Vice President, Customer Success

Overview

Appriss Retail is seeking a VP of Customer Success to lead an established, high-performing CS organization and drive continued customer retention, growth, and advocacy across a complex enterprise retail portfolio. This is a senior leadership role with full accountability for the customer lifecycle — from implementation handoff through renewal — built on a foundation of experienced, tenured CSMs who are deeply embedded in their accounts and consistently deliver strong customer outcomes.

The VP of Customer Success will lead the Director of Customer Success and the full CSM organization, overseeing relationships across a portfolio of enterprise retail clients. These are strategic, deeply embedded accounts requiring executive-level engagement, multi-stakeholder relationship management, and a consistent focus on demonstrating and communicating measurable value at every stage of the customer journey.

This role reports directly to the Chief Customer Officer and partners closely with Sales, Product, and Marketing to ensure alignment across retention strategy, customer advocacy, and go-to-market execution.

Essential Duties

• Leadership and development of the Director of Customer Success and the full CSM organization.
• Portfolio-level gross revenue retention (GRR) and net revenue retention (NRR).
• Commercial accountability: this is a revenue-generating CS function — the VP owns renewal execution strategy and directly supports expansion efforts in close partnership with Sales leaders.
• Executive sponsorship of the company’s most complex, high-value accounts — multi-banner, multi-region, multi-stakeholder retail relationships.
• Customer journey oversight — ensuring a consistent, high-quality experience from onboarding through renewal, with structured approaches to communicating and demonstrating value at each stage.
• CS playbooks: strategic account engagement, risk identification and management, escalation protocols, and expansion motions.
• Cross-functional partnership: collaborate with Sales on expansion pipeline, Product on customer feedback loops, Marketing on customer advocacy programs, and RevOps on forecasting and reporting.
• Long-term customer advocacy: developing customer champions, reference relationships, and advisory engagement that support broader go-to-market objectives.
• Organizational design: in partnership with the Director of CS and CCO, build toward a segmented or pod-based CS model aligned to customer complexity and growth stage.
• Talent development and succession planning within the CS organization.
• CS performance reporting to the CCO and executive leadership.

Required Qualifications

Knowledge, Skills, & Abilities

• 8+ years in Customer Success leadership in a B2B SaaS environment, with a track record of managing teams and driving measurable retention outcomes.
• Experience working directly with retail organizations.
• Demonstrated impact on GRR and NRR at portfolio scale.
• Experience managing managers and building CS organizational structure, process, and playbooks.
• Strong commercial acumen: experience in renewal strategy, pricing discussions, and executive-level customer engagement.
• Demonstrated ability to build long-term customer relationships and develop customer advocates at the executive level.
• Familiarity with CS platforms (Gainsight, Totango, or similar); Salesforce proficiency.
• Experience operating in a PE-backed, metrics-driven, high-accountability environment.

Tools & Systems

• Salesforce (account management, forecasting, and pipeline visibility).
• Gong (conversation intelligence and account health).
• Claude AI tooling (Appriss is an active AI-first organization).
• Microsoft Suite (Teams, Excel, PowerPoint, SharePoint).
• CS platform experience a plus (Gainsight, Totango, or equivalent).

Education & Experience

• Bachelor's Degree or equivalent.
• Master's Degree / MBA is a plus.

Benefits

At Appriss Retail, we offer a competitive and comprehensive benefits package designed to support your well-being at work and beyond. Benefits begin on your first day and include multiple medical plan options, dental and vision coverage, health savings and flexible spending accounts, paid parental leave, and supplemental coverage for life’s unexpected moments. We offer generous paid time off, a 401(k) with immediate vesting and company match, short- and long-term disability, and free access to health and wellbeing resources such as Calm and Sworkit. You’ll also have access to learning and development opportunities to help you grow your career. Our benefits support your well-being so you can perform your best in every part of life.

Reports to: Chief Customer Officer

Department: Customer Success

Supervisory Duties: Yes

Travel Required: 20%

Location/Work Region: Remote - US

Compensation range reflect base compensation. This job is also eligible for commission.

We are proud to be an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to protected characteristics.