The Challenge: Out-of-Policy Expense Claims

Finance teams are under pressure to control costs, but out-of-policy expense claims make that job significantly harder. Travel and expense policies are often long, complex, and full of exceptions. Employees submit claims in good faith, managers approve quickly to avoid bottlenecks, and finance only discovers problems weeks later during audits – if at all. The result is a steady trickle of non-compliant spend that is hard to see and even harder to correct after reimbursement.

Traditional approaches rely on manual checks, random audits, and basic rule engines embedded in expense tools. These methods struggle with real-world nuance: different per diems by country, special project rules, shifting travel classes by level or trip length, and exceptions like client entertainment or last-minute changes. Static rules can’t easily interpret notes on receipts or email approvals, and manual review doesn’t scale when thousands of line items hit the system every month.

The business impact is significant. Non-compliant spend quietly inflates travel and operating costs, approval cycles slow down when finance tightens manual controls, and late-stage disputes with employees damage trust. Finance leadership loses clear visibility into true cost drivers, making it harder to negotiate with vendors, optimise travel policies, or forecast cash flow accurately. In competitive markets, the inability to enforce expense policies at scale becomes a real disadvantage for profitability and governance.

The good news: this problem is solvable. Advances in AI for finance now make it realistic to read and interpret policies, receipts and expense exports with human-level nuance but machine-level consistency. At Reruption, we’ve seen how well-designed AI workflows can turn policy enforcement from a painful afterthought into an embedded, real-time control. In the sections below, you’ll find concrete guidance on using Claude to detect out-of-policy claims before they are paid – and to do it in a way that supports employees instead of policing them.

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Our Assessment

A strategic assessment of the challenge and high-level tips how to tackle it.

From Reruption’s work building AI-first workflows in finance functions, we’ve learned that tools like Claude shine where traditional rule engines struggle: understanding nuanced text, applying complex policies consistently, and explaining decisions in plain language. Used correctly, Claude can become a scalable expense control layer that reviews every claim against your travel and expense policy, flags exceptions, and guides employees towards compliant alternatives – all without drowning your finance team in manual checks.

Treat Expense Control as a Policy-Reasoning Problem, Not Just a Rules Engine

Many organisations approach out-of-policy expense control by adding more hard-coded rules into their expense tool. This quickly becomes unmanageable as policies change, countries differ, and exceptions multiply. Instead, frame it as a policy reasoning problem: can an AI read your policy like a human, understand the context of each claim, and reason about whether the expense makes sense?

Claude is particularly strong at ingesting long documents and applying them to specific cases. Strategically, this means you should invest time upfront in structuring and clarifying your policy, edge cases, and examples. Finance, HR, and Legal should align on what “compliant”, “requires justification”, and “out-of-policy” really mean, so that Claude’s reasoning mirrors your governance, not just a technical rule set.

Start with High-Risk Categories Before Expanding

Trying to automate checks for every single expense type from day one usually leads to complexity and resistance. A more strategic approach is to identify the highest-risk and highest-volume categories – such as travel, hotels, meals, and recurring subscriptions – and pilot Claude there first. These categories often carry the most policy nuance and financial impact.

By deliberately narrowing scope, you can validate Claude’s performance, tune prompts, and adjust thresholds for flagging issues without overwhelming the business. Once you demonstrate value – e.g. fewer late rejections, clearer explanations for employees, and measurable savings – it becomes much easier to extend AI checks to the long tail of other expenses.

Design for Collaboration Between Finance, Managers, and Employees

Out-of-policy enforcement can quickly become a cultural problem if employees feel they are being punished by a black box. Strategically, position Claude as an assistant that helps everyone play by the rules: it guides employees when they submit claims, gives managers clear rationales during approval, and provides finance with structured exceptions for review.

