Customer Engagement & Finance Specialist (Remote)

📍 Location: Remote (USA)
💼 Type: Full-time
💰 Compensation: Competitive salary + equity + premium benefits

This Isn’t Just a Job. It’s a Career Launchpad—With a Team That’s Got Your Back.

At most companies, customer billing and finance is transactional. Collections are combative. And the people doing it are stuck in the shadows.

Not here.

At Files.com, our customer finance team is a high-leverage, high-visibility, deeply supported role that sits at the intersection of customer success, revenue, and trust.

You won’t just send invoices and collect payments. You’ll prevent friction, solve real business problems, and protect customer relationships.

This is a role with daily momentum, direct impact, and zero dead weight.

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: Target, Canonical, UPS, GoPro, Marriott, and more.

We’re not a chaotic startup. We’re not a bloated big tech org.

We’ve built a $35M+ business with just 70 people by hiring smart, clear-thinking communicators who act fast and own their outcomes.

Backed by $46.5M from Riverwood Capital, we’re scaling with intention, and this role is core to that strategy.

Why This Role Is a Big Deal

When this job is done well:

• 💰 Revenue flows
• 💬 Customers feel supported
• 🧠 Internal teams operate in sync
• ✅ Our business stays healthy and respected

That’s why we’re only hiring someone excellent for this seat. Someone who communicates clearly, solves problems without drama, and gives a damn about getting it right.

What You’ll Actually Do (AKA: The Work That Moves the Needle)

Client Communication & Relationship Management

• Regularly speak with customers (yes, on the phone!) to resolve outstanding invoices
• Ask great questions, build rapport, and create action plans both sides can commit to
• Be professional and empathetic—even when the convo is tough

Documentation & Process Improvement

• Maintain clear, accurate records of all customer comms and decisions
• Log every call, every update, every plan—accurately and consistently
• Help improve the way we collect, communicate, and track payments over time

Cross-Functional Collaboration

• Work closely with Billing to fix errors and close gaps
• Know when to bring in Sales, Support, or Leadership for help
• Be the person who connects the dots—because no one else sees what you do

Remove Customer Payment Barriers

• Help customers solve why they haven’t paid—not just that they haven’t
• Prevent service disruptions before they happen
• Focus on customer success first—collections second

Who Thrives In This Role

✅ You communicate like it’s your superpower.
✅ You’re allergic to sloppiness and dropped balls.
✅ You lead with empathy, but don’t shy away from hard truths.
✅ You’re AI-fluent—or ready to learn FAST.
✅ You want feedback, and you actually use it.
✅ You move quickly, think clearly, and write like a pro.

What Happens If You Don’t Do This Job Well?

Let’s not sugarcoat it.

If this role is done poorly:

• Customers get angry, locked out, or churn altogether
• Revenue gets delayed, disrupted, or disappears
• Internal teams waste hours untangling messes
• Our audit readiness and reporting go out the window
• Company leadership loses confidence in operational reliability

This job matters, and that’s why we’re hiring someone great to do it.

Where This Role Can Take You (Growth Path)

We don’t sit on talent. When you perform here, we move fast to unlock your next chapter. 

Real paths include:

• Customer Engagement Manager – Coaching other customer-facing employees
• Finance / Accounting Roles, such as Controller – Manage process improvements, and own team outcomes

If you’ve got hunger and discipline, there is no ceiling.

This Role Is Not for You If...

Let’s be blunt. If any of these sound like you, you’ll struggle here:

• You avoid phone calls and try to solve everything over email
• You need to be reminded to follow up or log your work
• You wait for direction instead of taking ownership
• You get overwhelmed in fast-moving environments
• You don’t like feedback—or you get defensive when you hear it

That doesn’t mean you’re not talented. It just means this isn’t your team.

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