WAY Investor Day 2026 Presentation

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2 2WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. FORWARD-LOOKING STATEMENTSThis presentation contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995, including statements regarding Waystar’s expectations relating to future operating results, financial position, long-term financial targets, growth expectations, anticipated future investments, our industry, business strategy, goals, and expectations, capital allocation priorities, AI development and adoption, including the pace, scope, and commercial impact of our AI-powered and autonomous revenue cycle initiatives; our market position, total addressable market estimates, and profitability. This presentation also contains long-term financial targets and objectives, including expectations regarding revenue growth rates, Adjusted EBITDA margins, client retention rates, cross-sell contribution, pricing, utilization, free cash flow generation, and capital return programs. These targets and objectives are forward-looking statements and are based on management’s current expectations and assumptions, which may not be achieved. Forward-looking statements include all statements that are not historical facts and may be identified by words such as “anticipate,” “assume,” “believe,” “continue,” “could,” “estimate,” “expect,” “intend,” “may,” “plan,” “potential,” “predict,” “project,” “future,” “will,” “seek,” “foreseeable,” “outlook,” “target,” “goal,” “opportunity,” “vision,” the negative version of these words or similar terms. The forward-looking statements contained in this presentation are based on management’s current expectations, are not guarantees of future performance, and are subject to risks, uncertainties, and changes in circumstances that are difficult to predict or quantify. Our expectations, beliefs, and projections are expressed in good faith, and we believe there is a reasonable basis for them. However, there can be no assurance that management’s expectations, beliefs, and projections will result or be achieved. Actual results may differ materially from those indicated by these forward-looking statements as a result of factors including those discussed under the heading of “Risk Factors” in the Company’s most recent Annual Report on Form 10-K and Quarterly Reports on Form 10-Q filed with the Securities and Exchange Commission (the “SEC”), and in other reports filed with the SEC, all of which are available at investors.waystar.com. Forward-looking statements made by us in this presentation speak only as of the date of this presentation and are expressly qualified in their entirety by the cautionary statements included in this presentation. Factors or events that could cause our actual results to differ may emerge from time to time, and it is not possible for us to predict all of them. You should not place undue reliance on our forward-looking statements. We undertake no obligation to publicly update or review any forward-looking statement, whether as a result of new information, future developments, or otherwise, except as may be required by any applicable securities laws.This presentation includes certain non-GAAP financial measures, including Adjusted EBITDA, Adjusted EBITDA margin, and free cash flow. These non-GAAP financial measures are presented in addition to, and not as a substitute for or superior to, measures of financial performance prepared in accordance with U.S. generally accepted accounting principles (“GAAP”). There are limitations associated with the use of non-GAAP financial measures, including that other companies may calculate similarly titled measures differently. We encourage you to review the reconciliation of these non-GAAP financial measures to their most directly comparable GAAP measures, which can be found in our most recent Annual Report on Form 10-K and Quarterly Reports on Form 10-Q filed with the SEC, and in other reports filed with the SEC, all of which are available at investors.waystar.com. This presentation includes forward-looking non-GAAP financial measures, including long-term Adjusted EBITDA margin and free cash flow targets. We have not reconciled these forward-looking non-GAAP measures to their most directly comparable GAAP measures because certain items that impact these measures are uncertain or out of our control and cannot be reasonably predicted, including but not limited to stock-based compensation expense, acquisition-related costs, capital expenditures, and certain other non-recurring items. Accordingly, a reconciliation of these forward-looking non-GAAP financial measures is not available without unreasonable effort, and we are unable to address the probable significance of the unavailable information. You should consider the limitations of these forward-looking non-GAAP financial measures and not place undue reliance on them.This presentation contains estimates and other statistical data made by independent parties and by us relating to market size, growth, and other data about our industry. This data involves a number of assumptions and limitations, is subject to risks and uncertainties, and is subject to change based on various factors, including those discussed above. You are cautioned not to give undue weight to such estimates.This presentation is for informational purposes only and does not constitute an offer to sell, or a solicitation of an offer to buy, any securities of Waystar Holding Corp. or any of its affiliates. No representation or warranty, express or implied, is made as to the accuracy or completeness of the information contained herein. © 2026 Waystar. All rights reserved.

