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Chief of Staff
Sterling Capital Ltd. · Toronto, Canada, Toronto, ON, Canada · On Site · Active · $110,000–$130,000 / year · Rippling ATS
Job facts
| Field | Value |
|---|---|
| Company | Sterling Capital Ltd. |
| Title | Chief of Staff |
| Normalized title | - |
| Department / team | 760 Project Management Office |
| Location | Toronto, ON, Canada |
| Work model | On Site |
| Employment type | Full Time |
| Salary | $110,000–$130,000 / year |
| Status | active |
| ATS provider | Rippling ATS |
| Posted / first seen | 2026-04-08 / 2026-05-29 |
| Changed / last seen | 2026-06-20 / 2026-06-20 |
Related slices
| Page | What it contains | Open |
|---|---|---|
| Company jobs | Active postings from Sterling Capital Ltd.. | Open |
| Company breakdowns | Role, location, ATS, and work model facets for this company. | Open |
| ATS provider jobs | Active postings observed through Rippling ATS. | Open |
| Provider filtered search | The same provider as a filtered job collection. | Open |
| City jobs | Active postings in Toronto. | Open |
| Department jobs | Active postings in 760 Project Management Office. | Open |
| Work model jobs | Active On Site postings. | Open |
| Lifecycle events | Open, update, close, and reopen events for this posting. | Open |
| Original posting | Canonical source or apply URL captured from the ATS. | Open |
Linked records
| Company | Sterling Capital Ltd. |
| Source | b0c0b647-f32e-47e0-99dd-9e0d90b60168 |
| ATS provider | Rippling ATS |
Description
company
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.
role
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
Full job record
| Job ID | 35064a7c31b139c49a6e428b6e90a8bf0d69b111 |
| Org ID | bf914701-1ac4-43ed-b15b-8e64bb950533 |
| Source ID | b0c0b647-f32e-47e0-99dd-9e0d90b60168 |
| Board ID | b0c0b647-f32e-47e0-99dd-9e0d90b60168 |
| Provider | rippling |
| Provider Job Key | 930e23de-3d87-41ff-a8a7-4937812b89fe |
| Title | Chief of Staff |
| Normalized Title | — |
| Status | active |
| Active | yes |
| Location Text | Toronto, Canada, Toronto, ON, Canada |
| Department | 760 Project Management Office |
| Team | — |
| Employment Type | full_time |
| Workplace Type | on_site |
| Remote Policy | — |
| Country | Canada |
| Region | ON |
| City | Toronto |
| Salary Raw | COMPENSATION & BENEFITS – $110,000 – $130,000 base salary – Variable compensation tied to operational and business outcomes – |
| Salary Min | 110,000 |
| Salary Max | 130,000 |
| Salary Currency | USD |
| Salary Period | year |
| Source URL | https://ats.rippling.com/sterling-careers/jobs/930e23de-3d87-41ff-a8a7-4937812b89fe |
| Apply URL | https://ats.rippling.com/sterling-careers/jobs/930e23de-3d87-41ff-a8a7-4937812b89fe |
| First Seen At | 2026-05-29 07:15:33Z |
| Last Seen At | 2026-06-20 09:26:31Z |
| Last Checked At | 2026-06-20 09:26:31Z |
| Last Changed At | 2026-06-20 09:26:31Z |
| Inactive At | — |
| Source Posted At | 2026-04-08 22:00:34Z |
| Source Updated At | — |
| Raw Payload Uri | s3://job-postings-prod-raw-590183727216/raw/provider=rippling/board=sterling-careers/date=2026-06-20/2026-06-20T09-26-30-670Z-524997580d5832f4565d1552331912b2bd66a961d5b6ebcc9b217d1438aeb262.json |
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"role": "<meta><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"font-size:12pt;white-space:pre-wrap;\"> </strong></b><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">AI & Process Engineering</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">This is the core of the role. You will:</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Map current-state processes across the business and identify the highest-leverage automation opportunities</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Build AI-powered workflows using tools like Claude, GPT APIs, Make, n8n, and Zapier — you ship, not just recommend</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Own the AI and automation roadmap, setting priorities and driving accountability across teams</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Integrate AI capabilities with our proprietary platform — knowing when to build natively vs. integrate externally</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span 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Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">Executive Communications</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Draft, structure, and refine communications on behalf of the executive team — internal updates, partner communications, board materials, and external announcements</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Ensure consistency and clarity in how the executive team presents itself across all channels</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Prepare executive reporting, business performance dashboards, and operational briefings</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Build and maintain the rhythm of business: meeting cadences, follow-ups, and action tracking</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\"> </span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">Operations & Execution</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Translate executive team priorities into operational plans and drive cross-functional execution</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Identify the highest-leverage opportunities for improvement and make the case for investment</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Own ad hoc strategic projects as assigned by the executive team</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Be essential in delivering the business KPI’s across all key metrics</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\"> </span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">Business Development & Sales</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Redesign lead generation, outreach, and pipeline