Director of Customer Success

Overview

We are representing a confidential retail technology company in their search for a Director of Customer Success to lead their commercial customer success organization. This is a high-impact leadership role accountable for post-implementation growth, retention, and expansion across an enterprise software portfolio serving major North American retail chains.

In this highly visible position, you will lead a team of senior managers, Account Growth Managers, and Principal Growth Strategists who serve as the strategic and commercial face to retailer executives. You'll own critical outcomes including net revenue retention (NRR), gross revenue retention (GRR), expansion GTV, adoption velocity, and customer satisfaction. This is a remote opportunity available across the United States, with a preference for candidates who can collaborate closely with teams in Toronto.

Responsibilities

• Lead the customer success organization for the enterprise software portfolio, owning commercial outcomes end to end including NRR, GRR, expansion GTV, adoption velocity, CSAT, and renewal performance
• Build and develop a senior consultative customer success team by hiring and ramping Principal Growth Strategists who engage retailer executives on ecommerce strategy, merchandising, and operations
• Manage senior managers leading Account Growth Manager pods, setting standards for quality across account team layers including quarterly business reviews, growth planning, executive engagement, and renewal execution
• Operate as a commercial peer in a business development-led environment, owning post-sale accountability while surfacing churn, expansion, and escalation signals early
• Partner with technical customer success leadership on shared-account coordination, ensuring cross-functional account teams function cohesively with clear escalation paths
• Define and enforce strategic boundaries ensuring senior strategists remain focused on retailer-executive engagement and growth strategy rather than operational execution
• Own the consultative transformation roadmap including talent strategy, compensation structure, operating cadence, and tooling shifts to evolve customer success into a strategic business advisory function
• Partner on the implementation-to-success motion as a managed lifecycle, ensuring smooth account transitions with clear handoff criteria
• Operationalize tiered coverage models applying high-touch support for strategic accounts and scaled approaches for smaller accounts
• Build structured customer feedback loops into product development, surfacing durable patterns and instrumenting adoption of roadmap items
• Apply AI augmentation to scale customer success coverage and quality including health monitoring, account preparation automation, and insight generation
• Represent the post-sale narrative to senior leadership and serve as the director-level escalation point for retailer relationships

What We're Looking For

Required Qualifications:

• 8+ years of enterprise customer success, account management, or post-sale leadership at a B2B SaaS or enterprise technology company
• Direct, accountable leadership of a customer success organization responsible for post-live growth, NRR, and expansion
• Track record of managing managers at the Senior Manager level, with demonstrated ability to set standards and develop senior leaders
• Ownership of a customer success book or post-sale P&L of meaningful scale (e.g., $50M+ ARR) with documented outcomes on NRR, GRR, or expansion
• Proven success operating in a business development or sales-led commercial environment with clear understanding of customer success boundaries
• Demonstrated executive presence with enterprise customer counterparts at VP/SVP/C-level, including ability to deliver difficult messages and navigate escalations
• Experience designing and operating tiered customer success coverage models with capacity planning and exception handling
• Hands-on experience hiring senior consultative talent with clear understanding of profile, compensation, and ramp requirements
• Strong working knowledge of the implementation-to-success handoff and what breaks when coordination fails

Preferred Qualifications:

• Experience transforming a customer success function from reactive enablement into proactive business advisory, including talent, compensation, operating-model, and tooling changes
• Track record of building or scaling Principal-level strategist roles inside a customer success organization
• Experience operating with a separate technical customer success function on shared enterprise accounts
• Background applying AI to customer success workflows with measurable impact on coverage, throughput, or quality
• Familiarity with the business development/customer success interface in complex enterprise sales motions
• Deep familiarity with enterprise retail, grocery, ecommerce platforms, retail media, or adjacent complex B2B domains
• Experience instrumenting customer signal into structured product feedback and partnering with product leaders on adoption accountability

How We Work With You

When you apply through Get A Job.ai, our talent team will conduct an initial screening to understand your background and fit for this role. If we believe you're a strong match, we'll submit your profile to our client for consideration. Throughout the process, we'll serve as your advocate and guide. Please note that you should not contact the client directly—all communication will flow through our recruiting team to ensure the best experience for everyone involved.

Pay

This role is remote across the United States. Our client provides highly competitive compensation that varies by permanent work location. Get A Job.ai works on a fee-for-service model with the hiring company, and candidates are hired directly by the client at their standard compensation levels.

Equal Opportunity

Get A Job.ai is committed to inclusive recruiting practices. We partner with clients who value diversity and provide equal employment opportunities to all qualified candidates regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.