Selling an Artificial Intelligence Business

Based on hundreds of real buyer-seller conversations we’ve helped happen on Rejigg. These are the AI diligence topics that actually change price and terms: who owns the training rights, what transfers at close, how expensive inference gets at scale, and whether the product holds up in real enterprise deployments.

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What buyers ask and how to be ready

Each topic below comes from real buyer-seller conversations. Here's what they ask, what they're really evaluating, and how to prepare.

Data Rights

For every major data source, what’s the permission that allows training and ongoing use?

Buyers are underwriting whether the company can keep operating legally after the sale. They want proof that you’re allowed to collect, store, and use the data the way your product really works, including what happens if a customer terminates or revokes permission. If the answer is vague, buyers protect themselves with escrow, indemnities, or a lower price.

How to prepare

  • Map each dataset to the specific contract clause, consent language, or vendor terms that allow current use
  • Write a one-sentence allowed-use summary per source, including training, retention, and deletion timing
  • Document your fallback if a key data supplier changes terms, including degraded-mode behavior
  • List any gray areas and your containment plan, including updated customer language and counsel review

Great Answer

We maintain a data rights map for every meaningful source. For customer data, our terms are explicit about whether we can train across customers or only run processing for that single customer, and our pipeline follows that rule in practice. For third-party feeds, we can show the license terms, retention limits, and our backup plan if the feed goes away.

Okay

Most of our input is customer-provided data, and we believe our contracts cover our current use, but we have not tied every dataset back to specific language yet.

Gives Pause

We have access to the data, and our lawyer said it’s fine. We do not track which sources allow training versus one-off processing.

How Rejigg helps: Rejigg’s secure data room lets you share your data rights map, customer terms, and vendor contracts under NDA without email attachments. Learn more in the guide

Deal Perimeter

What are you actually selling: IP, customer contracts, data, and the right to keep operating the same way?

AI companies have more “what actually transfers?” issues than typical software. Customer data may be non-transferable or must be deleted, model access might sit in a vendor account, and internal tooling may never have shipped. Buyers want a clean list of what they get on day one, and what requires customer or vendor permission, so there are no late surprises that force a re-trade.

How to prepare

  • List what’s included: repos, trained artifacts, pipelines, evaluation tooling, transferable datasets, and customer agreements
  • List what’s excluded or conditional: vendor model accounts, marketplace approvals, non-transferable licenses, and prototypes
  • Document deletion obligations and how you execute them today
  • Write a simple 30-day “how we deliver value” narrative for a new customer

Great Answer

The sale includes the full codebase, deployment and monitoring tooling, customer contracts, and the evaluation harness we use to ship changes safely. We do not claim ownership of third-party model weights, and we’re explicit about which datasets are customer-provided and must be deleted on termination. We can walk through what works immediately post-close, and what requires vendor or customer consent.

Okay

You’d be buying the product, contracts, and our internal tooling. Some data and model components depend on vendor accounts that would need to be transitioned.

Gives Pause

You’re buying everything. We can sort out the model and data details later.

How Rejigg helps: Rejigg’s deal tracking keeps “what’s included” consistent across LOIs and drafts so the perimeter does not drift late in the process. Learn more in the guide

Product vs Services

Are you selling a product, a services team, or a hybrid—and what happens between “signed” and “live,” step-by-step?

Buyers are pricing your real delivery engine. If “software revenue” requires weeks of custom integrations, data cleanup, prompt tuning, and ongoing exception handling, they underwrite it like a services-heavy business with limited capacity. A clear implementation story helps a buyer separate repeatable product value from custom work, and it usually speeds up diligence.

How to prepare

  • Write the signed-to-live timeline step-by-step and name who owns each step, your team or the customer
  • Pull the last five implementations and quantify security review time, integration time, and engineering hours
  • Define what counts as standard setup versus custom work, and how custom work is scoped and priced
  • List the top 2–3 reasons go-lives slip and what you do differently now

Great Answer

A standard install is two integrations, one security review, and a guided workflow setup. The typical timeline is 4–6 weeks with about 40–60 engineering hours on our side, and we can show the last five deployments with those numbers. Custom work usually shows up when upstream data is messy or the customer wants a net-new workflow, and we scope and price that separately with a clear handoff to steady-state.

Okay

Onboarding is usually a month or two and involves some integration and tuning. It varies with the customer’s data quality and internal approvals.

Gives Pause

We’re flexible. Our engineers handle whatever comes up for each customer.

How Rejigg helps: Rejigg’s direct messaging and scheduling lets you walk buyers through the real signed-to-live path without a broker rewriting the story. Learn more in the guide

Cost-to-Serve

What drives your inference cost, and how does it change as customers grow?

