Tech-Savvy Executive Assistant / Business Operations & Automation Manager

Tech-Savvy Executive Assistant / Business Operations & Automation Manager AI + Automation + Executive Support | Long-Term Opportunity | Approx. 10 Hours/Week to Start ABOUT THE ROLE I am a Founder/CEO managing multiple businesses and investments across healthcare/wellness, real estate, consulting, e-commerce, and transportation/logistics. I am looking for an **exceptionally strong, highly tech-savvy Executive Assistant / Business Operations & Automation Manager** to become my administrative and operational right hand. **This is NOT a traditional Virtual Assistant position.** I need someone who can do much more than manage a calendar, send emails, enter data, and complete assigned tasks. I want someone who can look at how I currently operate and identify: **“This should be automated.”** **“These systems should communicate with each other.”** **“There is a much easier way to do this.”** **“You should not be spending your time doing this.”** **“I can build a system to handle this.”** And then actually implement the solution. Your primary objective: **Use technology, AI, automation, organization, and excellent executive support to reduce my workload and make my businesses operate more efficiently.** I am looking for someone who can eventually know my businesses well enough to anticipate what needs to happen before I have to ask. --- WHAT YOU WILL DO Your role will combine: **Executive Assistance + Business Operations + Project Management + AI + Automation + Technology Implementation** You should be equally comfortable handling a sensitive executive matter, organizing a complicated project, researching a business issue, creating a spreadsheet, and building a technology solution that eliminates repetitive work. --- # 1. EXECUTIVE & ADMINISTRATIVE MANAGEMENT You will help me manage the administrative demands of operating several businesses simultaneously. Responsibilities may include: * Manage calendars, appointments, meetings, reminders, and deadlines * Maintain a centralized executive task and follow-up system * Help prioritize activities across multiple businesses * Prepare concise daily/weekly executive priority summaries * Draft professional emails and business correspondence * Track outstanding requests, decisions, commitments, and deadlines * Follow up with employees, contractors, vendors, clients, attorneys, accountants, lenders, and other professionals * Coordinate meetings and prepare necessary materials * Capture meeting action items and ensure they are completed * Conduct research and summarize findings * Create spreadsheets, trackers, reports, and dashboards * Organize digital files and business records * Track renewals, contracts, registrations, insurance, and other important dates * Maintain organized documentation of important decisions and completed work Administrative support, however, is only one part of this position. --- # 2. TECHNOLOGY & BUSINESS AUTOMATION A major responsibility will be identifying ways technology can eliminate unnecessary manual work. I want you to continually evaluate how we operate and ask: **Can this be automated?** **Can AI handle part of this?** **Can these applications be integrated?** **Can we create a dashboard instead of searching through emails and spreadsheets?** **Can a form collect this information automatically?** **Can this follow-up happen automatically?** **Can we eliminate steps?** **Can we eliminate something the CEO is currently doing personally?** You may help evaluate, build, or improve: * AI-assisted workflows * Workflow automations * CRM systems * Project-management systems * Executive dashboards * Automated reporting * Forms and data collection * Automated email workflows * Scheduling systems * Electronic signature processes * Document-management systems * Cloud storage and filing systems * Automated reminders and follow-ups * Customer/client workflows * Lead-management systems * Vendor-management systems * E-commerce workflows * Internal knowledge bases * Standard Operating Procedures (SOPs) I am not interested in adding technology simply for the sake of having more software. **Technology should make the businesses simpler, faster, more organized, or less dependent on me.** --- # 3. AI IMPLEMENTATION I already use AI and want someone who can help me use it much more strategically throughout the businesses. You should have practical experience with tools such as: * ChatGPT * Claude * Gemini * Microsoft Copilot * Other business AI/productivity platforms I am particularly interested in candidates who understand how to use AI for: * Executive productivity * Research * Drafting and correspondence * Summarization * Document analysis * Meeting notes and action items * Email management * SOP creation * Data analysis * Spreadsheet assistance * Marketing support * Customer communication * Internal knowledge management * Business research * Workflow automation I am NOT looking for someone whose AI experience consists primarily of entering basic questions into ChatGPT. I want someone who understands how to incorporate AI into **actual business processes and workflows.