Order-to-cash process: How finance leaders can automate it

Revenue can be strong while cash flow still feels fragile. Payroll approvals can bring familiar tension even after a record month. A big deal can close, then stall because working capital is trapped in receivables. Forecasts look healthy, yet the bank balance does not match the plan.

This paradox is common in mid-market finance teams because order-to-cash (O2C) automation is often approached from the wrong angle. Many organisations still run “air gap” workflows that force manual coordination across systems. A signed quote lands in HubSpot, an internal note appears in Slack, and someone in finance manually creates a payment link and retypes line items. The sale is real, but cash collection is held together by human middleware.

That does not just create inefficiency. It creates unpredictability. AR teams can spend 15 or more hours each week sending reminders, tracking payment promises, and reconciling status across emails and spreadsheets, yet results remain inconsistent.

The core insight is simple. Most working capital problems live in the final stretch of order-to-cash, where finance controls sit. Invoicing, collections, and cash application determine whether revenue becomes cash quickly and predictably. This guide explains how to automate those finance-critical stages to improve cash flow.

Why most O2C automation misses the finance team's real problem

Order to cash process discussions often blend two distinct systems into one narrative.

Operational O2C focuses on order management, inventory allocation, fulfilment, shipping, and delivery confirmation. That is operations territory. It matters for customer experience and cost control, but it rarely fixes cash flow bottlenecks quickly.

Financial O2C focuses on invoicing, collection, and cash application. That is finance territory. It is where working capital gets trapped and where DSO quietly expands.

Most platforms labelled as “order to cash automation” are built for operations teams. They optimize how efficiently the business loads trucks, ships products, and tracks fulfilment milestones. Finance becomes a downstream afterthought. A finance team then inherits the consequences: delayed invoicing, invoice errors, missed follow-up, payment friction, and slow reconciliation.

Mid-market teams rarely need to automate the entire O2C cycle to see meaningful cash flow improvement. Automating everything can create multi-department dependencies, long implementation timelines, and a broad transformation scope that is difficult to sustain.

A more effective approach is targeted and finance-led: automate the 3 finance-critical stages where working capital gets trapped.

A useful analogy is this. Automating fulfillment is optimising how fast a business can load and dispatch trucks. Automating financial O2C is ensuring those trucks actually get paid.

The 3 finance-critical stages are the points of highest leverage.

Stage 1 - Invoicing and delivery gap

Cash collection timing starts when an invoice is issued and received in a payable form. Every day an invoice sits in draft pushes the entire timeline out.

If an invoice sits 5 days in draft and takes 3 days to reach the customer, eight days are lost before collections even begin. Those eight days are not a customer behaviour issue. Those eight days are because of a flaw in the process design.

The operational reality often includes disconnected systems, manual re-entry, and billing errors. A quote lives in a CRM, delivery confirmation lives in project tools, invoice creation happens in an accounting system, and payment links exist in a separate payment platform. Each handoff is a delay risk and an error risk. Payment expectations can also be unclear when invoices lack simple ways to pay.

Invoicing automation is not just about sending invoices. It is about speed, accuracy, and payment readiness.

Stage 2 - Collections delays and ineffective payment reminders 

This is where most capital gets trapped. Invoices often go unpaid not because customers refuse to pay, but because the invoice is not prioritised among dozens of competing payables. In practice, that can mean an invoice sits untouched for 45 to 60+ days past issue date, simply waiting its turn in an AP queue. Many customers receive 50 or more supplier invoices, and accounts payable teams triage based on urgency and friction, so anything that is not clearly due, easy to approve, and simple to pay can drift week after week.

Manual reminders are sporadic, inconsistent, and workload dependent. When the team is busy, reminders slip. When reminders slip, customers deprioritise. When customers deprioritise, DSO grows.

The day to day work is chaotic. Teams can spend 15+ hours weekly sending reminders, tracking payment promises across email and spreadsheets, and trying to figure out which accounts are genuinely at risk. Visibility is limited because data is fragmented.

Payment collection is not just about chasing. It is about designing a consistent system that makes payment the default outcome.

Stage 3 - Manually doing cash application and reconciliation

Even when customers pay, cash can remain “unusable” until it is accurately applied and reconciled.

Cash application becomes painful when customers pay without invoice references, pay multiple invoices in one lump sum, or short pay due to disputes. The finance team then spends hours checking bank feeds, cross referencing invoices, and sending messages like “please confirm which invoices this covers.”

