Two Chicks With A Side Hustle

Step into a high-impact role where your mission is simple but vital: keep invoices paid, cash flowing, and customers supported—not pressured.

About Files.com
Files.com is a profitable, founder-led SaaS company powering secure file transfer and automation for 4,000+ global brands like Michelin, Planet Fitness, Marc Jacobs, and KFC. With $35M+ in revenue and $46.5M in funding from Riverwood Capital, we’ve built a lean, fast-moving team of 70 people focused on impact, growth, and customer trust.

Schedule

  • Full-time, remote (USA only)
  • Standard business hours with flexibility

What You’ll Do

  • Troubleshoot payment issues by resolving PO errors, tax mismatches, procurement portal delays, or vendor miscommunication
  • Communicate directly with customers via phone and email, building trust through collaborative problem-solving
  • Document every call and decision with crisp CRM notes used by Finance, Sales, and Support teams
  • Partner with Billing, Support, Sales, and Leadership to clear roadblocks and maintain smooth processes

What You Need

  • 2+ years of office-based experience in finance, customer engagement, or operations
  • Strong communication skills, especially phone conversations that balance professionalism and empathy
  • Discipline in logging details, following through, and driving results
  • Ability to handle bureaucratic or ambiguous problems with clarity and persistence
  • A fast-moving, solutions-driven mindset that thrives in dynamic environments

Benefits

  • Competitive salary + equity grants for every employee
  • 100% employer-paid health, dental & vision (75% for family)
  • 401(k) with 4% company match
  • 20 PTO days + 11 holidays + full company winter break
  • Paid parental leave
  • $1,000 signing bonus + modern MacBook Pro
  • Anniversary gifts + company travel to NYC, Austin, San Diego, and more

This isn’t collections—it’s professional problem-solving that protects both revenue and relationships. If you’re hungry, disciplined, and ready to grow fast, this role is your launchpad.

Happy Hunting,
~Two Chicks…

APPLY HERE