Job Title: Contract Sales Representative (Lead Generation & Demo Scheduling)
Location: U.S.-based (Remote)
Contract Type: 1099 Contractor
Duration: 6–8 week trial with potential transition to part-time or full-time role
Compensation: Hourly (via Upwork)
About Upswing
Upswing is an education technology company focused on improving student success and retention through engagement tools, academic support, and actionable insights. We partner with colleges, universities, and nonprofits to help empower students to achieve their goals.
Role Overview
We are seeking highly motivated Contract Sales Representatives to support our outreach efforts. In this role, you will be responsible for generating scheduled demos from a provided list of leads. You’ll receive targeted sales training covering our messaging, buyer personas, product positioning, and outreach workflow.
This role is ideal for candidates who are self-starters, highly organized, and excited about contributing to a meaningful mission in higher education.
Responsibilities
Conduct outbound outreach (email, phone, LinkedIn) to a provided list of leads
Follow Upswing’s sales messaging and outreach cadence
Schedule demos for the sales team using our calendar tools
Document all outreach activity and lead notes in the designated system
Participate in training sessions and weekly check-ins
Meet weekly KPIs related to demo generation and documentation completeness
Qualifications
Based in the United States
Experience in sales, lead generation, or outreach-focused roles preferred; experience in higher education or higher education sales a plus
Strong communication and organizational skills
Ability to follow structured processes and meet weekly targets
Reliable time management and responsiveness
Comfortable working remotely and independently
Advancement Opportunity
Contractors who excel during the 6–8 week trial period may be invited to transition into a part-time or full-time role such as Jr. Account Executive or Account Executive, with expanded responsibilities including full sales cycle management.