The short answer: To prepare your IT before selling your business, start 12 to 18 months out. Document every system, retire unsupported hardware and software, lock down who has access, clean up vendor contracts, and collect proof that your security controls work. Buyers pay more for a company whose technology runs without the owner and holds up under due diligence.
If you're thinking about selling in 2027, you're in good company. Three out of four business owners say they want to exit within the next 10 years, yet only 13% have a formal exit plan.1 Most owners spend that planning time on the numbers: clean books, strong EBITDA, a tidy customer list. The technology usually waits until a buyer starts asking questions.
That's the expensive order of operations. Here's how to flip it.
Because buyers aren't just purchasing your revenue. They're purchasing the systems that produce it, and every risk inside those systems becomes their problem at closing.
Dealmakers know it. In a Q4 2025 survey of 150 senior investment banking executives, 47% said technology due diligence was their main priority over the previous 12 months, and 84% expect cybersecurity diligence to face even more scrutiny over the next one to two years.2 The buyer across the table will look under the hood.
Sentry CEO John Ohlwiler has seen this play out from both sides of the table. "We've worked with clients where, because of setting security standards and IT standards in place, they were able to present their company to different buyers and get a higher valuation," he says. "The easier you can show how it can operate without you, without certain people, or without single points of failure, the more it's going to help increase your valuation."
He's also seen the opposite. A pest control company Sentry knew was heading to sale ran on an old, highly manual customer and maintenance system. After the acquisition, the new owners were still pulling data out of the old system and re-entering it by hand a year and a half later. "The owner probably could have gotten a little more valuation if he was using a more standardized software set," John says.
Private equity buyers, in particular, want to see systems that are documented, supportable, and secure, because they're planning to integrate or scale what they buy. A strategic buyer may already own some of that infrastructure. Either way, clean technology makes you easier to buy.
Earlier than you think. Some fixes, like replacing a line-of-business application or renegotiating a multi-year contract, take months on their own. Here's a practical timeline for a 2027 sale:
| Time Before Sale | Focus | What Gets Done |
|---|---|---|
| 12 to 18 months | Inventory and assess | Full IT and security assessment, asset inventory, contract review, list of end-of-life systems |
| 6 to 12 months | Fix the big things | Replace unsupported systems, close security gaps, migrate off legacy software, renegotiate problem contracts |
| 3 to 6 months | Document and prove it | Build runbooks, test backups, run an incident response tabletop, assemble an evidence folder |
| During diligence | Answer with confidence | Respond to buyer IT questionnaires quickly, with documentation ready to hand over |
Starting at the 12 to 18 month mark lets you fix problems on your terms and your budget, instead of watching them turn into price reductions, escrow holdbacks, or a slower close.
These seven areas are where buyers find problems most often, and where a little work now pays off at the negotiating table.
Third-party risk deserves a special mention here. Breaches involving a third party, such as a vendor or supplier, reached 48% of all breaches in the 2026 DBIR, a 60% increase from the prior year.4 Knowing which vendors touch your data, and what access they hold, is part of the cleanup.
It depends on how serious the problem is and when it surfaces. Minor gaps usually become items on a remediation list. Bigger findings, such as evidence of a past breach, unsupported systems running core operations, or no tested backups, give the buyer leverage to lower the price, hold back part of the proceeds in escrow, or walk away.
The stakes are real. The average cost of a data breach in the United States reached $10.22 million in 2025, according to IBM.5 No buyer wants to inherit that exposure, and they'll price the risk accordingly. For a closer look at what acquirers dig into, see our guide to the IT due diligence red flags every acquirer should run down.
IT issues can also show up in the financial review. Unbudgeted upgrades, underpriced support contracts, and deferred technology spending can all affect adjusted earnings. We covered that in Inside the Quality of Earnings Conversation: Where IT Risk Hides.
Sentry's Technology Maturity Model (TMM) gives sellers a simple scorecard for where their technology stands and what to fix first. It has four stages:
A seller who can show a buyer solid Operate and Secure foundations, a clear Integrate story, and a start on Innovate is negotiating from strength.
You've spent years building something worth buying. Don't let the IT environment be the reason a buyer offers less for it. Sentry Technology Solutions helps business owners assess their technology, fix what matters most, and walk into due diligence with the documentation to back it up.
Planning to sell in the next two years? Talk with the Sentry team at sentryitsolutions.com about a pre-sale IT and cybersecurity assessment, and start your cleanup while time is still on your side.
Start 12 to 18 months before you plan to go to market. That gives you time to assess your environment, replace unsupported systems, and fix contract issues without rushing. Waiting until due diligence often means problems turn into price reductions instead of projects.
Expect requests for an asset inventory, network and system diagrams, software licenses and vendor contracts, security policies, backup and disaster recovery plans, incident history, and cyber insurance details. Having these ready speeds up the process and signals a well-run company.
It can, but it doesn't have to. Buyers are most concerned with how a breach was handled and whether the root cause was fixed. Disclosing it early, with documentation of the response and improvements, is far better than having a buyer discover it on their own.
For most sellers, yes. An assessment finds the issues a buyer's team will find, but early enough for you to fix them on your own timeline and budget. The cost is typically small compared to the price concessions a serious finding can trigger.
Not necessarily, but buyers increasingly ask about it. At minimum, know which AI tools your employees use and have a written policy for how company data is handled. A thoughtful AI plan can strengthen your growth story.