About the role

Trust is at the heart of every Pickle order. It drives our core product and has helped build a brand that people love. You'll be the architect of exceptional experiences, empowering users by preventing issues before they happen, resolving disputes with fairness, and turning challenges into opportunities for connection. By proactively maintaining trust and ensuring seamless interactions, you'll be a vital driver of Pickle's growth, fostering a community where owners and renters feel confident and supported in every exchange.

You'll own our customer support operation end to end: the team, the metrics, the strategy, and its impact on the P&L. Reporting to the Head of Ops, you'll manage a team of offshore agents, partner with Product and Operations to fix problems at the root instead of one ticket at a time, and personally own our hardest, highest-stakes cases: fraud, high-value damage, and complex disputes, where good judgment matters more than a script. Beyond running a tight day-to-day operation, you'll set the direction for what support becomes next: rolling out proactive, concierge-quality service and leveraging automation and AI to make the experience meaningfully better while driving cost per contact down.

It's a broad role for someone who likes designing the strategy, building a sharp operation across internal teams and external partners, and owning the calls that carry real risk.

What you'll own

• Support strategy and its P&L impact: scaling service quality as volume grows while driving cost per contact down through smarter routing, automation, and process, not just headcount
• Concierge-quality support: rolling out proactive, white-glove handling for the moments that matter most, rather than only reacting to inbound tickets
• Support automation (Intercom + Fin): continuously pushing AI further to deflect volume, speed up resolution, and free the team to focus on the cases that need a human
• Root-cause work with Product and Operations to cut recurring tickets and improve the experience
• Support metrics, SLAs, and the weekly reporting behind them
• Day-to-day management of a team of offshore agents: coaching, quality, and consistency
• The agent hiring, onboarding, and training pipeline as the team scales
• Our toughest cases: fraud and high-value disputes, including day-to-day use of our fraud tooling (SEON) and coordinating theft cases with law enforcement where needed
• Being the calm, senior owner who steps in when a rare, high-stakes escalation breaks outside normal hours

Requirements

• 4+ years in customer operations, support or CX, including 2+ years managing a team
• A track record owning metrics and hitting SLAs at scale
• Strong analytical skills: fluent in Sheets/Excel, and skilled at turning raw data into clear insights, and those insights into concrete recommendations and action
• Strong critical thinking, judgment, and EQ: you diagnose why issues happen and handle sensitive, high-stakes cases calmly
• Naturally curious about new tools, and comfortable driving AI-assisted automation
• Comfort with, or genuine interest in, fraud, risk, and dispute work - the hard cases don't faze you
• Based in NYC and able to work in-office 4 days a week

Nice to have

• Experience managing or working with offshore support teams, including hiring and developing agents
• Direct experience with Intercom, Zendesk, or similar support platforms
• Direct experience querying data in SQL, rather than relying solely on Sheets/Excel
• Experience supporting a two-sided marketplace or peer-to-peer platform
• Direct experience investigating fraud, handling chargebacks, or resolving disputes

Benefits

• Competitive compensation and equity
• Healthcare (Medical, Dental, Vision)
• Take what you need paid time off
• Meal Pal credits to cover the cost of lunch
• Stipend to help set up your office workspace
• Work directly with the founders and executive team
• Professional coaching, training, and development
• Real ownership from Day 1 and professional growth opportunities within a rapidly scaling, early stage startup
• Pickle credits for our employees, we love when the team uses Pickle!
• Fun team events, company parties, and offsites
• Downtown NYC office space (Tribeca)