This requires involving stakeholders early. Work with business units to understand common pain points in the current process and use them as design inputs. For example, ensure Claude’s outputs include human-readable explanations (“This exceeds the hotel cap for Berlin by 25%”) and, where possible, suggestions (“A compliant option would be up to 150€ per night or a documented client request”). This collaborative framing dramatically increases adoption.

Align AI Controls with Risk Appetite and Governance

Not every out-of-policy case has the same risk. A slightly too expensive taxi ride is not equivalent to repeated entertainment overspend or suspicious recurring SaaS charges. Strategically, define your risk tiers and escalation paths before configuring Claude: which cases should auto-block payment, which should require extra documentation, and which can be approved but logged for analytics?

Claude can be configured to apply different logic per tier, but the underlying design decision is governance, not technology. Finance, Compliance, and Internal Audit should co-create clear thresholds and escalation rules. This ensures that AI-driven controls reinforce your existing governance model, rather than introducing new informal rules that are hard to justify in audits.

Plan for Continuous Learning, Monitoring, and Policy Evolution

Expense policies and business realities change: new markets, updated per diems, different travel patterns, remote work norms. A one-time Claude configuration will drift over time if you do not plan for continuous monitoring and refinement. Strategically, treat Claude as a living control that you review periodically, just like you would any key financial control.

Set up feedback loops: finance analysts can tag incorrect flags or missed issues, which then feed into updated prompts, examples, or policy representations. Review summary metrics monthly – such as percentage of claims flagged, top violation types, and false positive rates – and adjust. This ongoing tuning is what turns Claude from an interesting experiment into a dependable part of your expense governance framework.

Used thoughtfully, Claude can transform how you control out-of-policy expense claims: from sporadic, manual checks to consistent, explainable, real-time reviews across all spend categories. The key is not just the model itself, but how you encode your policy logic, govern risk, and integrate AI into everyday workflows. At Reruption, we specialise in turning these ideas into working AI controls inside finance teams, from rapid PoCs to production-ready automations. If you want to explore what Claude could do for your own expense process, we’re ready to help you test it quickly, safely, and with clear business metrics.

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Real-World Case Studies

From Transportation to Automotive: Learn how companies successfully use Claude.

Waymo (Alphabet)

Transportation

Developing fully autonomous ride-hailing demanded overcoming extreme challenges in AI reliability for real-world roads. Waymo needed to master perception—detecting objects in fog, rain, night, or occlusions using sensors alone—while predicting erratic human behaviors like jaywalking or sudden lane changes. Planning complex trajectories in dense, unpredictable urban traffic, and precise control to execute maneuvers without collisions, required near-perfect accuracy, as a single failure could be catastrophic . Scaling from tests to commercial fleets introduced hurdles like handling edge cases (e.g., school buses with stop signs, emergency vehicles), regulatory approvals across cities, and public trust amid scrutiny. Incidents like failing to stop for school buses highlighted software gaps, prompting recalls. Massive data needs for training, compute-intensive models, and geographic adaptation (e.g., right-hand vs. left-hand driving) compounded issues, with competitors struggling on scalability .

Lösung

Waymo's Waymo Driver stack integrates deep learning end-to-end: perception fuses lidar, radar, and cameras via convolutional neural networks (CNNs) and transformers for 3D object detection, tracking, and semantic mapping with high fidelity. Prediction models forecast multi-agent behaviors using graph neural networks and video transformers trained on billions of simulated and real miles . For planning, Waymo applied scaling laws—larger models with more data/compute yield power-law gains in forecasting accuracy and trajectory quality—shifting from rule-based to ML-driven motion planning for human-like decisions. Control employs reinforcement learning and model-predictive control hybridized with neural policies for smooth, safe execution. Vast datasets from 96M+ autonomous miles, plus simulations, enable continuous improvement; recent AI strategy emphasizes modular, scalable stacks .

