Airframe
    By Paul Hsiao
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    Airframe·PE-held software·Q2 2026
    PE-held software stack · 2026

    $1.1T: private-equity software financing

    Medallia's lender handover. Eight other PE software deals under pressure.

    Private-equity firms hold $1.1 trillion of enterprise software value. Medallia's equity loss illustrates financing pressures that also affect other deals.

    PE-held value
    $1.1T
    PE-held leaders
    425
    Distressed software loans
    $46.9B
    Named deals on the watchlist
    9
    Medallia's lender handover

    On April 22, 2026, Thoma Bravo handed Medallia to its lenders.

    Similar financing structures apply to roughly a dozen other deals.

    Thoma Bravo took Medallia private in 2021 for $6.4 billion. By April 2026, the equity was worth roughly zero, and senior private credit lenders Blackstone, KKR, Apollo, and Antares owned the company. Thoma Bravo and its co-investors wrote off roughly $5.1 billion. A Payment-in-Kind relief arrangement expired at year-end 2025. It had allowed Medallia to add cash interest to principal; after it expired, the full cash interest bill came due against revenue and EBITDA below the 2021 underwriting assumptions. The capital structure failed while the company continued operating.

    Medallia was the first large example; we expect more. The register contains 425 PE-held software companies with combined enterprise value of $1.1 trillion. Moody's reports roughly $46.9 billion in distressed software loans. Distress is concentrated in Thoma Bravo's portfolio ($183 billion in AUM and 80 active companies) and Vista Equity Partners' portfolio (over $100 billion in AUM). The firms have invested more than $120 billion in software since 2019. Much of that capital entered at 2021 peak multiples, with debt financing up to half the purchase price at near-zero rates.

    Higher rates and slower expansion have weakened the debt assumptions. AI competitors are also reducing the growth that SaaS buyout models relied on.

    We expect those financing pressures to continue for roughly two years.

    Growth of the PE software portfolio

    Why private equity bought software.

    For fifteen years, private equity favored software's predictable recurring revenue, renewal rates above ninety percent, embedded customers, and pricing power. Those properties supported the leverage used to meet target returns.

    Early roll-ups included BMC, Infor, McAfee, and IFS, all founded before 2000 and now valued at $11 billion to $16 billion. SaaS take-privates followed: Anaplan, Avalara, Coupa, Zendesk, Smartsheet, New Relic, Proofpoint, Dayforce, and Splunk before its public-market exit. S&P Global Market Intelligence reports more than 450 annual software acquisitions and over $100 billion in deal value at the 2021 peak. Debt sometimes financed half the transaction. Thoma Bravo's $12.7 billion Dayforce acquisition, completed last year, was nearly half-financed with debt.

    The Airframe register shows where this capital sits now:

    PE cohort · by founding era
    Companies
    Combined value
    Pre-2000 (on-prem and earlier)
    170
    $488B
    2000–2009 (SaaS-era)
    167
    $415B
    2010–2018 (cloud-era)
    110
    $212B
    2019+ (AI-era)
    9
    $29B

    PE exposure includes 272 companies founded between 1985 and 2009, with $727B of value, competing with AI-native challengers. Roughly $730 billion of enterprise value faces the productivity benchmark established over the past three years.

    Financial reporting has followed the "PE software problem" for two years. The financing stress is already evident in a subset of the cohort.

    Figure 03·From total PE-held to first realized write-off · how the exposure cascades
    Source · Airframe register + Moody's + S&P Global · April 2026
    Total PE-held software stack · 2026
    $1.1T425 companies
    Every software vendor held by a private-equity firm in the airframeai/software-50 register.
    ↓ Cohorts the AI wave is most directly repricing
    Exposed cohorts · 1985–2009 vintage
    $727B272 companies
    SaaS-era + on-prem-era vendors, each now competing for the same budget against an AI-native challenger in their category.
    ↓ Financing assumptions under pressure from rates and AI
    Distressed software loans · private credit market
    $46.9BQ1 2026
    Held inside the publicly traded BDCs and the direct-lending market that financed the 2021 vintage.
    ↓ The first equity wipeout
    Realized write-off · Medallia · April 22, 2026
    $5.1BEquity to zero
    Senior lenders (Blackstone · KKR · Apollo · Antares) took the company. Thoma Bravo and co-investors wrote off the equity.
    The figure moves from total PE-held value to exposed cohorts, distressed loans, and the Medallia write-off. In our view, changing buyers and maturing substitutes could produce further write-offs over roughly two years, based on current category-displacement curves.

    Financial reporting has cited $574 billion in exposure for two years. Reconciliation with the full register puts the PE-held value at $1.1 trillion, roughly twice that estimate, alongside $46.9 billion in distressed loans and more than a dozen deals with similar financing structures.

    Our read
    In our view, the financing pressure extends across companies whose customers previously had few alternatives. AI challengers can change a category's productivity economics, requiring incumbents to rebuild products. Medallia's PIK expiration was its immediate trigger; we expect eight to twelve further deals to resolve through similar mechanisms over the next twenty-four months.
    The named deals · 9 capital structures at risk

    The deals on the watchlist.