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3 WAYSTAR INVESTOR DAY 2026 How our platform, data, and AI advantage drive durable growth Break following the client panel | Reception + dinner to follow Purpose-Built for This Moment: Advancing the Future of the Revenue CycleMatt Hawkins, Chief Executive OfficerFrom Intelligence to Action: The Waystar Platform AdvantageWilliam Chan,Chief Product + AI OfficerBrendan O’Connor,EVP, Product ManagementSean Joyce,SVP, Engineering The Waystar Go-to-Market EngineTodd Woods, Chief Commercial Officer Q+AWaystar leadership team Waystar Innovation LabLive product experience Client Panel: Real Revenue Cycle Impact Lisa Osborne, SVP, Product MarketingMODERATED BY 1 2 3 4 5 6 © 2026 Waystar. All rights reserved. Today’s agenda

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 5© 2026 Waystar. All rights reserved. A community built on results, partnership + innovationWAYSTAR TRUE NORTH™ 98%ofclientssaywedeliverontrust1 #1rank in product innovation + vision1 #1rank in client satisfaction1 74Waystar Net Promoter Score1 1ThirdPartyProviderSatisfactionSurvey,September2023 © 2026 Waystar. All rights reserved.

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 8© 2026 Waystar. All rights reserved. The journey to increasing shareholder value THE RIGHT MARKETLarge, growing market with rising demand for automation THE RIGHT PLATFORM + TEAMDifferentiated platform + commercial scale to drive durable growth THE RIGHTVISIONForging the path to an autonomous revenue cycle

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9 9WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. WAYSTAR TODAY 1M+providers¹ 30K+clients¹ 60%of U.S. patients¹1 in 3U.S. hospital discharges¹ 7.5B+annual healthcare payment transactions¹$2.4T+annual gross claims¹ HEALTHCARE IS PRIMED FOR TRANSFORMATIONLarge market, sustained growth, and accelerating automation demand A DIFFERENTIATED PLATFORM BUILT TO LEADPurpose-built platform, expansive data, and deep domain expertise MULTIPLE LEVERS TO DRIVE DURABLE GROWTHProduct innovation, client expansion, anddisciplined execution A PROVEN MODEL THAT COMBINES GROWTH + PROFITABILITYDouble-digit revenue growth and approximately 40% adjusted EBITDA margin1 1Waystar data2Represents long-term targets. See forward-looking statements and non-GAAP disclosures on slide 2

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 10© 2026 Waystar. All rights reserved. Revenue cycle pressure is intensifying © 2026 Waystar. All rights reserved. 1Third party market study, figures represent median values (2026) 2Centers for Medicare & Medicaid Services (2024) 3CAQH (2024) 4Sage (2024) 5American Hospital Association (2026 ) 6HFMA (2023) 7Kodiak Solutions (2024) 8Centers for Medicare & Medicaid Services (2023)

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 11© 2026 Waystar. All rights reserved. Substantial market opportunity with long-term growth runway 2Includes additional spend for payment processing and incremental claims management 1Independent third-party market study (2026) commissioned by Waystar, based on estimated U.S. provider spending on RCM software solutions. Not a forecast of company revenue. $103.3Btotal U.S. healthcare RCM spend1 Waystar RCM market opportunity $44.1BWaystar Segment TAM Services + Software1 $21.0Btotal addressable RCM software1,2 © 2026 Waystar. All rights reserved.

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 12© 2026 Waystar. All rights reserved. © 2026 Waystar. All rights reserved. $103.3Btotal U.S. healthcare RCM spend1 Waystar RCM market opportunity $44.1BWaystar Segment TAM Services + Software1 $21.0Btotal addressable RCM software1,2 Substantial market opportunity with long-term growth runway 2Includes additional spend for payment processing and incremental claims management 1Independent third-party market study (2026) commissioned by Waystar, based on estimated U.S. provider spending on RCM software solutions. Not a forecast of company revenue.

