Principal Customer Success Manager

Overview

Instacart’s Customer Success team partners with retailers to bring Caper’s in-store AI solutions—such as smart carts and computer vision–powered experiences—to life at scale. As a Principal Customer Success Manager, you will lead a team focused on driving measurable outcomes for our retail partners, from pilot to nationwide rollout, ensuring stores, shoppers, and operators see tangible value every day.

In this role, you will serve as a trusted advisor to executive retail leaders while orchestrating cross-functional execution with product, engineering, and sales. You will help shape how Instacart and Caper deliver operational excellence in stores, champion the voice of the customer, and guide strategic growth. This role is remote across the U.S. and Canada and includes periodic travel for store visits, pilots, and executive meetings.

About the Job

• Lead, coach, and develop a high-performing Customer Success team of 9 that supports enterprise retailers using Caper’s in-store AI solutions; establish goals, operating rhythms, and career development plans.
• Own executive relationships with retail Directors, VPs, and store leaders to drive adoption, expansion, and renewals; provide strategic guidance on store operations, change management, and value realization.
• Orchestrate end-to-end deployments—from pilot design through nationwide scale—aligning product, engineering, sales, and field operations; define success metrics, milestones, and risk mitigation plans.
• Build and refine playbooks, health scoring, and QBR/EBR cadences; forecast account health and surface voice-of-customer insights that inform product roadmaps and prioritization.
• Lead resolution of complex, cross-functional escalations spanning hardware, software, and store operations; run post-mortems and implement preventative improvements.
• Quantify ROI (e.g., labor savings, throughput, basket size) and present outcomes to executive stakeholders; influence multi-year commercial strategies and expansions.
• Travel up to 30% for onsite store visits, pilot support, and executive meetings as needed.

About You

Minimum Qualifications

• 10+ years of experience in Customer Success, Account Management, or Consulting for B2B technology, with 5+ years supporting enterprise retail clients.
• 3+ years of people leadership experience directly managing and developing customer-facing teams (hiring, performance management, coaching).
• Proven track record owning executive relationships and renewals for strategic accounts totaling $5M+ in annual contract value or equivalent scale.
• Hands-on experience delivering or operating in-store retail technology (e.g., POS, computer vision, smart carts, self-checkout, IoT) across 50+ locations.
• Demonstrated success leading complex rollouts and programs, including pilot design, change management, and store operations readiness.
• Proficiency with CRM and success tooling (e.g., Salesforce, Gainsight) to manage health, forecasting, and QBRs/EBRs.
• Bachelor’s degree in Business, Engineering, Operations, or related field, or equivalent practical experience.
• Willingness to travel up to 30% within North America.

Preferred Qualifications

• Experience with AI/ML or computer vision products in a retail environment.
• Background managing hardware–software deployments and coordinating field services or store operations.
• Analytical fluency with tools like Looker or Tableau; SQL proficiency to build/interpret dashboards and quantify ROI.
• Experience scaling programs from pilot to 100+ store deployments and leading enterprise change management.
• Commercial acumen across SOWs, pricing, and multi-year renewals; comfort presenting to C-suite stakeholders.
• MBA or relevant certifications (e.g., PMP, Prosci) are a plus.
• Track record influencing product and engineering roadmaps via structured voice-of-customer programs.