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TheinStartsandisgoingaByDavidLipman,ChristopherPerry,andGrantKiefferCopyright©2026Bain&Company,Inc.Allrightsreserved.AtaGlanceSoftwaredealmakinglimpedalonginearly2026asslowedrevenuegrowthandthethreatofAIdroveawedgebetweenbuyersandsellers.Butamidthetumult,patternsareemergingthatsuggesthowgeneralpartnersandtheirportfoliocompaniescannavigatethroughtheuncertainty.ManagingboththeriskandopportunityposedbyAIboilsdowntorethinkingduediligenceandvalue-creationplaybooks,whileretoolingmetricstovalidatesuccess.Ifinvestinghasanythingequitysofarin2026,itisthedisquietingcertaintythatthehasthatwasrunningaround20%annuallyistrendingathalfthat.(NRR)hasabout8pointssince2021(seeFigure1).DealmakingisataAgingaresuddenlyathingininvesting.loomingeverythingelseisthespecterofartificialintelligence,which,atbest,threatenstheonce-unassailableSaaSvalueand,atraisesfearsthatsomeusecasesareveeringobsolescence.Perhapsmostominousisthebuildingevidencethatislosingthestructuraladvantagesthatadecadetheshiniestreturns.Theassetsthataretransactinginthemarketscontinueattracthighprices,becausefocusedtheireffortssellingtheircompanies.dealsafterthepandemic,includingseasonedinvestments20202022,are,date,generatingreturnspre-Covid(seeFigure2).Whilemanyoftheseinvestmentsarenotfullyrealized,andperformancecouldtime,thatwillbeachallengethehighpricespaidassetsandthesector’sslowinggrowth.Whatcomesnext?Whilealotamidsafethatlivingthroughtheatmospherethatattendsanyperiodoftechnologicaldisruption.(thedot-comandtheshiftcloudcomputingmind)isthatwinningbusinesswillemergethechaos,andthewinnerswillallsomethinginadeepunderstandingofneedsandaclearvisiontheemergingcanthosewitheconomics.Figure1:Softwaresectorgrowthhasmoderatedsignificantly,andnetrevenueretentionisindeclineNotes:2025revenuegrowthdataasofFebruary2,2026;last12monthsrevenueusedfor2025ifQ4reportingunreleased;differentcompanysetsperyear;includesfirmswithSoftware(Primary)asindustryclassificationandmorethan$50millioninrevenueinthegivenyear;fornetrevenueretention,n=85;excludesanycompany/quartercombinationswithoutavailabledataSources:S&PMarketIntelligence;AlphaSenseFigure2:Itwillbechallengingforpostpandemictechbuyoutstoachievereturnsinlinewiththepriordecade,givenhighpricespaidandless-certaingrowthNotes:Includesfullyrealizeddealsanddealsthathaverealizedatleast25%oftheirreturns;includesalldealsizes;allfiguresinUSDSource:SPIbyStepStone(April2026)themoment,aboutimpacttradeoffalmostdailywithreportsthatcompaniesareseeingreturnstheirAIinvestments.Bid-asksomecategoriesmightasAIusecasesandbusinessbeginout.ButinmostcategoriesareessentiallyupgrabsrightThebiggestissueisthattheAIpaniesarestillinmode,searchingmeaningfullyAIsatisfyneeds(orwhattheymightneedsoon).againstthispatternsareemergingthatsuggestaofpracticalactionsequitycantakerightpressingenoughaboutdisruptiveinfact,startmakingno-regretsshiftsinphaseofthePEvaluegeneralpartners(GPs)aretakingstepsto:pragmaticallyreorientduediligenceunderwriteAIrisksandopportunities;value-creationinAIcanofferingsthroughadeeperunderstandingofandbankablemarshalingdataandmetricsthatcanthenextwithAIpoints,notjustnarrativesThenewduediligenceimperativeInthedecadesosincethesubscriptionsoftware,boostingvaluehasbeenallaboutmaximizingrecurringcamesteadilyasaddedseats,chargedfeatures,andcross-soldproducts.noeachdollarofinlargeparttheline.aSaaSwasestablishedwithathedeepenedintoamoatasbecameembedded,usershabitsaroundit,anddataaccumulatedwithintheAIischangingallthat.Thesejustthreatensomeallowingcompaniesswimacrossthosemoats(thinkserviceAIalsodifferenteconomics.ThecalculationsAIaddsubstantialcostwhichbasednotseatsbutactualusageandresults.Thatshrinksmarginsand,atleast,makesuncertain.TheisthattraditionalSaaSsignalsareincreasinglymisleadinginduediligence.multiples,annualrecurring(ARR),andNRRvaluewhenmoatsandmarginsstructurallyhigh.Buttheandisflattening,andtraditionalunderwritingfullycapturingtheelementsthatwillhelpwhichassetsareequippedinalandscapeAI.Diligenceinthisenvironmenthasstartwithanassessmentofthings:canAIimpacttheuserthesupports,andriskistherethatAIcoulddisplacethealtogetherwithinthoseStresstestingsincemoats,moats,anddatamoatseachunderdifferentdegreesofAI.diligencewillalsoupside:istheitself?IsitAIinternallyefficiency?IsitgainingtractionwithAItheside,eitheraddinglaunchingthatTheisevidence:ThemarketisbifurcatingcompaniesthatcanAItractionandthosethatarestillspinningawithoutbehindit.Indiligence,thequestionisnolonger“DotheyhaveanAIstrategy?”but“Cantheyshowmetheproofpoints?”AItransformationduringownershipAIinternallyefficiencyandisbecomingstakesanyinyourotherwise.Thetrulyinflectperformancestillsomeexperimentationandfaithinthebutstandingstillanoption.ThequestionisthegenerateAI-basedrevenue—andscalemeaningfulatspeed.Thatcanbeatallanincumbentusedoptimizingatraditionalseat-basedespeciallyallthedailyrequirementsofmanagingthecorebusiness.Thecompaniesseeingthemostsuccesstendalight-bulbmomentwhentheyrecognizethathelpinghumansdotasksfasterwithincrementalenhancementsisincreasinglymissingthepointinanAIIfanagenticinstance,canactuallymanageaendend,thegoalshouldbeenablingastepchangeinoutcomes,notjustuserThatmeansturningthetraditionalitshead.InsteadoffocusingusediscretewithinthemostcompaniesarelookingconnectthedotsacrosstheentireTheyaregoingdeeptheandtheircanberebuiltthatoutcome—sometimesfreeinguppursuits,sometimesthemZendesk,theservicethetippingpointarrivedacoupleofagowhenitbecameobviousthatmostinquiriesbeinghandledservicerepscouldbeusingAI.AddingAItheexistingmightspeeduphumaninteractionalimiteddegree.ButZendeskitselfoftheservicecouldbeandthewasclear:ItneededrebuildanAI-basedsortqueries,surfaceenterprise-wideknowledge,andacrosstheallatspeedsandaccuracyneverbeforepossible.Thequestionisnolonger“DotheyanAIbuttheyshowmetheproofpoints?”theAIcapabilitiesfastenoughposedamajorchallengeathatstillneededmaintainandservicealargeinstalledbase.Theastringoftargetedacquisitionsthatwouldexpertiseineverythingandqualitymanagemententerprisesearchandanalytics.DialingupthespeedalsorefocusingthesothatthanhalfthewasAI,uplessthan10%just15monthsearlier.Thatanervypruneinitiatives,collapsekillbetsthatnolongerstrategic,andotherwisethepainfultrade-offsneededupTheresultsbeenInroughly18months,Zendesk$200millioninARRAI,with20,000AIandnearly800millionAIinteractionsin2025.ThelessonisthatAIisnotagameofincrementalism.Capturingthestartswithzero-basingandreimaginingpossible.Thebearebuild.ButneeddecidecantakeoutcomesamatchingAIadeeperunderstandingoftheneedassesswhatthatwillintermsofaddingtalentandmakingorganizationalchangesrapidProvingitnosurprisethatGPsandtheirmanagementteamsareexpendingbandwidthAIandproducts.Butnotspendingenoughenergythemeansandmeasureimpactwithdata.Thathelpsexplainthewidegapinvalueexpectationsoftenseeingandsellers.BecausethetraditionalSaaSKPIstack(ARR,NRR,andgrossmargin)wasbuiltforadifferentvalue(aofnear-zeromarginalcost,seat-drivenexpansion,andretention),itfailsAIimpactARR,instance,isagreatmeasureofthesubscriptionseats.ButAIispricedactualusageandoutcomes,whichcanbeburstypaniestrytop-lineimpactbreakingoutacategorycalledButthattheanythanthe“cloud-associateddidadozenago.Understandingthetrueperformanceofthesetrackingatleastthreedistinctbuckets:traditionalAIandmachinelearningmodels,riskscores),AIadd-ons(copilots,assistantfeatures),andagenticexecution).Eachhasadistinctmarginprofile,anddynamics.Ifanagenticsystemcanactuallymanageaworkflowtoend,thegoalshouldbeenablingastepchangeinmeasurableoutcomes,notjustuserThecostside,isverydifferent.AIsignificantvariablecostsperusethatexisttraditionalSaaSAfullunderstandingofwhatspendingtrackinghostingandinfrastructurecosts,third-partycosts,andthefullyloadedcostofeachinfullinpartThelineisthatifchangeyourmetrics,AIimpact.TheandcostsdirectlyattributableAIfirstneedbeseparatedthebusinessandthenintotheirconstituentparts.Withoutthat,withthethreeessentialquestionsmind:IsAIdrivingincrementalIsAIchangingcoststructures?arescalingefficiently?ArmedwithfirmcompaniescannotdesignthebestandallocateresourcesbutGPscanstartbuildingthekindofevidence-basedexitaredemanding.AsandduediligenceprocessesAI-speci
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