Meet QuickFacts?
QuickFacts is a Software as a Service (SaaS) company that organizes information and presents it on a searchable web-based application. We develop intricate, innovative software that is simple to use and saves our clients hours each day. Currently, we provide the solution to the insurance industry, offering brokerages a one-stop location for organizational workflows as well as all their carrier underwriting information, including custom-made comparisons, documents, training, and helpful tools.
About The Role
We are looking for a highly analytical, systems-driven, and execution-focused Chief of Staff to join our leadership framework. In this role, you will act as the master coordinator of QuickFacts’ internal engine—bridging high-level strategy with day-to-day operational execution.
This is a permanent, high-leverage position designed for a unique operator who balances the structured, framework-driven mindset of a management consultant with the gritty, execution-first mentality of a SaaS builder. Reporting directly to the CEO (and collaborating closely with the Co-Founder/CRO), you will drive company-wide project delivery, protect our corporate compliance, maintain our strategic momentum, and directly manage our People & Culture Coordinator.
What You’ll Do
Strategic Project Management & Compliance
- Cross-Functional Execution: Act as the central project director for major corporate milestones, including our upcoming US incorporation and multi-state compliance setup.
- Security & Audits: Lead our SOC2 readiness and continuous audit workflows, coordinating yearly penetration testing and data room maintenance.
- AI & Automation: Drive our operational efficiency mandate—auditing internal workflows across all departments to identify, test, and implement AI tools that actively reduce manual administrative time.
- Corporate Governance: Serve as our internal legal liaison for initial contract prep, intellectual property, and trademarks, while managing company insurance and ESG initiatives.
- Tech & IT Infrastructure: Oversee organizational IT structures, device management systems, and vendor relations.
Culture, People, & Accountability
- Team Leadership: Directly manage, mentor, and support our People & Culture Coordinator to ensure daily administrative operations remain world-class.
- Organizational Rhythm: Own the implementation, tracking, and accountability metrics for our company-wide OKR framework to keep all departments aligned.
- Talent Strategy: Build out our company-wide progression planning matrices and design the operational infrastructure required for future US hiring.
- People Operations Oversight: Ensure company policies, EDI initiatives, and recruitment frameworks are updated annually, legally compliant, and reflective of our culture.
- Compensation Analytics: Run proactive market data research to ensure our compensation bands remain highly competitive.
Qualifications
Required:
- The Hybrid Toolkit: A proven track record that blends structured business/management consulting experience (frameworks, OKR tracking, process design) with hands-on operational execution inside a fast-growing Tech or SaaS company.
- Project Management Muscle: Exceptional ability to manage complex, multi-stakeholder projects simultaneously without letting details slip through the cracks.
- Compliance & Technical Agility: Direct familiarity or hands-on experience navigating rigorous compliance or audit frameworks (such as SOC2, ISO, or highly regulated corporate structures).
- AI & Automation Native: A strong curiosity and practical experience leveraging modern AI tools and software platforms to optimize workflows and eliminate manual data entry.
- Leadership & Influence: Strong emotional intelligence and communication skills, with the ability to manage direct reports and influence outcomes across senior leadership teams.
- Time Zone & Travel Alignment: Ability to maintain core working hours aligned with 9:00 AM to 5:00 PM AST (Atlantic Standard Time) from your remote location, and willingness to travel for in-person team events.
Nice to Have:
- Previous experience navigating cross-border corporate administration or US market expansion frameworks.
- Experience building employee leveling structures or performance frameworks from scratch.
How Will You Benefit?
- Be part of a company dedicated to improving brokerage operations.
- Get to work with a great team of self-proclaimed insurance nerds (we’re slightly biased).
- Be a part of the change in the insurance industry.
- Have an outlet for your creativity and organizational skills.
- True Work-Life Balance: Enjoy our permanent 4-day workweek
- Work from home (Open to exceptional candidates anywhere in Canada).
- Working with a Start-Up Company that is growing quickly!
- Extended health & dental benefits.
- MacBook and computer accessories provided.
- Base Salary: Starting at $90,000 / year + Employee Stock Options (Note: Final compensation to be calibrated based on the candidate's exact experience tier).
Why QuickFacts:
At QuickFacts, we believe a strong, supportive company culture is the foundation of success. Just as we uphold professionalism and excellence for our clients, we are equally committed to empowering our team. From day one, we provide the tools, training, and resources you need to thrive.
While experience is important, we value your enthusiasm, eagerness to learn, and willingness to take on new challenges just as much. At QuickFacts, we’re not just building a team—we’re shaping the next generation of leaders. Ready to grow with us? Take the next step in your career and join our dynamic, forward-thinking team today.
We Value Diversity
We are committed to building a diverse workforce that reflects our community at all job levels. We welcome applications from minorities and other racially visible persons, as well as persons with disabilities and women in underrepresented roles. If you are a member of one of these equity groups, we encourage you to self-identify in your application.
Pay: From $90,000.00 per year
Work Location: Remote