AI margins often look fine at low usage, then swing hard when customers scale, context windows get bigger, latency targets tighten, or GPU and model bills jump. Buyers want customer-level unit economics, not blended averages, plus proof that pricing protects you when a customer becomes a heavy user. If you cannot explain your cost drivers in plain terms, buyers assume gross margin is fragile.

How to prepare

  • Track cost-to-serve by customer, including model usage, cloud compute, storage, and meaningful support time
  • List the behaviors that spike cost and the guardrails you use, like limits, caching, routing, or smaller models
  • Pull the biggest cloud or model bill surprises from the last year and document what you changed
  • Align pricing to usage with tiers or overages and flag any upside-down customers with a reset plan

Great Answer

We track cost-to-serve per customer each month. The biggest drivers are model calls per workflow, long-document requests, and real-time latency requirements, and we can show how those map to our tiers and overages. We had two cost surprises last year around logging volume and vector storage, and we put guardrails in place so usage growth does not quietly wipe out margin.

Okay

Our biggest costs are model usage and cloud compute, and we know which customers are heavy users, but our per-customer reporting is not clean yet.

Gives Pause

Costs are low, and we do not focus on them. The cloud bill is what it is.

How Rejigg helps: Rejigg’s QuickBooks integration pulls clean financials into your data room so buyers can tie cost lines to the unit economics you describe. Learn more in the guide

Model Dependency

What parts are your own work versus third-party models and tools—and what happens if the main model provider changes tomorrow?

Buyers are pricing supplier risk, including price changes, deprecations, outages, policy shifts, and quality swings. Plenty of strong AI businesses run on third-party foundation models, but buyers still want to see that the dependency is understood and actively managed. If switching providers takes months and breaks key workflows, that risk shows up in price, escrows, or earnouts.

How to prepare

  • Document the stack in plain English, including what you built versus what you call externally
  • Quantify vendor costs at real usage and show how gross margin changes as usage grows
  • Write a fallback plan, including routing, smaller models, caching, and graceful degradation
  • Call out where dependency is concentrated, like one model endpoint, one vector store, or one data vendor

Great Answer

We use third-party models for generation, and our differentiation is the workflow, retrieval layer, and our evaluation and release process. If our primary provider changes pricing or quality, we can route core tasks to an alternate provider within days, and we already run a smaller-model fallback for non-critical steps. We can show the cost impact at current volumes and the vendor terms that matter.

Okay

We rely on a third-party model today and could probably switch, but we have not tested a full provider swap end-to-end recently.

Gives Pause

We use an API for the AI. If it changes, we’ll deal with it then.

How Rejigg helps: Rejigg’s data room is where you share vendor agreements, cost summaries, and a dependency map right after NDA so technical diligence moves faster. Learn more in the guide

Performance & Drift

How stable is model performance in the real world, and what triggers retraining or rollback when results get worse?

Buyers want evidence the system holds up in production, not just in a demo. They also want to understand how you catch performance decline before it turns into churn, escalations, and manual review work. A clear release gate and monitoring process tells a buyer the company can keep shipping safely after the founder steps back.

How to prepare

  • Pick 3–5 customer-facing outcomes and report them consistently with a baseline and current results
  • Document drift monitoring, including ownership, thresholds, and how often you see issues
  • Write your release process, including what you test pre-ship, what you monitor post-ship, and how rollback works
  • Log quality incidents and review trends so you can show patterns, not stories

Great Answer

We track outcomes customers care about, like time saved per case and percent of tasks auto-completed, and we review them weekly with baselines for each workflow. We monitor drift in production and trigger retraining when outcome metrics drop past defined thresholds, with a named owner who approves changes. We also have a rollback path when a release hurts performance.

Okay

We monitor performance and retrain when we see issues, but our thresholds and reporting are not consistent across customers yet.

Gives Pause

The model is good. We do not measure drift beyond customer feedback.

How Rejigg helps: Rejigg helps you package performance reporting and your release process in one buyer-ready set of materials inside the secure data room. Learn more in the guide

Security & Compliance

What’s the last security questionnaire you passed? Where does customer data live, and who can access it?

Enterprise AI deals often slow down on security because you touch sensitive internal data and generate outputs people rely on. Buyers are trying to separate normal procurement friction from real gaps, like weak access controls, missing audit logs, poor tenant separation, or no single sign-on. A specific, evidence-backed security posture reduces uncertainty and speeds up diligence.

How to prepare

  • Build a security packet covering access controls, encryption, data locations, incident response, and support access
  • Summarize recent security reviews, including what you provided, what you changed, and how long approval took
  • List known blockers like data residency or identity provider support and write a 60–90-day plan
  • Create plain-English data flow diagrams for your most common deployment patterns

Great Answer

Our last enterprise security questionnaire was with a regulated customer and took six weeks end-to-end. We can show the evidence we provided, the controls we implemented, and the few exceptions we negotiated. Customer data is isolated by tenant, access is least-privilege with audit logs, and support access is time-boxed and logged.