** You must also understand that AI-generated information needs to be reviewed for accuracy and used appropriately when working with confidential or sensitive information. --- # 4. AUTOMATION & SYSTEM INTEGRATION Experience with automation and no-code platforms is highly desirable. Examples may include: * Zapier * Make * Microsoft Power Automate * Airtable * Notion * ClickUp * Monday.com * Asana * Trello * HubSpot * GoHighLevel * Calendly * Microsoft 365 * Google Workspace * DocuSign * Dropbox * OneDrive * Google Drive You do NOT need experience with every platform listed. I care much more about whether you: * Understand how business systems work together * Can evaluate technology objectively * Learn software quickly * Can recommend better solutions * Can implement what you recommend I am especially interested if you have personally built: * Automated workflows * CRM pipelines * Executive dashboards * Automated reporting * Lead follow-up sequences * Client onboarding systems * Document-generation workflows * Automated reminders * Form-to-database workflows * Email automations * AI-assisted workflows --- # 5. MULTI-BUSINESS OPERATIONS You will work across multiple businesses and projects. These include: ### Healthcare / Wellness / Aesthetics Administrative systems, client workflows, vendors, scheduling, marketing coordination, e-commerce, reporting, documentation, and operational support. ### Real Estate Property administration, contractors, maintenance, leases, tenant matters, expenses, insurance, renewals, projects, and document management. ### Transportation / Logistics Company and vehicle documentation, insurance, registrations, compliance deadlines, driver/vendor administration, expense tracking, and operational records. ### Consulting Projects, research, proposals, correspondence, presentations, invoicing, client follow-up, and business development. ### E-Commerce Product and vendor coordination, customer workflows, marketing systems, reporting, inventory-related administration, and automation. You do not need to be an expert in every industry. You DO need to be able to learn quickly, research intelligently, ask good questions, and keep multiple businesses organized without confusing priorities or information. --- # 6. OWNERSHIP & FOLLOW-THROUGH This may be the most important part of the position. I do not want someone who requires step-by-step instructions for every assignment. If I say: **“Please handle this.”** I expect you to determine what needs to happen. Research what you don't know. Create the action plan. Contact the appropriate people. Track responses. Follow up. Escalate problems when necessary. Keep me informed when a decision is required. And bring the matter to completion. **Sending one email is NOT completing an assignment.** If someone doesn't respond, follow up. If something is approaching a deadline, address it before it becomes an emergency. If you discover a problem, bring me the problem AND your recommended solution whenever possible. ### I am hiring for ownership, not task completion. --- # 7. CONTINUOUS IMPROVEMENT I want you to actively look for opportunities to improve how I and the businesses operate. If you notice that I am repeatedly performing the same task, I expect you to ask: **“Why is the CEO still doing this?”** Then determine whether that task can be: * Automated * Delegated * Simplified * Standardized * Consolidated * Eliminated I would like this person to periodically present recommendations such as: **“Here are five things I noticed that we can automate, improve, consolidate, or take off your plate.”** The objective is NOT simply to help me manage a large workload. ## The objective is to systematically REDUCE my workload. --- # 8. DOCUMENT & INFORMATION MANAGEMENT I need someone who believes information should be easy to find. You may be responsible for: * Creating logical digital filing systems * Organizing existing documents * Establishing file naming standards * Maintaining version control * Tracking documents requiring signatures or responses * Organizing contracts, invoices, receipts, correspondence, and business records * Maintaining searchable business information * Developing internal knowledge bases * Creating SOPs * Making sure important information does not exist only inside someone's email inbox You must be extremely careful with confidential business, financial, personnel, healthcare-related, and personal information. --- # THE IDEAL PERSON You may be an excellent fit if you are: * Extremely tech-savvy * Highly organized * An advanced AI user * Naturally curious about technology * An excellent internet researcher * An excellent written communicator * Strong with spreadsheets * Comfortable troubleshooting technology * A process thinker * Proactive * Resourceful * Persistent * Detail-oriented * Comfortable making recommendations * Able to work independently * Excellent at managing multiple projects * Extremely dependable * Discreet with confidential information * Comfortable working with a fast-moving entrepreneur Most importantly: ### You naturally look for a better way to do things. --- # EXPERIENCE WE VALUE Strong candidates may have backgrounds such as: * Executive Assistant to a Founder/CEO * Tech-Savvy Executive Assistant * Executive Operations Manager * Business Operations Manager * Automation Specialist * Project Manager * Chief of Staff / Chief of Staff Assistant * Systems & Operations Coordinator * No-Code Automation Specialist * Senior Virtual Executive Assistant Experience supporting an entrepreneur with **multiple businesses simultaneously** is particularly valuable. --- # HOURS & WORKING RELATIONSHIP This position will initially begin at approximately: ## 10 HOURS PER WEEK I anticipate beginning with a paid trial period. I am intentionally starting with limited hours because part of your responsibility is to help us accomplish more with fewer administrative hours through better systems, AI, and automation. I am looking for