Your On-Call Tech Person
For $249 a month, your small business has an on-call developer who knows your systems — not a new chat every time something breaks. I'll tell you when the AI answer is safe, when it's about to cost you money, and I'll quote the work if talking isn't enough.
Why ChatGPT isn't enough
ChatGPT is a good first draft. It does not know your business, it does not remember last month's workaround, and it will not be there when a confident answer creates a mess. Small business technical support is mostly knowing which answers are safe.
01
You asked ChatGPT how to connect QuickBooks to your CRM. It gave you steps that looked right. A week later invoices are duplicated and your bookkeeper is untangling it.
02
A vendor sent a polished scope. ChatGPT said it seemed reasonable. You already had the feature in software you pay for.
03
Something on the website broke. ChatGPT said roll back the update. Now two other things are broken, and you are the unpaid project manager.
What $249 actually buys
You are not paying for an inbox. You are paying so the next question doesn't start from zero — and so you are not the person stitching together AI answers on a Sunday night.
01 · The website
You email me. I tell you whether to roll back, leave it, or fix the one thing that's actually broken — in plain English. If it needs hands-on work, you get a one-hour quote. You don't spend the evening in a chat thread.
02 · The vendor
You forward the proposal. I already know what you use. If Square, WordPress, or the tools you have can do it, I'll say so. If they can't, I'll tell you what I'd actually build — and what I wouldn't.
03 · The busywork
ChatGPT will happily design a Zapier maze. I'll tell you whether a simple automation is enough, whether the data is too messy for that, or whether a small custom tool is the cheaper path.
What's included
The subscription is the relationship. I learn how your business actually runs. You get an affordable developer for small business questions — and a faster path to a quote when the answer is “this needs to be built.”
01
Square, WordPress, the scheduling spreadsheet, the one weird workaround. Next time something breaks, you are not starting a new chat.
02
Not a ticket queue. Not a rotating help desk. Me — the same developer who can investigate, recommend, and quote the work.
03
ChatGPT is instant and unaccountable. You'll get a first response from someone who has to stand behind it.
04
Paste the ChatGPT plan, the vendor proposal, or the DIY idea. I'll tell you what's safe, what's expensive, and what to leave alone.
05
Help choosing tools, seeing how they should connect, and avoiding a bad fit — before you buy another subscription.
06
If talking isn't enough, the project quote comes from someone who already understands the problem. You don't brief a stranger.
Why $249
You are not choosing between this and an IT department. You are choosing between ChatGPT and your Sunday night, a freelancer you have to brief, or an agency that is too much for the question.
ChatGPT
$20/month
Instant answers. No memory of your business. No one accountable if the steps are wrong. You still do the work — and you become the QA department.
A freelancer you don't know
Often $100–150/hour
You write the brief from scratch. You hope they understood it. Next time you have a question, you start over with someone new.
An agency
Often $5k+ to start
A proposal, a queue, and a handoff to people you haven't met. Fine for a big project. A lot of overhead for “is this even worth doing?”
Your On-Call Tech Person
$249/month
Less than two typical freelancer hours. I already know the context. One avoided bad tool, bad Zap, or bad vendor pays for the year. If it needs to be built, you are not hiring a stranger.
Included vs. quoted
You are not paying a cover charge. You are paying so the person who understands the problem is the same person who can do the work — and so that work never starts without your approval.
Included in $249/month
Separately quoted
No surprise bills. No obligation to move forward with additional work. If it needs to be built, I'll quote it first — the same as the rest of how I help.
What you can bring
Bring the website issue, the integration that almost works, the report you still build by hand, or the vendor proposal you want a second set of eyes on. If it needs hands-on development, you get a separate quote before that work starts.
Building these is separately quoted.
Who this is for
You don't need a full-time developer. You need someone who keeps the context, tells you when to ignore the chatbot, and can do the work when it's worth doing.
This is not managed IT
I'm not a help desk, and I'm not here for computer repair, printers, or network administration. This is a personal working relationship with a developer who can investigate problems, recommend solutions, and quote the build when that's the right next step.