Ergebnisse

  • 450,000+ weekly paid robotaxi rides (Dec 2025)
  • 96 million autonomous miles driven (through June 2025)
  • 3.5x better avoiding injury-causing crashes vs. humans
  • 2x better avoiding police-reported crashes vs. humans
  • Over 71M miles with detailed safety crash analysis
  • 250,000 weekly rides (April 2025 baseline, since doubled)
Read case study →

UC San Francisco Health

Healthcare

At UC San Francisco Health (UCSF Health), one of the nation's leading academic medical centers, clinicians grappled with immense documentation burdens. Physicians spent nearly two hours on electronic health record (EHR) tasks for every hour of direct patient care, contributing to burnout and reduced patient interaction . This was exacerbated in high-acuity settings like the ICU, where sifting through vast, complex data streams for real-time insights was manual and error-prone, delaying critical interventions for patient deterioration . The lack of integrated tools meant predictive analytics were underutilized, with traditional rule-based systems failing to capture nuanced patterns in multimodal data (vitals, labs, notes). This led to missed early warnings for sepsis or deterioration, higher lengths of stay, and suboptimal outcomes in a system handling millions of encounters annually . UCSF sought to reclaim clinician time while enhancing decision-making precision.

Lösung

UCSF Health built a secure, internal AI platform leveraging generative AI (LLMs) for "digital scribes" that auto-draft notes, messages, and summaries, integrated directly into their Epic EHR using GPT-4 via Microsoft Azure . For predictive needs, they deployed ML models for real-time ICU deterioration alerts, processing EHR data to forecast risks like sepsis . Partnering with H2O.ai for Document AI, they automated unstructured data extraction from PDFs and scans, feeding into both scribe and predictive pipelines . A clinician-centric approach ensured HIPAA compliance, with models trained on de-identified data and human-in-the-loop validation to overcome regulatory hurdles . This holistic solution addressed both administrative drag and clinical foresight gaps.

Ergebnisse

  • 50% reduction in after-hours documentation time
  • 76% faster note drafting with digital scribes
  • 30% improvement in ICU deterioration prediction accuracy
  • 25% decrease in unexpected ICU transfers
  • 2x increase in clinician-patient face time
  • 80% automation of referral document processing
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UPS

Logistics

UPS faced massive inefficiencies in delivery routing, with drivers navigating an astronomical number of possible route combinations—far exceeding the nanoseconds since Earth's existence. Traditional manual planning led to longer drive times, higher fuel consumption, and elevated operational costs, exacerbated by dynamic factors like traffic, package volumes, terrain, and customer availability. These issues not only inflated expenses but also contributed to significant CO2 emissions in an industry under pressure to go green. Key challenges included driver resistance to new technology, integration with legacy systems, and ensuring real-time adaptability without disrupting daily operations. Pilot tests revealed adoption hurdles, as drivers accustomed to familiar routes questioned the AI's suggestions, highlighting the human element in tech deployment. Scaling across 55,000 vehicles demanded robust infrastructure and data handling for billions of data points daily.

Lösung

UPS developed ORION (On-Road Integrated Optimization and Navigation), an AI-powered system blending operations research for mathematical optimization with machine learning for predictive analytics on traffic, weather, and delivery patterns. It dynamically recalculates routes in real-time, considering package destinations, vehicle capacity, right/left turn efficiencies, and stop sequences to minimize miles and time. The solution evolved from static planning to dynamic routing upgrades, incorporating agentic AI for autonomous decision-making. Training involved massive datasets from GPS telematics, with continuous ML improvements refining algorithms. Overcoming adoption challenges required driver training programs and gamification incentives, ensuring seamless integration via in-cab displays.

