When a business realizes its software has no owner, three answers come up quickly. Hire a developer. Find a freelancer. Pay for a monthly support retainer. Each can be the right call. This post compares them for one specific kind of software: the application that mostly needs to keep running, with occasional fixes and small changes.
We sell retainers, so we have an interest. We will try to be fair about where the alternatives are better.
What this software usually needs
Most legacy business software does not need constant development. It needs a steady, modest amount of care:
- Someone watching the hosting, the backups and the expiry dates.
- Updates applied carefully when libraries or runtimes need them.
- Small fixes when a form, report or integration misbehaves.
- Occasional small changes when the business changes.
- Someone to ask when a question comes up.
That is a part-time job, spread unevenly across the year, and it requires someone who knows this particular system.
Option 1: hire a full-time developer
Where it wins. If your software is large, changing weekly and central to your product, a full-time developer is probably right. They become deeply familiar with it, they are available daily and they can grow with the business.
Where it struggles for this kind of software.
- A full-time salary is a large fixed cost for a part-time workload, and the role can be dull enough that good people leave.
- You then have the same single-person risk you were trying to escape. When they leave, the knowledge goes with them.
- Hiring takes time, and finding someone who wants to work on an old stack is hard.
Option 2: a freelancer
Where it wins. Freelancers can be excellent value for a clear, bounded task. A good one who already knows your system, at an hourly rate, is hard to beat for occasional work.
Where it struggles.
- Availability. A freelancer who is the only person on your system is a single point of failure, and the situation you are in now was probably caused by one.
- Process. Documentation, backup checks and access custody are rarely in an hourly scope, so they are rarely done.
- Hourly billing makes small questions feel expensive, so people stop asking.
Option 3: a monthly support retainer
Where it wins. For software that mostly needs to keep running, a retainer gives you a dedicated provider, a monthly check of the basics, a steady allowance of small fixes and a written note each month. The cost is predictable and the knowledge lives in documentation, not in one person's head.
Where it struggles.
- If you need a lot of new development, a retainer sized for upkeep will not cover it. You would move up to a higher tier or a project.
- You are paying for readiness, so in a quiet month it can feel like paying for nothing.
- A retainer provider is a company, not an employee. They do not sit in your office and will not know your business as intimately as a long-serving staff member.
What our retainers cost and include
| Retainer | Price | In short |
|---|---|---|
| Keep-Alive | $2,000 per month, 3-month minimum | Hosting, backup and access checks, patch pull requests, up to six small fix tickets, business-hours email and a monthly note |
| Support Plus | $4,500 per month, 3-month minimum | Keep-Alive plus about 12 hours a month of fixes and small enhancements, next-business-day priority |
| Own-It | $8,500 per month, 3-month minimum, by request | About 30 to 40 hours a month of AI-assisted development under human review |
Prices are in USD with a fixed scope. Out-of-scope requests are quoted as fixed-price projects first. More on the ongoing support page.
A simple way to decide
Ask these questions.
- How often does the software change? Rarely: a retainer or freelancer. Weekly: a developer.
- How bad would an outage be? If it is costly, you want more than one person who knows the system.
- Who looks after hosting, backups and access today? If the answer is nobody, a retainer's monthly checks add the most value.
- Do you want to manage someone? If not, a retainer is a way to buy the outcome, not the person.
Combining them
These are not exclusive. A common pattern is to use a retainer for upkeep and a freelancer or an in-house person for new features, with the retainer team holding the documentation and the access. Another is to start with a takeover assessment, put everything in your name and then decide who to hire from a position of knowledge. The assessment fee is credited in full toward your first three months of a retainer if you sign within 90 days.
Our recommendation
If your software is stable, matters to the business and nobody in-house can maintain it, start with an assessment and a Keep-Alive retainer. If it needs constant change, hire a developer and have us handle the documentation and the hosting around them. If it is about to be replaced, do the minimum and plan the replacement.
We use AI tools on first-pass work and a person reviews all of it. We tell you that on the first call. We do not offer security assessments or security testing. If you want to talk through your situation, tell us about your software, or see every option on the pricing page.
