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    Acquisitions

    When Search Funds Meet AI: A New Playbook for Acquisitions

    The traditional search fund model is overdue for an upgrade. We combine AI-powered operations with disciplined acquisition strategy to unlock value in overlooked businesses.

    Two executives reviewing acquisition documents in a boardroom above a city skyline
    Halle Abraham February 28, 2025 8 min read
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    The search fund model has produced strong risk-adjusted returns for decades by identifying well-run small businesses with stable cash flows and applying professional management. The core playbook, however, has changed little since its inception.

    The next generation of acquisitions will be defined less by management expertise alone and more by the technology deployed in the first year after close.

    Where the Classic Model Leaves Value Behind

    Traditional search underwriting focuses on revenue durability, customer concentration, owner dependence, and margin stability. These remain the right questions. What is typically missing is a rigorous view of how work actually flows through the business, and how much margin is consumed by coordination.

    In practice, an operator who inherits a business with manual intake, memory-based scheduling, and month-end financial visibility spends the first year firefighting. Value creation is deferred precisely when the cost of capital is highest and lender covenants are tightest.

    Underwriting technology alongside financials changes the shape of the first year. The operator arrives with a defined system to install rather than a set of problems to discover.

    The Target Profile

    What makes a business a strong candidate for a technology-led thesis.

    We look for businesses where the customer relationship is strong and the operations are manual. Those two conditions together indicate that demand is real and that the constraint is internal, which is the constraint an operator can actually fix.

    • Recurring or repeatable revenueService contracts, maintenance cycles, or high repeat rates that make retention improvements compound.
    • Manual operating coreOwner fields calls, dispatch runs from memory, invoicing is batched at period end.
    • Fragmented systemsMultiple disconnected tools with no single record of the customer or the job.
    • Clean enough dataHistorical records exist in some structured form, even if imperfect, so a baseline can be established quickly.

    Underwriting Technology Value Creation

    A technology value creation plan should be underwritten with the same discipline as a pricing or procurement initiative. Each initiative needs a named owner, a target metric, a baseline, a timeline, and a cost, and it should appear in the model rather than in the narrative.

    This discipline also protects against overstatement. If a scheduling improvement is expected to lift utilization, the model should reflect realistic ramp, the cost of change management, and the risk that adoption lags. Plans that assume immediate full adoption are the most common source of missed post-close targets.

    Window in which operating routines set for the new ownership period
    100 daysWindow in which operating routines set for the new ownership period
    Realistic horizon for the first full cycle of measurable operating improvement
    12 monthsRealistic horizon for the first full cycle of measurable operating improvement

    The First 100 Days

    Sequence matters more than scope. The first phase should stabilize the business, establish the operating baseline, and unify intake. The second should install decisioning for the single highest-volume workflow. Only then should automation extend across the operation.

    Change management is the determining variable. Systems introduced after new routines harden are rarely adopted, and adoption, not capability, is what produces cash flow. Frontline involvement in workflow design during the first phase materially improves the outcome.

    Diligence checkpoint

    Ask to observe a full day of operations before close. The gap between the documented process and the observed process is usually the clearest indicator of available value.

    What the Combined Model Produces

    Portfolio companies that pair disciplined acquisition with an operating system installed early tend to run with lower cost to serve, stronger customer experience, and meaningfully better free cash flow conversion within the first year.

    That is the compounding effect of treating technology as part of the underwriting rather than as a post-close project. It shifts value creation from a hope to a plan.

    Buy the customer relationship. Underwrite the operating system. Install it before the routines harden.

    Written by Halle Abraham

    Building the future of AI-powered business at Flatiron Foundry.

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