Inside Sales Representative – Trial Assist

Role Overview

• Proactively engage Dropbox trial users through phone, email, and digital channels to provide a personalized, high-touch customer experience throughout the trial lifecycle.
• Drive trial-to-paid conversion by understanding customer goals, identifying use cases, addressing objections, and guiding customers toward the best Dropbox solution for their business.
• Build relationships with trial customers by providing consultative support, answering product questions, and removing barriers to adoption.
• Partner closely with Sales to identify high-potential trial accounts, coordinate engagement strategies, and accelerate purchase decisions.
• Monitor trial engagement signals and prioritize outreach based on customer activity and likelihood to convert.
• Share customer insights and feedback with cross-functional teams to improve the trial experience and increase overall conversion rates.
• Consistently achieve trial conversion, customer engagement, and productivity goals while delivering an exceptional customer experience.
• Constantly strive to improve, proactively seeking coaching and guidance from peers and managers.
• Execute sales campaigns using various tactics including calling and emailing existing client customers.
• Leverage CRM and sales engagement tools (Salesforce, Outreach) to document customer interactions, maintain accurate pipeline data, and ensure timely follow-up.
• Adhere to daily, weekly, and monthly KPIs, maintaining high energy and flexibility in a fast-paced, constantly evolving team environment.
• Expertly serve as a product and service advocate for the client, building interest and awareness of the value proposition and assessing mutual fit.
• Learn quickly and maintain current, comprehensive knowledge of client’s products and services.
• Utilize tech platforms effectively: Outreach, Salesforce, Power BI, Slack, Calendar, Gmail, and Outlook.
• Other duties as assigned.

Requirements

• Minimum one year of B2B inside sales experience; some direct sales or trial conversion experience preferred.
• Solid understanding of cloud-based technology and tools, with a passion for the customer and customer experience.
• Prior experience nurturing leads, profiling customers, or managing a trial lifecycle to identify sales opportunities.
• Prior experience responding to customer requests for sales and service ensuring delivery of an exceptional customer experience by responding in a prompt, professional, and friendly manner.
• High confidence and ability to quickly build trust within the first call, using strong soft skills to drive impact on the spot.
• Strong organization and time management coupled with the ability to multitask, prioritize high-potential leads, and work under pressure.
• Excellent verbal and written communication skills with a professional telephone presence.
• Intermediate skills navigating tech platforms, including Salesforce.com, Outreach, Gmail, and other sales tech stack tools.
• High attention to detail and follow-through.
• Ability to take scheduled calls as needed.

Tech Stack

• Cloud
• SFDC

Benefits

• Structured learning and career development programs
• Mental health program
• Generous Paid Time Off policy
• Paid medical leave
• Child/Dependent care reimbursement
• Education reimbursement
• 401k match, hardship loan program, access to financial wellness advisor
• Comprehensive healthcare coverage including medical, dental, and vision