Ergebnisse

  • 100 million miles saved annually
  • $300-400 million cost savings per year
  • 10 million gallons of fuel reduced yearly
  • 100,000 metric tons CO2 emissions cut
  • 2-4 miles shorter routes per driver daily
  • 97% fleet deployment by 2021
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IBM

Technology

In a massive global workforce exceeding 280,000 employees, IBM grappled with high employee turnover rates, particularly among high-performing and top talent. The cost of replacing a single employee—including recruitment, onboarding, and lost productivity—can exceed $4,000-$10,000 per hire, amplifying losses in a competitive tech talent market. Manually identifying at-risk employees was nearly impossible amid vast HR data silos spanning demographics, performance reviews, compensation, job satisfaction surveys, and work-life balance metrics. Traditional HR approaches relied on exit interviews and anecdotal feedback, which were reactive and ineffective for prevention. With attrition rates hovering around industry averages of 10-20% annually, IBM faced annual costs in the hundreds of millions from rehiring and training, compounded by knowledge loss and morale dips in a tight labor market. The challenge intensified as retaining scarce AI and tech skills became critical for IBM's innovation edge.

Lösung

IBM developed a predictive attrition ML model using its Watson AI platform, analyzing 34+ HR variables like age, salary, overtime, job role, performance ratings, and distance from home from an anonymized dataset of 1,470 employees. Algorithms such as logistic regression, decision trees, random forests, and gradient boosting were trained to flag employees with high flight risk, achieving 95% accuracy in identifying those likely to leave within six months. The model integrated with HR systems for real-time scoring, triggering personalized interventions like career coaching, salary adjustments, or flexible work options. This data-driven shift empowered CHROs and managers to act proactively, prioritizing top performers at risk.

Ergebnisse

  • 95% accuracy in predicting employee turnover
  • Processed 1,470+ employee records with 34 variables
  • 93% accuracy benchmark in optimized Extra Trees model
  • Reduced hiring costs by averting high-value attrition
  • Potential annual savings exceeding $300M in retention (reported)
Read case study →

Associated Press (AP)

News Media

In the mid-2010s, the Associated Press (AP) faced significant constraints in its business newsroom due to limited manual resources. With only a handful of journalists dedicated to earnings coverage, AP could produce just around 300 quarterly earnings reports per quarter, primarily focusing on major S&P 500 companies. This manual process was labor-intensive: reporters had to extract data from financial filings, analyze key metrics like revenue, profits, and growth rates, and craft concise narratives under tight deadlines. As the number of publicly traded companies grew, AP struggled to cover smaller firms, leaving vast amounts of market-relevant information unreported. This limitation not only reduced AP's comprehensive market coverage but also tied up journalists on rote tasks, preventing them from pursuing investigative stories or deeper analysis. The pressure of quarterly earnings seasons amplified these issues, with deadlines coinciding across thousands of companies, making scalable reporting impossible without innovation.

Lösung

To address this, AP partnered with Automated Insights in 2014, implementing their Wordsmith NLG platform. Wordsmith uses templated algorithms to transform structured financial data—such as earnings per share, revenue figures, and year-over-year changes—into readable, journalistic prose. Reporters input verified data from sources like Zacks Investment Research, and the AI generates draft stories in seconds, which humans then lightly edit for accuracy and style. The solution involved creating custom NLG templates tailored to AP's style, ensuring stories sounded human-written while adhering to journalistic standards. This hybrid approach—AI for volume, humans for oversight—overcame quality concerns. By 2015, AP announced it would automate the majority of U.S. corporate earnings stories, scaling coverage dramatically without proportional staff increases.

Ergebnisse

  • 14x increase in quarterly earnings stories: 300 to 4,200
  • Coverage expanded to 4,000+ U.S. public companies per quarter
  • Equivalent to freeing time of 20 full-time reporters
  • Stories published in seconds vs. hours manually
  • Zero reported errors in automated stories post-implementation
  • Sustained use expanded to sports, weather, and lottery reports
Read case study →

Best Practices

Successful implementations follow proven patterns. Have a look at our tactical advice to get started.

Centralise and Structure Your Travel & Expense Policy for Claude

Claude’s strength is understanding complex text, but it still needs a well-prepared policy foundation. Start by centralising your travel and expense policy, approval rules, and country-specific guidelines into a single source of truth. Clean up contradictions, outdated sections, and ambiguous language (“reasonable”, “appropriate”) wherever possible.

