Head of Concierge Support & Trust — AI-Driven Ops

Pickle; New York (NY); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Healthcare

Equity

Paid time off

Meal Pal credits

Office in Downtown NYC

Pickle credits

Coaching & development

Team events

Job summary

Pickle, a NYC-based peer-to-peer rental marketplace, is seeking a senior leader to own customer operations end-to-end. You will manage offshore agents, partner with Product and Ops to fix root causes, and drive a concierge-quality support experience while lowering cost per contact.

Based in NYC and in the office four days a week, you will shape strategy, set SLAs, and lead a team through high-stakes cases such as fraud and disputes, using automation and AI to raise service levels.

Qualifications

• 4+ years in customer operations, support or CX with 2+ years leading a team.
• Track record of owning metrics and hitting SLAs at scale.
• Strong analytical skills: fluent in Sheets/Excel, translating data into insights and actions.
• Strong critical thinking, judgment, and EQ for high-stakes cases.

Responsibilities

• Own the customer support operation end to end: team, metrics, strategy, and its impact on P&L.
• Manage offshore agents and partner with Product/Operations to address root causes.
• Drive proactive, concierge-quality support and AI-assisted automation to deflect volume and speed up resolution.
• Lead hiring, onboarding, and training for the support team as it scales.
• Handle the toughest cases: fraud and high-value disputes, coordinating with law enforcement when needed.

Skills

Customer operations

Team management

Data analysis

SQL querying

AI automation

Fraud/risk handling

Tools

Intercom

Zendesk

SEON

SQL

Job description

Pickle, a NYC-based peer-to-peer rental marketplace, is seeking a senior leader to own customer operations end-to-end. You will manage offshore agents, partner with Product and Ops to fix root causes, and drive a concierge-quality support experience while lowering cost per contact.

Based in NYC and in the office four days a week, you will shape strategy, set SLAs, and lead a team through high-stakes cases such as fraud and disputes, using automation and AI to raise service levels.