AI Chatbot Development
AI Chatbot Development Services
Web, SMS, and voice chatbots that answer from your real content, run unlimited simultaneous conversations, and hand off to a human — with full context — the moment a question needs one. Founder-led since 2017.
AI chatbot development services build conversational software for web, SMS, and voice that answers from a business's real content, resolves routine questions automatically, and hands off to a human — with full context — the moment a question needs judgment a bot shouldn't make. Retailbox builds these across all three channels and keeps them accurate after launch under a managed plan.
What we build
Four channels, one underlying approach: answer from what you already know to be true, and hand off the rest.
Web chat
A chatbot on your site that answers from your actual FAQ and docs, qualifies visitors, and books meetings — not a generic widget with canned replies.
SMS chatbots
Text-based support and lead response that runs unlimited simultaneous conversations, so volume spikes and after-hours messages stop hitting a wall.
Voice agents
Phone-answering conversational agents that qualify callers and book appointments on your calendar, for the calls that come in outside business hours.
Multi-channel with human handoff
One bot personality across web, SMS, and voice, with full conversation context passed to a human the moment a query needs judgment a bot shouldn't make.
Chatbots we've shipped
Real builds with real numbers — not a general promise about what a chatbot can do.
AI SMS chatbot for a client's support line — unlimited conversations, 0% to 100% after-hours coverage
A ChatGPT-backed SMS bot on Twilio replaced a client's support line that could handle only one conversation at a time. It now resolves 78% of tier-1 queries automatically and escalates the rest to a human with full context — coverage went from zero overnight and weekends to 24/7.
AI voice agent for a client's phone line
A conversational voice agent that answers inbound calls, qualifies the caller, and books the appointment — built and maintained by our team.
Active Upwork chatbot contracts
Multiple ongoing Upwork engagements building conversational AI bots for clients, alongside the fixed-price and managed work below.
How Do You Build an AI Chatbot That Doesn't Hallucinate?
1 — Map what it should actually answer
We start from your real FAQ, docs, and past support tickets — not a blank prompt. The scope is what the bot resolves alone versus what it always escalates.
2 — Build with an escalation path from day one
Every bot ships with a human handoff — a bot with no escape hatch is how a bad answer turns into a bad review. The handoff carries full conversation context, not a cold transfer.
3 — Keep it answering correctly
Monitoring for drift and free fixes when a model or channel API changes, under a managed plan — so accuracy doesn't quietly degrade after launch.
Is a chatbot the right fit for your case?
The honest split we use on the first call:
Low volume, and a wrong answer barely costs anything
A simple FAQ widget or a documented macro might be enough — we'll say so on the call rather than sell a custom build you don't need.
Repeatable questions eating hours, especially after hours or on weekends
Strong fit. This is where a chatbot pays back fastest — coverage you don't currently have, on questions you already know the answers to.
Customer-facing, and a hallucinated answer would be a real problem
We scope the bot to answer only from your verified content and hand off anything outside it — a hallucinating bot in front of your clients is not a risk worth taking blind.
What it costs — real numbers
Priced by scope and channel count, not a flat "chatbot" rate:
Quick chatbot
$2,000–$5,000
1–2 weeks
Answers from your existing FAQ and calendar — books meetings, answers routine questions, escalates the rest.
Custom conversational agent
$15,000–$75,000
6–16 weeks
Retrieval over your documents, CRM actions, and multi-channel deployment (web, SMS, voice) with guardrails.
Managed operation
from $299/mo
Month-to-month
Accuracy monitoring, conversation review, and free fixes when a model or channel API changes. Cancel anytime.
Every engagement starts with a free 30-minute call that scopes the bot before any price is fixed. Need the decision-and-action layer behind the conversation, not just the front end? See AI agent development.
Who builds it
Michael Oskola — founder of Retailbox. He scopes every chatbot engagement personally; implementation runs with a small vetted team he's worked with for 5+ years. 400+ projects since 2017, Top 1% ranked on Upwork.
Based in Orlando, Florida — working with B2B teams across the US. Need the fuller build — CRM, workflows, and agents together? See the AI automation agency track, or browse the full services catalog.
Questions we get asked
How much does it cost to build an AI chatbot?+
A chatbot that answers FAQs and books meetings from your existing content runs $2,000–$5,000 and ships in 1–2 weeks. A custom agent with retrieval over your documents, CRM actions, and multi-channel deployment runs $15,000–$75,000 over 6–16 weeks, plus an optional managed plan from $299/month.
Which channels can the chatbot run on?+
Web chat, SMS, and voice — as one consistent bot or as separate deployments per channel. Our SMS chatbot work for a client moved their support line from one conversation at a time to unlimited simultaneous conversations, with 78% of tier-1 queries resolved automatically.
What happens when the bot doesn't know the answer?+
It escalates to a human with the full conversation attached — never a guess presented as fact. Every bot we ship is scoped to answer only from your verified content (docs, FAQ, CRM data) and to hand off anything outside that scope.
Can the chatbot connect to our CRM or calendar to actually book things?+
Yes — booking meetings, updating CRM records, and triggering follow-up workflows are common asks. We wire these in via API or webhook once the bot's answering behavior is solid, so we're not layering actions on an unreliable base.
Chatbot vs a full AI agent — which do we need?+
A chatbot is the conversational front end; an agent is the decision-and-action layer behind it. Many projects need both — a bot that talks to the customer, backed by an agent that qualifies or routes what it hears. If you need the fuller agent build, see AI agent development.
Will accuracy hold up after launch, or does it drift?+
It can drift as your content changes or the underlying model updates — that's what the managed plan exists to catch: conversation review and free fixes rather than a bot nobody's watching gradually giving worse answers.
Scope your chatbot on a free call
30 minutes. You leave knowing what the bot should answer, what it should escalate, and what it should cost.