Manual entries create downstream problems. If systems are out of sync, reminders can be sent for invoices that have been  paid. That can damage credibility and customer relationships, even when messaging is polite.

Automation in cash application and reconciliation compresses the time between payment and financial clarity. That improves cash flow visibility and reduces operational noise.

Common solutions finance teams try that fail

Most finance leaders are not ignoring the problem. Many teams have tried obvious fixes and found that those fixes do not scale.

Trap 1: Human middleware bridges between systems

The first trap is human middleware that acts as a bridge between systems. This can work at low volume, but growth turns those bridges into a bottleneck. A finance leader becomes the integration layer between CRM, ERP, invoicing, payment, and bank feeds. That is expensive and fragile.

Trap 2: The spreadsheet band-aid

The second trap is the spreadsheet band-aid. Spreadsheets can document the problem with aging buckets, risk rankings, and forecasting models. Spreadsheets rarely change customer behaviour. Spreadsheets also become stale quickly, which undermines confidence in cash flow projections.

Trap 3: Defaulting to enterprise platform adoption

The third trap is enterprise platform adoption as a default answer. Large O2C suites can require 18-month implementations, enterprise pricing, and cross-functional transformation. Mid-market teams often do not have the budget, the bandwidth, or the appetite for that scope.

Trap 4: Building custom internal tools

The fourth trap is building custom internal tools. Asking IT to build a debt collections workflow or a cash prediction model can seem attractive, but it creates technical debt and diverts resources from core product priorities. It also introduces dependency risk if the builder leaves.

Trap 5: Layering basic automation tools into new silos

The fifth trap is layering basic automation tools that create new data silos. A reminder tool here, a dashboard tool there, a separate payment tool somewhere else. Without a coherent system, automation fragments the process further.

Trap 6: Outsourcing to collection agencies

The method: Handing over difficult accounts to third-party debt collectors.
The problem: It erodes margins and damages relationships. Fees can take 15 to 50% of recovered amounts, and the tone and tactics can alienate customers you actually want to retain. It also pushes you into reactive recovery instead of building a repeatable, in-house escalation process.

Trap 7: Manual data entry from “chaos” formats

The method: Manually typing in orders from PDFs, Word docs, and emails because every customer sends a different format.
The problem: It is slow, demoralising, and error-prone. Teams can spend hours re-keying 20-line-item orders, then have to redo the work when terms change. The hidden cost is not just time, but downstream corrections in invoices, approvals, and cash application.

What effective O2C automation actually delivers (the principles that matter)

Effective order to cash automation is not defined by a specific feature list. Effective AR automation software is defined by the outcomes and the operating principles behind them.

The following principles matter most for mid-market finance automation.

Speed without chaos
Invoices should go out the same day work completes, not sit in draft for days. That requires automation that reduces handoffs and reduces manual re-entry. Speed must not come at the cost of errors.

Visibility without manual tracking
Instant answers should be available for questions like “which customers are at risk” and “what is expected to land next week.” Visibility should not require spreadsheet compilation and reconciliation marathons.

Consistency without burnout
Every overdue invoice should be chased according to policy regardless of workload spikes. Consistency matters more than intensity. The system should not depend on heroics.

Personalization at scale
Different customers require different treatment. A good payer might need a friendly nudge. A chronic late payer might require earlier reminders and tighter escalation. Automation should enable segmentation without forcing manual customization.

Accuracy without embarrassment
The system must know payment status before taking action. False reminders damage credibility. Accurate syncing and reliable reconciliation protect relationships.

Recovery without relationship damage
Aged debt recovery is sometimes necessary, but the approach must preserve goodwill where possible. The goal is firm and professional recovery, not aggressive tactics that compromise long-term revenue.

These principles establish a practical bar for evaluating automation. Any solution that cannot deliver on these principles will struggle to reduce DSO, improve cash flow predictability, and free finance teams from manual processes.

The 3-phase O2C automation process for finance leaders: Protect → Chase → Collect

A practical order to cash automation approach for mid-market finance leaders can follow 3 phases.

• Protect prevents cash flow problems before invoices age.
• Chase collects efficiently and consistently without damaging relationships.
• Collect recovers aged debt systematically when earlier efforts do not succeed.

Each phase benefits from a structured approach that moves from strategy to execution to enabling technology.