Okay

We’ve passed security reviews and have basic access controls and encryption. We still have a few enterprise asks in progress, like single sign-on.

Gives Pause

We take security seriously. We haven’t done a formal security review yet.

How Rejigg helps: Rejigg’s buyer vetting and digital NDAs let you share security materials only with serious, qualified buyers. Learn more in the guide

Pilots vs Production

How many customers are in production versus pilots, and why do pilots stall?

In AI, pilot-heavy revenue often behaves like experimentation and custom work, not durable software usage. Buyers want to see a repeatable path to production with clear timelines and integration steps, plus honest data on where things get stuck. Pilot-to-production conversion rates directly affect how a buyer underwrites growth and retention.

How to prepare

  • Tag every account as pilot, limited rollout, or production and define each status in one sentence
  • Record what each customer integrated and who uses the outputs weekly on the business side
  • List the top reasons pilots do not convert and what you changed to improve conversion
  • Calculate pilot-to-production conversion rate and median time-to-production for the last 12–24 months

Great Answer

We define production as weekly business usage tied to a live integration, not a demo environment. Today, we have 18 production customers, 6 limited rollouts, and 9 pilots, and we can show conversion rates and median time-to-production. Pilots stall mainly on security review and data access, and we shortened both with a standard integration package and a prepared security packet.

Okay

We have a mix of pilots and production customers, and we know the common stall reasons, but we have not quantified conversion rates and timelines yet.

Gives Pause

Most customers are basically in production. We count pilots as revenue and assume they convert over time.

How Rejigg helps: Rejigg’s data room lets you share a clean customer list with pilot and production tagging right after NDA so buyers do not have to guess. Learn more in the guide

Key Person Risk

If your lead ML (Machine Learning) engineer quits, what breaks first?

Buyers are underwriting whether the business transfers cleanly or runs on tribal knowledge. Many AI teams have one person who understands the pipelines and one person who owns the customer reality, and buyers usually find that quickly in diligence. If stability and deployments depend on heroics, buyers price in hiring risk and demand a heavier transition period.

How to prepare

  • Map ownership of production, deployments, model updates, and customer escalations to named people
  • Assign backups for each critical role and define what “backup-ready” means
  • Centralize runbooks for deployments, incidents, retraining, and customer integrations
  • Call out where knowledge is still concentrated and set a 60–90-day plan to spread it

Great Answer

The first pressure point would be deployments and retraining workflows, but we’ve documented them and have two engineers who can run them today. Production incidents follow a runbook with clear escalation and rollback steps. A couple customer-specific integrations still have concentrated knowledge, and we are cross-training and documenting those now.

Okay

It would hurt short term, but we have some documentation, and someone else could take it over with time.

Gives Pause

That person is the only one who understands the model and pipelines. We’d be in trouble for a while.

How Rejigg helps: Rejigg lets you share org charts, role ownership, and transition plans in the data room so buyers can underwrite transferability early. Learn more in the guide

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Questions Artificial Intelligence Owners Ask Us

AI software companies usually trade on a mix of growth, profitability, and risk. Multiples tend to be higher when revenue is repeatable, gross margin holds after real inference costs, and you have clean data rights and enterprise-ready security. If revenue leans on pilots or services-heavy implementations, buyers usually price more conservatively. Start with Rejigg’s free valuation calculator, then refine it with customer-level cost-to-serve and pilot-to-production conversion data.

Buyers can be comfortable with third-party model dependency, but they will price supplier risk. Expect questions about how fast you can switch providers, how quality shifts affect your workflows, and what happens to margins if per-token pricing moves. If you can show routing, fallbacks, and usage-based pricing that protects you as customers scale, the dependency usually becomes a manageable diligence item. Rejigg’s secure data room is a good place to share vendor terms and a simple dependency map after NDA.

Yes. You don’t need a broker to sell an AI company, and you don’t need to give up 5–10% of your sale price for introductions and forwarded emails. Rejigg supports a broker-free process: buyers are pre-vetted, NDAs are signed digitally, and you share diligence materials in a secure data room with tight control over access. Start with the finding buyers guide, then list once your diligence package is ready.

For AI, start with the docs that stop deals when they are missing: a customer list tagged by pilot versus production, a data rights map tied to contract language, a cost-to-serve summary that includes inference and cloud drivers, and a security packet that explains where data lives and who can access it. Most technical buyers ask for these early. Rejigg’s preparation guide plus the built-in data room helps you organize it without emailing files around.

