Chief of Staff, Online Grocery

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take ownership of and continuously enhance the operating rhythm for the General Manager and the Online Grocery division.

• Oversee the GM's operating cadence, prioritization, and delegation of various workstreams.

• Enhance organizational decision-making through established decision rights, frameworks, and pre-reads.

• Document, communicate, and monitor leadership decisions, priorities, and commitments.

• Design and facilitate leadership team offsite meetings, encompassing objectives, agendas, discussions, decisions, and follow-through actions.

• Act as a reliable thought partner to the GM and a problem-solving ally for product and R&D leaders.

• Prepare briefings and coordinate research for the GM's meetings.

• Collaborate with the GM, HR, and finance teams on headcount budgeting.

• Manage the calendar, planning, and content for C-suite and board communications.

• Assist the GM with content for speaking engagements.

• Identify and address organizational challenges, relationship dynamics, and cultural needs.

• Transform engagement survey insights into actionable plans and ensure their execution.

• Support the annual and long-term planning for Online Grocery.

• Convert vague initiatives into structured programs that include plans, ownership, decisions, stakeholder alignment, and operational rhythms.

• Identify and take ownership of emerging opportunities and risks before they escalate into obstacles.

⛳️ Requirements

• A minimum of 10 years of professional experience.

• Background in R&D within product, design, engineering, technical program management, or a related embedded role, or experience as Chief of Staff in R&D.

• Experience in consulting, corporate strategy/operations, or finance.

• Proven track record of working directly with executives.

• Proficiency in navigating product, design, and engineering organizations at scale.

• High emotional intelligence and a people-oriented approach to building trusted relationships and understanding organizational dynamics.

• Exceptional written and verbal communication skills suitable for executive-level interactions.

• Strong analytical abilities and a commitment to delivering high-quality work.

• Outstanding program management skills with the capability to drive multiple complex initiatives to completion within deadlines.

• Willingness to travel up to 10% of the time.

• Preferred: Experience in designing and facilitating leadership offsite meetings and driving organizational, cultural, or operating model transformations.

• Preferred: Experience in building with AI, including prototypes, automations, or agents.

• Preferred: Experience in high-growth, technology-driven organizations.

🏝️ Benefits

• Highly competitive compensation and benefits package.

• Equity grant for new hires.

• Annual refresh grants.

• "Flex First" work-location flexibility, allowing for work from home, an office, or a coffee shop.

• Regular in-person events to foster team collaboration.

• Comprehensive benefits offerings as highlighted by Instacart.