Stage 1 - Automate your key processes before problems start

The best way to reduce DSO is to reduce the volume of invoices that become overdue. Protect focuses on prevention. It reduces risk exposure, compresses invoicing cycle time, and reduces payment friction from day one.

Stop extending credit to the wrong customers

Strategy
Credit decisions should reflect real payment behaviour, not optimism. Extending credit to customers with poor payment history creates predictable DSO expansion and predictable stress.

How to succeed
A scalable approach uses automated credit assessment that flags high-risk customers before terms are granted. Credit limits and payment terms can be aligned to risk. The goal is not to block growth, but to price and manage risk intentionally.

A practical execution plan includes 3 elements:

• A structured risk classification for each customer
• Rules for adjusting terms and limits based on risk
• Early interventions for customers showing deteriorating payment patterns

How Chaser helps
Chaser includes Payer Rating that classifies customers as good, average, or bad payers based on payment behaviour. Chaser also includes a Late Payment Predictor that scores invoices using a risk score model, ranking each invoice with a risk score between 0-100%, enabling proactive attention before invoices become severely aged. These capabilities support consistent credit and collections policy application, especially when invoice volume grows.

Get invoices out the door instantly

Strategy
Invoice delays are often a hidden DSO tax. Every day lost before invoice delivery is a day added to the cash conversion timeline.

How to succeed
The goal is to eliminate delays between completing work and sending invoices by automating data flow between systems.

A practical approach includes:

• Defining clear invoice triggers, such as delivery confirmation, milestone completion, or contract dates
• Ensuring invoice data is complete and accurate at the point of creation
• Reducing manual re-entry by integrating source systems with accounting

Seamless integration between CRM, ERP, and accounting systems helps invoices go out the same day work completes. That improves cash flow and reduces disputes caused by missing or incorrect information.

How Chaser helps
Chaser supports integrations that sync invoice and payment data between accounting platforms and related systems. Native integrations exist for systems including Xero, QuickBooks, Sage, Dynamics 365, SAP, and many others, supported through two-way API synchronisation. The benefit is faster invoicing workflows with reduced manual entry and reduced errors. Faster invoice issuance shortens the time to payment without requiring an ERP overhaul.

Make payment expectations crystal clear

Strategy
Customers are more likely to pay on time when expectations are unambiguous and payment is easy.

How to succeed
Every invoice should make the next step obvious. That includes:

• Clear payment terms and due dates
• Simple instructions for payment
• A direct path to payment via a “pay now” option
• Multiple payment methods that align to customer preferences

Payment friction is often underestimated. If payment requires extra steps, an accounts payable team will postpone it. Making payment convenient reduces the behavioural barriers to paying promptly.

How Chaser helps
Chaser provides a Payment Portal and Chaser Pay that embed payment links directly into reminders and invoices. Payment options can include instant bank transfer and card payments, as well as methods such as Apple Pay and Google Pay where supported.

Chaser also supports Payment Plans, which help structure installment payments with automated tracking. This turns payment into a low-effort action from the moment an invoice is received.

Stage 2 - Collect payments without burning relationships

Most working capital becomes trapped during the collections stage. Many invoices go unpaid not because customers refuse, but because reminders are inconsistent, get ignored, or feel impersonal.

Chase is about designing a consistent system that nudges payment behaviour while preserving relationships.

Automate reminders across every channel

Strategy
Consistency drives outcomes. The objective is to ensure every invoice receives timely reminders based on policy, not based on capacity.

How to succeed
Effective automation uses multi-channel reminders that escalate naturally based on customer segment and invoice age. The tone should remain professional and aligned to your brand voice.

A practical framework includes:

• Pre-due reminders for customers with history of late payment
• Due date reminders that are clear and frictionless
• Post-due sequences that increase urgency without hostility
• Escalation steps that are rule-based and predictable
• Payment links included in every message to remove friction

Customer segmentation is essential. A long-standing good payer should not receive the same sequence as a chronic late payer. Automation should support these differences without manual effort.

How Chaser helps
Chaser supports multi-channel automation across email and SMS, with additional options such as letters and calls where appropriate. Reminder schedules can be customized based on customer history and invoice rules.

Messages can be personalised to reflect the sender identity and tone, which helps preserve relationships while maintaining persistence. Chaser also includes Recommended Chasing Times to help send reminders when customers are more likely to respond and pay.