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 13© 2026 Waystar. All rights reserved. Unmatched visibility drives better outcomes + durable advantage EligibilitycheckPatient costestimationPrior authorizationCo-pay collection Claim submissionClaimmonitoringPatient paymentDenial +appealPayerremittance Utilization managementClinical documentationintegrityRevenue capture WAYSTAR PLATFORM CONNECTS CRITICAL WORKFLOWS © 2026 Waystar. All rights reserved.

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 15© 2026 Waystar. All rights reserved. The next era of the revenue cycle is autonomousRIGHT AI. RIGHT MOMENT. Digitize, connect + standardize workflowsWorkflow enablementHISTORICAL Predict, prevent, prioritize + assist inside the workflowIntelligent automationTODAY Execute, adapt + resolve autonomously across the workflowAutonomous revenue cycleFUTURE Manually coordinated High human touch Reactive Statically configured FTE-constrainedworkforce Autonomously orchestrated Self-optimizing Highlyautomated Self-diagnosing 24/7 agent-led workforce

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 14© 2026 Waystar. All rights reserved.TRACEABLE, COMPLIANT, ADAPTABLE EXECUTED BY SPECIALIZED AGENTS INTELLIGENTLY ORCHESTRATED CONTINUOUSLY CREATING INTELLIGENCE + INSIGHTS POWERED BY CLIENT + WAYSTAR PROPRIETARY DATA The autonomous revenue cycle of the future is…

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 16© 2026 Waystar. All rights reserved. Durable growth + profitability create financial capacity © 2026 Waystar. All rights reserved. FINANCIAL CAPACITY CAPITAL AVAILABLE TOInvest in growthStrengthen the balance sheetReturn capital to shareholders Free cash flowgeneration TARGET FINANCIAL MODEL 40%+Adjusted EBITDA margin RULE OF 50 PERFORMANCE Low double-digit revenue growth 1DURABLE CLIENT RETENTION 2EXISTING CLIENT CROSS-SELL 3NEW CLIENT CONTRIBUTION4HIGHERUTILIZATION GROWTH ALGORITHM 5ANNUAL PRICE LIFT

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 17© 2026 Waystar. All rights reserved. Disciplined capital allocation supports long-term value creation © 2026 Waystar. All rights reserved. CAPITAL ALLOCATION PRIORITIES ORGANIC INVESTMENTDrive innovation + growth DEBT REDUCTIONStrengthen the balance sheet SHARE REPURCHASESActive capital return program DISCIPLINED M+AStrategic fit + value creationDIVIDENDSReturn capital when appropriate

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18 18WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS How Waystar creates + compounds valueTODAY’S AGENDA © 2026 Waystar. All rights reserved. How Waystar uses data + AI to strengthen its platform + power the autonomous revenue cycle Product + technology How Waystar wins, expands + turns platform adoption into durable growth Go-to-market How Waystar delivers measurable value + stronger outcomes —directly from the clients achieving them Client outcomesAn opportunity to dive deeper with an open forum for Q+A Q+A

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21 21WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. BACK-ENDAfter the encounterClaim + Payer Payment ManagementClaim management + monitoringRemittance +reconciliation Patient statementPost-service paymentsPatient Financial Care Denial + appeal managementRecoupment managementDenial Recovery One platform. Powerful AI. Proven results.WAYSTAR END-TO-END PLATFORM One Al-powered platform connects patient access, clinical intelligence, and reimbursement workflows © 2026 Waystar. All rights reserved. Analytics + reporting+Real-time visibilityacross the enterprise+Actionable insightsthat drive results+Benchmarks andbest practice KPIs FRONT-ENDBefore the encounterFinancial Clearance Patient Financial Care Coverage verificationPrior authorization Pre-service paymentsAffordability + propensity to pay MID-CYCLEDuring the encounterClinical Integrity + Revenue CaptureUtilization management Clinical integrity Revenue integrity

