This is a remote-friendly role. Ideally, candidates will sit in the following states: AL, AZ, CA, CO, DC, DE, FL, GA, ID, IL, LA, MA, MO, NC, NH, NJ, NV, NY, OR, OH, PA, RI, SC, TX, VA, WA, WI.
At this time, Tapcheck does not provide sponsorship for employment-based visas (e.g., H-1B, L-1, TN, etc.). Therefore, candidates must already possess the right to work in the United States without the need for employment-based visa sponsorship now or in the future.
About the Job
The VP, Customer Success is the executive owner of Tapcheck's entire post-sale organization: Customer Support, Onboarding, Customer Success, Account Management, and Payment Operations. Reporting to the COO, you will audit the current state of each function, then architect and lead the strategy that carries Tapcheck through its next phase of growth: scaling high-volume support, rebuilding the CSM motion, standing up a proactive Account Management and expansion engine, and tying every decision back to retention and revenue.
This role is for a leader who has built these functions before and wants to build them again with real ownership. In our B2B2C model, we win the employer, then we win adoption, engagement, and trust with their employees. You'll set direction across four functions at different maturity levels while developing a team of managers who run the day-to-day. You will not own individual accounts. Early on, expect to be hands-on: sitting in on executive customer relationships and save conversations, and working alongside your managers to establish the right playbooks and standards. As the team matures and your managers grow into their roles, your involvement shifts from doing the work to coaching the people who do it.
What You'll Do
Strategy & Executive Ownership
• Define and own the company-wide Customer Success strategy across the entire customer lifecycle including retention and expansion, building the playbook that will allow us to scale with excellence
• Audit the current state of all four functions all with the functional leaders, then set clear priorities: what gets invested in now, what gets deprioritized, and how finite resources are deployed across SMB, Mid-Market, and Enterprise segments
• Establish the metrics, operating rhythm, and early-warning systems that shift the organization from reactive to proactive
• Draw a straight line from every CS decision to revenue outcomes, with direct accountability to the executive team
Retention, Expansion & Account Management
• Define the Customer Success org structure: clarify roles and responsibilities, set performance expectations, and establish clear ownership and accountability
• Stand up the Account Management function from near-scratch alongside its director, defining the operating model, account segmentation, expansion playbook, and revenue targets
• Build an early warning system that identifies at-risk accounts early and the appropriate risk mitigating playbooks
• Convert organic, inbound expansion into a measurable, proactive growth motion across the existing client base
• Serve as the Executive Sponsor in strategic partnerships and facilitate intervention in high-level conversations
Support & Operations at Scale
• Set the Customer Support strategy for a high-volume organization, including workforce planning with a 6-12 month forward view
• Drive the AI and automation strategy in Support to scale capacity without proportional headcount growth
• Oversee Client Operations (technical onboarding and post-launch servicing), building capacity planning in collaboration with sales to staff, manage and measure programs effectively
• Partner with the Payment Operations leader on strategic prioritization for a client-facing team that owns repayments, reconciliations, and a proactive client auditing program
Leadership & Cross-Functional Partnership
• Coach and develop a team of managers, leveling up leaders while driving strategy
• Partner with Product and Engineering to close the loop between support volume and product quality, shaping the roadmap with customer and support data
• Align with Sales on pipeline visibility, handoffs, and staffing ahead of growth
• Represent the voice of the customer at the executive level, influencing company-wide decisions with firsthand customer insight
What You've Done
Required
• Spent 12+ years in post-sale leadership, including 5+ years in senior leadership, and have owned a multi-function customer organization at the VP level
• Owned both operational CS (support, onboarding, implementation) and commercial CS (churn, retention, expansion revenue) within the same role
• Led organizations with high-volume support, tens of thousands of tickets per month, with the operational discipline, workforce planning, and BPO or offshore experience that scale requires
• Built the systems and processes for retention and growth at a strategic level: early warning signals, save motions, and proactive playbooks
• Built or rebuilt a Customer Success function during a growth phase, operating comfortably through ambiguity and competing priorities
• Managed managers and developed leaders, not just ICs, while staying hands-on as a genuine player-coach: on customer calls, in save conversations, building executive relationships directly
• Operated as a strong cross-functional partner with Product, Engineering, Marketing, Finance and Sales
• Made resource and prioritization decisions tied directly to revenue outcomes in an extensive B2B or B2B2C environment
Preferred
• Worked in FinTech, payments, earned wage access, HRTech, or another regulated, high-growth environment
• Led post-sale teams in a B2B2C model, winning the client, then driving adoption and engagement through their end users
• Drove AI, automation, or bot strategy in a support or CS organization
• Managed segmented account models spanning SMB through Enterprise, including digital or tech-touch motions
• Experience with Salesforce, Zendesk, and data/BI tooling
Compensation
Compensation at Tapcheck is competitive and benchmarked to your role and the market. We're committed to a total rewards package that reflects your impact. Full details are shared as part of our hiring process.
