Chief of Staff, Online Grocery

We're transforming the grocery industry

At the company, 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 the company Personal Shoppers.

The company 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.

The company 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.

Overview

The company'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

The company 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 .

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 rea d more about our benefits offerings here .

For US based candidates, the base pay ranges for a successful candidate are listed below.

CA, NY, CT, NJ

$239,000 — $252,000 USD

WA

$229,000 — $241,500 USD

OR, DE, ME, MA, MD, NH, RI, VT, DC, PA, VA, CO, TX, IL, HI

$219,000 — $231,000 USD

All other states

$199,000 — $210,000 USD