Then, create a concise “AI-ready” version: bullet points for limits, explicit examples of allowed/not allowed, and clearly marked exceptions (e.g. “CEO exceptions”, “client events”, “emergency travel”). This structured document becomes the core reference Claude uses when evaluating each claim.

Example Claude system prompt snippet:

You are an Expense Policy Assistant for the Finance department.
You receive:
1) An excerpt of the Travel & Expense Policy
2) A list of expense line items

For each line item:
- Decide: COMPLIANT, NEEDS_JUSTIFICATION, or OUT_OF_POLICY
- Quote the exact policy section(s) that apply
- Explain your reasoning in 2-3 short sentences
- Suggest a compliant alternative if OUT_OF_POLICY

Expected outcome: Claude’s decisions become traceable back to specific policy clauses, which is critical for transparency with employees and auditors.

Build an Automated Review Workflow Around Expense Exports

Most finance teams can export expenses from their ERP or expense management tool (e.g. CSV with employee, cost centre, category, amount, date, notes). Use this export as the input for a Claude-powered batch review that runs on a set schedule (daily or after each expense run).

Design a small service or script that chunks the export into manageable batches (e.g. 100–200 line items), sends them to Claude with the relevant policy excerpt, and stores the results (status, explanation, recommended action) in a database or back into the ERP via API.

Example Claude request payload structure:

{
  "policy_sections": "[...consolidated relevant policy text...]",
  "expenses": [
    {
      "id": "EXP-10239",
      "employee_level": "Senior Manager",
      "country": "DE",
      "category": "Hotel",
      "amount": 230.00,
      "currency": "EUR",
      "city": "Berlin",
      "notes": "Conference hotel, booked last minute"
    },
    ...
  ]
}

Expected outcome: Finance receives a structured exception list with clear rationales instead of having to scan raw spreadsheets row by row.

Use Claude at the Point of Submission to Prevent Issues Early

While batch reviews are useful, the most effective control is prevention. Integrate Claude into your expense submission flow so that employees see potential out-of-policy issues in real time, before they hit approval.

A simple approach is to call Claude when an employee submits or edits a claim. Provide the expense details, employee role, and destination, plus the relevant policy section. Display Claude’s feedback in the UI: “This meal exceeds the per diem for Paris by 18€” plus suggestions (“Split between two employees”, “Change category to Client Entertainment with attached agenda”).

Example prompt for submission-time check:

You are assisting an employee submitting expenses. 
Given the policy and this expense, answer in JSON:
{
  "status": "COMPLIANT | WARNING | OUT_OF_POLICY",
  "summary": "Short explanation in user-friendly language",
  "required_action": "Any documents or changes needed",
  "policy_reference": "Section/paragraph"
}

Expected outcome: fewer out-of-policy submissions, less back-and-forth between employees, managers, and finance, and faster reimbursement cycles.

Classify Exceptions and Route Them to the Right Owner

Not every exception should land on the same finance inbox. Use Claude to categorise exceptions based on risk and required expertise. For example: “Minor limit exceedance”, “Missing documentation”, “Possible duplicate”, “Potential fraud/suspicious pattern”, “Subscription or recurring charge”.

Extend your prompt so that Claude assigns a risk-based category and a suggested routing target. Combine this with rules in your workflow tool (e.g. ticketing or ERP) so that documentation issues go to a shared finance queue, but suspected fraud routes directly to a designated controller or internal audit.

Prompt extension for exception routing:

For any NON-COMPLIANT item, add:
"exception_type": one of ["LIMIT_EXCEEDED", "MISSING_DOCS", "DUPLICATE_RISK", "SUSPICIOUS_PATTERN"],
"recommended_owner": one of ["FINANCE_ANALYST", "PEOPLE_MANAGER", "INTERNAL_AUDIT"]

Expected outcome: faster handling of real risks, and less time spent by senior staff triaging low-risk exceptions.

