[All remote jobs](https://jobicy.com/jobs.md)[![Instacart logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2023/03/fe39c2bc9bb5ebb0b5e24318b1f3b60d.jpeg)](https://jobicy.com/company/instacart.md)[Instacart](https://jobicy.com/company/instacart.md) # Chief of Staff, Online Grocery Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/instacart.md)ShareRemote from[Canada](https://jobicy.com/job-region/canada.md)SalaryCAD 203k–214k / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceDirectorPublished26 Oct 2026Apply before25 Nov 2026Listing views36Application actions2Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Instacart seeks a senior Chief of Staff to partner with the General Manager of its Online Grocery business and R&D organization of approximately 200 people. The role owns executive operating rhythms, planning cycles, decision frameworks, leadership communications, and follow-through on strategic priorities. It also supports organizational health, headcount planning, executive and board alignment, and ambiguous cross-functional initiatives. This is a high-impact individual-contributor position requiring strong product and R&D fluency, executive presence, analytical judgment, and exceptional program leadership. The role is remote within Ontario, Alberta, British Columbia, or Nova Scotia, with occasional travel of up to 10%. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis role requires influencing senior product, design, engineering, finance, and HR leaders without direct authority while simultaneously running high-stakes operating cadences. Success depends on independently converting ambiguous organizational issues into clear decisions, plans, and sustained execution. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job median (per year)Market rateC$208,500CA market range (per year)C$190k–C$240k0C$264k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses a base-pay range of CAD 203,000–214,000. Although the posting does not explicitly state the cadence, this is inferred as annual base pay based on the senior full-time Chief of Staff role and the magnitude of the Canadian compensation range. A reasonable estimated Canadian market range for a senior technology Chief of Staff is CAD 190,000–240,000 per year, excluding equity and benefits. ## Core skills Skills and capabilities most closely associated with this opportunity. [Executive partnership](https://jobicy.com/jobs?search_keywords=Executive%20partnership.md)[Strategic operations](https://jobicy.com/jobs?search_keywords=Strategic%20operations.md)[Operating cadence design](https://jobicy.com/jobs?search_keywords=Operating%20cadence%20design.md)[Program management](https://jobicy.com/jobs?search_keywords=Program%20management.md)[Organizational planning](https://jobicy.com/jobs?search_keywords=Organizational%20planning.md)[Leadership facilitation](https://jobicy.com/jobs?search_keywords=Leadership%20facilitation.md)[Executive communications](https://jobicy.com/jobs?search_keywords=Executive%20communications.md)[Stakeholder management](https://jobicy.com/jobs?search_keywords=Stakeholder%20management.md)[Decision frameworks](https://jobicy.com/jobs?search_keywords=Decision%20frameworks.md)[Product operations](https://jobicy.com/jobs?search_keywords=Product%20operations.md)[R&D collaboration](https://jobicy.com/jobs?search_keywords=RD%20collaboration.md)[Headcount planning](https://jobicy.com/jobs?search_keywords=Headcount%20planning.md)[Change management](https://jobicy.com/jobs?search_keywords=Change%20management.md)[Analytical problem solving](https://jobicy.com/jobs?search_keywords=Analytical%20problem%20solving.md)[Organizational health](https://jobicy.com/jobs?search_keywords=Organizational%20health.md) Sample interview questionsHow would you establish an effective operating rhythm for a 200-person product and R&D organization?I would first map the existing meeting, planning, and decision cadences, identify duplication and decision bottlenecks, and align the GM and leadership team on a small set of essential forums. I would define the purpose, inputs, decision rights, owners, and follow-up mechanism for each forum, then review effectiveness regularly using stakeholder feedback and execution outcomes. Describe how you would handle a strategically important initiative with unclear ownership and competing stakeholder views. I would clarify the intended outcome, constraints, and decisions required, then identify accountable DRIs and affected stakeholders. I would create a concise problem statement and options document, facilitate the needed decision forums, document the decision, and establish a milestone-based operating cadence that makes risks and commitments visible. How do you influence senior leaders when you do not have direct authority? I build credibility through preparation, sound judgment, and reliable follow-through. I seek to understand each leader's objectives and constraints, frame recommendations around shared business outcomes, present clear trade-offs, and make it easy for leaders to act by proposing concrete decisions and next steps. What approach would you use to turn engagement-survey findings into meaningful organizational improvement? I would segment the findings to distinguish systemic themes from local concerns, validate the interpretation through targeted discussions, and prioritize a limited number of actions with clear owners and measurable indicators. I would communicate both the insights and the plan transparently, track progress, and close the feedback loop with employees on what changed and why. How would you prepare a GM for a board or C-suite discussion on Online Grocery priorities? I would begin with the audience's likely questions and the specific decisions or alignment needed. I would synthesize performance, strategic context, risks, trade-offs, and recommendations into a concise narrative, pressure-test it with relevant functional leaders, and prepare the GM with clear talking points and responses to likely challenges. Opportunity details ## About this role. We’re transforming the grocery industry At Instacart, we invite the world to share love through food because we believe everyone should have access to the food they love and more time to enjoy it together. Where others see a simple need for grocery delivery, we see exciting complexity and endless opportunity to serve the varied needs of our community. We work to deliver an essential service that customers rely on to get their groceries and household goods, while also offering safe and flexible earnings opportunities to Instacart Personal Shoppers. Instacart has become a lifeline for millions of people, and we’re building the team to help push our shopping cart forward. If you’re ready to do the best work of your life, come join our table. Instacart is a Flex First team There’s no one-size fits all approach to