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 22© 2026 Waystar. All rights reserved. The foundation powering the next era of the revenue cycleWAYSTAR PLATFORM Best-of-breed platform breadth drove scale adoption, creating the proprietary network, data, and workflow integration that now power agentic automation and outcomes at scale Mission-critical InfrastructureFOUNDATIONAL PILLARS STRATEGIC UNLOCK POWERFUL OBJECTIVESOperate as clients' system of action for healthcare revenue cycle Deploy the right AI at the right time for every use caseRedeploy provider staff to focus on higher-impact priorities Create conditions for autonomous revenue cycle to be realized Unmatched Proprietary DataExtensively Deployed NetworkDeep Domain ExpertiseSeamlessly embedded in workflowsAPI-based capabilities + AI agents take corrective action on mission-critical workflows in real time Self-learning expands solution pipelineUnique combination of intelligence to unleash new products + market opportunities LLM-agnostic frameworkFlexibility enables continuous deployment of best-in-class frontier models Collaborating with AI hyperscalersMulti-year partnership with Google Cloud + more innovators engagement © 2026 Waystar. All rights reserved.

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 23© 2026 Waystar. All rights reserved. Extensively deployed network advantageBROAD CONNECTIVITY Waystar’s scaled payer network creates a continuously refreshed proprietary data asset, while deep EHR connectivity embeds that intelligence directly into provider workflows — enabling smarter automation and preventive action EXPANSIVE PAYER DATA CONNECTIONS Payer × workflow depth keeps intelligence current as adjudication behavior changes. EXPANSIVE EHR + PM INTEGRATION EHR native workflowSeamless integrationData + intelligence enrichment Deep integrations500+key integrations More connections → more payer-specific signals → smarter automation Connectivity creates a proprietary data asset © 2026 Waystar. All rights reserved. 5K+payersyears of data15+

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24 24WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Extensive proprietary dataBROAD CONNECTIVITY Breadth across care settings and geographies gives Waystar comprehensive visibility to identify patterns, act earlier, and unlock greater value Data assets from 30K providers across all settings of care unlock hard-to-replicate insights¹ SETTINGS OF CARE AcuteEmergency + urgent careAmbulatoryPost-acute Long-termHome-basedBehavioral healthRetail VirtualSpecialized1 in 3U.S. hospital discharges¹ 60%of U.S. patients¹ 7.5B+annual healthcare payment transactions¹© 2026 Waystar. All rights reserved. 1 Waystar data 2026

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 25© 2026 Waystar. All rights reserved. A four-layer intelligent agentic stack, powered by a shared data + product foundation Agent groups powered by a unified, platform-wide data layer Execution layer Agentic workflows Orchestration layer Intelligence layer Data sourcesBrings together internal + external data, rules, and policies that power every layer Routes + sequences work across agent workflows calling upon the 'next best action' Combines data, ontology + semantics to evaluate performance + inform where to act Claim rule librariesProvider contractsClaims + transactional dataPayer policy rulesClinical dataAdjudication behavior signals Clinical Integrity + Rev CaptureFinancial ClearanceClaim + Payer Payment MgmtDenial RecoveryPatient Financial CareAnalytics + Reporting

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26 26WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS Purpose-built for differentiated AI strategyAI MODEL INFRASTRUCTURE AI FOUNDATION ADVANTAGE Extensive data scale PAYER-SPECIFIC MODEL PORTFOLIO Shared AI model training layerEnables efficiency gains in model development PAYER A MODELPAYER C MODELPAYER B MODEL Sean 15+ years of network growth + shared AI infrastructure enable payer-specific intelligence at scale EXAMPLE•Payer A denies at claim level ~50% of the time•Payer B denies at claim-line level ~90% of the time. Each payer/denial combination is its own classification problem; the system must account for these differences to maintain strongpredictive performanceEach model trains on unique payer patterns and recommends the next best action to the provider MCP-native model interface Scaled, shared infrastructure Payer-specific LLM + ML models Behavioral drift tracking + accelerated retraining © 2026 Waystar. All rights reserved.