Docuflow is a useful proof point for this approach. Docuflow reduced DSO from 60 days to approximately 24 days and achieved invoices paid 54 days faster after implementing automated chasing sequences. That result illustrates how consistent reminders and reduced friction can unlock working capital quickly.

Prioritize with AI, not spreadsheets

Strategy
Collection time is scarce. Collections work should focus on invoices most likely to become late, not simply the oldest invoices on a report.

How to succeed
A risk-based approach uses predictive scoring to identify high-risk invoices early. That allows the team to intervene before invoices move into severe aging buckets.

A practical method includes:

• Risk scoring that accounts for payment history, invoice characteristics, and timing
• Prioritisation rules for high-value invoices and high-risk accounts
• Exception-based workflows that direct human attention to the most impactful work

This reduces wasted chasing on reliable payers and reduces the chance that high-risk invoices slip through until they become very late.

How Chaser helps
Chaser’s Late Payment Predictor assigns a risk score to invoices and helps identify which invoices are likely to be paid late. Payer Rating categorises customers into risk tiers. AR teams can sort and prioritise work by risk score rather than working through static aging buckets. This supports strategic allocation of effort and improves cash flow predictability.

Create your single source of truth

Strategy
Fragmentation creates wasted work. When chase history, customer communications, and payment promises live across inboxes and spreadsheets, the team spends time searching instead of collecting.

How to succeed
A single source of truth is a central system that logs every interaction and payment status update in a chronological timeline per customer. It should include:

• Reminder history and outcomes
• Customer responses and promises to pay
• Dispute notes and resolution status
• Payment status and reconciliation data
• Clear ownership and next actions

This “financial CRM” model reduces duplication, supports handoffs, and makes performance visible.

How Chaser helps
Chaser acts as a centralized receivables platform where communication timelines, chase history, and customer activity can be managed in one place. Chaser also includes an AI Email Generator to help draft responses to common debtor replies such as payment promises and disputes, reducing inbox management time.

Love Brands Limited provides relevant proof. Love Brands saved 15 or more hours per week on credit control work and reported that customer relationships improved. That matters because it directly addresses a common objection: automation can be relationship safe when messaging is consistent, clear, and professional.

Stage 3 - Recover aged debt while preserving goodwill

Even with strong Protect and Chase processes, some invoices will age past 60, 90, or 120 days. Collect is a systematic escalation approach that recovers cash without destroying relationships.

Use friendly collections, not aggressive agencies

Strategy
Aged debt recovery should preserve brand reputation and customer relationships whenever possible. Traditional collection agencies can be costly and aggressive, and they can damage future revenue.

How to succeed
A practical collections approach has 3 attributes:

• Professional and firm communication aligned to brand voice
• Clear visibility into outreach and outcomes
• A structured escalation path that avoids emotional decisions

Friendly collections services can operate as an extension of the finance team, focusing on resolution rather than confrontation.

How Chaser helps
Chaser Collections provides a no-win-no-fee approach to debt recovery with visibility into the process. The service is designed to protect customer relationships and maintain professional standards.

The Community Energy Scheme demonstrates the recovery potential. The Community Energy Scheme recovered £800,000 in previously written-off debt through a structured recovery approach. 

Additional examples include Huttie Group achieving response and payment rates above 80%for invoices escalated to collections and TaxAssist recovering £20,000 of debt in 30 minutes. These results illustrate how systematic escalation and professional recovery can unlock cash that manual processes have written off.

Offer payment plans that actually get you paid

Strategy
Some customers cannot pay in full immediately but can pay in structured installments. Payment plans can turn stalled invoices into predictable cash flow when managed correctly.

How to succeed
Successful payment plans require:

• A clear agreement that customers can accept easily
• Automated tracking of instalment due dates
• Automatic reminders for each instalment
• Clear consequences for missed payments

Manual payment plan tracking often fails because instalments are easy to lose in the noise of daily work. Automation is essential for consistency.

How Chaser helps
Chaser supports Payment Plans that enable weekly, monthly, or quarterly installments. The system can track each instalment and chase overdue installments automatically. This reduces manual tracking and improves the likelihood that plans stay on track.

Escalate systematically, not emotionally

Strategy
Escalation should be defined by policy, not by frustration. Emotional escalation creates inconsistent customer experiences and internal conflict.