someone who can provide reliable overlap with U.S. Eastern Time for communication and time-sensitive matters. Please clearly state the hours you are available in U.S. Eastern Time. --- # COMPENSATION & GROWTH This is intended to become a long-term working relationship. I am not measuring success by how many hours you work. I am measuring success by: * What you get completed * What you take off my plate * What you improve * What you automate * What problems you prevent * How much time you save * How reliably you follow matters through to completion As the businesses grow and you demonstrate measurable value, there is an opportunity for: * Increased hours * Increased compensation * Greater autonomy * Increased responsibility * Growth into a senior operations position Please include your normal Upwork hourly rate AND the rate you would offer for a consistent, long-term relationship of this nature. --- # FIRST 30 DAYS One of your first major assignments will be to help me conduct a **Technology & Workflow Audit**. Together, we will identify: * What I am currently doing personally * What can be delegated * What can be automated * What can be simplified * What software is duplicative or unnecessary * Where information is getting lost * Where follow-up is breaking down * What should be centralized * What technology could improve operations The result should become an: ## ELIMINATE • DELEGATE • AUTOMATE PLAN During the first 30 days, I want to begin implementing practical improvements that immediately reduce administrative work. --- # TO APPLY — READ CAREFULLY **DO NOT SEND A GENERIC UPWORK PROPOSAL.** Start your proposal with the exact words: ## “AUTOMATE IT.” Then answer ALL of the following questions. ### 1. Executive Experience Tell me about the most demanding Founder, CEO, entrepreneur, or executive you have directly supported. What were you personally responsible for? ### 2. Multi-Business Experience Have you managed responsibilities across multiple businesses, locations, properties, or major projects simultaneously? Explain. ### 3. Technology List the technology platforms you are genuinely proficient in. Do not simply list every application you have ever opened. ### 4. AI Which AI platforms do you currently use? Give me at least TWO specific examples of how you have used AI to improve an actual business process. ### 5. Automation Describe the most impressive business process you have personally automated. Tell me: * What was happening BEFORE? * What did you build? * Which technology did you use? * What happened AFTER? * Approximately how much time or manual work did it eliminate? ### 6. Automation Platforms Which automation platforms have you PERSONALLY built workflows in? Examples: Zapier, Make, Power Automate, Airtable, etc. ### 7. CRM Have you built or significantly improved a CRM? What platform did you use and what did you change? ### 8. Dashboards Have you built an executive or business dashboard? What did it track and what platform did you use? ### 9. Skill Ratings Rate yourself from **1–10** in each area: * Excel / Google Sheets * AI tools * Automation * Project-management software * CRM systems * Internet/business research * Written business communication * Executive administration ### 10. Availability What days and hours can you reliably work in **U.S. Eastern Time?** ### 11. Current Workload How many other clients are you currently supporting and approximately how many hours per week are committed to them? ### 12. Compensation What is your normal Upwork hourly rate? What hourly rate would you offer for a consistent, long-term relationship beginning at approximately 10 hours per week? ### 13. Long-Term Interest Are you interested in a role that could eventually grow into a senior business operations position? Why? --- # REQUIRED APPLICATION EXERCISE Imagine you have been working with me for two weeks and discover: * Important requests arrive through email and text. * I maintain several separate task lists. * Some deadlines are manually entered into my calendar. * Business documents are stored across multiple folders. * I frequently have to ask people for status updates. * Staff send information to me that I then manually forward to someone else. * I repeatedly answer similar questions. * Several businesses maintain separate spreadsheets. * I spend significant time researching vendors and services. * I personally follow up when people fail to respond. I tell you: ## “I need you to get as much of this off my plate as possible.” Tell me the **FIRST FIVE improvements** you would recommend. For EACH recommendation tell me: ### 1. What would you change? ### 2. What technology would you use? ### 3. How would you implement it? ### 4. What would become automated? ### 5. What work would this eliminate for me? Be specific. I am evaluating your ability to think like an **Executive Operations & Technology Partner**, not simply your ability to perform administrative tasks. --- # ONE FINAL QUESTION After reviewing this job description: ## What is ONE thing I have NOT asked for that you believe someone in this position should implement for a multi-business CEO — and why? I want people who think beyond the instructions they are given. --- Generic, copied, incomplete, or obviously mass-submitted applications will not be considered. I am looking for someone who wants to build a long-term relationship, learn the businesses, earn trust, introduce better technology, create better systems, and ultimately become someone I can rely upon to help keep the businesses moving without everything depending on me.