    Trade reporting in 2026 has identified PE-held software companies whose debt structures depend on growth or refinancing assumptions that current rates and category conditions have weakened. Values below come from the Airframe register; debt and lender details come from S&P Global Market Intelligence, SaaStr, and Octus.

    PE Watchlist · 9 named deals · 2026

    $66 billion of equity-plus-debt exposure, with financing assumptions under pressure from rates and AI competition.

    No. 01

    Medallia

    Customer survey
    Status · 2026
    Equity wiped · April 22, 2026
    Sponsor
    Thoma Bravo
    Take-private
    $6.4B · 2021
    Founded
    2001
    EV · today
    $2.80B

    Senior lenders (Blackstone, KKR, Apollo, Antares) now control the company. Customer survey software, a category directly threatened by AI-native voice-of-customer analytics.

    No. 02

    Proofpoint

    Cybersecurity
    Status · 2026
    Most-watched name in the portfolio
    Sponsor
    Thoma Bravo
    Take-private
    $12.3B · 2021
    Founded
    2002
    EV · today
    $12.3B

    Roughly $4 billion of buyout debt against approximately $150M of adjusted annual EBITDA. Interest coverage that only worked at near-zero rates. Total debt load now around $4.67B after a dividend recap and the Hornetsecurity acquisition. Six of the seven distressed private credit funds hold material exposure to it.

    No. 03

    Coupa

    Procurement
    Status · 2026
    Debt-to-equity ratio ~65/35
    Sponsor
    Thoma Bravo
    Take-private
    $8B · 2022
    Founded
    2006
    EV · today
    $8.00B

    Up to thirty percent of the workforce cut post-acquisition. Procurement and spend management is one of the categories autonomous agents threaten most directly, on the seat-based pricing model the entire LBO underwriting assumed.

    No. 04

    Anaplan

    Planning
    Status · 2026
    Loans near par — for now
    Sponsor
    Thoma Bravo
    Take-private
    $10.7B · 2022
    Founded
    2006
    EV · today
    $10.4B

    Same vintage, same sponsor concentration, same AI-exposed planning category as Coupa. Operationally executing better. The leverage is still in the capital stack.

    No. 05

    Zendesk

    Customer support
    Status · 2026
    ~$4.6–5B private credit
    Sponsor
    Hellman & Friedman + Permira
    Take-private
    $10.2B · 2022
    Founded
    2007
    EV · today
    $10.2B

    Customer support is ground zero for agent replacement of seats. Zendesk's own AI offering is reportedly generating $200M+ in ARR. The open question is whether that grows faster than the legacy seat revenue shrinks.

    No. 06

    Avalara

    Tax compliance
    Status · 2026
    ~$2.5B private credit · Blue Owl
    Sponsor
    Vista Equity Partners
    Take-private
    $8.4B
    Founded
    2004
    EV · today
    $8.40B

    Tax compliance is more defensible than most SaaS categories, but the leverage was structured at peak-vintage assumptions.

    No. 07

    Smartsheet

    Work management
    Status · 2026
    Loans on secondary bid/offer
    Sponsor
    Vista + Blackstone
    Take-private
    $8.4B · late 2024
    Founded
    2005
    EV · today
    $8.85B

    Loans have already appeared on private credit secondary bid/offer lists.

    No. 08

    New Relic

    Observability
    Status · 2026
    SOFR + 6.75% · ~$300M annual interest
    Sponsor
    Francisco Partners + TPG
    Take-private
    $6.5B · 2023
    Founded
    2007
    EV · today
    $6.50B

    A $2.65B debt package led by Blue Owl and Sixth Street, with Blackstone participating, priced at SOFR + 6.75%. Roughly $300M of annual interest against a business mid-transition to consumption pricing. Observability is one of the most directly AI-exposed categories: agents now write their own telemetry, and Datadog and Grafana are already cannibalizing the entry points.

    No. 09

    Sophos

    Cybersecurity
    Status · 2026
    Moody's downgrade B3 from B2 · March 2026
    Sponsor
    Thoma Bravo
    Take-private
    $3.9B · 2020
    Founded
    1985
    EV · today
    $3.61B

    In March 2026, Moody's downgraded the company to B3 from B2 ahead of $2.6B in upcoming maturities. The company is reportedly exploring private credit refinancing for a December 2026 revolver and $2.5B-equivalent senior secured first lien term loans due March 2027. Leverage projected to move toward 9× in fiscal 2026 from 6.3× in fiscal 2025.

    Numbers from the Airframe register; debt and lender details from S&P Global Market Intelligence, SaaStr, and Octus.

    The nine named deals represent roughly $66 billion of equity-plus-debt exposure. That excludes dozens of smaller deals from the same vintage with similar structures. SaaStr identifies at least twelve additional deals with more than $50 billion of combined debt at meaningful risk over the next two years.

    Growth, retention, and refinancing

    The assumptions behind the debt.