Buyers want to avoid a surprise license that forces you to publish proprietary code or limits commercial distribution. Inventory your key dependencies, flag anything with restrictive terms, and document how you comply today. This matters in AI stacks where model serving, vector search, and data pipelines pull in a lot of components. Put the inventory in your data room so the buyer’s technical team can review it quickly during due diligence.

An earnout means part of the price gets paid later if the business hits agreed targets, like revenue, renewals, or customer milestones. In AI, earnouts show up when buyers are uncertain about pilot conversion, retention without the founder, or whether margins hold as usage scales. Earnouts can be fine if the targets are easy to measure and you control the levers to hit them. Rejigg’s deal dashboard lets you compare offers side-by-side, including earnout terms and timelines.

Bring production proof: which workflows run weekly, who owns the outcome on the customer side, and what improved versus the baseline before you went live. Buyers also want to hear how you monitor quality in production and what you do when performance slips, including retraining or rollback. Keep it simple and consistent across customers. Store the reports in Rejigg’s data room so you can share them immediately after NDA.

Working capital is the short-term cash tied up in running the business, roughly what you have coming in soon minus what you owe soon. In AI software, the big swing items are often deferred revenue from prepaid contracts, accrued payroll, and unpaid cloud or model vendor bills. Buyers may ask for a “normal” level of working capital at close so they are not funding old payables on day one. Rejigg’s negotiation guide helps you prep for that ask.

Sometimes, but many AI deals are a tougher fit for SBA because lenders want stable, provable cash flow, and straightforward recurring revenue. If you have consistent profitability, clean books, and low reliance on pilots or founder-led delivery, SBA can work for some buyers. Before you negotiate, model the payment scenarios with Rejigg’s SBA loan calculator so you know what a buyer can afford.

Buyers look at revenue concentration, and in AI they also look at dependency concentration. One customer can matter because they provide unique data, labels, or edge cases that shaped the workflows and evaluation. Losing them can create a quality and roadmap problem, not just a revenue hit. Prepare a customer-by-customer view of revenue, integrations, and what the product would lose if the account disappeared. Rejigg’s data room is built to share that list under NDA with tight permissions.

Human review can be normal in regulated workflows or anywhere mistakes carry real liability. Buyers mainly want clarity on whether review is temporary, permanent, and who pays for it. Show who does the review, how many hours it takes per month, and how that changes as usage grows. If the review cost sits with you, tie it directly to pricing so margin does not compress as customers expand.

Most deals take a few months from the first serious buyer call to close, and longer when data rights, security reviews, or vendor dependencies are unclear. AI processes move fastest when you can share a data rights map, cost-to-serve summary, and security packet immediately after NDA, since technical buyers ask for them early. Rejigg helps with pre-vetted buyers, digital NDAs, and a built-in data room. See the due diligence checklist for timing drivers.

Common problems are contracts that allow processing for one customer but do not allow training across customers, unclear retention and deletion rules, and third-party data licenses that do not transfer on a change of control. Buyers also ask what happens if a customer revokes permission or terminates. The fix is usually straightforward: map each dataset to the actual terms and make sure the product workflow matches the contract. Rejigg’s data room helps you keep those documents organized and share them safely.

Translate cloud spend into customer behavior. Show what it costs to run model calls, store embeddings and logs, and pay any per-request vendor fees, then explain what drives spikes, like long documents, high volume, or low-latency requirements. If you have upside-down customers from early pilot pricing, call them out and show the reset plan. Rejigg’s QuickBooks integration helps you produce clean financials without spreadsheet churn.

No. Seller financing is optional, but it can expand the buyer pool when the business is smaller or when lenders are cautious about AI-specific risks like pilot-heavy revenue or inference-driven margin volatility. If you offer it, tie the structure to what you can verify, like contracted revenue and documented cost-to-serve, and keep clear protections in the agreement. Rejigg’s offer comparison view lets you evaluate seller financing terms against other offers in one place.

Buyers usually want a non-compete so you do not turn around and build the same product, and they want a transition period so knowledge transfer actually happens. In AI, the transition often centers on deployments, model updates, customer escalations, evaluation practices, and vendor relationships. A strong plan names who owns each operational area and what “handoff complete” means. Rejigg’s transition planning guide helps you lay this out in a buyer-friendly way.

Re-trades usually happen when buyers discover AI-specific risk late, like unclear data rights, a hidden services load in onboarding, or gross margins that fall apart once real inference and cloud costs show up at scale. None of that automatically kills a deal, but surprises make buyers look for price protection. The best prevention is to share the hard materials right after NDA. Rejigg supports that with pre-vetted buyers, digital NDAs, and a secure data room.