Were hiring a Chief of Staff with approximately five years of experience to sit at the intersection of strategy and execution. This is a senior, cross-functional role with direct access to the executive team and a clear mandate: identify where we can operate better, then build it. The two core responsibilities of this role are (1) driving AI-enabled process improvement across every part of the business - you will find the opportunities and build the solutions - and (2) supporting the effective communication of the executive team, both internally and externally. You will have real authority, real ownership, and real impact. **AI & Process Engineering** 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 **Executive Communications** - Draft, structure, and refine communications on behalf of the executive team - internal updates, partner communications, board materials, and external announcements - Ensure consistency and clarity in how the executive team presents itself across all channels - Prepare executive reporting, business performance dashboards, and operational briefings - Build and maintain the rhythm of business: meeting cadences, follow-ups, and action tracking **Operations & Execution** - Translate executive team priorities into operational plans and drive cross-functional execution - Identify the highest-leverage opportunities for improvement and make the case for investment - Own ad hoc strategic projects as assigned by the executive team - Be essential in delivering the business KPI's across all key metrics **Business Development & Sales** - Redesign lead generation, outreach, and pipeline workflows using AI - Eliminate manual CRM data entry through intelligent data capture and enrichment - Build intelligent prospecting, lead scoring, and follow-up sequences tailored to our buyer journeys - Streamline proposal generation and submission preparation **Client Service & Account Management** - Streamline client onboarding, policy documentation, and renewal workflows - Deploy document AI for extraction and routing of certificates, endorsements, and policy comparisons - Build automated touchpoint sequences for renewals, claims updates, and mid-term changes - Implement QA checkpoints that ensure consistency in client experience at scale **Platform & Product** - Partner with our Technology & Product teams to deliver improved product and technology adoption across the business - QA new platform features from a workflow and commercial impact perspective - Maintain a clear view of the technology roadmap and its alignment with business priorities **WHAT WE'RE LOOKING FOR** **Must-Haves** - ~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 **Nice-to-Haves** - 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 **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 **COMPENSATION & BENEFITS** - $110,000 - $130,000 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