On the Ground Specialist (Contractor)

Instacart

3d • $42 - $51 • Onsite

About The Position

The Caper Retail Go-to-Market Operations team is responsible for bringing our in-store technology to life inside partner retailers. We work at the intersection of product, store operations, and field enablement—ensuring launches are seamless, adoption is strong, and stores see measurable value from day one. Our team partners directly with retailers to implement smart cart programs that improve the shopper experience and drive incremental growth.

We are hiring an On-The-Ground Specialist (OTGS) to support a retailer's launches with Caper across Maryland. This role is the frontline operator for Caper deployments—owning in-store setup, associate training, launch execution, and early-stage performance stabilization. The OTGS will work directly with store managers, regional retail leaders, Caper GTM and Product teams, and cross-functional partners to ensure each launch meets operational standards and adoption targets.

This is a high-impact role for someone who thrives in fast-moving environments and enjoys turning strategy into execution. The OTGS will be responsible for driving strong first impressions at launch, accelerating shopper adoption, troubleshooting in real time, and feeding actionable insights back to Product and Ops. Their work directly influences GMV growth, retailer satisfaction, and the long-term success of the Weis partnership in the region.

Requirements

• 3+ years in field ops / retail operations / implementation (or equivalent). Proven experience running on-site rollouts in active stores or customer environments—training staff, coordinating stakeholders, and executing go-lives with minimal supervision.
• Comfort owning outcomes in a fast-moving, ambiguous environment. You can prioritize on the fly, make judgment calls with incomplete info, and stay effective when plans change, stores get busy, or constraints appear mid-launch.
• Strong on-the-floor communication + training ability. You can build trust quickly with store leaders and frontline teams, run clear trainings, and influence behavior change without formal authority.
• Hands-on technical aptitude. You can set up and validate hardware, follow SOPs precisely, troubleshoot first-line issues, and document/escalate cleanly—without freezing when something doesn’t work.
• Reliable travel and schedule flexibility. Able to support launches across a region, work in-store hours as needed (including early/late shifts when required), and maintain consistent performance across multiple sites.

Nice To Haves

• Experience launching new technology inside existing retail stores. Familiarity with introducing hardware/software into live environments and driving early adoption curves would accelerate impact, but is not required Day 1.
• Data fluency and performance orientation. Comfort interpreting adoption, GMV, or operational metrics and using them to coach store teams. The ability to move from “activity” to “measurable lift” within 3–6 months is a strong differentiator.
• Process improvement mindset. Experience refining SOPs, training materials, or rollout playbooks. Candidates who can help evolve the launch model—not just execute it—will stand out.
• Exposure to cross-functional HQ partnerships. Prior experience working with Product, Analytics, or GTM teams and translating field feedback into structured insights is a plus.
• Retail leadership or multi-unit experience. Background as a store manager, district leader, or regional trainer can accelerate credibility and influence, but is not mandatory.

Responsibilities

• Own in-store launch execution end to end: Lead hardware setup, cart staging, associate training, and go-live coordination inside existing retail stores. You are accountable for launch readiness, day-one performance, and setting the tone with store leadership.
• Drive adoption and early performance: Spend time on the floor coaching associates, educating shoppers, and removing friction in real time. You are responsible for accelerating usage, improving attachment rates, and stabilizing performance in the critical first weeks.
• Operate as the bridge between store teams and HQ: Surface operational insights, product gaps, and field learnings to GTM, Product, and Analytics partners. Your feedback directly influences roadmap priorities and future launch playbooks.
• Solve problems in live environments: Retail is unpredictable. You will troubleshoot hardware issues, navigate staffing constraints, adapt to store-level nuances, and make judgment calls without waiting for perfect information.
• Scale what works: Help refine training materials, launch checklists, and performance frameworks so each subsequent store improves. This role contributes to building the repeatable system behind regional expansion—not just executing one store at a time.

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed