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Sales Development Representative

📍 Location: Old Town Scottsdale, AZ (In-Office)
💼 Type: Full-time
💰 Compensation: $35,000 - $90,000 OTE (subject to qualifications and experience) + premium benefits

The first conversation can make or break a sale.

Sales Development Representatives at Files.com are the people who make those conversations count.

At a lot of companies, SDRs are treated like junior telemarketers, grinding through cold calls to people who don’t want to talk. That’s not how we work here. At Files.com, you won’t be dialing random lists — you’ll be engaging warm leads who have already shown interest in our platform. That means you spend your time having real conversations, not chasing ghosts.

Our SDRs are sharp, fast, and strategic. You’ll be qualifying opportunities from Fortune 500s, global brands, and fast-scaling enterprises — companies where file transfer and automation are mission-critical. You’ll research who you’re talking to, understand their business needs, and decide whether the opportunity is a fit. Then, you’ll hand off only the best-prepared leads to our Account Executives, protecting their time and directly influencing revenue growth.

This role is about more than filling the pipeline. It’s about learning the craft of enterprise sales from the inside. You’ll develop skills in research, qualification, and executive communication that will serve you for your entire career.

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, disciplined, and high-output teammates who act fast and own outcomes. Backed by $46.5M from Riverwood Capital, we’re scaling intentionally—and this role is a critical piece of that growth.

Our Scottsdale office sits in the heart of Old Town: a bright, modern space with huge windows ☀️, craft coffee ☕️, free drinks, and free catered breakfast every day 🍳🥓. Step outside and you’re surrounded by some of the best lunch and happy hour spots in Arizona. Twice a year, we bring the whole team together for energizing off-sites in cities like Austin, Nashville, and Miami.

What You’ll Actually Do

This isn’t about hammering phones all day. It’s about sharp thinking, fast judgment, and meaningful conversations with enterprise prospects.

In this role, you will:

  • Master the Product: Learn Files.com inside and out so you can confidently communicate its value.
  • Qualify Warm Leads: Engage inbound prospects over phone, email, chat, and social channels, asking the right questions to confirm fit.
  • Book High-Quality Meetings: Deliver well-prepared, high-value appointments to Account Executives that lead to real pipeline and closed deals.
  • Communicate with Impact: Represent Files.com with clarity, professionalism, and confidence in every interaction.

What Success Looks Like

  • Account Executives trust your meetings because they’re thoughtful, prepped, and high quality.
  • Prospects remember their first Files.com conversation as clear, professional, and worth their time.
  • You grow noticeably sharper at research, qualification, and communication every single quarter.

Why This Role Is Different

  • You’ll build confidence talking to executives at well-known companies — the kind of conversations most people don’t get this early in their career.
  • You’ll get exposure to big-name customers like Fortune 500s and global brands, giving you credibility and experience that makes your resume stand out.
  • You’ll learn enterprise sales without cold prospecting, focusing on warm leads who actually want to talk.
  • You’ll develop career-launching skills in research, qualification, and communication — with a clear path to Account Executive or beyond in 6–12 months.

Who Thrives in This Role

✅ You’re quick on your feet and can process information fast
✅ You’re disciplined about details, accuracy, and follow-through
✅ You communicate with confidence and clarity
✅ You thrive in a fast-paced, high-energy environment
✅ You want a career in enterprise sales and are hungry to grow

Where This Role Can Take You (Growth Path)

We don’t hire SDRs to stay SDRs. Perform here and you’ll set yourself up for rapid growth.

Real paths include:
SDR → Account Executive – run the full enterprise sales cycle, from qualification to close
SDR → Customer Success – manage long-term customer relationships and drive retention
SDR → Sales Leadership – coach, mentor, and scale the next generation of SDRs

Your trajectory here is only limited by your drive, discipline, and output.

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
🍳 Free catered breakfast every day in our Scottsdale office
✈️ Team Travel to NYC, Austin, Nashville, Miami, and more

Bottom Line: This isn’t “entry-level sales” the way other companies define it. This is high-output, high-impact sales development where accuracy meets speed. If you want to break into enterprise software sales, fuel the growth of a profitable SaaS company, and build a career that accelerates fast, this is your seat.

We would like you to tell us why this opportunity speaks to you. You don’t have to tell us now, but we promise we’ll read your story upfront. You’re more than a resume!

Our Employee Benefits At A Glance

We want you and your family to live longer, healthier, and happier lives. Providing our employees with top-tier benefits leads to improved productivity, long-term retention, and better decision making, so that's what we do.