How to succeed
Systematic escalation uses objective triggers such as:

• 60 days overdue
• Invoice value above a defined threshold
• Repeated broken payment promises
• Lack of response after a defined number of reminders

Escalation can include shifting the sender identity, copying additional recipients, applying late payment fees where contractually appropriate, and initiating collections steps when thresholds are met.

How Chaser helps
Chaser supports AR automation escalation workflows that shift reminders to escalated senders and escalated recipients based on defined triggers. This enables consistent escalation without relying on individual judgement at the moment. Late payment fees can be applied in line with configured rules, supporting a disciplined approach that is predictable and professional.

How finance teams use Chaser to automate order-to-cash without burning customer relationships

The Protect → Chase → Collect framework is practical. The outcomes become clear when mid-market finance teams implement financial O2C automation systematically.

The following examples show what changes when invoicing, collections, and cash applications move from manual processes to structured automation.

FHC for their client Docuflow

• Context: Docuflow were experiencing significant payment delays and high DSO.
• Problem: Invoices remained unpaid for extended periods, limiting working capital and increasing cash anxiety.
• What was implemented: FHC Accountants implemented automated chasing sequences and structured reminder cadences aligned to customer behaviour.
• Results: DSO reduced from 60 days to approximately 24 days, a 75% improvement. Invoices were paid 54 days faster. Many invoices were handled with minimal manual intervention through consistent sequences and reduced payment friction.
• Transformation: Cash flow became more predictable, and collections work shifted from reactive chasing to managing exceptions.
  
  

Community Energy Scheme

• Context: A business with severely aged receivables, including debt that had been written off.
• Problem: Stalled cash recovery and limited internal capacity to pursue difficult accounts without damaging relationships.
• What was implemented: A structured recovery process with professional escalation and collections support.
• Results: £800,000 recovered from previously written-off debt.
  Transformation: Aged debt recovery became a controlled process with visibility, rather than a last resort scramble.
  
  

Love Brands Limited

• Context: A growing organisation with limited finance bandwidth.
• Problem: Significant weekly time spent on manual credit control and follow-up.
  What was implemented: Centralised receivables workflows and automated reminders that maintained a relationship-safe tone.
• Results: 15+ hours per week saved on credit control. Customer relationships improved rather than deteriorated.
• Transformation: Finance capacity increased without hiring, enabling focus on forecasting and higher value work.

These results share a theme. Automation does not replace relationships. Automation replaces inconsistency. That is the difference between a process that scales and a process that breaks under growth.

Ready to automate O2C and accelerate cash flow? Here’s how Chaser helps finance teams

Order to cash automation does not require an 18-month transformation. A finance-led approach focuses on the 3 stages where working capital gets trapped: invoicing, collections, and cash application. The Protect → Chase → Collect framework provides a systematic path to reducing DSO, eliminating manual work, and improving cash flow predictability.

Chaser supports that framework with capabilities built for finance teams and designed for mid-market scale.

Protect phase support

• Payer Rating and Late Payment Predictor help identify high-risk customers and high-risk invoices early, supporting better credit decisions and proactive prevention.
• Integrations support faster invoicing workflows by reducing manual data entry and syncing invoice and payment data between systems.
• Payment Portal and Chaser Pay help remove payment friction by enabling customers to pay quickly using available payment methods, including instant bank transfer and card payments, with options such as Apple Pay and Google Pay where supported. Payment Plans support structured installments where appropriate.
  
  

Chase phase support

• Multi-channel automation supports consistent reminders through email and SMS, with options such as letters and calls where appropriate.
• Recommended Chasing Times can improve timing and response rates by prompting reminders when customers are more likely to engage.
• Custom schedules segment customers based on payment behaviour and risk, enabling different approaches for good payers, average payers, and bad payers.
• The platform functions as a central receivables system of record with a communication timeline and tools like AI Email Generator to reduce manual inbox work.
  
  

Collect phase support

• Chaser Collections supports professional, relationship-preserving recovery on a no-win-no-fee basis with visibility into the process.
• Payment Plans enable installments with automatic tracking and reminders.
• Automated escalation workflows support objective, policy-driven escalation paths, including escalated senders and recipients and late payment fee rules where applicable.

Chaser is designed for finance outcomes rather than operations workflows. Implementation can focus on finance-critical stages and can be structured to deliver value quickly. Two-way syncing helps prevent false reminders by aligning action with current payment status.

A practical next step is a short demonstration focused on current workflows, customer segments, and receivables risk patterns.