    Three buyout assumptions under pressure
    01
    Revenue growth has slowed
    2021 underwriting15–25%YoY
    2026 realitymid-singleor flat
    02
    Net retention has compressed
    LBO model110%+NRR
    At scale<100%in named cats
    03
    The refi window has closed
    2021 assumptionratesnormalize lower
    2026 refi cost~2×interest expense

    Software buyouts commonly assume modest revenue growth, net retention above 110%, and refinancing when debt comes due. All three assumptions face pressure.

    Revenue growth has slowed. Across the named companies, annual revenue growth has fallen from 15 to 25% at take-private to mid-single digits or flat. AI-native competitors are winning net-new projects in procurement, observability, customer support, customer feedback, and document management. Existing customers renew, but expansion has weakened.

    Net retention has compressed. The 110%+ retention assumed in buyout models depended on customers adding seats. Many now renew at flat seat counts while evaluating AI alternatives for whole workflows. Net retention is moving below 100% in categories that stayed above that level for a decade.

    The refi window has closed. The 2021 financing assumptions included lower future rates and an open IPO market for exits. Neither has materialized. Refinancing at 2026 rates roughly doubles interest costs, as Medallia experienced when PIK relief expired. Companies with debt due in 2026, 2027, and 2028 face the most immediate pressure.

    At Medallia, equity fell to zero, lenders took control, and the PE fund recorded the loss. Comparable write-offs lead LPs to examine similar assumptions elsewhere in their portfolios. Distributions and fundraising slow. The number of software buyout funds from the 2025 vintage is already the lowest since 2017, limiting capital for the model.

    Effects on private credit

    Lenders also bear losses.

    Roughly $1 trillion of private credit is extended to PE-backed companies, with software among its largest concentrations. Blue Owl, Blackstone Credit, Sixth Street, Golub Capital, Ares Capital, and other direct lenders hold most of it.

    Senior lenders have covenants and priority over equity, but recovery can still fall short of principal. Medallia's senior loan traded around par a year earlier and was last marked in the high seventies. Similar losses have pushed publicly traded BDCs with material software exposure below NAV, limiting new equity raising as portfolio marks fall. New private credit issuance premiums have widened roughly 0.83 percentage points since early 2025. Q1 2026 BDC bond issuance fell 22% year over year.

    Existing software deals face higher refinancing costs while the credit funds that would refinance them have less capital. AI-driven repricing in public software also limits IPO exits. These pressures reinforce one another.

    We see this as an unwinding of the original financing assumptions.

    Three developments over the next 24 months

    How the financing pressure could resolve.

    We expect three developments, at different times.

    The first is the named at-risk deals. We expect eight to twelve further watchlist deals to resolve over eighteen to twenty-four months. Some companies may complete an AI transition, refinance at higher cost, and preserve reduced equity value. Others may follow Medallia, losing equity and handing control to lenders. Debt structure and category exposure heavily influence that outcome. Portfolio analysis should test whether the debt remains viable through refinancing if revenue stays flat.

    The second is the broader category compression. The 272 PE-held companies founded between 1985 and 2009 face AI-native competitors even when their debt is not distressed. We expect weaker expansion and lower exit multiples across the vintage. Returns from 2018 to 2022 software buyouts could be the weakest since the 2007 to 2009 vintage; fundraising data already reflects that risk.

    The third is the playbook. New deals use lower leverage, more equity, AI operating plans that reduce headcount while maintaining products, and outcome or consumption pricing. We expect funds from the 2024 to 2026 vintages using these assumptions to fare better than firms that repeated the 2021 approach in 2022 and 2023.

    Our read
    We expect PE software to recover after repricing, as other PE categories have. Firms holding the 2018 to 2022 vintage face two to three difficult years, and LPs are already assessing that exposure before committing to another fund.
    Portfolio diligence

    Questions for LPs, deal teams, and operators.

    LP investment committees can examine existing vintage commitments exposed to the watchlist and continuation funds used to extend exits. Continuation funds can be useful, but can also defer recognition of economic losses. Their limited disclosures call for detailed diligence on valuations and underlying assumptions.

    Deal teams can identify portfolio companies still using seat-based pricing and assess how quickly their workflows can adopt AI before refinancing. Zendesk's $200M of AI ARR and Coupa's reported agent-first re-architecture illustrate that direction. The timing relative to debt maturity will determine whether the change is enough.

    Operators can review renewals at risk, seats that AI might replace, and expansion spending already going to challengers. Deployment records help answer those questions. Airframe maintains those deployment records.

    Financing pressure across the cohort

    Medallia illustrates the risk.

    We expect repricing across PE software over the next twenty-four months. As of February 2026, private credit includes roughly $46.9 billion in distressed software loans and about $1 trillion of total exposure to PE-backed companies. At least eight named deals depend on growth or refinancing assumptions current rates and category conditions have weakened.

    LPs, rating agencies, and trade reporting can already identify much of the financing exposure. Better disclosure would help establish how that risk is distributed.

    The watchlist identifies deals to follow as enterprise software financing pressures develop over the next two years.

    Operator-level data on the named deals available off-record on request. hello@airframe.ai

    Paul

    The companion piece on the $5.6T VC-private cohort examines limited LP liquidity and restricted market access. Read it at Trapped Trillions.