stage

Whether you're a bootstrapped startup or a publicly traded company, order-to-cash remains critically important—just for different reasons:

Early-Stage Companies:

• Focus on getting your product into customers' hands
• Easy to fall into the "do whatever it takes to get a deal signed" mindset
• Critical to begin establishing standardized processes even amid rapid growth

Mid-Stage Companies:

• Need to scale order processing with lower human touch
• Balancing customization with efficiency
• Often managing a mix of sales channels and payment methods

Late-Stage/Public Companies:

• Order-to-cash inefficiencies can mean the difference between beating or missing guidance
• Highly accountable to external stakeholders for bookings, revenue, and cash flow
• Need robust systems that can handle complex requirements while maintaining compliance

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Product-Led vs. Sales-Led: Different Models, Different Challenges

One particularly insightful part of the conversation focused on how order-to-cash differs between product-led growth (PLG) companies and traditional sales-led organizations.

For product-led companies like Dropbox (in its consumer business):

• Customer pays almost instantaneously at the time of order
• Focus on preventing fraud and chargebacks
• Pricing experimentation directly impacts conversion rates

For sales-led companies like Komodo Health:

• Payment typically occurs days or weeks after order placement
• Managing payment terms becomes critical
• Customers can "stretch" their payables to improve their own cash flow

Many modern companies use a hybrid approach, which creates its own challenges. As Eileen noted: "You might start with product-led growth, and then as you move upmarket, you attract larger customers. What works for your product-led customers doesn't work for an outbound-driven enterprise-level customer, and vice versa."

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Common Pitfalls in Order-to-Cash Management

Throughout the conversation, several recurring challenges emerged:

Allowing Too Much Variation:"If you let your sales reps do whatever they want when they fill out an order form, that gets you into very manual work process hangups," Eileen explained. Simple things like locking down dropdown fields for payment terms or price lists can eliminate significant downstream issues.

Ignoring Customer Payment Processes:Large customers often have specific requirements for invoicing and payment. "Very large customers out there in any industry have their idiosyncrasies about their procure-to-pay process," Eileen noted. "They may have their own internal portal—you need to make sure your invoice is in there by the 5th day of the month, and if it's not, then you're not going to get paid until next month."

Not Performing Credit Checks:Early-stage companies are often reluctant to perform credit checks, but Eileen strongly recommends this practice: "It will help ensure that you'll get paid and that this is a good customer to do business with, that they'll be around for a long time."

Poorly Structured Payment Terms:"If you typically offer 30-day payment terms but one customer negotiates 60-day terms, if you think about it, many customers don't pay on time—and they don't pay on time on purpose," Eileen pointed out. "If your average time to get paid is 45-50 days, now with 60-day terms, you're not going to get paid for 75, 80, 90 days."

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Best Practices for an Effective Order-to-Cash Workflow

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Standardize Where Possible

Even for early-stage companies in land-grab mode, standardization pays dividends. "At any stage of a company, even early stage, even if you are in the mindset that a one-off deal is better than no deal at all, you can still make an effort to standardize and have processes where possible," advised Eileen.

Specific areas to standardize include:

• Order terms and formats
• Payment options and terms
• Customer onboarding procedures

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Require Purchase Orders

While it might seem easier to skip formal POs, especially for smaller deals, Eileen recommends requiring them: "Most companies with a level of maturity for their procure-to-pay process will require their employees to issue POs. Your collections process can get hung up because your customer won't pay you if they can't match a PO with an invoice."

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Maintain Customer-Specific Catalogs

For B2B companies, especially those selling physical goods, maintaining customer-specific catalogs is crucial. Many enterprise customers assign their own SKUs to your products, and your ability to reference these in your invoicing can determine whether you get paid promptly.

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Focus on Cash

If you're resource-constrained, prioritize the cash collection aspect of order-to-cash: "If you don't have time to look at order accuracy or invoicing accuracy or different metrics, then focus on cash," Eileen advised. "Especially in the current environment, it's really important to get a lot of rigor around your receivables and collections—look at them weekly at minimum."

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Align Sales, Finance, and Operations

Perhaps most importantly, create alignment between the three key stakeholders in the order-to-cash process:

"These three organizations, if they're really working well together, can ensure that 80% of the orders and transactions are just going through smoothly," explained Eileen. "Then everybody can focus their brainpower, problem-solving, and creativity on that last 10 to 20% of those large deals or one-off deals."

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Leveraging Technology for Order-to-Cash

Modern technology can dramatically improve order-to-cash processes through:

Automated Invoicing: Systems that can automatically generate accurate invoices based on completed orders eliminate manual errors and accelerate payment cycles.

Embedded Payments: "The embedded payment link in an invoice is just a huge step forward in making it easier for your customer to get an invoice and for them to pay you," noted Eileen.

Dynamic Rules and Workflows: Advanced systems can apply different rules to different customer segments, such as offering early payment discounts that automatically adjust based on when payment is received.

Data Insights and Dashboards: Visual representations of order and payment data help spot anomalies: "We have this really big amount of unpaid items from this one customer, and I've never seen them do that before in this chart. I'm going to just call them up and ask what's going on."

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Looking Forward

As we look to the future of order-to-cash, several trends are emerging:

• Faster time to insight through better analytics
• More flexible payment options to meet customer preferences
• Increased automation of repetitive tasks
• Better integration between systems across the entire workflow

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Whether you're a startup founder or a finance leader at a public company, the order-to-cash process deserves your attention. By standardizing processes, leveraging technology, and creating alignment between teams, you can turn this critical workflow from a source of friction into a competitive advantage.

As Eileen summarized: "This workflow is so critical... it's the lifeblood of any company."

Looking to improve your order-to-cash workflow? Book a demo to learn how our platform can help automate and optimize your entire process, from order entry to cash collection.

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