workflows using AI</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Eliminate manual CRM data entry through intelligent data capture and enrichment</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Build intelligent prospecting, lead scoring, and follow-up sequences tailored to our buyer journeys</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Streamline proposal generation and submission preparation</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\"> </span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">Client Service & Account Management</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Streamline client onboarding, policy documentation, and renewal workflows</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Deploy document AI for extraction and routing of certificates, endorsements, and policy comparisons</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Build automated touchpoint sequences for renewals, claims updates, and mid-term changes</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Implement QA checkpoints that ensure consistency in client experience at scale</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\"> </span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">Platform & Product</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Partner with our Technology & Product teams to deliver improved product and technology adoption across the business</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">QA new platform features from a workflow and commercial impact perspective</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Maintain a clear view of the technology roadmap and its alignment with business priorities</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><br></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(27,58,107);font-size:11pt;white-space:pre-wrap;\">WHAT WE'RE LOOKING FOR</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">Must-Haves</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">~5 years of experience in business operations, management consulting or process engineering type role</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">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</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Proven ability to write and communicate clearly — you can draft a polished executive update and a process spec in the same afternoon</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Comfortable working with proprietary platforms and technical teams — you understand and can learn our technology and business and make connections</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">High ownership mentality — you define the problem, build the solution, and measure the outcome</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\"> </span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">Nice-to-Haves</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Experience in insurance, employee benefits, or regulated financial services</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Background in prompt engineering and LLM-based workflow design</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Proficiency in Python or JavaScript for custom integrations and scripting</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Experience with document AI for extracting data from policies and structured documents</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\"> </span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(46,109,180);font-size:11pt;white-space:pre-wrap;\">What You're Like</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Sharp communicator — clear, concise, and effective whether presenting to leadership or writing a process doc</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Action Oriented — you are most comfortable when you are shipping something</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Strategically focused — you prioritize the things that actually move the needle</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Discreet — you will operate with full context and full trust</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Low ego — you lead through results, not title</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Decisive — you don't wait for perfect information to move forward</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><br></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><b><strong style=\"color:rgb(27,58,107);font-size:11pt;white-space:pre-wrap;\">COMPENSATION & BENEFITS</strong></b></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\"> </span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">$110,000 – $130,000 base salary</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Variable compensation tied to operational and business outcomes</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Equity participation — Long Term Incentive Plan (LTIP)</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">Remote-first with direct access to the executive team</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"white-space:pre-wrap;\">–</span><span style=\"font-size:7pt;white-space:pre-wrap;\"> </span><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">The opportunity to shape how a fast-growing brokerage operates at every level</span></p>",
"company": "<meta><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">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.</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">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.</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><span style=\"color:rgb(45,45,45);white-space:pre-wrap;\">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.</span></p><p style=\"font-family:"Basel Grotesk",Arial,sans-serif;font-size:11pt;font-weight:400;line-height:1.6;letter-spacing:0.25px;margin:4px 0px;padding:0px;\"><br></p>"
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