how we do our best work. Our employees have the flexibility to choose where they do their best work—whether it’s from home, an office, or your favorite coffee shop—while staying connected and building community through regular in-person events. [Learn more about our flexible approach to where we work.](https://www.instacart.careers/flex-first) ### Overview Instacart’s mission is to create a world where everyone has access to the food they love and more time to enjoy it together. Online Grocery is the heart of that mission — the products millions of customers rely on every day and the team that builds them. We’re looking for a Chief of Staff, Online Grocery to partner with the General Manager who leads this business and its product and R&D organization of ~200 people across product, design, research and technical program management. People, operations and programs are the core of the work — but what should energize you is what that work makes possible. A Chief of Staff here helps the organization operate at its best: more cohesive, clearer in its purpose, sharper and faster in how it makes decisions and operates, and enabled to do the thing that matters most — building products our customers love. If you’re motivated by improving how a team works, and serve as a multiplier on everything the team can ship, this is your role. This is a highly strategic and operational individual-contributor role (no direct reports) for someone exceptionally organized, has strong business and strategic sense, high in empathy, and who has an understanding of how product, design, and engineering teams work. ### About the Job Run the operating rhythm * Own and continuously improve the business rhythm for the GM and the organization — leadership team syncs, all-team meetings, monthly and quarterly business reviews, planning reviews, organizational communications, and Online Grocery segments of company-wide all-hands. * Manage the operating cadence for the GM — prioritizing and delegating workstreams, ensuring the right things get the right attention at the right time. * Improve how the organization decides: clarify decision rights and the questions that matter, build the frameworks and pre-reads that bring options into focus, and remove the friction that slows good calls. * Once decisions are made, capture and sharpen them, ensure they’re communicated to the right stakeholders, and close the loop on execution — keeping leadership priorities, decisions, and commitments visible and on track (R&D execution itself is owned by TPM). * Shape and run the substance of the leadership team offsites: objectives, agenda, pre-reads, the hard discussions, decisions, and follow-through (logistics and events are handled separately). * Be a trusted thought partner to the GM and a credible problem-solving partner to product and R&D leaders, and build strong relationships with chiefs of staff across the organization to partner effectively in getting your responsibilities done. * Prepare briefings and coordinate research for the GM’s meetings with partners and key leaders — identifying goals, talking points, and relevant context. * Partner with the GM, HR and finance to manage the organization’s headcount budget Plan executive communication * Drive the calendar, planning, and content for upward communication and alignment with the C-suite and the board on Online Grocery priorities. * Support the GM in preparing content for speaking engagements (working with our comms team). Strengthen people, culture, and organizational health * Help the GM spot, diagnose, and get ahead of issues across the organization — bringing structured, candid read-outs and early signals, not just status. * Partner with the GM and HR to address relationship and culture dynamics across the team and create a high-trust, high-performance leadership team culture. * Turn signals like engagement surveys into action — working across the organization to develop the right plans, pressure-test them, and ensure they get executed and the loop gets closed with teams. Drive priority programs * Help the GM kick off and drive annual and long-range planning for Online Grocery. * Take ambiguous new efforts for the GM from unclear to fully underway — creating clarity and a plan, identifying DRIs, setting up the decisions that need to be made, aligning stakeholders, and developing the right operating rhythm to track progress. * Proactively identify and take ownership of emerging opportunities and risks before they become blockers. ### About You Minimum Qualifications * 10+ years of work experience * R&D experience — earned in a direct R&D role (product, design, engineering, or technical program management), an adjacent role embedded with R&D teams, or as a Chief of Staff within an R&D organization * Consulting, corporate strategy/operations, or finance background and experience working directly with executives * Working fluency to navigate a product, design, and engineering organization at scale, and to be a true problem-solving partner to R&D leaders rather than a coordinator. * High EQ and a genuinely people-oriented instinct — builds trusted relationships, reads organizational dynamics, and bridges leadership and teams. * Outstanding written and verbal communication at an executive level * Strong analytical skills, and a commitment to consistently high-quality work. * Exceptional program management: organized, effective, and relentless at driving multiple hard initiatives forward to deadline at once. * Ability to travel 10% Preferred Experience * Experience designing and facilitating leadership offsites and driving organizational, culture, or operating-model change. * Experience building with AI (e.g., prototypes, automations, or agents) in a professional setting. * Experience within high-growth, technology-driven companies. #LI-Remote Instacart provides highly market-competitive compensation and benefits in each location where our employees work. This role is remote and the base pay range for a successful candidate is dependent on their permanent work location. Please review our Flex First remote work policy [here](https://instacart.careers/flex-first/). Currently, we are only hiring in the following provinces: Ontario, Alberta, British Columbia, and Nova Scotia. Offers may vary based on many factors, such as candidate experience and skills required for the role. Additionally, this role is eligible for a new hire equity grant as well as annual refresh grants. Please read more about our benefits offerings [here](https://instacart.careers/taste-of-instacart/). For Canadian based candidates, the base pay ranges for a successful candidate are listed below. CAN $203,000—$214,000 CAD Show more [Apply now >](https://jobicy.com/jobs/157245-chief-of-staff-online-grocery.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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