Customer Experience Lead

Must be located in NYC (we are in office Monday - Thursday).

Please apply by emailing [email protected] with "Customer Experience Lead" in the subject line and include the following:

• Share 1-3 (max) bullets on why you think you're a standout applicant for this role.
• Share 1-2 (max) bullets summarizing a customer experience initiative you're most proud of and the impact it drove (we love metrics!)
• Share your Pickle username and your favorite app feature

Pickle is a rental marketplace that aims to monetize the billions of underutilized assets sitting in consumers closets and brands inventory. Users can easily tap into shared closets within their community through flexible and/or on-demand delivery options. Our goal is to provide affordable and convenient access to quality items exactly when our users need them. We are starting with P2P clothing/accessories and expanding to other categories.

We're looking for a passionate and experienced Customer Experience Lead to be the voice of our customers and the champion of their happiness. This role goes far beyond traditional support—you'll uncover customer pain points, identify usage trends, and partner with Product and Operations to continuously improve our service. You'll ensure every new feature, ops flow, and delivery change is rolled out with our customers' needs at the center.

Role Overview:

As Customer Experience Lead, you'll be the internal advocate for our community of renters and lenders. You'll lead customer support operations, but more importantly, you'll be embedded in strategic decisions across the company—from product roadmap discussions to operational changes. Your deep understanding of customer needs will inform how we build, what we prioritize, and how we communicate changes.

You'll interview customers regularly, analyze trends in support tickets and product usage, and translate insights into actionable recommendations. When we launch a new delivery option, update our trust & safety policies, or ship a product feature, you'll ensure our customers understand it, love it, and benefit from it.

• 5+ years of experience in Customer Experience, Customer Support, or related roles (marketplace, e-commerce, or tech a plus)
• Proven experience leading and scaling customer support teams
• Track record of uncovering customer insights and translating them into product or operational improvements
• Deep passion for solving customer problems and creating delightful experiences
• Strong analytical skills—comfortable identifying trends in customer feedback, support data, and product usage
• Excellent cross-functional collaborator; experience working closely with Product, Operations, and Engineering teams
• Outstanding communication skills—comfortable conducting customer interviews, presenting insights to leadership, and advocating for user needs
• Empathetic and user-obsessed; you genuinely care about how people feel when they use Pickle
• Experience managing change management and customer communication for new product launches or operational rollouts
• Comfortable working in a fast-moving, dynamic startup environment where you'll wear many hats
• Bonus: experience with peer-to-peer marketplaces or two-sided platforms
• Bonus: familiarity with support tools like Zendesk, Intercom, or similar platforms

Responsibilities

• Serve as the internal voice of the customer across Product, Operations, and the broader company
• Conduct regular customer interviews and feedback sessions to uncover pain points and opportunities
• Analyze support trends, product usage data, and customer sentiment to identify systemic issues and improvement areas
• Partner with Product to ensure customer insights inform roadmap decisions and feature development
• Collaborate with Operations on new delivery flows, logistics changes, and process improvements—ensuring they're customer-friendly
• Own change management and communication for new features, policy updates, and operational rollouts
• Lead and scale the customer support team, setting the tone for empathy, speed, and quality
• Build and refine support processes, workflows, and documentation to scale efficiently
• Own all customer support channels (email, chat, in-app messaging) and ensure timely, helpful responses
• Track and improve key customer experience metrics (CSAT, NPS, response time, resolution time)
• Develop policies and best practices for handling disputes, trust & safety issues, and edge cases
• Create a culture of customer obsession across the company, championing user needs in every decision
• Report on support performance, customer sentiment, and strategic insights; define and drive improvement targets

• 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 desk and office environment
• Work directly with the founders and executive team
• Professional coaching, training, and development
• Grow with the company
• Pickle credits for our employees, we love when the team uses Pickle!
• Fun team events and company parties
• Company offsites
• Office space in NYC