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27 27WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS AI is accelerating engineering productivityAI-POWERED PRODUCT DEVELOPMENT More engineering output translates into faster product delivery, accelerating innovation from idea to client impact Faster buildAI agents draft code, APIs, data mappings, and documentationHigher qualityAI expands testing, detects defects earlier, and strengthens release confidence Sharper focusEngineers spend less time on boilerplate and more time on hard product problems More innovationTeams can test more ideas, learn faster, and scale what works ENGINEER PRODUCTIVITY RECOUPMENT MANAGER LAUNCHCase study example commits per engineer1code per commit115%+output per engineer11.8x © 2026 Waystar. All rights reserved. time savings for providers180%Unlocks meaningful client outcomes faster product development cycle1from 14 months to under 62.4xAccelerate development time1.6x 1 Waystar data 2026

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28 28WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Brendan How our roadmap is leveraging this advantageNEAR-TERM INNOVATIONS Prioritizing high-impact workflow automation opportunities that drive cleaner claims, faster payments + fewer denials FRONT-ENDFinancial clearance + paymentsMID-CYCLEClinical integrity + revenue captureBACK-ENDRevenue recovery + realization ROADMAP EXAMPLES Omnichannel billing agent for data-driven patient payment interactions powered by AltitudeAI Automated Medicaid eligibility monitoring + redetermination verification Coding agent for CDI reviewers closes the gap between coding +documentation workflows Enable faster ED status decisions with predictive patient trajectory insights Visualize ROI in real-time with conversational analytics powered by AltitudeAI Auto claim resubmission to accelerate reimbursement + reduce downstream denials Claim rejection + denial prediction powered by AltitudeAI that uncover missing information prior to submission © 2026 Waystar. All rights reserved.

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29 29WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. WaystarAltitudeAI enables monetization expansion AltitudeAI drives greater platform monetization by deepening client value, expanding share of wallet, and enabling new product adjacencies SHARE OF WALLET EXPANSION CATEGORY CREATIONPREBILL ANOMALY DETECTION Monetization: Performance-based pricing RECOUPMENT MANAGERMonetization: Subscription-based pricing aligned to value generated AUTO COVERAGE DETECTIONMonetization: Increased transaction volume + higher priced premium SKU PERSONALIZED PATIENT DISCOUNTSMonetization: Increased transaction volume 1For users of this capability 2Model estimations. Actual results will vary. 3Waystar client results. Actual results will vary. 20%+increase in coverage detection transactions1 50%increase expected in applicable collections2 $3.7Midentified per 10k discharges3 80%reconciliation time savings3 © 2026 Waystar. All rights reserved.

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WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS 30© 2026 Waystar. All rights reserved. Launchpad for the future of healthcare revenue cycleVISION As autonomy increases, so does the opportunity to transform both provider economics and Waystar’s growth modelVALUE + AUTONOMY TIME 1TODAY+Predictive, generative, and agentic AI+Dependent on manual touchpoints 2AGENTIC LAUNCHPAD+Deploy agents across high-value workflows+Connect agent workflows and data sets+Shift to agent-led model 3AUTONOMOUS REVENUE OPERATIONS+Agents orchestrate workflows end-to-end+Disrupt labor-intensive business models+Outcome-oriented monetization © 2026 Waystar. All rights reserved.

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33WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. A broad market with common buying prioritiesOUR MARKET Healthcare organizations vary in size and complexity, yet their core challenges and desired outcomes remain consistentWHO WE SERVEAcute care Ambulatory careMedical specialties + ancillary carePost-acute + home-based care Healthcare support orgsPatients WHO BUYSFinancial leadershipOperational leadershipIT leadershipClinical leadership COMMON BUYING PRIORITIES Lower cost-to-collectAccelerated + increased reimbursementFewer denials + underpaymentsEnhanced cybersecurityImproved staff efficiency + productivityIncreased patient financial clarity © 2026 Waystar. All rights reserved.

