Customer Engagement & Finance Specialist (Remote)

Location: Remote (USA only) Type: Full-time Compensation: $70,000 - $90,000 (subject to qualifications and experience) + equity + premium benefits The Customer Engagement & Finance Specialist role at Files.com is a high-impact generalist position with one mission: make sure invoices get paid. When they don't, this isn't about hounding customers with reminders. It's about digging in and fixing what's broken. That could mean detangling purchase orders, resolving sales tax issues, navigating procurement portals, or finding the right person inside a complex corporate hierarchy. You'll be on the front lines every month, working hundreds of accounts that fall into gray areas where payment is delayed or uncertain. Your job: clear the roadblocks, keep cash flowing, and make sure customers feel respected—not pressured. This isn't "collections." It's professional problem-solving, persistence, and communication that protects both revenue and relationships. Who We Are We're Files.com, a profitable, founder-led SaaS company powering secure file transfer and automation for 4,000+ brands you know: Marc Jacobs, GrubHub, Michelin, Hot Topic, Stamps.com, Planet Fitness, KFC, and more. We've built a $35M+ business with just 70 people by hiring smart, clear-thinking communicators who act fast and own outcomes. Backed by $46.5M from Riverwood Capital, we're scaling intentionally—and this role is a core part of that growth. What You'll Actually Do

• Troubleshoot Payment Issues: Investigate why payments are missing. That could mean invoice confusion, missing paperwork, sales tax mismatches, vendor delays, or technical hiccups. Find the real blocker and remove it.
• Client Communication (Phone + Email): Pick up the phone. It's faster, builds trust, and resolves issues. You'll talk with customers about invoices and payments in a collaborative, solutions-focused way. Professional, empathetic, persistent—never heavy-handed.
• CRM Logging & Documentation: Capture every call, email, and decision with clarity. Our finance, audit, and support teams depend on your records. No fluff, no gaps—just crisp documentation that anyone can follow at a glance.
• Cross-Department Coordination: Work closely with Billing, Support, Sales, and Leadership. You won't solve everything alone—but you will keep issues moving through the right lanes so customers always feel supported.

What Success Looks Like

• Invoices are paid on time—or quickly recovered when delayed
• Customers leave billing conversations feeling respected and supported
• Cash keeps flowing, revenue stays predictable, and the business stays healthy
• Teams across Finance, Sales, and Support trust your notes and depend on your follow-through

Who Thrives In This Role ✅ You communicate like it's your superpower—especially on the phone ✅ You can detangle messy, bureaucratic problems without losing momentum ✅ You stay positive and empathetic—even in tough conversations ✅ You're disciplined about logging details and following through ✅ You move quickly, think clearly, and keep your eye on the goal: timely payment Where This Role Can Take You (Growth Path) We don't sit on talent. Perform well here and doors open fast. Growth paths from this role include:

• Customer Engagement Manager – Coaching and leading other customer-facing employees
• Finance/Accounting Leadership – Driving process improvements, managing outcomes, even stepping into Controller-track work
• Operations or Customer Success – Expanding into adjacent high-visibility, high-impact roles

If you've got hunger and discipline, there's no ceiling. What This Job Is Not This isn't for you if:

• You avoid phone calls and try to solve everything over email
• You need to be reminded to follow up or log work
• You freeze in fast-moving, ambiguous environments
• You dislike feedback or take it personally

We move fast, communicate clearly, and hold a high bar—for ourselves and each other. Perks & Benefits 100% Paid Health, Dental & Vision (75% for family) 401(k) with 4% Company Match Equity Grants for Every Employee Paid Parental Leave 20 PTO Days + 11 Holidays + Full Company Winter Break $1,000 Signing Bonus + Modern Apple Laptop + Anniversary Gifts ✈️ Team Travel to NYC, Austin, San Diego, and More Bottom Line: This role matters. Done well, it keeps customers happy, cash flowing, and the business strong. If you want a career launchpad where you'll solve real problems every day and grow fast, we want you in this seat. Apply tot his job Apply To this Job