Head of Dealer Success — Card Dealer Pro

Head of Dealer Success — Card Dealer Pro

Full Time

Remote / Haddonfield, NJ

About the role

Card Dealer Pro is building the operating system for modern card dealers—helping them ingest, identify, list, and sell cards faster across channels. The Head of Dealer Success owns dealer outcomes end-to-end and is directly accountable for increasing Gross Retention and Net Retention through adoption, value realization, engagement, and expansion.

This is a senior, cross-functional leader role that blends strategic account management, programs, support operations, and dealer-driven QA into one tight feedback loop.

What success looks like (primary measures):

You will be accountable for:

• Gross Revenue Retention (GRR) and Net Revenue Retention (NRR) improvement (primary KPIs)]
• Dealer adoption and value realization (time-to-value, feature adoption, workflow completion)
• Expansion outcomes from key accounts (upsell/cross-sell, usage growth, seat/location growth)
• Support effectiveness (resolution time, deflection, CSAT, quality) in an AI-first support model
• CDP > CollX GMV lift driven by dealer activation and ongoing execution

What you’ll do:

1) Own retention and customer health across segments

• Define and operate a customer health model across our three core segments (e.g., Part-Time sellers, Full-Time sellers (online and local card shops / shows), Enterprise)
  
• Instrument leading indicators (usage, workflow completion, listing velocity, inventory throughput, support signals)
• Build programs that move health scores and reduce churn risk (onboarding, reactivation, training, playbooks). Collaborate with Growth Marketing team to deliver lifecycle messaging.

2) Form and execute Dealer Success Plans (DSPs) for key accounts

• Create Dealer Success Plans (DSPs) with key/strategic accounts: goals, milestones, adoption plans, ROI, and operating cadence
  
• Run QBRs/EBRs with enterprise dealers and ensure measurable value delivery
• Coordinate cross-functionally to unblock dealers (Product, Engineering, Ops, GM)
• Own strategy, operations, incentives, and performance for the CDP Ambassador program
  
• Build a scalable engine for referrals, training, enablement content, and community feedback
• Track program ROI, conversion impact, and retention lift attributable to community initiatives, including collaboration closely with the CollX Ambassador Program

4) Oversee Support delivery across CDP and CollX (AI-first)

• Oversee the support experience end-to-end across CDP and CollX
  
• Partner closely with the Head of Operations and GM, Card Dealer Pro to define and implement a modern, AI-first support delivery model
  
• Lead on delivery of all Tier-2 support (more advanced issues)
• Drive support tooling strategy (knowledge base, AI agent workflows, ticketing/CRM, in-product help, automation)
• Improve response/resolution times, quality, and self-serve rates while reducing cost-to-serve

5) Be the key enterprise contact and adoption owner

• Serve as the primary success leader for enterprise customers and strategic dealers
  
• Ensure adoption of CDP’s core workflows and advanced capabilities
• Identify expansion opportunities based on value delivered and operational maturity
• Develop dealer playbooks that increase sell-through and GMV through CollX pathways
• Track and improve conversion funnels from CDP inventory/listing workflows into CollX monetization

7) Oversee dealer-driven QA feedback loops for new features

• Own the dealer-facing QA process for new CDP releases (UAT with real dealers)
  
• Build a repeatable testing regimen and feedback pipeline with Product/Engineering
  
• Ensure new features ship with the polish, reliability, and workflow clarity dealers expect

Who you are

You’re a dealer-obsessed operator who can drive outcomes across strategy, people, programs, and systems. You love cards. You love people. You love helping people make money selling cards.

Required qualifications

• 7+ years in Customer Success / Customer Experience / or Customer-facing Managerial role
  
• Proven track record improving NRR/GRR with measurable results
• Experience leading strategic/enterprise accounts or customer-facing operational function
• Strong operational rigor: metrics, health scoring, segmentation, playbooks, and program design
• Experience building or modernizing Support (tooling, workflows, escalation, QA, KB, self-serve)
  
• Excellent cross-functional leadership with Product/Engineering/Operations
• Data-driven decision maker; comfortable in analytics tools and dashboards

Strongly preferred

• Experience in marketplaces, e-commerce, or seller/dealer ecosystems (cards, collectibles, resale, SMB operations)
  
• Experience implementing AI-first support (agent workflows, deflection, KB strategy, automation)
  
• Familiarity with dealer workflows: inventory ingest, scanning, listing, repricing, shipping, and multi-channel selling

Core competencies

• Dealer empathy + high standards
  
• Process design and accountability systems
  
• Ability to move between hands-on execution and strategy
• Comfort in fast-moving, high-ownership environments

Working relationships

This role reports to the GM, Card Dealer Pro and partners tightly with:

• Head of Operations
  
• Product & Engineering leadership
  
• CollX leadership (for shared support + GMV outcomes)

Equal opportunity

Card Dealer Pro is an equal opportunity employer. We value diverse perspectives and build better products when our team reflects the broad set of dealers we serve.