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

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

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