Upwork Growth Specialist (Automation & Proposal Systems)

Before applying, please answer honestly: -Have you worked inside Upwork as either a freelancer, proposal writer, bidder, or lead generation specialist? -Have you personally built automations using Make.com? -Have you used LLMs or Custom GPTs as part of a business workflow? -Are you comfortable evaluating opportunities and making judgment calls without constant supervision? -Can you write clearly in English and communicate professionally with a U.S.-based business owner? -Are you comfortable working inside ClickUp and following documented systems? If not, this role is probably not a fit. About Us Blue Ocean Automators helps small businesses streamline operations through automation, AI systems, and workflow design. We build solutions using Make.com, Zapier, LLMs, CRMs, Google Workspace, scheduling systems, payment systems, and other business software. Our mission is simple: help businesses scale without requiring the owner to do everything manually. Over the last year, we've developed a repeatable process for generating clients through Upwork. The process works. The challenge is increasing volume while maintaining quality and speed. We're looking for the right person to help us build and scale that system. This is not a traditional virtual assistant role. Think of it as an opportunity to become a key part of our growth engine. What You'll Be Doing You will play a direct role in helping Blue Ocean Automators generate new business through Upwork. You will be helping evaluate opportunities, prepare proposal materials, improve systems, and ultimately help us scale a lead generation process that already produces clients. Your responsibilities will include: -Reviewing and qualifying Upwork opportunities -Scoring opportunities using established criteria -Identifying the strongest opportunities worth pursuing -Managing opportunity records inside ClickUp -Maintaining proposal pipeline data and reporting -Organizing and selecting relevant project examples, screenshots, and proof assets -Working with AI tools and custom GPTs to create proposal materials -Drafting proposal first drafts -Selecting the strongest project examples for each opportunity -Creating proposal support materials -Creating proposal video scripts -Assisting with proposal video production -Helping manage and improve our overall Upwork application process -Continuously identifying ways to improve speed, quality, and conversion rates throughout the workflow We're looking for someone who can think critically, exercise good judgment, and take ownership of outcomes—not someone who simply completes administrative tasks. The right person will gradually take ownership of larger portions of the lead generation and proposal process, allowing the founder to focus on client delivery, sales conversations, and business growth. If you're excited by AI, automation, systems, process improvement, and building something that can scale, you'll likely enjoy this role. Required Experience - Upwork - Make.com - Custom GPTs If you do not have experience with all three, this position is probably not a fit. Strongly Preferred - Zapier - ClickUp - Descript - CRM systems - Proposal writing - AI-assisted workflows - Lead generation - Sales systems - Operations management - What Success Looks Like Success in this role means helping us: - Increase proposal volume - Maintain proposal quality - Improve response speed - Keep our sales pipeline organized - Reduce the amount of founder time required per proposal Our current process generates strong results when executed consistently. Your job is to help us increase volume while maintaining quality. Long-term, we'd like to scale from approximately 10–15 quality proposals per week to 20–30 quality proposals per week. Growth Opportunity This is not intended to be a simple admin position. The right person could eventually grow into roles such as: - Lead Generation Manager - Proposal Manager - Automation Project Coordinator - Operations Specialist - Growth Operations Manager We prefer building long-term relationships with great people rather than constantly hiring and replacing contractors. Hours We expect this role to begin at roughly 10 hours per week There is significant opportunity for additional hours and responsibility as the relationship develops. Important to note - we care far more about: Judgment Reliability Initiative Communication Speed Attention to detail Problem-solving ability than years of experience, degrees, or impressive resumes. To Apply Please answer the following: 1. Upwork Experience What experience do you have with Upwork, either as a freelancer or supporting freelancers? 2. Make.com Experience What types of automations have you personally built in Make.com? Please provide specific examples. 3. AI Experience Which AI tools do you use regularly, and how do you use them in your work? 4. ClickUp Experience Have you worked inside ClickUp before? If yes, describe how you've used it. 5. Process Improvement Tell me about a process you helped improve, automate, or systemize. What was the problem? What did you change? What was the result? 6. Availability How many hours per week are you currently available? 7. Compensation What hourly rate are you seeking? Practical Screening Question A client says: "I need a Zapier automation that takes leads from Facebook Lead Ads, sends them into Google Sheets, and automatically emails the lead." In 2–3 paragraphs, explain: - How you would think through the request - What questions you would ask before building it - Any potential issues or edge cases you would want to clarify We are not looking for a perfect technical answer, here, we're just looking to understand how you think. Final Instructions: Begin your proposal with the phrase: "Speed creates opportunities." Applications that do not include this phrase will not be considered. We look forward to meeting you!