Chief of Staff

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 – $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