Pilot Store Operations Specialist, Caper (Contract)



windsor, ct, usa
Posted on Friday, February 9, 2024

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.


The Pilot Store Operations Specialist is responsible for in-store operational success as we bring Caper Carts to new retail stores. In this client-facing role, your on-the-ground presence in partner grocery stores will be pivotal to planning and launching new pilots while also collaborating remotely with Caper’s operations, product, and business teams for enduring performance.

This role will be a temporary contractor role for up to 3 months with the ability to extend if required. This is a unique opportunity for individuals with a passion for retail, technology, and continuous improvement to impact our operations at the grassroots level.

Location: Various locations within Ohio (must be willing to travel to multiple store locations)


Caper builds smart shopping carts powered by deep learning and computer vision to enable a seamless grab-and-go retail experience. Caper’s unique technology is a plug-and-play solution that does not require retail store renovation, operational overhaul, heavy computing, and endless image labeling & training. Retailers simply purchase smart shopping carts and the entire store is upgraded with cashierless capabilities!

Caper is one of the fastest-growing retail automation technology products in the market, costs less than 1% of our competition’s infrastructure and is already widely adopted in the marketplace. Our cross-functional team solves challenging problems in ways that our customers love.


  • Engage with store teams throughout the launch and implementation cycle of pilot programs.
  • Provide hands-on, on-site observation to identify, troubleshoot, and resolve operational challenges.
  • Serve as a crucial link between local store teams and broader strategic operations, ensuring clear communication and feedback loops.
  • Oversee the execution of local initiatives and the rollout of new programs, ensuring alignment with company goals and standards.
  • Conduct technical testing and troubleshooting, following guides to problem-solve issues with technology, and potentially build or repair elements as needed.
  • Utilize performance metrics and data analysis to drive continuous improvement and operational excellence within pilot store locations.
  • Document processes, issues, and resolutions in clear notes and other media as required.


  • Demonstrates a passion for operations, an eagerness for continuous improvement, and a strong interest in e-commerce and retail technology.
  • Proven autonomy, ability to multi-task and excel in a fast-paced, ever-evolving environment.
  • Experience and comfortability in handling technology challenges using guides and troubleshooting resources.
  • Customer-focused orientation that aims to over-deliver on expectations
  • Collaborative attitude who enjoys working with a team to solve problems

Minimum Qualifications

  • Minimum 3 years of retail experience in management, regional, or corporate roles.
  • Demonstrated experience in driving program implementation, change management, and successful execution of training, as well as measurement of success.
  • Exceptional written and oral communication skills with the capacity to adjust messaging based on audience needs.
  • Flexibility to travel and spend significant time in retail environments, especially during peak periods.
  • Proficient in performance monitoring, reporting, and leveraging data for operational improvements.

Preferred Qualifications

  • Bachelor’s degree in related field or equivalent work experience
  • Proven track record with process mapping, measurement, and documentation, with a firm grasp of continuous improvement tools and methodologies.
  • Experience in a client-facing role

This contract position requires a flexible schedule, including availability during store peak hours, weekends, and holidays as needed to meet project demands. It includes significant on-site presence at store locations within the designated region.