Chief of Staff

Sterling Brokers•Toronto, ON

36d•$100,000 - $120,000•Remote

About The Position

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

Requirements

~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

Responsibilities

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
Own the AI and automation roadmap, setting priorities and driving accountability across teams
Integrate AI capabilities with our proprietary platform
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
Draft, structure, and refine communications on behalf of the executive team
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
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
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
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
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