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34 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Patient hurts knee falling down the stairs Administrator manages claim, denial, and collection Provider sees patient and renders service FRONT-END MID-CYCLEBACK-END The challenge of the healthcare revenue cycleA COMPLEX SERIES OF INTERACTIONS Every step of a patient’s journey requires multiple processes to be executed flawlessly for the provider to be paid for the care they delivered EligibilitycheckPatient costestimationPrior authorizationCo-pay collection Claim submissionClaimmonitoringPatient paymentDenial +appealPayerremittance Utilization managementClinical documentationintegrityRevenue capture PAIN POINTS•Insurance coverage shifts•Prior authorization demands•Patient estimate confusion•Pre-service collection challenges •Clinical documentation requirements•Coding complexity•Revenue leakage•Clinical denial risk •Claim errors and rejections•Denial appeal challenges•AR follow-up burdens•Payment delays

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35 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Activates revenue cycle workflows with financial, clinical, and administrative intelligenceData in Insights + actions Actions + transactions Responses + outcomes Waystar is the system of action for the revenue cycleEHRs record the care journey — Waystar uses that data to activate workflows across providers, payers, and patients, driving reimbursement and efficiency SYSTEMS OF RECORD Capture and maintainpatient and clinical records 500+ EHRs, PMs, HISintegrations CONNECTION NETWORKSYSTEM OF ACTION Providers + revenue cycle teamsPatients + payment gateways 5K+ Payer connections © 2026 Waystar. All rights reserved. BEFORE CAREDURING THE ENCOUNTERAFTER THE ENCOUNTER Improved staff efficiencyReduced denials + underpaymentsFast + accurate reimbursementLower cost-to-collect Turning data into action to drive:

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36 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Performing across a fragmented landscapeOUR RIGHT TO WIN Solving end-to-end revenue cycle challenges, providing clients with a comprehensive platform driving meaningful outcomes 1 Bain & Company, 2023 15%YoY growth in clients with $100K+ in LTM revenue3 100%ofhealth systems using an end-to-end RCM platform report positive ROI2 67%of health systems are looking to streamline their tech stack1 2 The Health Management Academy, 20243 Waystar data as reported in 10-Q, July 2026© 2026 Waystar. All rights reserved. 1 – 2 vendors2 – 3 vendors1 – 4 vendors1 – 3 vendors1 – 2 vendors1 – 2 vendors Financial ClearancePatient Financial CareClinical Integrity + Revenue CaptureClaim + Payer Payment ManagementDenial RecoveryAnalytics + Reporting end-to-end software platform Platform clients’ reality prior to Waystar 15+Vendor displacement potential for providers that adopt Waystar’s platform

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37 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Multiple points of entry + clear expansion pathsCOMPLEXITY CREATES OPPORTUNITY Waystar solves for specific pain points throughout the revenue cycle, creating numerous entry points while establishing a foothold for client platform expansionFRONT-ENDMID-CYCLEBACK-ENDCOMMON POINTS OF ENTRYFinancial ClearancePatient Financial CareClinical Integrity Revenue CaptureClaim + Payer Payment ManagementDenial RecoveryPatient Financial Care VALUE CREATEDFewer denials Staff efficiencyFaster patient clearanceReduced leakageAccurate documentationStronger claimsStaff efficiencyDenial recovery COMMON CLIENT EXPANSION PATHS Mid-cycle: Utilization ManagementBack-end: Claim Manager Front-end: AuthorizationsBack-end: Denial + Appeal Management Front-end: Eligibility + Coverage DetectionMid-cycle: Clinical Documentation Integrity © 2026 Waystar. All rights reserved.

