Chief of Staff at Sterling Capital Ltd. – Toronto, Ontario

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