Virtual assistant experienced in Otter.ai Fireflies Chicago IL is one of the most common requests we get from business owners. Here is what the work involves, the role that handles it and our real prices. For Chicago, IL businesses, that means someone who works your Central time business hours, without adding a desk or payroll.
What a AI Assistant & Prompt Specialist Does
Best for business owners and teams who want to use AI but don't know where to start or how to prompt. Typical work includes:
- Choosing the right AI tools and keeping private data out of them
- Setting up ChatGPT, Claude, Gemini or Microsoft Copilot for your business
- Writing a library of ready-to-use prompts for your everyday tasks
- Custom GPTs, Claude Projects and AI chatbots trained on your documents
- AI-drafted emails, proposals, blog posts and social content, checked by a person
They already work in tools like Notion AI, Claude and Perplexity. See the full AI Assistant & Prompt Specialist page for every task.
Working in Otter.ai Fireflies
Your assistant works in Otter.ai Fireflies with a login you share through the encrypted vault in your account, so you control access. Every setup is different, so during onboarding they learn your naming rules, templates and automations and write them into a checklist.
Need someone with deep experience? Choose the Senior Specialist level: 5+ years in the field and certified in the tools you use, from $486 a month.
AI Assistant & Prompt Specialist Support for Chicago, IL Businesses
Chicago companies hire executive assistants for calendar and inbox management, and teams want assistants
Your assistant works Central time. See our Chicago page for every role available locally. We also serve Schaumburg, Naperville, Springfield and Rockford.
AI Assistant & Prompt Specialist Prices
Our current monthly prices for an AI Assistant & Prompt Specialist at the Skilled VA level. They are the same in Chicago, IL as in every other city.
- Starter, 20 hours a month: $360 ($18.00 an hour)
- Growth, 40 hours a month: $684 ($17.10 an hour)
- Professional, 80 hours a month: $1,296 ($16.20 an hour)
- Full-Time Dedicated, 160 hours a month: $2,448 ($15.30 an hour)
A Senior Specialist starts at $486 a month and a US-Based Specialist at $684. Prepay 3, 6 or 12 months to save up to 12%. Build your package to see your exact price.
How to Hire in Four Steps
- Build your package: pick the role, hours and experience level and see the price
- Pay the itemized invoice by card or crypto
- Your account manager contacts you within one business day, and most assistants are matched within 1 to 3 business days
- Share access through the vault and give your first tasks
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For the bigger picture, read our full guide: Hiring a Virtual Assistant in Ohio, Michigan, Illinois, Indiana, Wisconsin and Minnesota.