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38 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. A purpose-built growth engine combining specialized sales teams, 500+ integrations, and 200+ channel relationships to expand market share EXAMPLE EHRsEXAMPLE CHANNEL PARTNERS EXAMPLE AMBULATORY + SPECIALTY CLIENTSEXAMPLE ACUTE CLIENTSEXAMPLE SERVICE CLIENTS Proven, repeatable growth model 1 Waystar data as reported in 10-K, Feb 2026.2 Waystar data. 108-110% NRR from 2024-2026. See the 10-Q filed July 2026 for definition and reconciliation to GAAP measures. NEW CLIENT ACQUISITIONCLIENT EXPANSION108-110% net revenue retention285%win rate1 Direct | 6-18 month cycleHEALTH SYSTEMS + HOSPITALSDirect | 1-6 month cycleUP-MARKET AMBULATORY + SPECIALTYDirect + channel | 1-3 month cycleHIGH-VELOCITY AMBULATORY + SPECIALTYDirect | 6-18 month cycleBPOs + SERVICES PROVIDERSSpecialized teams with proven playbooks

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39 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Capitalizing on our right to winRECENT WAYSTAR GROWTH CASE STUDIES Academic health system7 hospitals1 in NY6M+ patients per year1 SolutionsFull Waystar platform expansion NEW MODULE ADOPTION Successfully compounding growth across new and existing clients through platform sales, module adoption, and upgrades 1Based on publicly available data, August 20262Represent illustrative examples and are not necessarily representative of results achieved by all clients. Individual client outcomes vary based on organization size, product mix, and implementation scope. Existing client expansion Skilled nursing facilities190+ locations1 across the U.S.15K+ concurrent patient residents1 SolutionsUpgrade to AltitudeAITM capabilities AI OFFERING UPGRADEExisting client expansion 3x5x+ Community health system 2 hospitals1 in NJ + PA150K+ patients per year1 SolutionsFull Waystar platform PLATFORM SALENew client acquisition 7-figureexpected ACV2 increase in ARR2 increase in ARR2 Performance improvementInnovative technologyVendor consolidationPURCHASE DRIVERS

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40WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Scale drives performance + earns the right to winGROWTH THROUGH IMPROVED CLIENT PERFORMANCE Waystar’s growth is self-driving — as more clients send more data, all clients benefit, creating a virtuous cycle of increased client value, client retention, client expansion, and net new client additions #1 RCM platform for trust + satisfaction1 Demonstrable client ROI + financial impactContinued growth in market share + large contracts Waystar delivers value 1 Qualtrics survey, 2025 WAYSTARGROWTHENGINE More clients More data Sharper insightsBetter client outcomes Broader client portfolio Longer client relationships

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WAYSTAR TRUE NORTH™ INVESTOR DAY We'll resume shortlyUp next — Client Panel: Real Revenue Cycle ImpactThe webcast will resume automatically.No need to refresh.

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44WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Waystar Early Adopter ProgramWaystar Advisory BoardClients gain early access to emerging innovations and help validate them through real-world useProminent healthcare organization leaders provide insight that helps guide Waystar platform innovation ~60active healthcare organization members 100%new product launches reviewed by Waystar Early Adopter Clients Innovation shaped by client communityTRUSTED PARTNERSHIP Waystar partners with clients to ensure innovation is practical, trusted, and built for performance impact © 2026 Waystar. All rights reserved.

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45 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Meet today’s speakersWAYSTAR CLIENT PANEL Candice Brown Davis Chief Revenue Cycle Officer LisaGriffin Chief Consumer Officer Chris Kiser Enterprise Vice President Genevieve Sagett Chief Revenue Cycle Officer SteveBurr Senior Vice President, Revenue Cycle LisaOsborne Senior Vice President Product Marketing MODERATORPANELISTS © 2026 Waystar. All rights reserved.

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49 WAYSTAR | SIMPLIFY HEALTHCARE PAYMENTS © 2026 Waystar. All rights reserved. Meet today’s speakersQ+A MattHawkins Chief Executive Officer ToddWoods Chief Consumer Officer WilliamChan Chief Product + AI Officer BrendanO’Connor EVP, ProductManagement SeanJoyce EVP,Engineering Edward Parker SVP, Investor Relations MODERATORPANELISTS © 2026 Waystar. All rights reserved.

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