Right Hand to the Managing Director: Client Ops, Onboarding & Admin at an AI-Driven Investment Firm

Right Hand to the Managing Director: Client Ops, Onboarding & Admin at an AI-Driven Investment Firm (Remote)

Company: SkySail Strategies Applied Quantitative Research and Investments Location: Remote. We prefer Brazil and Lebanon. Candidates elsewhere are welcome to apply if they can work US Eastern hours. Hours: Full time, Monday to Friday, 9:00 am to 5:00 pm US Eastern Engagement: Independent contractor, paid monthly in USD Compensation: USD $2,000 to $3,000 per month depending on experience, with a review after 90 days

About SkySail Strategies

SkySail Strategies is a quantitative research and investment firm based in Tampa, Florida. We build proprietary AI-driven market models and run a client program built on them. Our clients are individual investors and partners who connect their own brokerage accounts to our systems, and the experience they have from first contact through their first months with us is the heart of what we deliver.

We are a small, fast-moving firm that runs on AI tools. We use Claude and ChatGPT every day to draft, organize, automate, and analyze, and we expect the person in this role to do the same.

The role

You will own client operations and act as the right hand to our Managing Director. In practice that means two things.

First, you make sure every client gets onboarded completely, on time, and without anything falling through the cracks. You guide them through our onboarding process, help them connect their brokerage accounts to our platform, track where each client is in the process, and follow up until every required step is done. Many of our clients invest through self-directed IRAs, which means coordinating between the client, an IRA custodian (Equity Trust), a futures broker (StoneX), and our trading platform (MetaTrader 5). You will become the person who knows that process cold.

Second, you keep the business running smoothly behind the scenes: invoicing, payment tracking, client requests, task management for the Managing Director, and building the processes that let all of this run without constant supervision. Our client operations live in a CRM (GoHighLevel), and you will own it: the pipelines, the automations, the follow-up sequences, and the reporting that tells us where every client stands.

Most of your day is spent communicating: writing to clients, replying in chat, and keeping the Managing Director informed. How you come across in writing and on a call is a large part of how our clients experience the firm, so we care a lot about it.

This is an operations and client service role. It does not involve soliciting investors, giving investment advice, or discussing investment performance. Those conversations are handled by the firm’s principals.

What you will do

• Run our client onboarding process end to end: welcome new clients, walk them through each step, and help them integrate their brokerage account connections with our platform
• Coordinate with custodians and brokers on the client’s behalf, by phone, chat, and email, to get accounts opened, funded, and connected
• Monitor every client’s onboarding status, chase incomplete tasks, and make sure nothing stalls
• Be the friendly, responsive first point of contact for clients over email and chat, and route anything outside your scope to the right person quickly
• Keep clients on track with the actions they need to take, with clear reminders and follow-ups
• Prepare and send invoices, record client payments, reconcile what is owed and what has been paid, and flag anything overdue
• Organize and track client needs and requests so every item has an owner, a status, and a deadline
• Manage the Managing Director’s task list, calendar, and miscellaneous administrative items
• Document our processes, spot where they break, and improve them. You will be expected to build checklists, templates, and automations rather than just follow them
• Use AI tools (Claude, ChatGPT, and others) as a core part of your daily work: drafting client communications, summarizing, organizing, building workflows, and automating repetitive steps

Who we are looking for

• 3+ years in an executive assistant, operations coordinator, client onboarding, customer success, or administrative management role, ideally supporting a founder or executive directly
• You have run client or sales operations out of a CRM (HubSpot, GoHighLevel, Pipedrive, Zoho, Salesforce, or similar) and you have built or modified pipelines, automations, …