Who you're emailing
Not a bench. Not a bot. Not a handoff to someone you've never met.
I'm Jess. I'm based on Long Island, New York, and I work with small businesses here and remotely. I've spent 20+ years across software, product, and digital marketing, including more than five years as a CTO. In that role I helped grow a SaaS business from roughly $300K to $1.5M+ in annual revenue.
I can write the code. I can also tell you whether the thing that's bothering you should be fixed, automated, built, replaced, or left alone — including when ChatGPT's plan is the wrong one.
If we decide to work together, I'll confirm the terms with you in writing before anything is billed. This starts with a note. More about me.
Which service
They are different levels of help — not two prices for the same inbox. The full breakdown is in On-Call Tech vs Fractional CTO. If you're weighing a hire, see on-call developer vs hiring.
$249/month
Someone to email when something breaks, you're choosing software, or you want a second opinion. Development is quoted separately.
On-call developer — $249/monthStarting at $3,000/month
Someone to guide the technology decisions and strategy — ongoing leadership, not more support hours.
Fractional CTO for small businessQuestions
The short version is below. The longer one is when ChatGPT isn't enough.
You should, for first drafts and late-night questions. ChatGPT doesn't know your systems, doesn't remember last month's workaround, and isn't accountable if the steps are wrong. This is for the questions where a confident answer could cost you money — and for the moment talking isn't enough and you need the same person to quote the work.
If you need someone to email when something breaks, you're choosing software, or you want a second opinion, that's an on-call developer — $249/month. If technology decisions are getting expensive and you need ongoing leadership, that's a fractional CTO, starting at $3,000/month. They're different levels of help, not two prices for the same inbox.
A working relationship with an on-call developer for small business: I learn your stack, you email me directly, you get an initial response within 24 business hours, troubleshooting and technical guidance, software and integration recommendations, a second opinion on ChatGPT plans and vendor proposals, and a faster quote when something needs to be built. It is not unlimited development or implementation hours.
Because the expensive part is usually the wrong decision, not the invoice for doing it right. $249 is less than two typical freelancer hours, and you don't spend those hours re-explaining the business. When work is needed, the quote comes from someone who already understands the problem. You approve it before anything starts.
No. The monthly subscription does not include unlimited development hours or unlimited hands-on implementation. Actual development, implementation, and substantial technical work are quoted and billed separately.
Guidance is. I'll answer questions about the problem, help identify likely causes, give you troubleshooting steps, and tell you whether it needs development. Logging in to do extensive debugging, writing code, or implementing a fix is separately quoted.
You'll get an initial response within 24 business hours. This is not emergency or after-hours coverage — it's a reliable first reply from the person who can actually help.
Yes. I'll help you choose software, understand an integration, and decide how your tools should work together. Building or implementing the integration itself is quoted separately.
Yes. You can bring website issues, WordPress questions, and ideas for new functionality. I'll help you figure out what's going on and what to do next. Substantial website changes and new features are scoped and quoted separately.
If the right answer is to build or implement something, I'll send you a quote. Work only starts after you approve it. You're not starting over with a freelancer who has never seen your systems.
Hourly or fixed-price project quotes, depending on the work. You approve the scope before anything begins. No surprise invoices.
You can inquire without any commitment — this starts with a note, not a contract. If we decide to work together, I'll confirm the billing terms with you in writing before anything is billed.
Yes. I'm based on Long Island, New York, and I work with small businesses here and remotely. Most of this starts over email. If we need to look at a system together, we can do that online.
No. This is not a help desk, an emergency IT line, or overnight coverage. You'll get an initial response within 24 business hours.
Get in touch
Tell me how your business actually runs and the kind of technical help you need. I'll reply by email. No subscription starts from this form.
For $249/month, you have a person who keeps the context. If something needs to be built, I'll quote it first — and I won't start until you approve it.
Prefer email? jess@sitelifters.com