VP, Customer Success

This is a fully remote position, open to applicants in Alabama, +23 more states.

📋 Description

• Take ownership of Tapcheck's complete post-sale organization, which includes Customer Support, Onboarding, Customer Success, Account Management, and Payment Operations.

• Report directly to the COO and assess the current state of each post-sale function.

• Design and implement a strategy for scaling high-volume support, revitalizing the CSM motion, creating proactive Account Management and expansion efforts, and connecting decisions to retention and revenue.

• Define and manage the company-wide Customer Success strategy throughout the customer lifecycle, focusing on retention and expansion.

• Set priorities and allocate limited resources across SMB, Mid-Market, and Enterprise segments.

• Establish metrics, operational rhythms, and early-warning systems to transition the organization from a reactive to a proactive stance.

• Define the structure, roles, responsibilities, expectations, ownership, and accountability for the Customer Success organization.

• Collaborate with the director to develop the Account Management function, including operating models, segmentation, expansion playbooks, and revenue targets.

• Identify accounts at risk and implement risk-mitigation strategies.

• Transform inbound expansion into a measurable, proactive growth initiative.

• Act as the Executive Sponsor for strategic partnerships and facilitate high-level interventions.

• Establish the Customer Support strategy for an organization handling approximately 40,000 tickets monthly, including workforce planning for the next 6–12 months.

• Spearhead the AI and automation strategy within Support.

• Supervise Client Operations, which includes technical onboarding and post-launch servicing, ensuring alignment with sales capacity planning.

• Collaborate with Payment Operations on prioritizing repayment, reconciliation, and proactive client auditing.

• Mentor and develop managers, enhancing organizational leadership capabilities.

• Work alongside Product and Engineering teams, leveraging support and customer data to shape product quality and roadmap decisions.

• Coordinate with Sales on pipeline visibility, handoffs, and staffing needs.

• Represent the customer perspective at the executive level.

• Initially engage directly in executive customer relationships and retention discussions, transitioning to coaching managers as the team grows and matures.

⛳️ Requirements

• 12+ years of experience in post-sale leadership, including over 5 years in senior leadership roles.

• Have led a multi-functional customer organization at the VP level.

• Demonstrated experience managing both operational CS (support, onboarding, implementation) and commercial CS (churn, retention, expansion revenue) within the same role.

• Experience leading high-volume support teams managing tens of thousands of tickets monthly.

• Strong operational discipline, workforce planning skills, and experience with BPO or offshore operations.

• Developed strategic retention and growth systems, including early-warning indicators, save initiatives, and proactive playbooks.

• Experience building or restructuring a Customer Success function during a period of growth, managing ambiguity and competing priorities.

• Proven ability to manage managers and cultivate leadership talent while remaining actively involved as a player-coach.

• Strong cross-functional collaboration with Product, Engineering, Marketing, Finance, and Sales teams.

• Resource allocation and prioritization directly linked to revenue outcomes in a significant B2B or B2B2C environment.

• Candidates must possess the right to work in the United States without current or future employment-based visa sponsorship.

• Preferred: experience in FinTech, payments, earned wage access, HRTech, or another regulated, high-growth sector.

• Preferred: B2B2C post-sale leadership experience that drives client adoption and end-user engagement.

• Preferred: familiarity with AI, automation, or bot strategies in Support or Customer Success.

• Preferred: experience with segmented account models ranging from SMB to Enterprise, including digital or tech-touch approaches.

• Preferred: experience with Salesforce, Zendesk, and data/BI tools.

🏝️ Benefits

• Flexible PTO: No accrual caps, no counting days. Take the time you need.

• 10 paid holidays, including Christmas Eve and New Year's Eve.

• Comprehensive medical coverage through Blue Cross Blue Shield of Texas, with PPO and HDHP options and employer HSA contributions.

• Dental and vision coverage through MetLife.

• Flexible Spending Account (FSA).

• Basic Life/AD&D insurance.

• Employee Assistance Program (EAP).

• 401(k) with a 100% match up to 3% of salary through Mutual of America; eligibility after 90 days.

• Engage in mission-driven work that enhances financial wellness and access to earned wages.

• Join a team culture focused on humility, resilience, raising the bar, and fostering growth.