[Hiring] Chief of Staff @Sterling Brokers

Role Description

This is the core of the role. You will:

• Map current-state processes across the business and identify the highest-leverage automation opportunities
• Build AI-powered workflows using tools like Claude, GPT APIs, Make, n8n, and Zapier — you ship, not just recommend
• Own the AI and automation roadmap, setting priorities and driving accountability across teams
• Integrate AI capabilities with our proprietary platform — knowing when to build natively vs. integrate externally
• Translate frontline operational pain points into clear, prioritised product requirements for the dev team
• Measure the impact of every automation you ship and iterate based on results

Qualifications

• ~5 years of experience in business operations, management consulting or process engineering type role
• Hands-on with AI tools and the ability to learn new technology quickly (Claude, GPT APIs, document AI) and automation platforms (Make, Zapier, n8n, or similar) — you build, not just direct
• Proven ability to write and communicate clearly — you can draft a polished executive update and a process spec in the same afternoon
• Comfortable working with proprietary platforms and technical teams — you understand and can learn our technology and business and make connections
• High ownership mentality — you define the problem, build the solution, and measure the outcome

Requirements

• Experience in insurance, employee benefits, or regulated financial services
• Background in prompt engineering and LLM-based workflow design
• Proficiency in Python or JavaScript for custom integrations and scripting
• Experience with document AI for extracting data from policies and structured documents

Benefits

• $100,000 – $120,000 base salary
• Variable compensation tied to operational and business outcomes
• Equity participation — Long Term Incentive Plan (LTIP)
• Remote-first with direct access to the executive team
• The opportunity to shape how a fast-growing brokerage operates at every level

What You're Like

• Sharp communicator — clear, concise, and effective whether presenting to leadership or writing a process doc
• Action Oriented — you are most comfortable when you are shipping something
• Strategically focused — you prioritize the things that actually move the needle
• Discreet — you will operate with full context and full trust
• Low ego — you lead through results, not title
• Decisive — you don't wait for perfect information to move forward