Analyse Expense Narratives and Attachments with Claude

Many crucial details live in free-text fields (“client dinner after workshop ran late”) or in attached documents (invitations, agendas, approvals). Traditional tools often ignore this nuance. Use Claude to read and interpret notes and documents alongside structured data.

For each expense line, pass the description text and, where possible, OCR’d content from receipts or attached approvals. Ask Claude whether the justification supports an exception (e.g. client request, emergency, no alternatives), and whether the documentation seems sufficient based on your policy.

Example prompt for narrative & attachment analysis:

For this expense, consider the description and receipt text. 
Answer:
- Is the justification consistent with a valid exception in the policy? (YES/NO)
- Is the level of detail sufficient? (YES/NO)
- What additional documentation, if any, should be requested?

Expected outcome: more consistent handling of exceptions, fewer missing documents, and stronger audit trails without adding manual review steps.

Define Metrics and Dashboards to Track Impact

To prove value, instrument your Claude-based control with clear KPIs. Typical metrics include: percentage of expenses flagged, breakdown by category and entity, average time from submission to approval, savings from reduced out-of-policy spend, and false positive rate (flags that finance later deems acceptable).

Export Claude’s decisions and explanations into your BI tool and build a dedicated expense compliance dashboard. Over time, this will highlight where policy may be unrealistic (e.g. persistent small overages in certain cities) or where specific teams need targeted training.

Expected outcome: realistic improvements such as a 20–40% reduction in non-compliant spend in focus categories within 6–12 months, a meaningful cut in manual line-item checks, and faster, more predictable reimbursement cycles – without sacrificing control or employee experience.

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Frequently Asked Questions

Claude evaluates each expense line item against your travel and expense policy and approval rules. It can read limits, exceptions, and per diems, then apply them to real data like amount, location, employee level, and description text.

For every claim, Claude can output a status (compliant, needs justification, out-of-policy), a short explanation, and the exact policy sections it used. This makes its decisions transparent for employees, managers, finance, and auditors.

You typically need three ingredients: a reasonably up-to-date expense policy document, access to your expense data exports or APIs, and someone from finance who understands current approval flows and edge cases. Technical integration can start small (e.g. file-based exports and imports) and mature over time.

Reruption usually begins with a short scoping phase to understand your policy structure, systems (ERP/expense tool), and risk appetite, then designs a Claude-based workflow that fits into your existing processes rather than forcing a complete overhaul.

Most organisations can run a focused proof of concept within a few weeks and start seeing value in a single category such as travel or hotels. Once the first workflow is tuned, extending it to other expense types is much faster.

Realistic outcomes include: significantly fewer late-stage rejections, measurable reductions in out-of-policy spend in targeted categories, and a noticeable drop in manual line-item reviews for finance teams. Many finance leaders also report clearer visibility into cost drivers and more constructive conversations with employees about policy design.

The direct usage cost of Claude is driven by the volume of expenses you process and how often you run checks (e.g. real time vs. daily batches). In most finance environments, the cost per reviewed expense is low compared to the time saved in manual review and the savings from reduced non-compliant spend.

ROI typically comes from three areas: avoided out-of-policy spend, reduced reviewer workload, and fewer employee disputes. Ongoing maintenance mainly involves updating prompts and policy references when your rules change, plus periodic tuning based on false positive/negative rates – tasks that can be scheduled into your regular finance control reviews.

Reruption supports clients end-to-end, from idea to working solution. With our AI PoC offering (9,900€), we first validate that Claude can reliably interpret your specific policies and expense data. This includes use-case definition, feasibility checks, a working prototype, and clear performance metrics.

From there, we apply our Co-Preneur approach: we embed with your finance and IT teams, design the workflow around your existing ERP/expense systems, and engineer the automations, prompts, and monitoring needed for production use. The goal is not just a demo, but a tangible expense control capability that lives inside your organisation and evolves with your policies.

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