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Pickle is a peer-to-peer rental marketplace enabling consumers to rent high-quality items on-demand, with 400K+ items live nationwide and rapid scaling in NYC, LA, and Miami. The company has raised $20M from top-tier investors and is expanding beyond fashion into all categories.
As Customer Support Manager, you'll own the entire support operation end-to-end: team management, metrics, strategy, and P&L impact. Reporting to the Head of Ops, you'll manage a team of offshore agents while personally handling the highest-stakes cases—fraud, high-value damage disputes, and complex escalations where judgment matters more than scripts.
Key responsibilities include:
- Designing and executing support strategy that scales quality while driving down cost per contact through smarter routing, automation, and process optimization
- Building concierge-quality, proactive support for high-impact moments rather than reactive ticket handling
- Driving support automation using Intercom and AI tools to deflect volume, accelerate resolution, and free agents for complex cases
- Partnering with Product and Operations on root-cause analysis to reduce recurring tickets and improve user experience
- Managing support metrics, SLAs, and weekly reporting
- Leading day-to-day offshore agent team: coaching, quality assurance, consistency, hiring, onboarding, and training as the team scales
- Owning fraud investigation, dispute resolution, and high-value cases using fraud tooling (SEON) and coordinating with law enforcement when needed
- Serving as the calm, senior escalation owner for rare, high-stakes situations outside normal hours
You'll need 4+ years in customer operations, support, or CX with 2+ years managing a team. Strong analytical skills (Sheets/Excel fluency), critical thinking, and EQ are essential. You should be naturally curious about new tools and comfortable with AI-assisted automation. Experience with offshore teams, Intercom/Zendesk, SQL, two-sided marketplaces, or fraud/dispute work is a plus. Based in NYC with 4 days/week in-office (Tribeca).