Categories :

High Starting Salaries

As a successful, profitable business that believes in over-investing in our team, we choose to offer industry-leading base salaries for all positions.

Performance-Based Raises

We reward our high performers for one simple reason: they've earned it.

Equity Option Grants

As a private equity-backed business, we expect to have a major exit event within the next 5 years. We have set aside a substantial pool of equity options to grant to our employees so they are able to share in the value created.

401(k) With Generous Employer Match

Most employer-sponsored 401(k) plans crush you with fees. Our plan features extremely low-fee ETFs, ensuring that you actually keep the money that you save for retirement. Plus, we will match your contributions up to 4% of your salary to encourage you to invest for your retirement.

Starting Bonus

New Hires receive a $1,000 starting bonus. No strings attached.

Company-Issued MacBook Pro

You will receive a fully loaded MacBook Pro, reducing time wasted setting up individual rigs.

Legal Assistance

Option to participate in an employee paid legal plan to gain access to a network of attorneys who assist with basic legal needs including wills, trusts, contracts, tickets, and documents.

Employee Assistance Program

We provide a confidential and no cost avenue for you to receive 24/7 assistance with issues regarding behavioral and emotional health, family, legal, financial, wellness or other personal matters. You will have access to a certified clinician who can help you one-on-one or refer you to someone in your area for longer-term help.

Medical Insurance

Comprehensive coverage with low premiums for employees and families. Ability to choose between a Preferred Provider Organization (PPO), Exclusive Provider Organization (EPO), or Health Maintenance Organization (HMO)

Dental Insurance

Coverage for preventive and diagnostic services like semi-annual exams, x-rays, cleanings, and coverage for more major events like fillings, extractions, or root canals.

Vision Insurance

Plans designed to encourage you to maintain your vision through regular eye exams and help with expenses for contacts, lenses, frames or surgery.

Life insurance

Employer-provided $50,000 Basic Life & AD&D policy, which employees have the option to supplement.

Disability Insurance

Coverage for short-term and long-term disability available for purchase.

Flexible Spending Account (FSA)

Ability to set aside pre-tax money for out-of-pocket medical expenses, such as prescriptions, over-the-counter medicine, or vision care.

Healthcare Providers

Access to providers based on region including Aetna, Blue Cross Blue Shield, Cigna, Delta Dental, Guardian, Group Health, Kaiser Permanente, MetLife, Tufts Health Plan, VSP, WageWorks, and UHC among others.

Vacation and Holidays

We encourage our employees to take time off and enjoy all that life has to offer. Employees are eligible to accumulate up to 4 weeks (20 days) of paid time off (PTO) and receive 11 company holidays.

Growing A Family

We offer paid time off for growing a family, whether by birth, adoption, or fostering. Eligible employees may take between 2 to 10 weeks of paid leave.

Bereavement Leave

Employees may take up to 4 days of paid bereavement leave for the death of an immediate family member. Bereavement days do not count toward an employee's PTO.

Paid Business Trips

You will travel to in-person meetings with your team and the entire company to meet and work together face-to-face. These meetings are in cities that are fun to visit. In the last few years, we've been to Austin, Orlando, New Orleans, San Diego, Las Vegas, New York City, and Nashville among other destinations. We also support attending trade shows and conventions, especially if you are willing to speak at such an event.

Continued Learning

We invest in continued learning opportunities for our staff. We reimburse employees who attend conferences, participate in speaking events, and pursue certifications to improve their skills.

"You're surrounded by intelligent and driven people who genuinely want to see you succeed. Everyone here is invested in helping you grow and perform at your best. It's rare to find that combination of high talent and supportive culture in one place."

— Karan Mangat, Account Executive

“It's really about being able to work with really smart people on really interesting problems and feeling like you're actually contributing to something big.”

— Gabe Purrenhage, Principal Infrastructure Engineer

“Files.com gives me opportunities to solve big problems, build real products, and see the direct impact on customers and growth. It’s work that truly matters.”

— Dustin Zeisler, Principal Engineer

"The level of excellence across the team encourages me to keep learning, try new ideas, and become better at what I do. I also appreciate how quickly our products move from concept to real customer use. Seeing something you helped build get adopted almost immediately creates a strong sense of pride and connection to the work."

— Claudio Tinnirello, Product Manager

"I am truly proud to work for Files.com. We’re creating technology that genuinely helps people. You can see your work go from idea to impact so quickly, it's awesome."

— Jesse Harris, Senior Engineering Manager