Important: Only applications submitted through the official application link will be considered.

Wentwood Capital is a Miami-based private real estate lender. We are a team of rockstar A+ performers from top companies, driven by a culture of hard work and teamwork!

Here's a glimpse of our last company meetup in Vietnam:

www.facebook.com/share/r/1E4jcnmm2P/

We are looking for an AI Chief of Staff to work directly with our CEO and build, operate, and continuously improve his personal operating system, which we call AbbasOS. This role reports directly to the CEO.

AbbasOS is the system around the CEO's executive workflows, communications, calendar, follow-ups, personal administration, household and family logistics, vendors, and other recurring responsibilities that consume time and attention. The goal is to systematically reduce recurring administrative and cognitive load while preserving the CEO's visibility and control over the things that actually require his judgment.

This is not a traditional Chief of Staff or Executive Assistant role. You will not become a gatekeeper between the CEO and the people he already works with. You will review how recurring work currently happens, document it, improve it, build playbooks and prompts, create practical AI agents and automations, and work with our AI Automation Engineer and other technical team members when deeper technical development is required.

We are looking for an operator who combines strong judgment, organization, process thinking, and practical AI ability. You should be comfortable taking an unclear recurring problem, understanding how it works, designing a better system, building what you reasonably can yourself, and coordinating with others when needed.

What You'll Do:

- Own the ongoing development and operation of AbbasOS, the CEO's personal operating system
- Review how the CEO currently manages email, calendar, scheduling, follow-ups, executive workflows, personal administration, household and family logistics, vendors, travel, research, and other recurring responsibilities
- Identify where the CEO's time and attention are being consumed and prioritize recurring problems that can return the most time or reduce the most cognitive load
- Turn recurring workflows into clear SOPs, playbooks, decision rules, prompts, ownership, handoffs, and escalation paths
- Build practical AI agents, automations, and multi-step workflows using tools such as ChatGPT, Claude, Gemini, n8n, Make, Zapier, Power Automate, and similar tools




- Build workflows that summarize information, identify priorities, prepare recommendations, draft responses, route tasks, track follow-ups, and surface items that actually require the CEO's judgment
- Develop an AI-assisted email operating model that can triage and prioritize messages, summarize what matters, identify required actions, prepare drafts where appropriate, route work to the right person, and track follow-up
- Improve calendar and scheduling workflows so commitments, preparation requirements, conflicts, priorities, reminders, and follow-ups are handled systematically
- Create systems that convert conversations, emails, meetings, decisions, and commitments into clear actions and make sure those actions are tracked through completion
- Build systems around recurring household, family, vendor, travel, document, renewal, and personal administration workflows without replacing the people already responsible for those areas
- Determine what should be handled by AI, automation, the AI Chief of Staff, an existing team member, an outside resource, or the CEO
- Personally build useful first versions of simpler AI workflows and agents without waiting on an engineer for every improvement
- Work with our AI Automation Engineer and other technical team members when a workflow requires deeper technical development or more sophisticated automation
- Test workflows in real use, identify where they fail, and continuously improve them
- Maintain transparent documentation so AbbasOS remains organized, repeatable, and not dependent on one individual

What We're Looking For:

- 2-4 years of real hands-on experience in business operations, founder or executive support, chief of staff work, AI automation, systems operations, or a similar role
- Strong practical experience using AI to improve real workflows, not just using ChatGPT for drafting or research
- Hands-on experience personally building AI agents, automations, or multi-step workflows
- Experience with tools such as ChatGPT, Claude, Gemini, n8n, Make, Zapier, Power Automate, or similar AI and automation tools




- Ability to take an unclear or manual recurring process and turn it into a structured, repeatable workflow
- Strong process thinking and the judgment to determine what should be automated, delegated, standardized, or kept human
- Excellent written English and the ability to summarize complex information clearly and concisely
- Exceptional organization, follow-through, attention to detail, and ability to keep track of multiple open loops without losing control
- Strong judgment and discretion when working with confidential business, financial, family, and personal information
- Self-directed and comfortable identifying problems, recommending solutions, and implementing improvements without significant hand-holding
- Comfortable working directly with a CEO whose business and personal workflows are constantly evolving
- Comfortable collaborating with technical team members and knowing when something should be handed off for deeper development
- Someone who keeps up with AI because they genuinely enjoy finding practical ways to use it

If your AI experience is primarily prompting ChatGPT, drafting content, or experimenting with tools but you have not personally built working agents, automations, or repeatable workflows, this is not the right role. Goal: Build and continuously improve AbbasOS so information, requests, commitments, and recurring responsibilities are converted into automated execution, delegated action, organized follow-up, or concise decisions requiring the CEO's judgment. Success means fewer things require the CEO to remember, organize, chase, review, or manually process, while maintaining appropriate visibility and control.

Hiring Process:

1. Application
2. Intro Call
3. Phase I: AbbasOS Workflow & Systems Design
4. Phase II: Practical AI Workflow Build
5. Final Interview with CEO
6. Offer

Benefits:

- Competitive salary
- Annual performance-based bonus
- Paid time off
- All-expense-paid annual company trip

Important: Only applications submitted through the official application link will be considered.

To Apply:

Please fill out the Google Form link here: https://forms.gle/5pdMscpMX8NBH1XP7

To learn more about us, you may check us out here:

- Facebook: www.facebook.com/profile.php?id=61576600761011
- Tiktok: www.tiktok.com/@wentwoodcapitalcareers?is_from_webapp=1&sender;_device=pc
- Wentwood Capital Careers Official Website: wentwood-capital-careers.webflow.io/
- Wentwood Capital website: www.wentwoodcap.com

📌 AI Chief of Staff (Mumbai)
🏢 Wentwood Capital
📍 Mumbai