Principal Customer Success Manager

Instacart is transforming the grocery industry by providing innovative solutions for grocery delivery. As a Principal Customer Success Manager, you will lead a team to ensure the successful adoption and expansion of AI solutions in retail environments, working closely with executive retail leaders and cross-functional teams.

Responsibilities:

• 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

Requirements:

• 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
• 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