Chief of Staff

Sterling Capital Brokers is a Canadian employee benefits distribution platform. We operate with a proprietary technology platform at the core and we're growing fast — through direct sales, acquisitions, and channel partnerships with payroll and HRIS companies across Canada.

We're 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

• 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 enrichmentBuild 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
• 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

• 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