Inside Sales Representative – Trial Assist – DropBox

Join MarketStar as an Inside Sales Representative specializing in trial customer conversion and account development for Dropbox in the United States. In this full-time role, you'll nurture prospective small and mid-market clients through their evaluation phase, translating their business goals into Dropbox solutions and closing the sale.

Role Overview

As an Inside Sales Representative focused on trial assistance and customer conversion, you'll take ownership of a dedicated pipeline of trial accounts and qualified prospects. Your mission is to accelerate customers from evaluation to purchase by providing expert guidance, identifying product-market fit, and removing adoption barriers. This is an ideal opportunity for someone ready to deepen their inside sales expertise with a leading cloud services company.

Day-to-Day Responsibilities

• Reach out to active trial users via phone, email, and digital touchpoints, delivering personalized engagement tailored to their business needs and timeline.
• Convert trial evaluations into paid agreements by discovering customer challenges, presenting relevant Dropbox capabilities, and addressing purchase objections.
• Cultivate customer trust through consultative problem-solving, product education, and clear communication around platform value and implementation.
• Coordinate with the broader sales function to identify high-momentum opportunities, align messaging, and accelerate deal progression.
• Analyze trial activity and engagement metrics to prioritize outreach and forecast conversion likelihood.
• Deliver feedback from customer conversations to cross-functional stakeholders to refine the trial onboarding experience and boost conversion performance.
• Meet and exceed weekly and monthly conversion targets, customer satisfaction goals, and pipeline productivity metrics.
• Execute targeted outreach campaigns via email and phone to existing and prospective accounts using a mix of proven sales methodologies.
• Maintain detailed, accurate account data in Salesforce and Outreach, ensuring timely follow-ups and complete pipeline visibility.
• Embrace a growth mindset—actively seek feedback from leadership and peers, refining your approach based on coaching and market response.
• Master the technology stack quickly, including Salesforce, Outreach, Power BI, Slack, Gmail, Outlook, and other sales tools.

What You Bring

• At least one year of B2B inside sales or sales development experience; trial conversion or direct sales background is a plus.
• Working knowledge of cloud-based platforms and a genuine commitment to exceptional customer outcomes.
• Proven success in lead qualification, customer profiling, and trial-to-revenue pipeline management.
• Experience managing customer inquiries with professionalism, responsiveness, and a service-first mindset.
• Natural confidence and the ability to establish credibility and rapport in first conversations.
• Strong organizational skills and the ability to juggle competing priorities, manage time effectively, and stay focused under pressure.
• Clear verbal and written communication with a polished phone presence.
• Comfort navigating sales tech platforms—Salesforce, Outreach, and similar tools—at an intermediate level or higher.
• Meticulous attention to detail with consistent follow-through on commitments.
• Flexibility to take scheduled calls as business needs require.

More About MarketStar

For over 35 years, MarketStar has fueled revenue growth for the world's leading technology companies through outsourced demand generation, sales enablement, customer success, and revenue operations. Our 3,000+ team members span offices in Utah, India, Ireland, Bulgaria, Mexico, the Philippines, and Australia. We invest deeply in career development, mentorship, and leadership pathways for our employees, and we contribute to social good through the MarketStar Foundation. Our workplace culture has earned recognition as a top employer, built on six core values that guide everything we do. We support employee well-being through structured learning programs, mental health resources, generous paid time off, paid medical leave, dependent care reimbursement, education assistance, 401(k) matching, and comprehensive healthcare coverage including medical, dental, and vision benefits.

Ready to Apply?

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