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
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
