Job Description
Job Overview
We're seeking a contract Chief of Staff to work closely with the CEO and executive team,
driving strategic priorities and ensuring organizational alignment as we scale. This is a high-
impact role that combines strategic insight, operational execution, and cross-functional
coordination.
As Chief of Staff, you'll act as a force multiplier for leadership, bridging the gap between
vision and execution. You'll oversee critical initiatives, manage key stakeholder relationships, facilitate decision-making, and ensure organizational effectiveness during a pivotal growth phase. This role is ideal for someone who excels in fast-moving, mission-focused environments.
Responsibilities
Partner with the CEO and other executive to define, prioritize, and execute strategic initiatives aligned with company goals
Lead cross-functional projects from conception to completion, ensuring timely delivery and measurable outcomes
Manage the executive calendar, coordinate leadership meetings, and drive accountability for action items
Prepare and coordinate materials for board meetings, investor updates, and strategic presentations
Serve as a trusted liaison between the CEO, executive team, board members, investors, and key partners
Streamline operational processes and enhance organizational effectiveness across all functions
Foster cross-functional collaboration and break down organizational silos
Conduct research and analysis to inform strategic decisions, competitive positioning, and market opportunities
Support business development activities including partnership negotiations and strategic collaborations
Lead high-priority special projects that require executive oversight and cross functional coordination
Qualifications
5+ years of progressive experience in management consulting, strategy, operations, or leadership roles
Experience in fast-paced, high-growth startup environments or complex organizational settings
Bachelor's degree required; MBA or advanced degree preferred
Exceptional analytical and problem-solving skills with ability to synthesize complex information
Outstanding written and verbal communication skills, including executive-level presentations
Proven ability to manage multiple high-priority projects simultaneously with strong attention to detail
Strong project management skills with experience leading cross-functional initiatives
High emotional intelligence, professionalism, and discretion when handling confidential information
Self-starter with ability to work independently and drive initiatives without close supervision
Preferred Qualifications
Prior Chief of Staff or Strategic Operations experience in a high-growth startup
(Series A-C)
Experience in healthcare, health-tech, digital health, or regulated industries
Familiarity with startup fundraising processes, investor relations, and board
governance
Experience with regulatory environments (FDA, Health Canada) or clinical operations
Existing network in Canadian healthcare ecosystem or digital health communityThis position is integral to our leadership team and offers an engaging environment for professionals eager to make a significant impact within our organization.
Pay: $65,064.97-$157,186.03 per year
Benefits:
Dental care
Work Location: In person
We're seeking a contract Chief of Staff to work closely with the CEO and executive team,
driving strategic priorities and ensuring organizational alignment as we scale. This is a high-
impact role that combines strategic insight, operational execution, and cross-functional
coordination.
As Chief of Staff, you'll act as a force multiplier for leadership, bridging the gap between
vision and execution. You'll oversee critical initiatives, manage key stakeholder relationships, facilitate decision-making, and ensure organizational effectiveness during a pivotal growth phase. This role is ideal for someone who excels in fast-moving, mission-focused environments.
Responsibilities
Partner with the CEO and other executive to define, prioritize, and execute strategic initiatives aligned with company goals
Lead cross-functional projects from conception to completion, ensuring timely delivery and measurable outcomes
Manage the executive calendar, coordinate leadership meetings, and drive accountability for action items
Prepare and coordinate materials for board meetings, investor updates, and strategic presentations
Serve as a trusted liaison between the CEO, executive team, board members, investors, and key partners
Streamline operational processes and enhance organizational effectiveness across all functions
Foster cross-functional collaboration and break down organizational silos
Conduct research and analysis to inform strategic decisions, competitive positioning, and market opportunities
Support business development activities including partnership negotiations and strategic collaborations
Lead high-priority special projects that require executive oversight and cross functional coordination
Qualifications
5+ years of progressive experience in management consulting, strategy, operations, or leadership roles
Experience in fast-paced, high-growth startup environments or complex organizational settings
Bachelor's degree required; MBA or advanced degree preferred
Exceptional analytical and problem-solving skills with ability to synthesize complex information
Outstanding written and verbal communication skills, including executive-level presentations
Proven ability to manage multiple high-priority projects simultaneously with strong attention to detail
Strong project management skills with experience leading cross-functional initiatives
High emotional intelligence, professionalism, and discretion when handling confidential information
Self-starter with ability to work independently and drive initiatives without close supervision
Preferred Qualifications
Prior Chief of Staff or Strategic Operations experience in a high-growth startup
(Series A-C)
Experience in healthcare, health-tech, digital health, or regulated industries
Familiarity with startup fundraising processes, investor relations, and board
governance
Experience with regulatory environments (FDA, Health Canada) or clinical operations
Existing network in Canadian healthcare ecosystem or digital health communityThis position is integral to our leadership team and offers an engaging environment for professionals eager to make a significant impact within our organization.
Pay: $65,064.97-$157,186.03 per year
Benefits:
Dental care
Work Location: In person
💡 Quick Summary
Seeking a career-building opportunity? The Chief of Staff position is now open for candidates interested in the Operations Executive Jobs sector. This role in Toronto offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in Operations Executive Jobs is a plus.