Customer Support Manager

About Pickle

Pickle is a peer-to-peer rental marketplace unlocking the value of the billions of underutilized items sitting in consumers' closets. We make it easy to rent high-quality items exactly when you need them — with fast, convenient fulfillment and an on-demand experience that's as seamless as shopping.

We're building a new kind of commerce layer: one powered by dynamic local supply, where access is more convenient than ownership. Pickle is now live nationwide and scaling rapidly in key local markets including NYC, LA, and Miami. Our marketplace already features 400K+ items, and we're just getting started. We're excited to extend our vision beyond fashion into every category.

What makes Pickle different is the combination of incredible peer-to-peer inventory, industry-leading convenience (under 2 days nationwide and under 2 hours locally), and an on-demand model with no subscriptions — users rent what they want, when they want it. We've raised $20M to date from FirstMark, Craft, Burst Capital, FJ Labs, and others, and we're scaling quickly to build the future of access-driven shopping.

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)