Careers
Technical Customer Success Lead
About In The Loop (ITL)
We’re In The Loop, a vertical software suite transforming the massive, overlooked world of secondhand retail. Thrift stores move billions of items every year, yet many still rely on handwritten tags, guess-based pricing, and fragmented systems. We’re changing tht.
Over the past year, we’ve partnered with some of the largest thrift operations in the country and have helped process 85,000+ garments per month. Now, with demand surging and new product modules shipping, we’re officially in scaling mode.
We’re backed by leaders in the industry: including eBay, the former CTO of Depop, and the former CTO of Hepsiburada.
What We Build
Our system plugs directly into the workflows of thrift processors, POS systems, and e-commerce marketplaces. We help stores go from:
handwritten tags → automated listings,
guess-based pricing → dynamic, data-driven pricing,
lost revenue → recovered value
external, messy data dashboards → dynamic, daily views
Why This Space Matters
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Massive, broken industry: $211B re-commerce market and growing.
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Complex workflows: Every store and warehouse looks different, making it the perfect playground for problem-solvers.
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First movers: No one else is building a purpose-built production system for thrift.
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Clear ROI: Customers see velocity increases and revenue lift in months, not years.
About the Team
We’re a small, product-obsessed team with deep experience in AI, resale, reverse logistics. We’ve built and scaled startup products from 0→1. At ITL, everyone wears multiple hats and is passionate about driving success for our customers.
The Role
We’re hiring a Technical Customer Support Specialist to serve as the frontline partner for our thrift store customers, ensuring they get the most out of ITL’s pricing, production, and inventory tools. You’ll troubleshoot issues, go on-site with clients and observe real workflows, communicate customer needs to engineering, and help us scale support as demand grows.
This role is perfect for someone who loves solving problems, thrives in operational environments, and wants to be foundational at a fast-moving startup.
What You’ll Do
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Serve as the primary support contact for our thrift customers
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Lead customer calls to understand workflows, pain points, and opportunities for process optimization
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Lead customer calls to present data in Power BI and our internal dashboard
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Assist with onboarding and configuration for new stores alongside the CEO
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Support on-site installs or training (~25% Travel)
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Troubleshoot product issues the web app and ecosystem integrations
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Diagnose technical problems (API errors, sync issues, data inconsistencies) and communicate them clearly to engineering
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Maintain help documentation, support playbooks, and internal tooling
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Surface recurring customer feedback and help turn it into product improvements
What We’re Looking For
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Experience in retail operations, thrift, warehouse workflows
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Highly organized and able to juggle multiple support requests while keeping customers informed
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Comfortable with basic technical tasks (API logs, CSV validations, debugging user flows) or eager to learn quickly
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Intermediate to advanced proficiency in PowerBI
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Bonus: Familiarity with SQL, EDI flows, or data mapping
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Bonus: Startup experience or supporting 0→1 products
Why Join Us Now
This is a unique chance to join early and help build the support function from scratch. You’ll have real ownership, constant customer exposure, and the ability to influence product decisions.
If you care about operational excellence, sustainability, and building tech that actually matters to real people, you’ll thrive here.
Comp
Base salary of $80K plus competitive equity package.
High ownership, remote work (preferably East or Central Time Zones)
How To Apply