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

–     $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